Category: Travel Hacking

By Josh November 12, 2018

It was only 10 days ago, on a Friday evening after work, when I learned my internet friend Dumpster Doggy was going to be in New York City for a week, visiting her friend from college this week. It made me think “I’ve never flown across the country to visit a friend before” and “I should totally do that sometime!” In that instant, I remembered that my new job affords me the benefit of a paid holiday for Veteran’s Day, which was coming up the following weekend, and observed on the Monday (today) that I write this. A three-day weekend – I should totally take advantage of that extra day and travel somewhere!

Being somewhat unimaginative myself, I borrowed Dumpster Doggy’s idea – I would travel to NYC! As you are probably aware by now, I have tons of points and miles from various hotel and airline programs, plus the beneficial “transferable points” from a couple different bank/credit card programs. So, I set out searching for routes and times for flights that would work, and award availability at hotels in the City that would make for spectacular redemptions.

As a cardholder of the Chase IHG credit card, I receive a certificate good for a free night at any hotel in their portfolio around the world. They have recently changed the terms to make it work for hotels with a maximum of 40,000 IHG points per night, but I used it at the Intercontinental New York Barclay that charges 70,000 points per night. I pay a whopping $49 per year for that card, and I saved over $450 (plus taxes and fees) using my certificate.

For my second night, I transferred the valuable Chase Ultimate Rewards points (that I earn from Sapphire Reserve, Freedom and Freedom Unlimited cards) to World of Hyatt. I had over 4,000 Hyatt points sitting in my account, so I needed to send over another 26,000 Ultimate Rewards points to Hyatt (transferred instantaneously) to book the Park Hyatt New York City that goes for $895 per night (plus taxes and fees). Chase Ultimate Rewards points are typically valued around 2-2.1c each, but this redemption was 2.98 (call it 3) cents per point, and I got to stay in the swankiest hotel I’ve ever stepped foot into! For FREE!

To get to New York City, I looked at a few options. I could have used my Southwest Rapid Rewards points that I have sitting in my account, but I also hold the Chase Southwest Priority card that has an annual benefit of a $75 credit on flights purchased on Southwest. I had been looking for a one-way trip to buy a cash ticket on Southwest and get that automatic $75 credit, so I bought a ticket from RSW to LaGuardia for $156.80 and was only charged $81.80 for the trip. (This card comes with a $149 annual fee, so I earned back half of that fee with this flight. It also comes with 4 reimbursed upgrades to A1-A15, so I can skip the “early bird” gimmick and take my chances checking in at 24 hours ahead of the flight… if I don’t get a decent boarding position, I can buy an upgrade to the front of the boarding line, and it will be reimbursed 4x per year. Other benefits include 7,500 Rapid Reward points as a cardmember anniversary bonus, and 20% off in-flight purchases). I used UberPool to get from LaGuardia airport to the Intercontinental Barclay hotel in Manhattan for $16.99, including a $5 tip.

To get home, I am flying on JetBlue using some accumulated TrueBlue points I mostly earned from the JetBlue Plus credit card from Barclay. I got 40,000 points for only $1,000 in purchases, and I have earned smatterings of additional points from actual flights on JetBlue, filling out surveys, and doing my grocery shopping with that card. For 10,000 TrueBlue points, I flew home to Fort Myers, FL from Newark, NJ. My JetBlue credit card also gives me 50% off in-flight purchases, so I bought a Mile-High Mule and an Angry Orchard for only $3.50 each. To get to the airport, I booked a shuttle bus called the Newark Airport Express for $18 that picked me up at Bryant Park (42^nd Street and 5^th Avenue) and brought me to Newark in a charter bus that took about 45 minutes.

So all of the above is the “how” of travel hacking my trip, and I spent a whopping $156.79 (including $33 for parking at my home airport) for a 3-day weekend of luxury accommodations in one of the most expensive cities in the world! (I don’t count the cost of meals, since I would still be eating at home if I wasn’t traveling.) Below, I will provide a run-down of the activities I took part in, and the wonderful people I met (excluding 2 guys in Times Square that took all my remaining cash).

Saturday afternoon, upon landing at LaGuardia, I pulled out my phone to find a Twitter DM from Zero2Fire to say that she and Felicity from Fetching Financial Freedom were hanging out a café in Midtown, about ¾ mile from where my hotel was located. After checking in and dropping off my bag (traveled once again with my convertible backpack from ebags.com, which I can wear like a backpack or carry like a duffel), I went to Café Zaiya and met Zero and Felicity (whom I’d met at FinCon18), where we shared an ice cream and chatted for a while, before setting out to explore the City a bit. We checked out a Japanese grocery store, where Felicity and I both bought Japanese candies), and the New York Public Library at Bryant Park, which had awesome architecture and a big gift shop.

We wandered south a little bit and saw the Flatiron Building (which was once the tallest building in the world) and we stopped at Sweaty Betty’s (women’s athleisure) and the Fujifilm store, which took our picture on their knock-off Polaroids and gave us hot chocolate and a voucher for 10 free 4×6 prints from our phones. By then, it was time to go meet The Luxe Strategist at Tacombi Flatiron, a taco joint that allowed us to sit and visit for 2 hours (it started to get crowded towards the end), before we settled up the bill, each with our own Chase Sapphire Reserve cards (I had never seen another one of these out “in the wild” until FinCon, and now it’s a regular occurrence 😉).

We walked a few blocks south to get some dessert, aka doughnuts, at a place called Dough. We stayed there until the place closed at 9, and the workers were literally taking away the chairs all around us… Haha! After walking and talking a little while longer, we said our goodbyes to Luxe, and turned to walk north towards a subway station that would take Zero and Felicity back to Zero’s apartment. By the time we split up, I only had about 10 more blocks to walk, but I ended up walking about 15 more because I got a little confused about where I was headed, but I didn’t want to make an about-face in the middle of the sidewalk, so I just continued to the next corner and turned North and walked back on the next block 😉

Saturday, I checked out of my hotel early and left my bag with the Bell Stand, then grabbed some Starbucks on my way South along Madison Avenue. I reached Madison Square Park, then walked down 5^th Avenue in the direction of Washington Park.

After crossing through Washington Park,  I kept going south until I found myself surprised by the World Trade Center Memorial pools. It might sound strange to be “surprised” to be at the foot of the tallest building in North America, but I was walking through cute neighborhoods filled with a tree canopy and then all of the sudden: bam! I hit 10k steps as I was walking to the 2^nd memorial pool, and then I went inside to take a little break while checking out the One World Observatory and the See Forever Theater.

 

After spending about an hour at the One World Observatory taking in all of the sights from 102 stories in the sky, I headed south to Battery Park to get a glimpse of the Statue of Liberty and Ellis Island. I also grabbed a $1 hotdog as I kept walking towards the Charging Bull statue. I didn’t really get close to the bull, since there was a line about 50 people deep to get your picture with the bull, unless you were a total tourist and stood at the back-end of the bull to get a picture! (Seriously, people did this!!)

Heading North on Broadway, I walked through the Wall Street area and continued north through SoHo and NoHo before reaching Union Square Park. I veered right and kept walking north on Park Avenue, ending at Grand Central Terminal. I’d been there before in 2002, but I still wanted to walk inside and marvel at the sea of humanity, all heading in different directions at different speeds, and never seeming to bump into each other. From there, I turned east and walked to the top of the Isaiah Wall in Tudor City where I took a photo of the United Nations building before heading back to the hotel to grab my bag and head towards hotel #2.

On the way to the Park Hyatt on 57^th Street, I walked past Trump Tower and proceeded to extend my middle finger in protest. A few blocks later, a couple hundred steps away from my hotel, I almost bumped right into Wayne Brady, but instead of saying anything to him, I just chuckled and muttered “Wayne.”

The Park Hyatt is so fancy; you walk in and they escort you to an elevator to the lobby on the 3^rd floor. I had already walked almost 29,000 steps at this point, and I was sweating from walking so much and carrying my backpack for the past 3,500 steps of that journey. I just wanted to get to my room, take a shower and rest… but I also knew I needed to take pictures to show off how fabulous these accommodations were (again, for free!). The shower was incredible, with a wand AND a rain shower in the ceiling.

I relaxed for a while in pajamas before putting on fresh clothes to go check out the Ed Sullivan Theater (Stephen Colbert), the Hello Deli (made famous by David Letterman when he was in the Ed Sullivan Theater), and I grabbed an Italian sausage sandwich from a street vendor. After finishing the sandwich, I walked south to Times Square, where I was just trying to grab a few photos before hustling out of the mob of people. I truly hate crowds, and for good reason: a street vendor/hustler came up to me, and when I said “not interested” and kept walking, he pulled the race card and said “at least shake a Black Man’s hand when you speak to him,” so I stopped and shook his hand. He was peddling crappy cd copies of his “album” and “music video” and encouraged me to follow him on YouTube. He signed the CD sleeve and so did his buddy that showed up once I stopped. I didn’t want either CD, but I didn’t want to cause a situation, either, and they both knew it… suddenly I was hit up for a “suggested donation” of $20, and I said I didn’t have any cash, so he pulled out his Square credit card reader and pointed out a police officer standing behind me saying he was legit. I didn’t want to hand over my credit card, and I didn’t want to give him anything besides his CDs back, but I took the fastest escape valve I could think of, and handed him a $20 bill and tried to walk away, but then he said “Anything for him? He’s separate” but I only had $20 left in cash and I didn’t want to give all of it away. The second guy gave me a $5 back and I scurried away, upset and nearly broke. As soon as I found a trashcan, I threw away those damn CDs and vowed that any time this happens again, I will hand back the CDs and leave, even if I must be rude about it. This situation really ruined what was otherwise a WONDERFUL day of exploring NYC.

I walked quickly back to my hotel and changed back into pajamas, content to call it a day at 5PM and just go to bed… but after a cooling off period, I decided I really wanted something to eat and to explore a tiny bit more. I saw on Google Maps that there was a Chipotle just 3 blocks away, and I had a gift card I could use to pay for it (since I no longer had enough cash). I was surprised to find that Chipotle prices in NYC aren’t that much different than Chipotle in Fort Myers, so I even had $1.18 left on the card, which I handed over to the young man in line behind me, because I’d rather give it away than try to track gift cards with $1.18 left on them. After Chipotle, I wanted a drink from Starbucks to help keep me warm on the walk back to the hotel, but after I placed my mobile order and walked next door, the lady said they were out of apple cider to make my Caramel Apple Spice. Boo! So I got a hot chocolate and went back to my room for the night.

The bed had an integrated reading light built into the headboard, which was helpful as I read a few chapters from Jen Sincero’s You Are a Badass at Making Money, before falling asleep at 9:11pm “in the City that doesn’t sleep” that the ol’ crooner Frank Sinatra used to sing about. I got over 9 hours of sleep, which wasn’t too surprising considering the 36,538 steps I walked over the course of 20.11 miles on Sunday.

Monday was a much lighter day of sight-seeing, as my legs and feet were killing me. I stayed in my room and read some more of the book before getting cleaned up and checking out of my hotel around 9:20. I left my bag with the Bell Staff again and set out for the Starbucks across the street to grab that Caramel Apple Spice that I’d wanted the night before. Starbucks in hand, I walked a couple blocks north and entered Central Park. I marveled at the City skyline from inside the park, both on the trails and atop some of the bedrock. I wandered around and saw the Wollman ice skating rink.

Then I walked along 5^th Avenue on the east side of Central Park, up to 72^nd Street, where I crossed through Central Park, past the Bethesda Fountain and into the Strawberry Fields (John Lennon), before escaping the park and walking south to Columbus Circle, and back to the Park Hyatt to retrieve my bag. The concierge staff seemed WAY too excited to help me with transportation, but I already had my own plans. With bag in tow, I walked 15 blocks south to Bryant Park to grab the Newark Airport Express shuttle bus, which priced out at $18 one-way, versus about $68 with Uber. To be honest, it was more comfortable on the charter bus too, so I saved $50 and had a more enjoyable trip.

Newark Airport was a breeze, getting from the curb to my gate in only 8 minutes, thanks to my TSA Pre-Check that was reimbursed by my Chase Sapphire Reserve card ($85 fee). Unfortunately my flight was delayed, so I had plenty of time to knock out this 2,700+ word blog post 😊

Highlights of the trip:

Hanging with Zero/Felicity/Luxe. No question, my FIRE friends on Twitter are my favorite people on the planet.

One World Observatory. Definitely worth the $38 bucks plus taxes/fees (41.37 in total).

Walking all over the City and never getting bored. I’m at over 65,000 steps in my ~50 hours here in the City, with over 17,000 on Saturday afternoon/evening, the aforementioned 36,500 on Sunday, and over 11,600 as I sit here writing. Most days I struggle to get to 10,000 steps, and here I am averaging over 20,000 steps per day, even with all of the time spent on planes and in airports waiting for planes.

Wayne Brady

Japanese candy

It was the best 3-day weekend I’ve ever had!

By Josh July 24, 2018 (This post will be maintained periodically)

I thought it would be a good idea to share a list of the trips that my travel hacking [obsession] has allowed me to cover in the past few years, since really taking up the hobby in March 2016. If you are interested in finding out more the various points and miles programs I use, please browse this page (contains referral links that may benefit me, at no cost to you).

So I lied. My very first travel hacking booking actually happened before I started this hobby. I was traveling a lot for work starting in December 2014, so by August of 2015 I had a lot of Hilton Honors points. I used 80,000 for 2 nights at the Embassy Suites in downtown Indianapolis to attend my cousin’s wedding. My parents stayed in the room with me, and I slept on the pull-out couch in the “living room” portion of the suite. But the points came free from my work travel, so it didn’t cost me anything to be able to help out my parents with lodging expenses and we all stayed a couple blocks away from the wedding reception venue (the Eiteljorg Museum).

August 2016 – I used Southwest Airlines Rapid Rewards points to fly back “home” to Indiana to attend my 15-year High School Class Reunion. The reunion was co-located with a local non-profit’s wine, craft and music event at a local winery, but thunderstorms throughout the day kinda ruined the evening plans. We had 100 students in our graduating class, and 13 of us showed up for the 15 year reunion…

October 2016 – 2 nights in Downtown Orlando using Hilton Honors points. I was a Diamond member at the time, so I was able to book a special Diamond rate for 40,000 HHonors points per night, instead of the listed rate of 66,000/night.

Christmas-New Years 2016/17 – I live in Florida, but grew up in rural Indiana. I always get the mom-guilt-trip about coming home for Christmas, so I used Southwest Airlines Rapid Rewards points for my flights. I only paid $11.20 out of pocket to cover the September 11th security fee, both ways $5.60.

October 2017 – 2 nights in Orlando, across the street from Universal Studios. I used 80,000 HHonors points for a deluxe room with a view of the theme park. I could have saved (I think) 5,000 points per night by going with a standard view room, and I will actually do that going forward. It was impressive, but a little further away from the action at the park than I expected.

Christmas/New Years 2017/18 – If you haven’t noticed the theme, this is just a continuation of that same pattern. Moving along…

February 2018 – A change in my travel theme! This trip was a 2-day trip to Indianapolis, but for a very special reason. My hometown high school girls basketball team was playing at Bankers Life Fieldhouse (where the Indiana Pacers play!) in the State Championship game at the Class 2A level. I booked my flights on Southwest (again) for about 25,000 RRs. This was booked only 7 days in advance, so tickets were a little bit more expensive than I had seen only a few days earlier, but I waited until the buzzer sounded in their THRILLING OVERTIME VICTORY at the Semi-State game to book my flights. I also used 40,000 Hilton Honors points for a single night at the Homewood Suites in Downtown Indy, just 2 blocks away from Bankers Life Fieldhouse. Unfortunately the Lady Falcons did not win the State Championship, but they led at halftime and were very close the whole way, despite our two best players competing with torn ACLs. These girls are TOUGH!

April 2018 – My parents were visiting with me in Southwest Florida, but their best friends (and practically my second set of parents) were in Orlando at the Gaylord Palms Resort, so we planned to spend a day with them at their resort and in the general area of International Drive. I used 35,000 of my IHG points to book 1 night at the Holiday Inn Resort near Disney Springs. By carrying my IHG card, I automatically have Platinum Elite status, which gave us free drink coupons, free parking, and expedited check-in & check-out. We had an awesome time visiting with our friends, had margaritas with chips & salsa at Señor Frogs, and the 5 of us were able to beat an escape room in 48 minutes and change! This was an amazing trip for just burning some IHG points.

May 2018 – I’ve got a whole post on My Freedom Trip to Los Angeles, Seattle and Boston. To recap, I used Delta Skymiles (AKA SkyPesos), IHG points, Hilton Honors points, JetBlue TrueBlue Miles, and transferred a couple thousand Chase Ultimate Rewards to Hyatt for a second Hyatt redemption. JetBlue TrueBlue points (again) rounded out the trip.

June 2018 – I had a business trip to Phoenix, with a very early morning flight scheduled out of Tampa. Since I live about 2 hours away from the Tampa airport, I didn’t want to leave my house at about 3AM to get there in time, so I drove up the night before and stayed at the Holiday Inn Westgate – Tampa airport, which allowed me to sleep in until almost 5AM and still make it with plenty of time to spare. This was a 20,000 point IHG redemption, and I stayed on a floor reserved for Platinum Elite members, with a complimentary lounge.

Upcoming trips (planned so far):

Thanksgiving 2018 – Fly home on Southwest Rapid Rewards points (a little over 17k) to be with family on Thanksgiving, but also to celebrate my parents 40th wedding anniversary on the Sunday after Thanksgiving.

By Josh July 17, 2018

Sorry for the click-baity headline, but I truly committed a sin in the world of travel hacking earlier today: I bought POINTS with cash! To be more specific, I bought Starwood Preferred Group (SPG) Starpoints, and I used a card that will earn Chase Ultimate Rewards for the purchase today.

A little bit of backstory: SPG Starpoints are considered one of the most valuable travel rewards points/currencies in the game, for many reasons. First, they are difficult to obtain in large numbers, so they are relatively rare. Second, they are transferable at a 1:3 ratio with Marriott (which is absorbing/merging Starwood into the Marriott family of properties and closing down the SPG program completely on August 1). Third, and one of the most popular redemptions, SPG points can be transferred to several airline programs at a 1:1 ratio, but they will give you a 5k bonus in airline miles when you transfer your SPG points in bundles of 20k.

Since SPG is folding at the end of this month, I started to consider what I wanted to do with my Starpoints in terms of redemption. I started collecting Starpoints in February of 2017, when I signed up for the SPG personal card from American Express. It comes with a $95 annual fee, but I originally earned 35k Starpoints upon opening the card, and I called for a retention offer at the 1 year mark and they gave me another 7k Starpoints for spending $1,000 in 90 days. In addition to those 42k Starpoints, I also had earned some points by spending on non-bonus categories with the SPG card, earned a few points from stays at Marriott properties, and I completed the Sunday Twitter promotion with Marriott Rewards and the NFL last fall for 1,000 Marriott points per weekend.

But most recently, I have spent a total of 11 nights in Starwood properties (Sheraton Downtown Phoenix and Four Points by Sheraton San Diego – Sea World) for two work-related conferences. In addition to earning Starpoints for my stays, I earned Starpoints for participating in the Green Choice program, which offered 250 or 500 points per night for declining room cleaning services. I also signed up for a double-dip promotion that Starwood and Delta Airlines has had for the past couple years, and I chose to be awarded extra Starpoints. The sum total of these actions left me with 76,101 Starpoints when I woke up this morning. Remember that Starpoints are worth 3x as many Marriott reward points, so that means I had the equivalent of 228,303 Marriott points.

So why did I commit the cardinal sin of buying points? SPG is currently running a 35% off sale on Starpoints purchased between now and July 20th (THIS FRIDAY), if you purchase more than 5k Starpoints. I ended up buying 14,000 Starpoints for $318.50 (regular price $490) so that I could bring my total up to 90,000 Starpoints. By transferring my 90,000 Starpoints to Marriott this morning, I was able to bring my Marriott total to 270,000. WHY 270,000?? That happens to be the price of a “hotel & flight package” that will reward me most handsomely with a certificate good for a 7-night stay in any Marriott Category 1-5 property PLUS 120,000 Southwest Airlines Rapid Rewards points. Marriott has several of these packages available, with a couple dozen airlines, and different redemption values if you want a smaller amount of airline miles/Avios, or if you want a fancier hotel. My main goal was to get a “good” redemption for my Starpoints, while maximizing my Southwest miles.

So the math comes out like this: $0.022 per Starpoint, which is actually less than the value “The Points Guy” places on them at $0.027, so the sale is worth it from the start. If I had made the Marriott hotel and flight package redemption with only my 228,303 point balance from before the purchase, I would have received 70,000 Southwest RR miles. By buying those 14k Starpoints (equivalent to 42k Marriott points) I was able to get an additional 50,000 Rapid Rewards. The Points Guy values Southwest Rapid Rewards at $0.015 per mile, so I gained an additional $750 in value of Rapid Rewards for paying $318.50 to Starwood this morning. A great deal, if you can find a valuable redemption like I found.

A big warning to anyone who reads this: The SPG program is folding on August 1, 2018, as I mentioned at the top. Marriott has released the category charts for hotels as of August 1, and they will be adding additional categories and “off-peak” and “peak” pricing as time goes along. They also recently released the news that the hotel and flight packages are getting more expensive, and/or you won’t receive as many airline miles. That was the sole cause of my rush to use these Starpoints before August 1.

By Josh Published June 30, 2018

Hello reader! As I began typing this post, I was sitting on an Amtrak train on the Coast Starlight route, from Los Angeles, California to Seattle, Washington. The trip took 34 hours, and included magnificent sights including the Pacific Ocean, Silicon Valley, and Mt. Rainier.

The trip was possible because I had scheduled 15 days of “Funemployment” between jobs. I needed to turn in my work vehicle and all of my work materials and computer equipment when I left employment with the State of Florida. But since I live in Southwest Florida, and the State Capitol is in Tallahassee (in the Panhandle), I started my trip with a 400-mile drive to Tallahassee for one last work day.

Day 2, in the morning I turned in my stuff and said goodbyes. In the afternoon, I took an Uber to the Tallahassee airport, and then I flew to Atlanta, Georgia, which is a hub for a large portion of trips to/from the Southeast US. I booked the flight on Delta, using 32,000 Delta Skymiles I had accumulated over the years, mostly from a 30,000 Skymiles offer on the Gold Delta Skymiles credit card from American Express a couple years ago. Don’t be like me, wait for a 60,000 or 70,000 point offer before you sign up for this card. American Express cards are usually only available once per “lifetime”.

While in Atlanta, I was able to use my Priority Pass Select membership (free with my Chase Sapphire Reserve credit card) to spend a free hour in the Minute Suites in Terminal B at Atlanta Hartsfield-Jackson International Airport. It was nice to unwind a bit, kick my shoes off, and have room to spread out, without having to keep a vigilant eye on my luggage.

From Atlanta, I could arrive in just about any major city in the US, so I caught a cheap flight on Southwest for only $130. I had a voucher for $51 from finding a fare reduction on a previous business trip, so I only had to pay $79 out of pocket. I have developed the habit of arriving early and asking the gate agent if there are any available seats on the plane, and this time there were 32 empty seats. So my next question for the agent is to see if I can get an extra seat and pre-boarding due to my height and large frame. This has worked on each of my last 6 flights with Southwest. This way, I’m able to raise the armrest between the two seats and sit diagonally to gain some extra legroom.

I arrived at LAX and caught a quick Uber to my hotel a couple miles away. I had initially booked 5 nights of lodging at 3 different hotels in the Los Angeles area, but when I left a Facebook message for my cousins living in the Anaheim/Buena Park area that I was flying in that night, they reached out to me to have me cancel my stays and sleep in their guest bedroom. One night at the Holiday Inn LAX ran me 30,000 IHG points (and I got 2,000 back from an Accelerate promo), earned from the Chase IHG credit card last fall (100,000 point offer for $2,000 spend in 90 days), and I was able to check-out early and recoup the points that would have been spent for my second night stay. I was able to cancel my 4th & 5th nights stay easily and got the points refunded, but unfortunately I changed my plans too late for the cancellation window on my 3rd night stay at the Hotel MdR – a DoubleTree Hotel in Marina del Rey. I used 50,000 Hilton Honors points, and since I couldn’t get them refunded, I went ahead and borrowed my cousin’s car (she had left on a trip to Ohio the night prior) and I went exploring in that area, and went ahead and stayed in the hotel, since the points had been spent, anyway.

On Day 4, I set out to adventure with my counsin’s car. From Buena Park, I drove to the Santa Monica Pier, then went on the Pacific Coast Highway to Malibu, turned around and came back towards Hollywood via Sunset Boulevard to the UCLA campus, and on to Rodeo Drive before driving back to Marina del Rey to beat the evening rush hour. After checking in, I walked about 2 miles to Venice Beach and grabbed an early supper at Cabo Cantina, to munch on some chips & salsa and a quesadilla, while sipping a margarita and watching the Cavs-Raptors Game 2. I walked back to the hotel and spent the majority of the evening relaxing poolside and called my parents to fill them in on my trip so far.

Day 5, after checking out of the hotel and grabbing the breakfast buffet (should have been a $4 upcharge from the complimentary continental breakfast I receive for my Gold status at Hilton properties, but the waiter was gracious to upgrade me for free), I drove back to Buena Park and went golfing with my cousin’s husband. We played “Dad Miller Golf CLub” which is where Tiger Woods played when he was in high school. Apparently the guy named Dad Miller was a 93 year-old golfer who hit a hole-in-one on the 11th hole, and they named the course after him! I hadn’t really planned on golfing during this trip, so I didn’t have my normal golf clothes, shoes, hat, glove, golfballs, or golf clubs(!) so I played in a too-heavy shirt, tennis shoes, no hat, and with borrowed clubs, on a club I’d never heard of before that morning, so I was fairly pleased with my 93 I carded that day. My playing partner shot 108 and he’s a member, so I felt decent about the round, given all of those limiting factors.

That evening, I went to a school carnival at my little cousins’ elementary school. They are finishing up 1st and 6th grades, so they were excited to show off their school projects from the whole year to their parents and their unexpected-visitor/cousin from Florida 🙂

Day 6 happened to be Cinco de Mayo, and being in Southern California, I knew there’d be a party! This time, my other cousin hosted a bunch of us at her (very nice) house with a pool in the backyard. All of my little cousins were jumping onto and playing with their “Cous-uncle Josh” because I’m the age of their uncles, but I’m officially their cousin (2nd cousin, once removed?). I got way too much sun, and had way too much fun. Ate way too much chips & salsa and had a few adult beverages to wash it all down.

Day 7, before heading to Union Station, my golf buddy (cousin’s hubby) took me to see Huntington Beach, where the AVP was hosting the annual Huntington Beach Open beach volleyball tournament. Action had not yet started for the day, but it was cool to see it up-close, since I’ve seen it on TV several times in the past. Upon arriving downtown at Union Station, I checked in to get my seat assignment and grabbed a handful of snacks for the train. I found my train platform and fairly quickly found my seat (and the empty one next to me, which I definitely will not complain about!). I booked this train trip (LA–>Seattle) on the Amtrak website for $122 cash out of pocket. I went with a regular coach seat, knowing that there is ample legroom and wider-than-airline seats, 120v outlets, and it’s possible to get up and explore the train (dining car, observation car with floor-to-ceiling windows, and a café lounge car that operates like a mini 7-Eleven onboard the train). We got delayed by more than an hour in the Oakland area, and have been gradually losing more time between stops. But this caused us to be near Mt. Shasta as the sun was rising, and I got to see some cool sights that would normally have been passed by during the dark.

Around 9pm on Day 8, I arrived in Seattle, and checked in at the Grand Hyatt Seattle for two nights, with a list price of $548/night. I paid 15,000 Hyatt points per night instead, which I earned from the 40,000 point sign-up bonus on the Chase Hyatt credit card (plus a 5,000 point bonus for adding an Authorized User when I opened the card). I can’t believe I got nearly $1,100 in value out of that Hyatt card signup bonus, with another 15,000 points remaining that I used for Day 11 in Boston.

On Day 9, I purchased the CityPass for $89, which includes admission to 5 top destinations, including the Space Needle, Chihuly Museum & Gardens, Museum of Pop culture, Seattle Aquarium, and the Argosy Harbor Cruise (the 5 options I chose; you can opt for a different museum in place of Chihuly and #MoPop), and these are valued at over $160. I woke up to a perfect weather day, sunny and in the upper 50s. Working through the list of suggestions from friends and locals I had tapped via Twitter (Shoutouts to @CeceMcKiernan, my friend Kelli @FloodGeek101, Angela from @TreadLightly_RE, and Ty Roberts from @CampFIREfinance, along with some Twitterless peeps), I started out in search of breakfast at Biscuit Bitch. These Bitches are very popular, and there was a line out the door for people to get their hands on some scrumptious fixin’s and coffee. I Tweeted to the OG Bitches (@bitchesgetrich) that I found their Mothership!

Moving on from there, I walked 2 blocks to Pike Place Market, which was full of merchants getting set up for the day. I walked around for a bit and checked out the GumWall, which might be cool to some people, but I’ve seen more gum on one wall at a loose-meat sandwich shoppe in Greenville, Ohio (Shoutout to Maid-Rites). From there, I walked through Belltown to check out the Space Needle in Seattle Center. The Space Needle is undergoing a “Spacelift” (facelift) right now, so my views were partially obstructed by construction workers and ongoing construction, but it was such an amazing view. Mt. Rainier stands so much higher than, and closer to, Seattle than I expected! With the morning’s marine mist still showing up, the peak of Mt. Rainier looked like a perfectly-painted mountain from a Bob Ross painting, sticking its head above the clouds.

After Space Needle, I checked out the Chihuly Museum and Gardens, which were impressive, but I had already seen a large collection of Chihuly works at the Morean Museum in St. Petersburg, Florida. I also went to the Museum of Pop Culture, but felt underwhelmed by it :/ Last on the agenda for sight-seeing was a one-hour harbor cruise around the Elliott Bay, which was full of opportunity to take more pictures of the Seattle skyline and enjoy the nice sunny day. The onboard bar didn’t hurt, either!

As cool as those sights were, the highlight of my day came later, around Happy Hour, when I met up with a fellow Personal Finance blogger for the first time. Ty Roberts had a meeting downtown, and met me for a beer at Yard House. Honestly, this was the first time I’ve ever been able to talk to someone In Real Life about FI, FIRE, blogging, and this PF community that I honest-to-goodness LOVE. Ty was so easy to talk to, encouraging, and I just had the most amazing chat with him. I can’t wait to experience more of that at FinCon in Orlando this September!

Day 10, I wanted to check out more sights that were recommended to me, so I walked to Pier 51 to catch the Ferry to Bainbridge Island for $8.35 (round-trip).

The ride over & back were the most enjoyable part for me, because I arrived so early in the morning that most, if not all, of the local shops had not opened for the day (around 10-10:30AM). In fact, I hopped back on the return ferry by 10:25 and made it back to Seattle by 11. After that, I used up the last ticket in my CityPass to check out the Seattle Aquarium just a few piers away. In the early afternoon, I went back to the hotel to shower up and pack my bag so I could check out of the hotel room by 2pm (late checkout granted for my World of Hyatt Discoverist status). I left my bag with the front desk, and took the Link over to the University of Washington campus to check it out.

After walking around campus for about an hour, I went back to the hotel, grabbed my bag, and took the Link to the Seattle-Tacoma International Airport. Arriving at the airport 7 hours before my flight was not ideal, but I was able to once again use my Priority Pass Select to gain entry to an airport lounge with free snacks and beverages. The Priority Pass app shows 5 lounges that we are supposedly able to access, but the Alaska Airlines lounges had signs at the entrance that said they were not accepting Priority Pass holders that day. So I walked up and down every terminal (C, D, B and then A) except N & S, and counted at least 10 airport lounges in that airport. I finally gained access to The CLUB at SEA where I spent a couple hours charging my devices, listening to a podcast, called my grandma (awww) and took advantage of somde free snacks.

At the end of Day 10, at one minute until midnight(!) I flew on a JetBlue flight in Mint class (first class with a lay-flat seat) to Boston. I booked the flight using JetBlue TrueBlue points, only 33,700 points, when that class was listed on other flights the same day for 70,000-110,000 points). I figured for my first-ever Red-Eye flight, it was a good idea to trade-up for some comfort, and I really wanted to check out Mint, anyway.

Arriving in Boston on Day 11, I will use some additional Hyatt points (15,000/night) at the Hyatt Regency Boston in downtown. Unfortunately I was about 1900 points shy of having the 15,000 needed for my second night, so I transferred 2,000 Chase Ultimate Rewards Points at a 1:1 transfer ratio to Hyatt from my accumulated Chase points (reminder: I have Chase Sapphire Reserve, Freedom and Freedom Unlimited, and I transfer all of my rewards to my Sapphire Reserve points balance to allow the points transfers to Chase’s travel partners). I was pretty exhausted from the overnight travel, but I did manage to walk 2+ miles to Fenway Park to take the tour of a sports and cultural icon, with some amazing views of the city.

 

Day 12, having caught up on sleep, I set out for a day of exploring. I had previously visited Boston in 2003, on a family trip before I turned 21, so I knew I had to stop at Cheers and have an adult beverage. I checked out the Freedom Trail and walked over to Bunker Hill and the USS Constitution. I also killed at least an hour watching various street performers in the Quincy Market area. I explored Chinatown a little bit and grabbed a local hard cider to go along with my dinner.

Day 13, I took the Silver Line MBTA bus to Boston-Logan International airport for $2.75 instead of the $23 and change that I paid a (terrible) Uber drive on Day 11 morning when I arrived in Boston. For my return flight to Southwest Florida (RSW airport), I used 8,600 TrueBlue points from JetBlue. I had these points plus the Day 10 red-eye flight points from the Barclays JetBlue Plus card, which came with a 40,000 point bonus for spending only $1,000 in 90 days. I forgot that the card also gives me a 10% refund on award redemptions, so I ended up getting  over 4,000 TrueBlue points back into my account (over $80 worth at 2c a piece).

So I share this whole story to say that I went overboard on a 13 day trip to celebrate the end of my previous job. I worked in a position that was effectively a full-time temp for almost 3.5 years. Due to this work status, I did not have any paid holidays or vacation time in that time, so I had this pent-up urge to hit the road, skies and rails to see more of this magnificent country. I could probably do without the overwhelming scent of weed/pot in the various cities/states I visited, but that only minimally reduced my enjoyment of these fine places. I’m excited to be moving into a position where I will be earning a standard 2 weeks of vacation and 11 paid holidays to help me get back on the road moving forward. I’m glad I had the opportunity to bank all of these various points so I could use them in this blowout trip around the US. Many in the travel-hacking community chirp the mantra of “earn and burn” or “churn and burn,” because there are constant devaluations occurring in the many points & miles programs. But for someone like me, there were zero opportunities to use the points/miles over the past 3 years (except for a few quick trips “home” to Indiana for the holidays) so the points were worthless to me until I could actually use them. And it was SOOO worth it once I could actually use them on a trip that will be in my memory bank until the day I die.

By Josh March 10, 2018

For a long time, I avoided the whole world of travel hacking. I don’t know if it was the word “hacking” in the name, or if I was just OK with earning 1% cash-back or some points to spend at Best Buy (a former addiction) with all of my usual purchases. I didn’t shy away from it for the “Anti-Credit Cards” reasons that D.R. preaches, because I had already been responsibly using credit cards since 2005, when I first got out of college.

Once I made up my mind to try it, I fell down the rabbit hole. If you’re interested in starting, don’t open any cards until you’ve taken the free course at TravelMiles101.com. It will change your life! I also have a resources post here on the blog if you’re looking for more digestible information on some of the top cards on the market.

Once you have a stash of points burning a hole in your pocket, you might start making all sorts of travel plans. Confirmations for flights, hotels, and event tickets start to clog up your inbox. This is where TripIt can be a huge help. TripIt is a product of Concur, one of the largest travel and expense management service companies for businesses, and it feels like they’ve made this product for both leisure and business travelers.

I travel frequently for business, and I have a mixture of business and personal hotel reservations floating around in my inbox at any given time. I also get email confirmations on my parents’ travel plans, especially when they come here to Florida to visit me. Sometimes I will also reserve a hotel room *just in case* because it’s a busy time of year such as the Legislative Session in the state capital city. Once you link TripIt to your email inbox, they do all of the rest.

Take a look at the screenshot below. It shows all of my upcoming travel plans that involve a flight or an already-booked hotel and/or event ticket. The trip in September in Orlando is my first FINCON! 🙂

As you can see, I have some upcoming workshops and conferences already in my travel plans. If you click on any of the individual trips, it will show you an itinerary of all of your related travel confirmations, as shown below.

I upgraded to TripIt Pro in August 2017, and I am thankful that I did. They were running a special at the time, $34 for the first year, regular price $49. Now I receive “Go Now Alerts” which tell me when to leave for the airport, Terminal and Gate reminders (which help when traveling through an unfamiliar airport or when gates suddenly change), Check-in reminders (24 hours before on Southwest Airlines flights to get a good boarding position, amirite?), automatic trip sharing with your network that you set up in the app (great for work or for personal reasons), and best-of-all: Flight Refund Monitoring!

Last night, I received an email from TripIt at 9:18pm stating that my upcoming flight to Atlanta had decreased in price by $51, and they gave me the steps to follow to request that refund. I called Southwest and they were able to quickly make the change, and gave me a $51 flight voucher, good for one year from the purchase date of this flight. This one refund more than paid for my $34 annual fee on TripIt Pro! I’m totally sold.

In case you’re not quite sold, here’s a few more benefits:

1. Point Tracker – once you get involved in the travel hacking game, you will have points spread across multiple hotel, airline and flexible bank point programs. This saves a lot of time spent manually tracking your various points.
2. Seat Tracker – helps you find a better seat on flights
3. LoungeBuddy – Comes with a free $25 airport lounge credit
4. CLEAR – Not all airports have this service, but TripIt Pro comes with a 4 month free trial for the fastest way through airport security, even faster than TSA Pre-Check!