I have lived in Southwest Florida for the better part of the past 15 years, but it wasn’t until last weekend that I finally visited one of the most famous locations in South Florida – Key West. Due to its location at the literal end-of-the-road in the Florida Keys, Key West is approximately 6 hours away from Fort Myers by car, and that’s if you don’t run into traffic on the many bridges and narrow roads through the Keys. But I’ve had my eye on a different route, through the Gulf of Mexico and Florida Bay. The Key West Express fit that bill perfectly, and it is faster by a couple hours. Win-win!

The Key West Express makes a daily route between Fort Myers Beach and Key West, several days a week. My parents are currently visiting from Indiana, and since they had never been to the Keys either, I decided it would be a fun trip for us to take together over the Veterans Day weekend.

Day One

We arrived around 7am for an 8am departure, and after a little bit of a bumpy ride thanks to the passing cold front, we arrived in Key West around noon. It sure beats that 6 hours of sitting in traffic on I-75 (Alligator Alley) and the Overseas Highway (US-1). We purchased tickets for the Conch Train Tour and caught the first one after disembarking from the boat. Our tour guide/driver Doug lived most of his life in New York City, but has been visiting Key West ever since he was 5 years old, in the late 1950s, and he gave an excellent, if punny, tour. I really enjoyed it!

After the tour, we decided to head to the Harry S. Truman Little White House tour, which was so much better than we would have guessed. Truman made a huge impact on our country at the end of WWII and in the post-war years. He spent considerable time in Key West, at his doctor’s suggestion (originally), but came back another 10 times throughout the rest of his life, both before and after the end of his Presidency.

I now introduce – President Skip!

But after the early start to our day and the tours, we were getting a bit hungry. We made our way down Duval Street and stopped for sandwiches and drinks at Sloppy Joe’s Bar.

Rum Punch

After some rest, we explored the shops on Duval Street some more before catching the sunset at Mallory Square.

Sunset in Mallory Square

After that, we caught an Uber to our hotel for the stay, a Hilton Garden Inn on the east side of Key West away from the busy tourist areas. We were all tired, so we watched a few episodes of “Love it or List it” on HGTV for a while before heading down to the pool bar, just 20 minutes before it was going to close. It also turns out that our bartender had been to my small hometown of Winchester, Indiana (population less than 5,000) several times when he used to live in nearby Dayton, Ohio. I crashed in bed at exactly 9pm 🙂

Day Two

The next morning, I woke up early thanks to the roosters that run around all over Key West. We took our time getting ready and checked out around 9. Then we grabbed breakfast in the hotel lobby before heading out (via Uber) to the Southernmost Point. The line was shorter than we had seen the day before, and we quickly found out why! Due to the winds and high surf, waves were crashing up against the seawall and spilling into the area around the large concrete buoy. But it took less than 10 minutes to wait our turn for our photo-op, and we moved along to the Ernest Hemingway house.

Being tourists at the Southernmost Point

After a very interesting guided tour of the house, grounds, and cat condos, we made our way to Papa’s Pilar Rum Distillery for a free tour (included with the price of the Conch Train Tour ticket) and rum tasting. The tour guide was funny, and he shed some more insights into Hemingway’s life along with the exhibits in the distillery.

Dad in the Fighting Chair in front of the social media mural

After rum, we made over to Duval Street to people-watch and grab a late lunch at Amigos (home of the square taco) which is across the street from Capt. Tony’s bar, the original location of Sloppy Joe’s Bar from 1933-37. We had curbside seats and people-watched some more while eating chips/salsa/guac. After lunch, we had to have some dessert, so we went to Key West Key Lime Pie Co., previously featured on CNBC’s show The Profit a few years ago. A famous saying in my hometown says “Try the Pie” because it’s the home of Wick’s Pies, Inc. so I tried the Key Lime pie, and it was the best I’ve ever had 😊

Key West Key Lime Pie Co.

At this point, we were getting pretty tired, but we still had a couple hours to kill before loading back up onto the Key West Express, so we slowly made our way back to the port through some of the various shops. We stopped by a marina where many of the powerboat racing boats were showing off their vessels. One speedboat even had FIVE 400-HP motors on the back, for a total of 2,000 Horsepower! We also checked out Dante’s pool bar, if only from outside the gates to watch the beautiful people for a few minutes.

Dante’s pool bar during golden hour

Back inside the ferry terminal, I guess we weren’t the only ones worn out from exploring Key West, because close to 200 people had already arrived and taken their seats in the boarding area of the building. Even still, we were able to load the boat 30 minutes earlier than scheduled, got seats on the mid-deck at the front of the boat and watched the Packers/Panthers game for most of the ride home. We made it back home by about 10:30PM, and I was glad to have the Monday off to recuperate from a fun weekend in Key West.

The End of the Road

Travel Hacking

But since I never go anywhere without some travel hacking tricks, I wanted to share the two tips I used to bring down the cost of our 38-hour trip to the Keys.

First off, we booked early. Way early. The Key West Express sells vouchers during the holiday season for only $99 round-trip. This is considerably less than the typical $145-155 that a round-trip will cost during the rest of the year. The voucher is good for two years, January 1, 2020 through December 31, 2021 if purchased now. You’ll still need to book the trip, but you apply the voucher as payment when you make the reservation.

Second, and perhaps much more boring, I used accumulated Hilton Honors points for the hotel. While a 60,000-point redemption seemed quite high, it was a deal compared to many of the cash rates available for the holiday weekend, plus the offshore powerboat racing brought a lot of extra tourists to the area for the week. The redemption came out to .5c per point, which is at the high end of the normal range for Hilton Honors points, but we also saved around $50 in taxes and fees by using points.

All in all, it was a very fun trip and we were able to keep costs relatively low by employing some travel tips. I’m not in a rush to go back anytime soon, but I’m glad we finally went down there to check it out!

  1. Aww, that looks like a great trip with your parents! I visited Key West once when I was a teenager and we drove down from Daytona Beach, where we were staying. I remember going over all those many bridges, and I can see where a ferry would be a really nice alternate option.

    1. I saw those everywhere! My mom was creeped out by the thought of them 🤔 but I was just fine trying the real deal with a load of whipped cream on top!

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