First Time Exploring Key West, Florida
My husband and I took a trip to Key West, Florida, and let me just say, it was incredible. From the rich culture to the mouthwatering food and stunning sunsets, it was an adventure filled with unforgettable moments! Here’s a recap of our amazing Key West itinerary, along with some tips if you’re planning your own trip to the southernmost point of the U.S.
Day 1: Arrival & Sunset Views in Key West
We flew from Birmingham, Alabama to Key West, with a brief layover in Atlanta. During our stopover, we visited The Club at Terminal F using our Priority Pass. Overall, the lounge was comfortable, and we enjoyed a couple of free drinks and light snacks.
FYI: The lounge is usually busy and sometimes you have to wait to get in. It’s not the best airport lounge, but with a free membership, taking advantage of the free snacks and beverages is a no-brainer. You might not find luxury amenities, but it’s a nice spot to relax, recharge, and grab a quick bite before your next flight. Just be prepared for the crowds, as seating can fill up fast, especially during peak times.
Arriving at Key West Airport in the late afternoon, I used the Key West Rides ride-share app to get us to our hotel, Kimpton’s Winslow’s Bungalows, which was an easy ride. Upon arrival, the hotel staff welcomed us with two cans of Cayo Hueso, a refreshing passion fruit shandy—just what we needed after a day of travel.
Our room was in a bungalow on Elizabeth Street, nestled at the back of the property, where lizards darted around the lush landscaping.
After quickly dropping off our luggage, we hurried over to Bistro 245 for our 6:30 pm dinner reservation. Our waiter, Einar from Russia, made the meal memorable, serving Truffle Crusted Grouper for Jeff and Lemon Garlic Mahi for me.
After dinner, we wandered to Mallory Square to catch a glimpse of the sunset and enjoy the street performers. Exhausted from the day, we left before the sun fully set, deciding to hop on the Free Duval Loop bus back to our hotel.
Day 2: Exploring Key West on Foot, Bike, and Sunset Cruise
Our first full day in Key West began with me (Lynda) donning my new She Bird dress—a great travel outfit with pockets and a built-in bra, though in retrospect, I should have worn something else. Our first stop was a walk to the Southernmost Point Buoy for the must-have photo op. After snapping a few shots, we headed back to the hotel for breakfast, where we were treated to a simple continental spread of cereal, oatmeal, and fresh fruit.
Next on the agenda was a visit to the Key West Butterfly & Nature Conservatory. The conservatory was magical, with fluttering butterflies everywhere, and we were particularly charmed by the resident flamingos, Scarlett and Rhett.
Later, we went back to the hotel to reserve bicycles for the afternoon. On our way, we passed the Key West Firehouse Museum, the Wildflower Garden, and the Basilica of Saint Mary Star of the Sea.
Our main event of the day was the Southernmost Food Tasting & Cultural Walking Tour, which gave us a delicious introduction to the local cuisine, including the iconic conch fritters and Key lime pie. We even made a few new friends from Tennessee and South Carolina during the tour.
Afterward, we grabbed our bikes and rode to the Ernest Hemingway House, where we saw the famed polydactyl cats, descendants of Hemingway’s cat, Snow White.
Right across the street, we climbed the Key West Lighthouse, where the view from the top was worth the 88 steps it took to get there. If you are out of shape, it will take your breath away. And I am not just talking about the view.
After returning our bikes to the hotel, we wrapped up the day with a stunning sunset cruise from Danger Charters, sailing into the horizon while sipping wine and enjoying the breeze.
Day 3: Museums, Roosters, and Island Vibes
Breakfast was at La Creperie in Bahama Village, where Jeff had the American Breakfast and I had the Benedict Galete. While waiting for our food, I dashed across the street to Blue Heaven and picked up some banana bread for later. We spent the morning walking down Duval Street and passed Willie T’s, a bar covered with dollar bills similar to McGuire’s in Pensacola.
Afterward, we hopped on the Old Town Trolley, a fun way to see all the famous sights, including Sloppy Joe’s, the bar that once hosted Hemingway. We stopped at Caroline’s Café for lunch—Jeff got a Cuban sandwich, and I enjoyed a refreshing Bamboozled Salad. Along the way, we spotted chickens, which roam freely all over the island!
In the afternoon, we visited the Harry S. Truman Little White House, where we took a guided tour and met a vlogger named Sunflower. We continued our exploration at the Mel Fisher Maritime Museum, learning about treasures from shipwrecks, and finished our museum day with a stop at the Key West Aquarium.
Dinner that evening was at Conch Republic Seafood Company, where I tried a Pineapple Margarita and had the Blackened Shrimp for dinner. Jeff ordered the Coriander Crusted Tuna, both dishes delicious but the Strawberry Tempura dessert stole the show.
Day 4: Parasailing and Thrilling Scooter Ride
We started the day with coffee and banana bread in our room before heading out for some adventure. First up was tandem parasailing with Sebago Water Sports—such a thrill! We paid extra for photos and definitely felt it was worth it.
Afterward, we enjoyed breakfast at Pepe’s, where Jeff ordered an omelet, and I opted for the chocolate bread, although it wasn’t quite what I expected.
Unable to hail a ride back, we ended up walking down Elizabeth Street back to the hotel, passing the incredible Paradise Tree on the way. I am grateful for that unexpected surprise.
Feeling adventurous, we decided to rent a scooter from A & M Scooters of Key West and zipped around the island. One of our stops was Fort Zachary Taylor Historic State Park, where we explored the fort.
In the afternoon, we embarked on a tarpon fishing trip with Reel Easy Fishing Charters. But before we set sail, we made a detour for lunch and stopped to explore the Key West Tropical Forest & Botanical Garden. I have to say, our food at Hogfish Bar & Grill on Stock Island just might have been the best food we had in the Keys.
We didn’t catch any tarpon, and overall the experience was just “meh.” The most excitement was when saw an iguana and manatee at the marina before our trip. That night, we had a late dinner at Duffy’s Steak & Lobster House, grateful that we survived the motorscooter ride. (Those who have driven/ridden a scooter in Key West will know what I am talking about.)
Day 5: Farewell to Paradise & Last Island Delights
Our last day started with a delicious breakfast at Harpoon Harry’s—I indulged in Key Lime Pie French Toast, while Jeff had Harry’s Special. FYI: If you dine there, be sure to have cash. They don’t take credit cards.
After breakfast, we packed up, returned our scooter, and waited for A & M Scooters to pick us up. (Complimentary transportation to the airport because we rented a scooter was an unexpected bonus.) There was a brief moment of panic when they were running late, but they arrived just in time to take us to the airport.
After an amazing few days in Key West, it was time to head home. I won’t go into detail about how our flight was delayed, causing us to miss our connection in Atlanta. But I will suggest this: if you’re flying with a connection, allow extra time in your schedule for any unexpected delays. Even better, travel insurance is essential! Key West’s airport is quite small, with only around 33 flights daily, so I also recommend booking an early flight in case cancellations or delays affect your travel plans.
Tips for Visiting Key West
- Use Key West Transit: The free Duval Loop is super convenient for getting around town. It stops at all the major attractions and restaurants, and it’s an easy way to see the island without worrying about parking.
- Catch a Sunset: Whether it’s at Mallory Square, from a sailboat, or right on the beach, make sure you plan to catch one of Key West’s breathtaking sunsets.
- Plan for Adventure: If you’re into water sports, make sure to book a parasailing trip or one of the famous sunset sails. The views are worth it!
- Take a Food Tour: The Southernmost Food and Cultural Tour was a fantastic way to sample local cuisine and learn more about the island’s history.
If you’re looking for a laid-back yet adventure-filled getaway, I can’t recommend Key West enough. It’s the perfect blend of relaxation and excitement, and we had an amazing time exploring the island. Until next time, Key West!
