I always wanted to go to Key West and explore the cute but lively city. Finally, Casey and I decided to take the trip over a long weekend. There is so much to do in the city and so much I wanted to see! I worked up a schedule that allowed us to pack everything we wanted to see into just 4 days. And, if I’m being honest, 4 days was plenty of time to see and do majority of what we wanted!
Listed out below is our perfect but busy itinerary to fit it all in! I have also listed out our options for Brunch, Dinner, Snacks and places to explore! I hope this helps you plan your next trip!
DAY ONE: ARRIVING & DINNER
Flying into Key West and landing around mid-day offers the perfect opportunity to immerse yourself in the vibrant atmosphere of this tropical paradise. It’s an ideal time to explore without the intense heat. Once you’re checked in and settled at your hotel, take a leisurely stroll through the charming streets, adorned with colorful houses and swaying palm trees. Don’t miss the chance to visit Kermits for a delightful slice of Key Lime Pie, a renowned delicacy in this region. It’s the perfect way to start off your weekend in Key West, savoring the unique flavor of this iconic dessert. After treating yourself, head over to Robbie’s Marina to explore, and then to The Stoned Crab for dinner, where the inviting ambiance and culinary offerings never disappoint. This was one of my favorite spots for dinner, and the experience of being able to feed the sharks that frequent the area adds an adventurous touch to the evening. You can also indulge in some delicious crab legs, savoring the delightful flavors while taking in the serene coastal setting.
After this, enjoy the view of the water as the sun sets and head back to the room! Tomorrow will be a busy day!
DAY TWO: SNORKELING, KAYAKING & EXPLORING THE CITY
To make the most of this exhilarating day, consider waking up with the sun. But don’t worry, it will be truly rewarding. First, set out promptly at 8AM to Glazed Donuts to treat yourself to some of the most delectable donuts you’ve ever tasted. After indulging in this delightful breakfast, make your way to Sebago Watersports to kick off your day of adventure. Be sure to pre-book a tour with them! We had an incredible time on the Island ‘Ting Eco Tour. During this tour, you will be treated to breakfast, lunch, and snacks, as well as an open bar. Our adventure began with snorkeling in the open reef, where we encountered numerous reef sharks and a myriad of colorful fish. Following this, we all boarded the boat and enjoyed a delicious lunch as we headed to the Mangrove Island for some kayaking. Exploring the groves and learning about the history of these islands was a truly fascinating experience. Upon completing your kayaking adventure, you’ll return to the boat to relax with snacks and drinks as you journey back to the island. We even had the opportunity to spot a few dolphins and sea turtles on the trip back!
Once you get back to the island, head on back to your hotel or airbnb to freshen up! After you are ready for the evening, head out to dinner! There are so many great spots that are perfect for dinner. I have listed them all out at the bottom of this article for you! Depending on if you want somewhere more casual, you can check out places like Louies Backyard or somewhere more fancy like Latitude’s Restaurant. After you enjoy dinner, stop by one of the many rental shops and pick up a golf cart or moped to explore the city. It is so fun to take your time and enjoy the coastal air in the evening while riding around. Once it starts getting dark, you can venture back down to the city and check out some of the night life. You can almost always find some live music and dancing to end the night!
DAY THREE: BRUNCH, MUSUEMS & AQUARIUMS
After the packed day, you can sleep in just a little bit and then enjoy brunch at one of the many places in Key West this morning. But, don’t sleep in too late if you don’t want to wait. Brunch is a popular mealtime in Key West, so there is typically a wait, but it’s worth it!
After you enjoy a good brunch, check out the Museums and Aquarium. It doesn’t take much time to get through the museums. We wanted to see more, so we took the drive down the highway to the Florida Keys to explore their Aquarium, and it did not disappoint! You get to see so much more wildlife and learn so much about the sea life! The drive there and back is also so relaxing with great views!
Once you are back, grab a bite to eat (or more ice cream for a sweet treat!) and head over to the pier! It’s the perfect place to watch the sunset and try to spot dolphins or sea turtles! End the night with Ben & Jerry’s Ice Cream!
DAY FOUR: COFFEE & HEADING HOME
Start your morning off with a good cup of joe from Cuban Coffee Queen and take one last stroll through the beach or pier before you head over to the airport to head home! If you have time before your flight, drive over to the southern most point and check out the sign. I would try to hit this spot early in the morning because it gets more and more crowded as the day goes on!
I hope you enjoyed these recommendations and enjoy the fun adventures that this little but lively city as to offer!
- Blue Heaven
- Sarabeths
- Louies Backyard (casual)
- Shor American Seafood Grill (in a hotel)
- Latitude’s Resturant (nice place – you will need to take a ferry to it)
- Hot Tin Roof (in a hotel)
- Southernmost Beach Cafe (in a hotel)
- Sunet Pier (in a hotel)
- Half Shell Raw Bar (casual)
- The Stones Crab (casual)
- The Thirsty Mermaid
- Seven Fish (a little nicer)
- Kermits
- Key West Key Lime Pie Co.
- Cuban Coffee Queen
- The Rum Bar (for night time)
- Glazed Donuts
- Better Than Sex (an intimate restaurant for you and your spouse, best to get to-go since it is usually booked up!)
- Ben and Jerry’s Key West
- Smathers Beach
- Higgs Beach
- Feed Sharks at the Stoned Crab
- Climb the stairs at the Key West Lighthouse
- Shipwreck Musuem
- Key West Aquarium
- Hemingway House Tour
- Truman Little White House
- Robbies Marina
- Florida Key’s Aquarium Encounters