New Chat

Download App

Ask me about your trip!

There are no messages for this conversation.

AI Travel Planner

5 Days in Key West and the Florida Keys

5 Days in Key West and the Florida Keys Itinerary

Last updated: 2024 Jun 14

Exploring Key West's Historic Charm

Morning
Start your adventure with a visit to Ernest Hemingway Home and Museum. This historic home offers a glimpse into the life of one of America's most famous authors. Explore the lush gardens and meet the famous six-toed cats that reside here. Afterward, head to Blue Heaven for a delicious breakfast in a charming outdoor setting.
Afternoon
Continue your exploration with a visit to Key West Lighthouse and Keeper's Quarters Museum. Climb to the top for stunning views of the island. Next, take a leisurely stroll through Key West Historic District, where you can admire the beautiful architecture and vibrant street life. For lunch, stop by Santiago's Bodega for some delightful tapas.
Evening
As the sun sets, make your way to Mallory Square for the famous Sunset Celebration. Enjoy street performers, local artists, and breathtaking views of the sunset over the Gulf of Mexico. End your evening with a dinner at A&B Lobster House, known for its fresh seafood and elegant ambiance.
Bedtime
Find amazing hotels in Key West.

Nature and Adventure in Key West

Morning
Begin your day with a visit to Key West Butterfly and Nature Conservatory. Walk among hundreds of butterflies in this serene environment. Afterward, head to Banana Cafe for a delightful breakfast featuring French-inspired dishes.
Afternoon
Embark on an exciting adventure with Key West Afternoon Sail, Snorkel, Kayak & Sunset Excursion. This tour offers snorkeling in crystal-clear waters, kayaking through mangroves, and a relaxing sail as you watch the sunset. For lunch before your excursion, grab a quick bite at Fisherman's Cafe, known for its fresh seafood sandwiches.
Evening
After returning from your excursion, unwind with a visit to Duval Street. Explore its lively bars, shops, and galleries. Don't miss out on trying some local cuisine at El Meson de Pepe, which offers delicious Cuban dishes in a vibrant setting.
Bedtime
Find amazing hotels in Key West.

Cultural Immersion in Key West

Morning
Start your day with an insightful experience at Harry S. Truman Little White House. Learn about its historical significance as President Truman's winter retreat. Enjoy breakfast at nearby Cuban Coffee Queen, famous for its strong coffee and tasty breakfast sandwiches.
Afternoon
Take part in an engaging activity: Key West Hemingway's Life and Local Food Walking Tour. This tour combines history with culinary delights as you explore Hemingway's favorite haunts while sampling local food specialties. For lunch during your tour, savor some authentic flavors at one of the stops included in the tour.
Evening
Conclude your day with a peaceful evening at Fort Zachary Taylor, where you can enjoy both history and nature. Stroll along the beach or explore the historic fortifications. For dinner, dine at Latitudes, located on Sunset Key—a short ferry ride away—for an unforgettable dining experience by the water.
Bedtime
Find amazing hotels in Key West.

Island Hopping in the Florida Keys

Morning
Begin your island-hopping adventure with a drive to Marathon, located in the heart of the Florida Keys. Start your morning with a visit to the Turtle Hospital, where you can learn about sea turtle rehabilitation and conservation efforts. Afterward, enjoy breakfast at Keys Fisheries, known for its fresh seafood and stunning waterfront views.
Afternoon
Continue your journey by heading to Bahia Honda State Park, one of the most beautiful natural areas in the Florida Keys. Spend your afternoon exploring the park's pristine beaches, snorkeling in crystal-clear waters, and hiking along scenic trails. For lunch, pack a picnic or grab a bite at Sunset Grille & Raw Bar, which offers delicious food and panoramic ocean views.
Evening
As evening approaches, make your way to Islamorada, known as the 'Sportfishing Capital of the World.' Visit Robbie's Marina to feed the tarpon and enjoy some local shopping. End your day with dinner at Morada Bay Beach Cafe, where you can dine on fresh seafood while watching a breathtaking sunset over Florida Bay.
Bedtime
Find amazing hotels in les Keys de Floride.

Exploring Key Largo's Natural Wonders

Morning
Start your final day with a visit to John Pennekamp Coral Reef State Park in Key Largo. Take a glass-bottom boat tour or go snorkeling to explore the vibrant coral reefs and marine life. Enjoy breakfast at Bagel Street Deli, which offers a variety of delicious bagels and coffee.
Afternoon
In the afternoon, embark on an exciting activity: Key West Search for Dolphins on a Cruise with Snorkeling. This tour departs from Key Largo and provides an opportunity to see dolphins in their natural habitat while also enjoying some snorkeling. For lunch before your tour, stop by The Fish House, renowned for its fresh seafood dishes.
Evening
Conclude your trip with a relaxing evening at Harry Harris Park. Enjoy a leisurely stroll along the beach or have a picnic while taking in the serene surroundings. For dinner, head to Sundowners, where you can savor delicious cuisine while watching one last sunset over the beautiful waters of Key Largo.
Bedtime
Find amazing hotels in les Keys de Floride.

Top Key West & The Florida Keys Travel Videos

kayakFind the right stay during your trip.
Got a question about your trip?