New Chat

Download App

Ask me about your trip!

There are no messages for this conversation.

AI Travel Planner

5 Days in Key West Florida Itinerary

Last updated: 2024 Jun 14

Exploring Historic Key West

Morning

Start your day with a visit to the Ernest Hemingway Home and Museum. This iconic site offers a glimpse into the life of one of America's most famous authors. Enjoy breakfast at the nearby Blue Heaven, known for its delicious pancakes and relaxed atmosphere.

Afternoon

In the afternoon, explore the Key West Lighthouse and Keeper's Quarters Museum. This historic lighthouse offers stunning views of the island. For lunch, head to Latitude's Restaurant on Sunset Key for a unique dining experience.

Evening

End your day with a visit to Mallory Square to enjoy the famous sunset celebration. For dinner, dine at El Meson de Pepe, which offers authentic Cuban cuisine and live music.

Bedtime

Find amazing hotels in Key West, Florida.

4.68
Ernest Hemingway Home and Museum
Book Now

4.74
Key West Lighthouse and Keeper's Quarters Museum
Book Now

Nature and Adventure in Key West

Morning

Begin your morning at the serene Key West Butterfly and Nature Conservatory, where you can walk among hundreds of butterflies. Enjoy breakfast at Six Toed Cat, known for its hearty breakfast options.

Afternoon

Spend your afternoon exploring the underwater world with a visit to the Vandenberg Wreck, perfect for diving enthusiasts. For lunch, try B.O.'s Fish Wagon for some fresh seafood.

Evening

In the evening, take part in the Key West Ghosts of Key West Walking Tour to learn about the haunted history of Key West. Have dinner at A&B Lobster House, renowned for its seafood dishes.

Bedtime

Find amazing hotels in Key West, Florida.

4.94
Key West Butterfly and Nature Conservatory
Book Now

4.88
Vandenberg Wreck
Book Now

Cultural Immersion in Key West

Morning

Start your day with a visit to the historic Harry S. Truman Little White House. Enjoy breakfast at Bagel Island Cafe for some freshly baked bagels.

Afternoon

Afterward, explore the vibrant art scene at the Key West Garden Club. For lunch, head over to Santiago's Bodega for tapas-style dishes.

Evening

Conclude your day with an exciting sail on the Key West Windjammer Champagne Sunset Sail. Dine at Louie's Backyard, offering oceanfront views and gourmet cuisine.

Bedtime

Find amazing hotels in Key West, Florida.

4.67
Harry S. Truman Little White House
Book Now

5.00
Key West Garden Club
Book Now

Relaxation and Leisure Activities

Morning

Visit one of Key West's most iconic landmarks: The Southernmost Point Buoy at 90 miles from Cuba. Then have breakfast at nearby cafe: Cuban Coffee Queen.

Afternoon

Spend time relaxing on Smathers Beach soaking up sun or engaging in water sports like parasailing or paddleboarding before grabbing lunch from Salute! On The Beach.

Evening

Take leisurely stroll down Duval Street filled shops bars restaurants including Hard Rock Cafe where you can enjoy dinner while listening live music.

Bedtime

Find amazing hotels in Key West, Florida.

Final Day Adventures

Morning

Explore Fort Zachary Taylor Historic State Park where you can learn about Civil War history swim snorkel picnic among beautiful surroundings followed by breakfast from Date & Thyme Organic Cafe.

Afternoon

Head over Mel Fisher Maritime Museum discover treasures shipwrecks have lunch Garbo’s Grill food truck offering variety delicious dishes.

Evening

Finish trip magical sunset sail Fury Water Adventures savor last moments paradise dining Alonzo’s Oyster Bar known fresh oysters seafood fare.

Bedtime

Find amazing hotels in KeyWest.