New Chat

Download App

Ask me about your trip!

There are no messages for this conversation.

AI Travel Planner

Key West Adventure 5 Days Itinerary

Last updated: 2024 Jun 14

Welcome to Key West

Morning

Start your Key West adventure with a visit to the Southernmost Point of the Continental USA. This iconic landmark is perfect for a morning photo-op and offers a great introduction to the southern charm of Key West. Afterward, head over to Cuban Coffee Queen for a delicious Cuban coffee and breakfast sandwich.

Afternoon

In the afternoon, explore the Ernest Hemingway Home and Museum. This historic site provides insight into the life of one of America's most famous authors. Enjoy lunch at Blue Heaven, known for its eclectic atmosphere and delicious Caribbean-inspired dishes.

Evening

Conclude your first day with a sunset sail on the Key West Windjammer Champagne Sunset Sail. Experience breathtaking views of the sunset over the water while sipping on champagne. For dinner, indulge in fresh seafood at Conch Republic Seafood Company.

Bedtime

Find amazing hotels in Key West, Florida.

4.72
Southernmost Point of the Continental USA
Book Now

4.68
Ernest Hemingway Home and Museum
Book Now

Historic Sights and Local Flavors

Morning

Begin your day with a visit to the Key West Lighthouse and Keeper's Quarters Museum. Climb to the top for panoramic views of Key West. For breakfast, stop by Garbo's Grill for their famous fish tacos.

Afternoon

Spend your afternoon at Fort Zachary Taylor, exploring its historic fortifications and relaxing on its beautiful beach. Grab lunch at Hogfish Bar & Grill, known for its laid-back vibe and delicious hogfish sandwiches.

Evening

In the evening, join the Key West Ghosts of Key West Walking Tour to learn about the spooky history of this charming town. End your day with dinner at Latitudes, where you can enjoy fine dining with stunning ocean views.

Bedtime

Find amazing hotels in Key West, Florida.

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

3.97
Fort Zachary Taylor
Book Now

Nature and Nautical Adventures

Morning

Start your day surrounded by butterflies at the enchanting Key West Butterfly and Nature Conservatory. Enjoy breakfast at nearby The Flaming Buoy Filet Co., offering creative takes on classic dishes.

Afternoon

Head out for an adventurous afternoon with the Key West Afternoon Sail, Snorkel, Kayak & Sunset Excursion. This tour offers a mix of sailing, snorkeling in crystal-clear waters, kayaking through mangroves, and ending with a beautiful sunset view. Have lunch onboard as part of this excursion.

Evening

After returning from your nautical adventure, unwind with dinner at Louie's Backyard, known for its elegant setting and delectable cuisine.

Bedtime

Find amazing hotels in Key West, Florida.

4.94
Key West Butterfly and Nature Conservatory
Book Now

5.00
Key West Afternoon Sail, Snorkel, Kayak & Sunset Excursion
Book Now

Cultural Exploration Day

Morning

Dive into local culture with a visit to the vibrant Duval Street, lined with shops, galleries, bars, and cafes. Stop by Nine One Five for a delightful breakfast in an inviting atmosphere.

Afternoon

Continue exploring cultural sites like the fascinating exhibits at the Mel Fisher Maritime Museum. For lunch, head over to El Siboney Restaurant to savor authentic Cuban cuisine.

Evening

Wrap up your cultural exploration day by attending an evening show or live music event on Duval Street. Finish off with dessert at Better Than Sex - A Dessert Restaurant Key West, where you can indulge in decadent treats.

Bedtime

Find amazing hotels in Key West, Florida.

4.83
Duval Street
Book Now

4.45
Mel Fisher Maritime Museum
Book Now

Farewell to Key West

Morning

Begin your final day with a peaceful visit to the Basilica of Saint Mary Star of the Sea. This beautiful church offers a serene atmosphere and stunning architecture. For breakfast, enjoy a hearty meal at Cuban Coffee Queen, known for its delicious Cuban coffee and breakfast sandwiches.

Afternoon

Spend your afternoon exploring the Key West Garden Club, where you can stroll through lush gardens and enjoy the tranquility. Have lunch at Santiago's Bodega, famous for its tapas and relaxed ambiance.

Evening

End your trip with a memorable dinner at A&B Lobster House, offering exquisite seafood dishes with waterfront views. After dinner, take a leisurely walk along the Edward B. Knight Pier to soak in the final moments of your Key West adventure.

Bedtime

Find amazing hotels in Key West, Florida.