New Chat

Download App

Ask me about your trip!

There are no messages for this conversation.

AI Travel Planner

8-Day Adventure in Key West and Beyond 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. Wander through the beautiful gardens and meet the famous six-toed cats that call this place home.

Afternoon

Head over to Blue Heaven for a delightful lunch. This quirky restaurant is known for its delicious brunch options and laid-back atmosphere. Afterward, take a leisurely stroll down Duval Street, where you can explore unique shops, galleries, and historic sites.

Evening

End your day with a visit to Mallory Square for the famous sunset celebration. Enjoy street performances, local crafts, and stunning views of the sunset over the Gulf of Mexico. For dinner, dine at Latitudes, located on Sunset Key, offering an unforgettable dining experience with breathtaking views.

Bedtime

Find amazing hotels in Key West, Florida.

4.68
Ernest Hemingway Home and Museum
Book Now

4.83
Duval Street
Book Now

Nature and Culture in Key West

Morning

Begin your day at the serene Key West Butterfly and Nature Conservatory. Walk among hundreds of butterflies in this tranquil environment. Follow it up with breakfast at Cuban Coffee Queen Waterfront, known for its strong coffee and delicious Cuban sandwiches.

Afternoon

Visit the historic Fort Zachary Taylor, where you can explore Civil War-era fortifications and relax on one of Key West's best beaches. For lunch, head to Hogfish Bar & Grill for some fresh seafood in a casual setting.

Evening

Spend your evening on an adventure with the Key West Windjammer Champagne Sunset Sail. Enjoy sailing on a classic schooner while sipping champagne as the sun sets. For dinner, indulge in fine dining at Louie's Backyard, offering exquisite cuisine with oceanfront views.

Bedtime

Find amazing hotels in Key West, Florida.

4.94
Key West Butterfly and Nature Conservatory
Book Now

3.97
Fort Zachary Taylor
Book Now

Underwater Adventures and Local Flavors

Morning

Kick off your day with an underwater adventure by exploring the famous Vandenberg Wreck. This popular diving spot offers an exciting experience for both novice and experienced divers. Grab breakfast at Azur Restaurant & Patio Dining before heading out.

Afternoon

After your dive, take some time to relax at Smathers Beach, one of Key West's largest public beaches. Have lunch at Garbo's Grill, known for its gourmet food truck offerings like fish tacos and burgers.

Evening

In the evening, join the spooky fun on the Key West Southernmost Ghosts Haunted Walking Tour. Discover haunted sites around Old Town Key West while hearing eerie tales from local guides. Finish off your night with dessert at Better Than Sex - A Dessert Restaurant Key West, where you can indulge in decadent sweets.

Bedtime

Find amazing hotels in Key West, Florida.

4.88
Vandenberg Wreck
Book Now

4.76
Smathers Beach
Book Now

Cultural Insights and Sunset Views

Morning

Start your morning by visiting the historic landmark of Southernmost Point of the Continental USA. Snap some photos at this iconic spot before heading to breakfast at Bagatelle, known for its charming ambiance and delicious morning fare.

Afternoon

Explore more cultural heritage by visiting Harry S. Truman Little White House, where President Truman spent his winters during his presidency. Have lunch nearby at El Siboney Restaurant, which serves authentic Cuban cuisine that will leave you satisfied.

Evening

End your day by joining Key West Schooner Sunset Sail with Food & Drinks for another beautiful sunset experience but this time aboard a schooner complete with food & drinks . For dinner , enjoy fresh seafood dishes at A&B Lobster House , offering waterfront dining with excellent service .

Bedtime

Find amazing hotels in Key West, Florida.

4.72
Southernmost Point of the Continental USA
Book Now

4.67
Harry S. Truman Little White House
Book Now

Relaxation and Local Experiences

Morning

Start your day with a leisurely visit to Key West Garden Club, where you can stroll through beautiful gardens filled with native plants and flowers. Have breakfast at Cafe Marquesa Key West, offering gourmet breakfast options in an elegant setting.

Afternoon

Spend some time relaxing on Edward B. Knight Pier, enjoying ocean views and perhaps some fishing or people-watching. For lunch, head to The Flaming Buoy Filet Co., known for its creative seafood dishes.

Evening

Join the Key West 2-Hour Sunset Sail with Live Music for another unforgettable sunset experience accompanied by live music onboard . For dinner , savor fine dining at Nine One Five , offering innovative cuisine in a charming historic house .

Bedtime

Find amazing hotels in Key West, Florida.

5.00
Key West Garden Club
Book Now

4.77
Edward B. Knight Pier
Book Now

Final Day of Exploration

Morning

Begin your final day by visiting Basilica of Saint Mary Star of the Sea , one of Florida's oldest Catholic churches . Enjoy breakfast at Little Pearl Key West , known for its intimate setting and delicious morning fare .

Afternoon

Explore more local history by visiting Mel Fisher Maritime Museum , where you can learn about shipwrecks and treasure hunting . Have lunch nearby at Azur Restaurant & Patio Dining , which offers Mediterranean-inspired dishes .

Evening

End your trip with a relaxing evening on Key West Southernmost Food and Cultural Walking Tour , where you can sample local delicacies while learning about Key West's rich cultural heritage . For dinner , enjoy one last meal at Louie's Backyard , offering exquisite cuisine with oceanfront views .

Bedtime

Find amazing hotels in Key West, Florida.

4.85
Basilica of Saint Mary Star of the Sea
Book Now

4.45
Mel Fisher Maritime Museum
Book Now

Exploring Miami's Vibrant Culture

Morning

Begin your day with a visit to the iconic Art Deco Historic District in South Beach. Wander through the colorful buildings and learn about the history of this unique architectural style. Enjoy breakfast at The Front Porch Cafe, known for its hearty breakfasts and ocean views.

Afternoon

Head to the Pérez Art Museum Miami (PAMM) to explore contemporary art exhibitions from around the world. For lunch, dine at Verde, located within the museum, offering delicious meals with stunning views of Biscayne Bay.

Evening

Spend your evening in Little Havana, experiencing Cuban culture through music, dance, and food. Dine at Versailles Restaurant, a staple for authentic Cuban cuisine, and enjoy live music at Ball & Chain, a historic bar with a lively atmosphere.

Bedtime

Find amazing hotels in Miami, Florida.

Adventure in Dry Tortugas National Park

Morning

Take an early ferry or seaplane from Key West to Dry Tortugas National Park. Start your adventure by exploring Fort Jefferson, one of the largest masonry structures in the Americas. Learn about its history and significance.

Afternoon

Enjoy snorkeling in the crystal-clear waters around Garden Key. Discover vibrant coral reefs and marine life that make this area a snorkeler's paradise. Pack a picnic lunch to enjoy on the beach while taking in the natural beauty of this remote location.

Evening

Return to Key West in the evening and relax after your adventurous day. Have dinner at Santiago's Bodega, known for its tapas-style dishes and cozy atmosphere.

Bedtime

Find amazing hotels in Dry Tortugas National Park.