New Chat

Download App

Ask me about your trip!

There are no messages for this conversation.

AI Travel Planner

Ultimate 5-Day Key West Adventure and Relaxation

Ultimate 5-Day Key West Adventure and Relaxation Itinerary

Last updated: 2024 Jun 14

Sunset Sailing and Duval Street Delights

Morning
Start your day with a delightful breakfast at the iconic Blue Heaven, known for its unique atmosphere. After breakfast, embark on a Key West Conch Train Tour to get an overview of the island's history and key landmarks.
Afternoon
For lunch, head to El Siboney Restaurant for authentic Cuban cuisine. Afterward, explore the Key West Historic District at your own pace, visiting the Hemingway Home and Museum and the Key West Lighthouse and Keeper's Quarters Museum.
Evening
Enjoy a magical sunset sailing experience on a Key West 2-Hour Sunset Sail with Live Music. After the cruise, have a delicious dinner at Latitudes on Sunset Key and take a leisurely walk along Mallory Square to experience the vibrant sunset celebration.
Bedtime
Find amazing hotels in Key West.
Visit Key West Conch Train Tour in Key West
star4.59

Key West Conch Train Tour

Book Now
Visit Key West Historic District in Key West
star4.57

Key West Historic District

Book Now
next arrow

Snorkeling and Beach Day

Morning
Indulge in a delightful breakfast at Blue Heaven before heading out for a Key West Reef Snorkel Morning Tour with Breakfast & Mimosas. Spend the morning exploring the underwater world of the Florida Keys National Marine Sanctuary.
Afternoon
For lunch, enjoy fresh seafood at Hogfish Bar & Grill. Afterward, relax and unwind at Smathers Beach, where you can soak up the sun and take a refreshing dip in the crystal-clear waters.
Evening
In the evening, savor a casual dinner at Garbo's Grill, known for its gourmet street food. End the day with a leisurely stroll along Duval Street, exploring the shops and vibrant nightlife.
Bedtime
Find amazing hotels in Key West.
Visit Key West Reef Snorkel Morning Tour with Breakfast & Mimosas in Key West
star4.47

Key West Reef Snorkel Morning Tour with Breakfast & Mimosas

Book Now
Visit Florida Keys National Marine Sanctuary in Key West
star4.75

Florida Keys National Marine Sanctuary

Book Now
next arrow

Island Adventure and Sunset Celebration

Morning
Start your day with a delicious breakfast at Blue Heaven before embarking on a Key West Jet Ski Island Tour. Experience the thrill of jet skiing around the island and taking in the scenic views.
Afternoon
For lunch, enjoy a taste of the Caribbean at Bien Caribbean Latino. Afterward, visit the Southernmost Point of the Continental USA and take a leisurely walk through the Key West Butterfly and Nature Conservatory.
Evening
Witness a breathtaking sunset at Mallory Square and enjoy the lively sunset celebration. For dinner, savor the flavors of the Mediterranean at Azur Restaurant. After dinner, take a romantic Key West Sunset Dinner Cruise with Open Bar & Live Music.
Bedtime
Find amazing hotels in Key West.
Visit Key West Jet Ski Island Tour in Key West
star4.68

Key West Jet Ski Island Tour

Book Now
Visit Southernmost Point of the Continental USA in Key West
star4.72

Southernmost Point of the Continental USA

Book Now
next arrow

Historic Sites and Sandbar Relaxation

Morning
Enjoy a leisurely breakfast at Blue Heaven before visiting the Fort Zachary Taylor. Explore the historic fort and relax on the beautiful beach.
Afternoon
For lunch, have a picnic at the fort or enjoy a meal at Garbo's Grill. In the afternoon, take a Key West 4-Hour Private Sandbar Cruise on a Tiki Bar Boat for a unique and relaxing experience.
Evening
Enjoy a casual dinner at Garbo's Grill or Garbo's Grill and spend the evening at your leisure, perhaps taking a romantic walk along the beach.
Bedtime
Find amazing hotels in Key West.
Visit From Fairbanks Chena Hot Springs Northern Lights Tour in Key West
star3.97

Fort Zachary Taylor

Book Now
Visit Key West 4-Hour Private Sandbar Cruise on a Tiki Bar Boat in Key West
star4.78

Key West 4-Hour Private Sandbar Cruise on a Tiki Bar Boat

Book Now

Cultural Exploration and Farewell to Key West

Morning
Start your last day in Key West with a delightful breakfast at Blue Heaven before taking a Key West Old Town Trolley 12-Stop Hop-On Hop-Off Tour. Visit the Key West Shipwreck Treasure Museum and the Key West Aquarium.
Afternoon
For lunch, enjoy a meal at Mangia Mangia Pasta Cafe. Afterward, take a Key West Food Tasting and Cultural Walking Tour to immerse yourself in the local food and culture.
Evening
Conclude your Key West adventure with a farewell dinner at Latitudes on Sunset Key, savoring the stunning views and delicious cuisine. Reflect on your unforgettable trip as you enjoy a leisurely evening in this tropical paradise.
Bedtime
Find amazing hotels in Key West.
Visit Key West Old Town Trolley 12-Stop Hop-On Hop-Off Tour in Key West
star4.45

Key West Old Town Trolley 12-Stop Hop-On Hop-Off Tour

Book Now
Visit Key West Shipwreck Treasure Museum in Key West
star4.58

Key West Shipwreck Treasure Museum

Book Now
next arrow

Top Key West & The Florida Keys Travel Videos

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