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 Culinary Delights

Ultimate 5-Day Key West Adventure and Culinary Delights Itinerary

Last updated: 2024 Jun 14

Island Introduction and Sunset Spectacle

Morning
Begin your Key West journey with a delightful breakfast at Blue Heaven, known for its quirky ambiance and delicious cuisine. Afterward, embark on the Key West Old Town Trolley 12-Stop Hop-On Hop-Off Tour to get an overview of the island's main attractions at your own pace.
Afternoon
For lunch, head to Mangia Mangia Pasta Cafe for some of the best Italian food on the island. Post-lunch, visit the historic Fort Zachary Taylor, where you can explore the fort, relax on the beach, and even do some snorkeling.
Evening
Experience the famous Key West sunset on the Key West 2-Hour Sunset Sail on Schooner America 2.0. Enjoy complimentary drinks and take in the breathtaking views. After the sail, savor a sumptuous dinner at Latitudes on Sunset Key, a perfect spot to end your first day in Key West.
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 From Fairbanks Chena Hot Springs Northern Lights Tour in Key West
star3.97

Fort Zachary Taylor

Book Now
next arrow

Underwater Wonders and Culinary Delights

Morning
Start your day with a hearty breakfast at Firefly Key West, known for its Southern cuisine. Afterward, join the Key West Dolphin Watching and Snorkeling Eco Cruise Tour to encounter the local marine life in their natural habitat.
Afternoon
After the cruise, enjoy a delightful lunch at La Creperie French Cafe, where you can indulge in sweet and savory crepes. Post-lunch, visit the Key West Aquarium to learn about the diverse marine species found in the Florida Keys.
Evening
Dine at Nine One Five, a contemporary restaurant offering a diverse menu. After dinner, take a leisurely stroll along Mallory Square and enjoy the nightly Sunset Celebration, where local artists and performers showcase their talents as the sun dips below the horizon.
Bedtime
Find amazing hotels in Key West.
Visit Key West Dolphin Watching and Snorkeling Eco Cruise Tour in Key West
star4.55

Key West Dolphin Watching and Snorkeling Eco Cruise Tour

Book Now
Visit Key West Aquarium in Key West
star4.31

Key West Aquarium

Book Now
next arrow

Thrills on the Water and Historic Haunts

Morning
Enjoy a classic Key West breakfast at Pepe's Cafe and Steakhouse, a local favorite. Fuel up for an adventurous morning as you embark on the Key West Jet Ski Island Tour, zipping through the crystal-clear waters and exploring the island from a different perspective.
Afternoon
For lunch, head to Garbo's Grill, a food truck offering mouthwatering gourmet sandwiches. Afterward, immerse yourself in Key West's history with a visit to the Harry S. Truman Little White House, the former winter White House for President Truman.
Evening
Experience the spookier side of Key West with the Key West Ghosts & Gravestones Guided Trolley Tour. This entertaining and informative tour takes you to the island's most haunted locations. Afterward, lighten the mood with dinner at The Flaming Buoy Filet Co., known for its unique dishes and vibrant atmosphere.
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 Harry S. Truman Little White House in Key West
star4.67

Harry S. Truman Little White House

Book Now
next arrow

Nature's Beauty and Duval Street Delights

Morning
Start your day with a breakfast at Cafe Marquesa, offering a refined and tranquil dining experience. Post-breakfast, enjoy a morning of relaxation at Smathers Beach, one of the largest and most popular beaches in Key West.
Afternoon
For lunch, head to Blackfin Bistro, where you can enjoy a meal in a historic building with a contemporary twist. Afterward, take a guided Key West Guided Bicycle Tour with Key Lime Pie to explore the charming streets and taste the iconic Key Lime Pie.
Evening
Enjoy a lively evening on Duval Street, known for its vibrant nightlife and eclectic mix of bars, restaurants, and shops. Have dinner at Bien Caribbean Latino, offering a fusion of Caribbean and Latin flavors. Cap off the night with the South Beach experience, where you can relax and enjoy the island's warm evening breeze.
Bedtime
Find amazing hotels in Key West.
Visit Smathers Beach in Key West
star4.76

Smathers Beach

Book Now
Visit Key West Guided Bicycle Tour with Key Lime Pie in Key West
star4.88

Key West Guided Bicycle Tour with Key Lime Pie

Book Now
next arrow

Key West Culinary Journey and Farewell Fun

Morning
Indulge in a breakfast at Better Than Sex - A Dessert Restaurant Key West, a unique spot known for its decadent desserts and intimate setting. After breakfast, take a walk to the Southernmost Point of the Continental USA to capture the quintessential Key West photo.
Afternoon
For lunch, visit Hogfish Bar & Grill, a local gem where you can enjoy fresh seafood in a casual, laid-back atmosphere. Afterward, spend your afternoon at the Key West Shipwreck Treasure Museum, where you can learn about the maritime history of the island and even climb the lookout tower for panoramic views.
Evening
Conclude your Key West adventure with a memorable dinner at Louie's Backyard, an iconic restaurant with stunning ocean views. After dinner, join the Key West Sunset Party Cruise by Catamaran to celebrate your time in Key West with live music, dancing, and a festive atmosphere.
Bedtime
Find amazing hotels in Key West.
Visit Southernmost Point of the Continental USA in Key West
star4.72

Southernmost Point of the Continental USA

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?