New Chat
Download App
Ask me about your trip!
There are no messages for this conversation.
5-Day Key West Adventure with Sunset Sails and Culinary Delights Itinerary
Last updated: 2024 Jun 14Island Introduction and Sunset Celebration
Morning
Begin your Key West journey with a delightful breakfast at Half Shell Raw Bar, known for its fresh seafood and waterfront views. Afterward, immerse yourself in the island's history with a visit to the Key West Shipwreck Treasure Museum. Explore the exhibits and climb to the top of the lookout tower for panoramic views.
Afternoon
For lunch, head to Island Dogs Bar, a quirky spot with a diverse menu. Post-lunch, take a leisurely stroll through the Key West Historic District, admiring the charming architecture and browsing the boutiques and art galleries.
Evening
As the sun begins to set, join the Key West Sunset Party Cruise by Catamaran. Enjoy live music, drinks, and the stunning sunset views. After the cruise, savor a delicious dinner at Milagro Restaurant and Bar, offering a fusion of Latin American flavors.
Bedtime
Find amazing hotels in Key West.
4.58Key West Shipwreck Treasure Museum
Book Now
4.58Key West Shipwreck Treasure Museum
Book Now
4.57Key West Historic District
Book Now
4.57Key West Historic District
Book Now
Snorkeling, Dolphins, and Culinary Delights
Morning
Start your day with a hearty breakfast at First Flight Island Restaurant & Brewery, a unique eatery with a historical aviation theme. Then, gear up for an exciting Key West 3-Hour Snorkeling Adventure to explore the vibrant underwater world of the Florida Keys.
Afternoon
After drying off, enjoy a light lunch at The White Tarpon Bar & Restaurant, known for its casual atmosphere and fresh catches. Post-lunch, embark on the Key West's Dolphin & Snorkel Combo Boat Tour for a chance to spot dolphins in their natural habitat.
Evening
For dinner, indulge in the flavors of the Key West Old Town Secret Food Tour. This guided walking tour will take you to hidden culinary gems, allowing you to sample a variety of local dishes and drinks.
Bedtime
Find amazing hotels in Key West.
4.09Key West 3-Hour Snorkeling Adventure
Book Now
4.09Key West 3-Hour Snorkeling Adventure
Book Now
4.38Key West's Dolphin & Snorkel Combo Boat Tour
Book Now
4.38Key West's Dolphin & Snorkel Combo Boat Tour
Book Now
Historical Landmarks and Sunset Sails
Morning
Enjoy a classic Key West breakfast at Sloppy Joe's Bar, a historic establishment with a lively atmosphere. Fuel up for a morning of exploration that begins with a visit to the iconic Southernmost Point of the Continental USA. Take the obligatory photo and then continue to the serene Smathers Beach for a relaxing start to the day.
Afternoon
For lunch, head to El Meson De Pepe's Restaurant & Bar for authentic Cuban cuisine in a vibrant setting. Post-lunch, take a guided tour of the Harry S. Truman Little White House, where President Truman spent 175 days of his presidency.
Evening
Experience the magic of a Key West sunset on the Key West Sunset Sail with Buffet Dinner and Open Bar. Relax on the deck, enjoy the food and drinks, and witness the sky ablaze with color. After the sail, have a late dinner at Dante's Key West Pool Bar & Restaurant, known for its laid-back poolside ambiance.
Bedtime
Find amazing hotels in Key West.
4.72Southernmost Point of the Continental USA
Book Now
4.72Southernmost Point of the Continental USA
Book Now
4.76Smathers Beach
Book Now
4.76Smathers Beach
Book Now
Outdoor Adventures and Evening Entertainment
Morning
Start with breakfast at Boat House Bar & Grill, offering a menu of American favorites with a waterfront view. Then, spend the morning at the Key West Butterfly and Nature Conservatory, where you can admire the beauty of tropical butterflies in a lush, climate-controlled environment.
Afternoon
For lunch, visit Mary Ellen's Bar & Restaurant, a local favorite known for its comfort food and welcoming atmosphere. Afterward, take a guided Key West Old Town Trolley 12-Stop Hop-On Hop-Off Tour to get an overview of the island's top attractions.
Evening
Dine at Rams Head Southernmost, which offers a menu of Southern-inspired dishes. After dinner, enjoy the vibrant nightlife of Duval Street, hopping between the various bars, live music venues, and entertainment spots.
Bedtime
Find amazing hotels in Key West.
4.94Key West Butterfly and Nature Conservatory
Book Now
4.94Key West Butterfly and Nature Conservatory
Book Now
4.45Key West Old Town Trolley 12-Stop Hop-On Hop-Off Tour
Book Now
4.45Key West Old Town Trolley 12-Stop Hop-On Hop-Off Tour
Book Now
Cultural Exploration and Farewell to Key West
Morning
Begin your last day with breakfast at Hard Rock Cafe Key West, where you can enjoy classic American fare surrounded by music memorabilia. Then, visit the Key West Lighthouse and Keeper's Quarters Museum to learn about the island's maritime history and enjoy panoramic views from the top.
Afternoon
Have a leisurely lunch at Fogarty's, a Key West institution known for its Irish pub fare. Afterward, take a self-guided tour of the Ernest Hemingway Home and Museum, where the famous author lived for more than a decade. Marvel at the six-toed cats and the beautiful gardens.
Evening
Conclude your Key West adventure with a memorable dinner at Tavern N Town, offering a sophisticated dining experience with live music. Raise a glass to the wonderful time you've had in Key West and reminisce about the highlights of your trip.
Bedtime
Find amazing hotels in Key West.
4.74Key West Lighthouse and Keeper's Quarters Museum
Book Now
4.74Key West Lighthouse and Keeper's Quarters Museum
Book Now
4.68Ernest Hemingway Home and Museum
Book Now
4.68Ernest Hemingway Home and Museum
Book Now
Top Key West & The Florida Keys Travel Videos
Adjacent Cities
Find the right stay during your trip.