Cruises & Boat Tours, Drinking Tours, Evening Experiences, Key West, Sunset Sails & Cruises, Tiki Boat & Pontoon Tours, Tour ReviewsKey West Tiki Bar Sunset Cruise (by the seat) BYOB Adventure 5.0Key WestKey West Tiki Bar Sunset Cruise (by the seat) BYOB Adventure2 hours (approx.)$80.58 May 24, 2026
Cruises & Boat Tours, Evening Experiences, Key West, Photography & Live Music Experiences, Sunset Sails & Cruises, Tour ReviewsKey West: Sunset Sail with Live Band, Drinks, and Appetizers 4.7Key WestKey West: Sunset Sail with Live Band, Drinks, and Appetizers$80 May 24, 2026
Cruises & Boat Tours, Key West, Sailing, Tour Reviews, Tours, Wildlife, Wildlife & Shark ToursKey West: Shark and Wildlife Viewing Catamaran Tour 4.8Key WestKey West: Shark and Wildlife Viewing Catamaran Tour2 hours$99 May 24, 2026
Cruises & Boat Tours, Drinking Tours, Evening Experiences, Food & Drink, Key West, Reef Snorkeling Tours, Sunset Sails & Cruises, Tour Reviews, Tours, Wine ToursKey West 2 Reef Snorkel Tour & Sunset Cruise with Beer & Wine 4.5Key WestKey West 2 Reef Snorkel Tour & Sunset Cruise with Beer & Wine3 hours (approx.)$69.95 May 24, 2026
Cruises & Boat Tours, Dolphin Watching, Dolphin Watching Tours, Key West, Tour ReviewsKey West’s Favorite Afternoon Dolphin Sail 4.5Key WestKey West’s Favorite Afternoon Dolphin Sail2 hours 30 minutes (approx.)$59.00 May 24, 2026
Cruises & Boat Tours, Drinking Tours, Key West, Sandbar Tours & Cruises, Tiki Boat & Pontoon Tours, Tour ReviewsKey West Tiki Bar Boat to Popular Sand Bar with Turquoise Waters 5.0Key WestKey West Tiki Bar Boat to Popular Sand Bar with Turquoise Waters4 hours (approx.)$564.90 May 24, 2026
2-Hour Experiences, Concerts, Cruises & Boat Tours, Evening Experiences, Key West, Photography & Live Music Experiences, Sunset Sails & Cruises, Tour ReviewsKey West: 2-Hour Sunset Sail with Live Music 4.7Key WestKey West: 2-Hour Sunset Sail with Live Music2 hours$79 May 25, 2026
Cruises & Boat Tours, Dolphin Watching, Dolphin Watching Tours, Key West, Sailing, Tour ReviewsKey West: Afternoon Catamaran Sail and Dolphin Watch 4.5Key WestKey West: Afternoon Catamaran Sail and Dolphin Watch2.5 hours$59 May 25, 2026
Cruises & Boat Tours, Evening Experiences, Historical Tours, Key West, Schooner Cruises, Sunset Sails & Cruises, Tour ReviewsKey West Historic Schooner When And If Sunset Cruise 5.0Key WestKey West Historic Schooner When And If Sunset Cruise2 hours (approx.) May 25, 2026
2-Hour Experiences, Cruises & Boat Tours, Key West, Mangrove & Kayak Eco Tours, Sailing, Tour Reviews, Tours2 Hour Key West Mini Catamaran Eco Tour 4.5Key West2 Hour Key West Mini Catamaran Eco Tour2 hours (approx.)$264.95 May 25, 2026
2-Hour Experiences, Cruises & Boat Tours, Evening Experiences, Florida Keys Day Tours, Key West, Sailing, Sunset Sails & Cruises, Tour Reviews, Wine Tours2-Hour Sunset Sailing With Wine In Stock Island 5.0Key West2-Hour Sunset Sailing With Wine In Stock Island2 hours (approx.)$125.00 May 26, 2026
Canoes & Kayaks, Cruises & Boat Tours, Key West, Mangrove & Kayak Eco Tours, Schooner Cruises, Tour Reviews, Tours, Wildlife & Shark ToursKey West Schooner Backcountry Eco Tour Sail Snorkel and Kayak 5.0Key WestKey West Schooner Backcountry Eco Tour Sail Snorkel and Kayak5 hours (approx.) May 26, 2026
Boat Charters & Rentals, Cruises & Boat Tours, Drinking Tours, Key West, Schooner Cruises, Tour ReviewsSchooner Appledore Day Sail with Full Bar in Key West 5.0Key WestSchooner Appledore Day Sail with Full Bar in Key West2 hours (approx.) May 26, 2026
2-Hour Experiences, Cruises & Boat Tours, Evening Experiences, Key West, Private, Private & Small-Group Tours, Sunset Sails & Cruises, Tour Reviews, Wine ToursPrivate 2-Hour Wind and Wine Sunset Sail in Key West 5.0Key WestPrivate 2-Hour Wind and Wine Sunset Sail in Key West$4,000.00 May 26, 2026
Cruises & Boat Tours, Key West, Safari, Sandbar Tours & Cruises, Tiki Boat & Pontoon Tours, Tour ReviewsKey West Sandbar Safari on One of a Kind Tiki Boat 4.5Key WestKey West Sandbar Safari on One of a Kind Tiki Boat3 hours 30 minutes (approx.)$139.00 May 26, 2026
Cruises & Boat Tours, Key West, Morning, Reef Snorkeling Tours, Tour ReviewsKey West Morning Snorkel Sail with Mimosas and Gourmet Breakfast 4.5Key WestKey West Morning Snorkel Sail with Mimosas and Gourmet Breakfast3 hours (approx.)$49.00 May 26, 2026
Cruises & Boat Tours, Drinking Tours, Evening Experiences, Key West, Private, Private & Small-Group Tours, Sunset Sails & Cruises, Tiki Boat & Pontoon Tours, Tour ReviewsKey West: Private Sunset Cruise on an Authentic Tiki Bar Boat 4.5Key WestKey West: Private Sunset Cruise on an Authentic Tiki Bar Boat2 hours (approx.)$456.88 May 27, 2026
Cruises & Boat Tours, Evening Experiences, Glass Bottom Boat Tours, Key West, Tour Reviews, ToursKey West: Glass Bottom Boat Reef Tour with Sunset Option 4.0Key WestKey West: Glass Bottom Boat Reef Tour with Sunset Option$70 May 27, 2026
Cruises & Boat Tours, Evening Experiences, Key West, Private, Private & Small-Group Tours, Sunset Sails & Cruises, Tour ReviewsPrivate Sunset Cruise around Key West 5.0Key WestPrivate Sunset Cruise around Key West2 hours (approx.)$400.00 May 27, 2026
Cruises & Boat Tours, Evening Experiences, Florida Keys Day Tours, Historical Tours, Key West, Sunset Sails & Cruises, Tour ReviewsMarathon: Historic 7-Mile Bridge Sunset Cruise 5.0Key WestMarathon: Historic 7-Mile Bridge Sunset Cruise1 hour 30 minutes (approx.)$124.99 May 27, 2026
Cruises & Boat Tours, Evening Experiences, Key West, Private, Sunset Sails & Cruises, Tour ReviewsPrivate Key West Sunset Sail 4.5Key WestPrivate Key West Sunset Sail2 hours (approx.) May 27, 2026
Cruises & Boat Tours, Evening Experiences, Key West, Reef Snorkeling Tours, Sunset Sails & Cruises, Tour ReviewsKey West: 2 Reef Snorkel With Sunset Cruise, Includes Drinks 4.7Key WestKey West: 2 Reef Snorkel With Sunset Cruise, Includes Drinks$70 May 28, 2026
Cruises & Boat Tours, Florida Keys Day Tours, Key West, Sandbar Tours & Cruises, Tour ReviewsMarathon FL Sandbar Cruise & Sightseeing Adventure 5.0Key WestMarathon FL Sandbar Cruise & Sightseeing Adventure4 hours (approx.)$113.90 May 28, 2026
Cruises & Boat Tours, Key West, Parasailing in Key West, Tour ReviewsKey West Parasailing: Ideal For Cruise Ship & Downtown Guests 5.0Key WestKey West Parasailing: Ideal For Cruise Ship & Downtown Guests1 hour (approx.)$49.95 May 28, 2026
Canoes & Kayaks, Cruises & Boat Tours, Key West, Mangrove & Kayak Eco Tours, Private, Sandbar Tours & Cruises, Tour ReviewsPrivate Key West Sandbar and Paddle by Boat 5.0Key WestPrivate Key West Sandbar and Paddle by Boat3 hours 30 minutes (approx.)$600.00 May 30, 2026
Cruises & Boat Tours, Dolphin Watching, Dolphin Watching Tours, Evening Experiences, Key West, Sunset Sails & Cruises, Tour ReviewsCaptain’s Choice: Dolphin Watch Sunset Sail 4.5Key WestCaptain’s Choice: Dolphin Watch Sunset Sail2.5 hours$89 May 29, 2026
Cruises & Boat Tours, Dolphin Watching, Dolphin Watching Tours, Evening Experiences, Key West, Sailing, Sunset Sails & Cruises, Tour ReviewsKey West Dolphin Watch and Sunset Sail on Catamaran 4.5Key WestKey West Dolphin Watch and Sunset Sail on Catamaran3 hours (approx.)$117.17 May 30, 2026
Cruises & Boat Tours, Key West, Sandbar Tours & Cruises, Tour Reviews, ToursKey West Sandbar Excursion & Island Adventure Cruise 5.0Key WestKey West Sandbar Excursion & Island Adventure Cruise4 hours (approx.)$1,200.00 May 29, 2026
Boat Charters & Rentals, Cruises & Boat Tours, Key West, Sailing, Tour ReviewsDay Sailing Adventure in the Florida Marine Sanctuary 5.0Key WestDay Sailing Adventure in the Florida Marine Sanctuary3 hours (approx.)$120.00 May 30, 2026
Cruises & Boat Tours, Evening Experiences, Key West, Reef Snorkeling Tours, Sandbar Tours & Cruises, Sunset Sails & Cruises, Tour ReviewsKey West: Sunset Sail + Reef Snorkel & Sandbar 5.0Key WestKey West: Sunset Sail + Reef Snorkel & Sandbar4 hours 30 minutes (approx.)$143.05 May 30, 2026