11 Best Wine Tours In Key West

Cruises & Boat Tours, Evening Experiences, Key West, Sunset Sails & Cruises, Tour Reviews, Wedding Cruises, Wine Tours

Key West Small-Group Sunset Sail with Wine and Hors d’oeuvres

/ June 4, 2026

1.Key West Small-Group Sunset Sail with Wine and Hors d’oeuvres

Key West small-group sunset sail with up to eight wines, beer, and hors d'oeuvres on a schooner. Intimate, romantic start to night.

Key West Sunset Sail: Dolphin Watching, Wine, and Tapas

/ June 4, 2026

2.Key West Sunset Sail: Dolphin Watching, Wine, and Tapas

Key West sunset sail with dolphin watching, premium wine, champagne and tapas on a luxury catamaran, small group max 50.

★ 4.5

“Captain Daniel and John were outstanding and very accommodating. The tapas were exceptional, much more than we anticipated and would give the chef 5 stars!”

699 reviews2 hours 30 minutes (approx.)From $89.00by Sebago Key West

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Bachelorette Party Cruises, Birthday Party Cruises, Catamaran Cruises, Cruises & Boat Tours, Evening Experiences, Key West, Party Boat Cruises, Sailing, Sunset Sails & Cruises, Tour Reviews, Wedding Cruises, Wine Tours

Key West Champagne Sunset Catamaran Cruise

/ June 4, 2026

3.Key West Champagne Sunset Catamaran Cruise

Sail Key West’s harbor to chase the champagne sunset from a 69-foot catamaran, with included drinks, a restroom, and great photo views.

★ 4.5

“You may want a sweatshirt or light jacket after the sun sets. The wind is fairly strong and the temperature gets a little cooler. We booked a 1.5 hour champagne cruise but it didn’t sail that evening so we were given a complimentary upgrade to the 2 hour sail with live music and hors d’oeuvres.…”

586 reviews1 hour 30 minutes (approx.)From $59.00by Sebago Key West

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Cruises & Boat Tours, Drinking Tours, Evening Experiences, Food & Drink, Key West, Reef Snorkeling Tours, Sunset Sails & Cruises, Tour Reviews, Tours, Wine Tours

Key West 2 Reef Snorkel Tour & Sunset Cruise with Beer & Wine

/ June 4, 2026

4.Key West 2 Reef Snorkel Tour & Sunset Cruise with Beer & Wine

Snorkel two Key West reef spots on The Miss Valyn, then sail into sunset with beer, wine, and champagne on a 3-hour catamaran.

★ 4.5

“The captain and crew was oustanding! Very knowledgeable about snorkling activities. We felt safe during the entire trip.”

146 reviews3 hours (approx.)From $69.95by Sunset Watersports

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2-Hour Experiences, Cruises & Boat Tours, Evening Experiences, Florida Keys Tours, Key West, Sailing, Sunset Sails & Cruises, Tour Reviews, Wine Tours

2-Hour Sunset Sailing With Wine In Stock Island

/ June 4, 2026

5.2-Hour Sunset Sailing With Wine In Stock Island

2-hour sunset sailing from Stock Island, Key West with wine, beer, and charcuterie on a small schooner crew by Danger Charters.

★ 5.0

“This was an awesome experience. The food and wine selection was great! Staff was awesome! And the views of the sunset were top notch! Would highly recommend!”

94 reviews2 hours (approx.)From $125.00by Danger Charters

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2-Hour Experiences, Cruises & Boat Tours, Evening Experiences, Key West, Private, Sunset Sails & Cruises, Tour Reviews, Wedding Cruises, Wine Tours

Private 2-Hour Wind and Wine Sunset Sail in Key West

/ June 4, 2026

6.Private 2-Hour Wind and Wine Sunset Sail in Key West

Private 2-hour Key West sunset sail on a 65-ft schooner with global wines, craft beers, and hors d’oeuvres for your group.

★ 5.0

“This was our third sunset, wine tasting, cruise with Danger in the last two years. Comfortable boat, fun and accommodating staff, good wine, tasty food, beautiful sunset.”

87 reviewsFrom $4,000.00by Danger Charters

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Cruises & Boat Tours, Evening Experiences, Key West, Sunset Sails & Cruises, Tour Reviews, Wine Tours

Key West: Windjammer Champagne Sunset Sail

/ June 10, 2026

7.Key West: Windjammer Champagne Sunset Sail

Sail the Schooner Appledore II on a Key West sunset cruise with champagne, sangria, and hands-on sail-raising by the crew.

★ 5.0

18 reviews2 hoursFrom $89by Schooner Appledore

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Cruises & Boat Tours, Evening Experiences, Key West, Schooner Sailing, Sunset Sails & Cruises, Tour Reviews, Wine Tours

Key West Wind and Wine Sunset Sail aboard classic Schooner

/ June 11, 2026

8.Key West Wind and Wine Sunset Sail aboard classic Schooner

Wind and Wine sunset sail in Key West: classic schooner, eight wines, premium beer, charcuterie, and sunset sailing magic.

★ 5.0

16 reviews2 hoursFrom $133by Danger Charters

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Cruises & Boat Tours, Dolphin Watching, Dolphin Watching Tours, Key West, Reef Snorkeling Tours, Sunset Sails & Cruises, Tour Reviews, Wine Tours

Champagne Dolphin Sail and Reef Snorkel

/ June 16, 2026

9.Champagne Dolphin Sail and Reef Snorkel

Key West champagne catamaran: wild dolphin spotting, about 1 hour reef snorkeling with sanitized gear, easy lessons, small group.

★ 5.0

“we had a truly fantastic time. our captains/guides were Bailey and Micah who facilitated a lovely experience, the views were top notch, and the provisions were plenty. we will be return customers for similar excursions when we return to Key West. thanks for a great day!”

5 reviews3 hours (approx.)From $108.91by Dolphin Echo Inc. (Catamaran Echo)

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