6 Best Wine Tours In Key West

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

“So much fun and the crew is fantastic!! If you do nothing else, DO THIS! I really can’t say enough good things. It’s just a really good time.”

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

“We had a wonderful time on the Wind and Wine Sail! It was great meeting new people while enjoying delicious wine and tasty hors d’oeuvres. One of the highlights was seeing baby dolphins jumping out of the water—such a special surprise. The sunset was absolutely stunning, and the crew was incredibly attentive and knowledgeable throughout…”

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, 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

“The crew was friendly and there was a good variety of wine. The atmosphere was reserved without the obnoxious crowds. One thing to improve upon was the food. There was not many choices and one can only have so many cheeses. Read more”

87 reviewsFrom $4,000.00by Danger Charters

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Wine Tours