Category Wine Tours

Key West · WINE TOURS

Top 6 Wine & Tasting Tours in Key West

6 reviewed

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

Key West Small-Group Sunset Sail with Wine and Hors d'oeuvres - What You’re Paying For: $125, All-In Drinks and Snacks

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

★★★★★★★★★★5.0 · 1,366 reviews · 2 hours (approx.) · from $125Our pick

Key West small-group sunset sail with wine tasting, beer, and hors d’oeuvres on a schooner-like boat for about two hours.

“Go on the sunset sail! You won’t regret it! Our friend group of 6 went on a sunset sail with captain Mary, Lexi, and Connor. It was the highlight of everyone’s Key West trip! The crew was amazing. You could tell that they absolutely love what they do and truly care about their passengers experience. I’m sure that they could cater to any age group and make any sailing experience worthwhile. We loved the way that they served wine and appetizer courses. The appetizers were creatively served skewer style, but still kept taste in mind by pairing things such as fig and cheese, mozzarella and tomato, as well as apples…”

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

Key West Sunset Sail: Dolphin Watching, Wine, and Tapas - Getting On Board: Historic Seaport Start, What to Bring, and Simple Comforts

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

★★★★★★★★★★4.5 · 699 reviews · 2 hours 30 minutes (approx.) · from $89

Key West sunset sail with dolphin watching plus premium wine and chef’s tapas. Small group, landmark views, and an easy 2.5-hour plan.

“The sunset cruise was a lot of fun. We enjoyed the views, the beautiful sunsets, and the dolphins. The appetizers were delicious and the staff were knowledgeable and fun!”

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Key West Champagne Sunset Catamaran Cruise

Key West Champagne Sunset Catamaran Cruise - Boarding on a 69-Foot Catamaran: Room, Comfort, and Practical Wins

3.Key West Champagne Sunset Catamaran Cruise

★★★★★★★★★★4.5 · 586 reviews · 1 hour 30 minutes (approx.) · from $59Best value

A 69-foot Key West catamaran at sunset with captain-led views, included champagne-style drinks, and a laid-back 1.5-hour sail from the harbor.

“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. The crew was amazing and on point attending to any needs we had. Highly recommend this cruise.”

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

Key West 2 Reef Snorkel Tour & Sunset Cruise with Beer & Wine - The Boat: The Miss Valyn and the Feel of a Real Catamaran

2-Hour Sunset Sailing With Wine In Stock Island

2-Hour Sunset Sailing With Wine In Stock Island - What’s Included Onboard: Wine, Beer, and Sodas

5.2-Hour Sunset Sailing With Wine In Stock Island

★★★★★★★★★★5.0 · 94 reviews · 2 hours (approx.) · from $125

2-hour sunset schooner sail from Stock Island with wine, beer, and charcuterie included. Small group, attentive crew, big views.

“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!”

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

Private 2-Hour Wind and Wine Sunset Sail in Key West - Wind and Wine: Drinks, Beer Styles, and How the Pairing Works