Savvy travelers will find Key West’s wine-tasting sailing tours both practical and memorable. The standout choices blend fine wines with stunning Gulf views. A top pick is the 65-foot schooner experience, offering 8 wine varieties and a quality cheese spread – perfect for small groups seeking an intimate atmosphere. The private 2-hour sail delivers excellent value for couples or families wanting their own space, while the adults-only cruise stands out for its generous unlimited beverage service. For active travelers, the combination snorkel-and-wine sail provides great bang for your buck. Let’s look at the best wine-themed sailing options in Key West.
Key Points
- Key West Sunset Sails offers a 2-hour small-group sunset sail with wine tastings, a gourmet cheese buffet, and a personalized experience for up to 26 guests.
- The Key West Wind & Wine Sunset Sail provides breathtaking coastal views, premium wines, and gourmet appetizers, departing from the Bad Boy Taqueria & Tequila.
- The Private Wind and Wine Sunset Sail is an exclusive 2-hour private tour for one group, featuring a variety of hors d’oeuvres and a global wine selection.
- The Schooner Appledore Star Champagne Sunset Sail offers a 2-hour cruise with complimentary champagne, boutique wine, and hors d’oeuvres, as well as opportunities to interact with the vessel.
- The 2-Hour Sunset Sailing in Stock Island features wine sampling from eight wines, a charcuterie board, and a maximum of 20 travelers aged 13 and older.
Key West Small-Group Sunset Sail With Wine
One of the most popular wine-tasting experiences in Key West is the small-group sunset sail aboard a 65-foot schooner. During this 2-hour cruise, guests can sample up to eight wines and five beers while enjoying the scenic views and a gourmet cheese buffet.
The maximum of 26 travelers ensures a personalized experience, and gratuities are covered in the package. The tour departs from the Opal Key Resort, with participants advised to arrive 30 minutes early for check-in. The activity concludes at the same meeting point.
Participants must be at least 21 years old, and the cruise isn’t wheelchair accessible but is near public transportation.
With over 1,145 reviews and a 4.9 overall rating, this sunset wine-tasting sail has earned a 98% traveler recommendation rate. Guests praise the friendly crew, wine selection, and overall experience, though some suggest a broader range of wine options.
Notable highlights include the chance to spot dolphins and the romantic atmosphere as the sun dips below the horizon.
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Key Wests Schooner Appledore Star Champagne Sunset Sail
Key West’s Schooner Appledore Star Champagne Sunset Sail offers a truly unique and unforgettable experience. Priced from €106.92 per person, this 2-hour cruise aboard a romantic 2-masted schooner provides stunning views of Key West’s iconic sunset.
Guests can enjoy spacious and comfortable decks, complimentary drinks like champagne and boutique wine, and a chef’s selection of hors d’oeuvres.
The Appledore Star is the only bugeye schooner in Key West, with an experienced captain who positions the vessel for optimal sunset viewing. Participants can even take a turn at the wheel or help hoist the sails, making this an interactive and memorable experience.
The tour sails past notable landmarks, including Mallory Square, Navy Mole, and Fort Zachary Taylor.
With free cancellation up to 24 hours in advance and the option to reserve now and pay later, this sunset sail is a must-do activity for visitors to Key West. Don’t miss the chance to enjoy this unique and picturesque experience.
Read our full review: Key Wests Schooner Appledore Star Champagne Sunset Sail Review
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Adults Only Sunset Cruise From Key West With Champagne
Although Key West offers a wide variety of sunset cruises, the Adults Only Sunset Cruise From Key West With Champagne stands out as a truly memorable experience.
Limited to just 14 passengers, this 2-hour cruise aboard a comfortable catamaran provides an intimate setting to enjoy breathtaking views of the sunset from the water. Theres some good a gourmet cheese buffet, complemented by unlimited champagne, premium wines, and ice-cold beer.
The crew is praised for their friendliness and attentiveness, ensuring an exceptional level of service. With an average rating of 4.9/5 based on 849 reviews, this cruise is a must-do activity for adults seeking a sophisticated and relaxing way to experience Key West’s famous sunsets.
At $108.91 per person, the Adults Only Sunset Cruise offers excellent value, though non-refundable payment and a 2-week cancellation policy apply.
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Key West: Sunset Snorkel Cruise With Draft Beer & Wine
For travelers seeking a unique blend of adventure and relaxation in Key West, the Key West: Sunset Snorkel Cruise with Draft Beer & Wine offers an exceptional experience.
Lasting 3 hours, this cruise takes guests to the world’s third-largest coral barrier reef for 1 hour of snorkeling. Afterward, they can enjoy unlimited cold draft beer and wine while admiring unobstructed sunset views over the Gulf of Mexico.
The relaxing boat ride includes music and passes by Mallory Square. Priced at $69.95 per person, the cruise includes snorkeling gear, soft drinks, water, and hotel transportation.
With a 4.7/5 overall rating from 47 reviews, guests praise the beautiful reef, dolphin sightings, and overall fun experience. The cruise’s 5/5 guide rating and 4.8/5 transportation rating further attest to its quality.
For those looking to combine sightseeing, snorkeling, and drinks, this sunset cruise is an excellent choice in Key West.
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Champagne Sunset Catamaran Cruise in Key West With Cocktails!
Sailing aboard a 69-foot catamaran, the Champagne Sunset Catamaran Cruise in Key West offers travelers a unique way to experience the island’s stunning sunset views.
With a 92% recommendation rate from past guests, this 2-hour cruise has earned a Badge of Excellence and positive reviews from 576 travelers.
The cruise includes complimentary wine, champagne, beer, sangria, and soft drinks, as well as a cash bar for cocktails. Guests can also use the restroom on board and enjoy the included gratuities.
The cruise departs from 205 Elizabeth St, with boarding starting 30 minutes prior to the 2-hour experience.
While the cruise generally receives high praise for its friendly crew, enjoyable atmosphere, and beautiful sunsets, some guests have expressed concerns about communication and value for upgrades.
The quality and consistency of the experience seem to vary, with mixed reviews on the food.
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Stock Island Wind & Wine Sunset Sail Aboard Classic Schooner
Offering a unique twist on the traditional sunset sail, the Stock Island Wind & Wine Sunset Sail aboard a classic Schooner provides travelers a captivating experience. Priced from $128.89 per person, this 2-hour cruise features premium wines, upscale beers, and gourmet appetizers, allowing guests to mingle with friends or enjoy a romantic evening.
The sail has been ranked as one of the top two in North America by Coastal Living Magazine, showcasing eight varieties of wine and five premium beer options.
Guests meet the Captain at Bad Boy Taqueria & Tequila 30 minutes prior to departure, then are escorted through the Perry Hotel & Marina to the boat at slip J5. Recommended items to bring include a sweatshirt, sunglasses, and a camera.
Bathrooms are available before boarding and on the schooners. While gratuities aren’t specified, they’re typically appreciated by the crew.
Read our full review: Stock Island Wind & Wine Sunset Sail Aboard Classic Schooner Review
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Key West Sunset Sail: Dolphin Watching, Wine, and Tapas
Travelers seeking a memorable sunset experience in Key West can embark on the Key West Sunset Sail, which offers a unique blend of dolphin watching, wine, and tapas.
This intimate cruise, limited to 50 guests, showcases stunning views of Key West landmarks like Mallory Square and Fort Zachary Taylor. Aboard a luxury catamaran, guests can relax and enjoy premium wine, beer, champagne, shrimp cocktail, and other hors d’oeuvres as they witness the sun dipping below the horizon.
While dolphin sightings aren’t guaranteed, the knowledgeable crew provides an educational and engaging experience. With an average rating of 4.6 out of 572 reviews, the Key West Sunset Sail is a highly recommended activity for families and couples visiting the area.
The cruise departs from the meeting point at 205 Elizabeth Street, offering convenient access and a hassle-free return to the starting location.
Read our full review: Key West Sunset Sail: Dolphin Watching, Wine, and Tapas Review
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Key West Wind and Wine Sunset Sail Aboard Classic Schooner
While the Key West Sunset Sail offers a delightful dolphin-watching experience paired with wine and tapas, the Key West Wind and Wine Sunset Sail aboard a classic schooner presents a distinct and captivating opportunity.
This 2-hour excursion departs from the Opal Key Resort & Marina, allowing guests to set sail into the stunning “Floribbean” sunset.
Aboard the classic schooner, attendees can indulge in an impressive selection of premium wines, upscale beers, and gourmet appetizers. The wine list features eight varieties, including four reds, three whites, and a Champagne, while the beer selection offers five premium imported and domestic options.
Charcuterie boards with meats, cheeses, crackers, fruit, crudités, and chocolate provide the perfect accompaniment.
With a 5/5 rating based on rave reviews, the Key West Wind and Wine Sunset Sail promises an unforgettable experience.
Couples and friends alike can mingle and bask in the breathtaking coastal vistas as the sun dips below the horizon.
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Key West Sunset Snorkel With Unlimited Draft Beer & Wine
The Key West Sunset Snorkel with Unlimited Draft Beer & Wine tour provides travelers with the unique opportunity to combine a sunset sail and snorkeling in the vibrant coral reef.
With a maximum capacity of 70 guests, the 3-hour experience offers a relaxing atmosphere, music, and the chance to mingle with other participants.
Travelers will receive snorkeling equipment, alcoholic beverages, and gratuities as part of the $56.95 per person price tag.
Positive reviews highlight the crew’s friendliness, knowledgeable staff, and the beautiful views, with many guests enjoying the great snorkeling, sunset, and social atmosphere.
While some suggestions mention improving the check-in process and clarifying premium drink upgrade policies, the tour maintains an impressive 4.7-star rating based on 111 reviews, earning a Badge of Excellence.
Travelers can take advantage of the free cancellation policy and pay-later option, and are encouraged to bring cameras to capture the sunset.
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2-Hour Sunset Sailing With Wine In Stock Island
A 2-hour sunset sailing tour in Stock Island, Key West, allows guests to enjoy picturesque views while sipping on a variety of wines. Recommended by 100% of travelers, this experience includes appetizers and wine sampling from around the world.
Travelers can expect a selection of eight wines, five types of beer, and sodas, as well as a charcuterie board with meats, cheeses, crackers, and chocolate.
The tour has a maximum of 20 travelers and is only open to those 13 and older. Operated by Danger Charters, this activity is likely to sell out, so booking in advance is recommended.
Confirmation is received at booking, and free cancellation is available up to 24 hours before the tour. Guests should arrive 30 minutes prior to departure at the Perry Hotel and Marina, J dock, slip 5, and the activity ends back at the same meeting point.
Priced from $133.89 per person, the tour offers a lowest price guarantee, and guests can reserve now and pay later for flexibility.
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Private 2-Hour Wind and Wine Sunset Sail in Key West
Although it operates exclusively for your group, this private 2-hour wind and wine sunset sail off Key West provides a memorable experience.
Departing just before sunset from the Opal Key Resort, you’ll board a 65ft schooner and enjoy the beautiful scenery as you sail beside the shoreline.
The experience includes a variety of hors d’oeuvres like assorted cheese skewers and a selection of wines and beers from around the globe.
With a 4.9 rating from 77 reviews and a Badge of Excellence, this tour is highly recommended by 99% of travelers.
While not wheelchair accessible, the tour is near public transportation, and most travelers can participate.
Priced at $4,000 per group (up to 1 person), you can secure your spot with free cancellation up to 24 hours before.
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The Sum Up
Key West offers a variety of wine-infused sunset sails and cruises. Visitors can enjoy champagne, beer, and cocktails while taking in the picturesque views. Whether you’re seeking a private sail or a group experience, there are options to suit different preferences and budgets. These sunset excursions provide a unique and relaxing way to experience the beauty of Key West.