Key West isn’t just about lively bars and conch fritters — it’s also a surprisingly good spot for wine tours and relaxing sunset sails. The island’s scenic waterways, warm climate, and laid-back vibe make for perfect sailing conditions and memorable sipping experiences. We love the Adults Only Sunset Cruise with Champagne for its intimate setting and top-notch champagne, providing a refined way to toast the end of the day. Meanwhile, the Key West Sunset Snorkel with Unlimited Draft Beer & Wine offers a fun combo of reef exploration and sunset views, ideal if you want more activity with your wine. Whether you prefer a peaceful, small-group sail or an energetic dolphin cruise with wine on tap, Key West’s waters offer something for every wine lover.
Quick Overview
This list covers a variety of sunset cruises, sailing experiences, and snorkel-plus-wine trips. Some tours focus on luxury and romance (like the Champagne Sunset Catamaran Cruise), while others combine dolphin watching with wine tasting (Key West Sunset Sail: Dolphin Watching, Wine, and Tapas). There are also classic schooner sails with boutique wines, and even historic schooners with a touch of American history (Key West: Classic Schooner Sail With Boutique Wines). Keep reading to find the right fit for your style and budget.
1. Adults only Sunset Cruise from Key West with Champagne
At number one, this adults-only sunset champagne cruise is a top choice for couples or anyone looking for a refined, peaceful evening on the water. The small group of just 14 passengers ensures a personal vibe, perfect for quiet conversations or celebrating a special occasion. The cruise features house champagne, premium red and white wines, and ice-cold beers, complemented by a gourmet cheese buffet with berries, seafood dip, and fresh-baked bread. You can also buy bottles of Moët & Chandon if you want to splurge.
What makes this cruise stand out is its intimate setting and the consistently high reviews. Travelers praise the friendly crew, the relaxing atmosphere, and the stunning sunset views. One guest notes, “It’s a fun way to enjoy the sunset with many selections and a fabulous crew.” For around $109 per person, it offers excellent value for a luxurious, adults-only experience that’s perfect for a romantic evening. The quiet waters and gourmet snacks make this one of the most memorable ways to see the sunset.
Bottom Line: If you’re after a small-group, upscale, and romantic sailing experience, this cruise delivers. Book early — it’s very popular.
2. Key West Sunset Sail: Dolphin Watching, Wine, and Tapas
Number two on our list is the Key West Sunset Sail: Dolphin Watching, Wine, and Tapas. This tour combines the magic of dolphin sightings with the beauty of the sunset, all on a luxury catamaran. It’s slightly longer at about 2.5 hours and includes tapas such as shrimp cocktail along with wine and champagne. Since it’s limited to a small group, the atmosphere is relaxed, and you get a chance to see Key West landmarks like Mallory Square and Sunset Key from the water.
Guests frequently comment on the crew’s friendliness and the quality of the food and drinks. One reviewer says, “Great atmosphere and music — no dolphin sightings, but that’s out of their control.” The price of $89 makes it an affordable option for those who want a combination of wildlife, sunset views, and good eats. It’s ideal for travelers who want a lively yet mellow experience, including families or first-time visitors.
Bottom Line: This tour offers a lively, scenic, and tasty way to enjoy the water with opportunities to spot dolphins and enjoy tapas. Perfect for families or groups wanting more action.
3. Champagne Sunset Catamaran Cruise in Key West
Coming in at number three, the Champagne Sunset Catamaran Cruise presents a shorter, 1.5-hour sail, perfect if you’re short on time but still want a memorable experience. This cruise includes wine, champagne, beer, or sangria as you cruise along Key West’s waters. The captain will take you to the best sunset viewpoints and share insights about the island, making it both scenic and educational.
Guests rave about the friendly crew and the smooth sailing. One says, “Nothing but positive vibes — the staff was wonderful, and the scenery was stunning.” At $79 per person, it provides a relaxed, elegant way to toast the sunset without the longer commitment of some tours. A cash bar is available, and the friendly atmosphere makes it suitable for couples and solo travelers.
Bottom Line: For a quick, stylish sunset with drinks and great views, this is a solid pick. It’s well-suited for those with limited time or looking for a more casual, yet classy experience.
4. 2-Hour Sunset Sailing With Wine In Stock Island
At number four, this peaceful 2-hour sail from Stock Island is for wine lovers who want a more intimate experience. The tour includes eight different wines and five types of beer, along with charcuterie boards of meats, cheeses, and chocolates. The small group creates a cozy, relaxed environment perfect for unwinding as the sun dips below the horizon.
Guests praise the knowledgeable crew, with one reviewer noting, “Tony and Maria made the trip fantastic. The views, wine, and snacks were perfect.” The $134.89 price reflects its premium quality and personalized vibe. It’s ideal for travelers seeking a luxurious, quiet evening with a focus on fine wines and scenic views.
Bottom Line: Best suited for wine aficionados wanting a tranquil, small-group sail with excellent wine options and gourmet snacks.
5. Key West Sunset Snorkel with Unlimited Draft Beer & Wine
Number five combines reef snorkeling with a sunset cruise — a great pick if you want a bit of adventure along with your wine. For around $57, you get to cruise the Atlantic, snorkel at a coral reef, and enjoy unlimited draft beer and wine. The tour lasts about three hours, making it a longer, more active option.
Reviewers love the snorkeling experience, with one commenting, “The snorkeling was awesome, and the sunset views spectacular.” The crew is praised for being friendly and attentive. This tour is perfect for active travelers or those who want both reef exploration and a relaxing sunset.
Bottom Line: A good choice if you’re interested in combining marine life with wine, especially for those who enjoy a mix of activity and relaxation.
6. Key West: Windjammer Champagne Sunset Sail
Number six features a classic windjammer schooner experience, offering a 2-hour sunset sail aboard a historic wooden ship. The tour includes drinks like wine and champagne and the chance to participate in the traditional raising of the sails. It’s a beautifully nostalgic way to enjoy the sunset, especially if you appreciate maritime history.
The reviews highlight the iconic experience and the stunning sunset views. One guest says, “The colors of the sunset were amazing, and helping raise the sails made it special.” Priced at $90, this is a romantic, nostalgic tour perfect for those who want a taste of traditional sailing.
Bottom Line: Ideal for history buffs and romantics who want a scenic, classic schooner experience with drinks included.
7. Key West Wind and Wine Sunset Sail aboard classic Schooner
Number seven on our list offers a luxurious sail aboard a classic schooner with premium wines, upscale beers, and gourmet hors-d’oeuvres. This 2-hour experience is about indulgence, with the crew hoisting sails and serving high-quality drinks as you relax on the water.
Guests comment on the enchanting atmosphere and the friendly crew. One reviewer notes it’s perfect for a romantic evening or celebration. At $134 per person, it’s a bit pricier but well worth it for those seeking an elegant, memorable experience on the water.
Bottom Line: For lovers of fine wine and a touch of luxury, this sail offers an upscale, unforgettable experience.
8. Champagne Dolphin Sail and Reef Snorkel
Number eight combines dolphin spotting, reef snorkeling, and champagne on a luxury sailing catamaran. It’s the most exclusive tour, with only 17 passengers on a yacht initially used for luxury cruises. Ideal for those wanting a mix of adventure, wildlife, and champagne, it’s a three-hour journey that promises memorable wildlife encounters.
Reviews call this a fantastic trip with “top-notch views and plenty of provisions.” The small group and the chance to see dolphins in their natural habitat make it stand out.
Bottom Line: Perfect for wildlife lovers and those seeking a high-end, intimate yacht experience with champagne.
9. Stock Island Wind & Wine Sunset Sail aboard classic Schooner
Number nine offers a romantic sail into the “Floribbean” sunset with premium wines and gourmet hors-d’oeuvres. Similar to the earlier schooner experience, it’s a cozy, elegant choice for lovers of fine wine and classic sailing, departing from Stock Island. It’s a very intimate option for those wanting to avoid crowds.
Guests describe it as an unforgettable experience with stellar crew service. At $134 per person, this tour emphasizes comfort, sophisticated drinks, and the romance of a traditional schooner.
Bottom Line: Best for couples and quiet celebrants who want a scenic, upscale sailing experience.
10. Key West Small-Group Sunset Sail with Wine and Hors d’oeuvres
Number ten offers a small-group, wine-tasting sunset cruise on a 65-foot schooner. It includes up to eight wines and five beers, along with a gourmet cheese buffet and other snacks like summer sausages and green apples with honey. The crew’s friendly service and the calm waters make it a top-rated choice.
Reviews are glowing, with one saying, “Fabulous sail, excellent service, and a beautiful sunset.” At $120.50, it combines personalized service and quality drinks for a memorable evening.
Bottom Line: Great for wine lovers who want a personalized, relaxed cruise with excellent snacks and drinks.
$120.50 per person
11. Key West: Catamaran Champagne Sunset Sail
Number eleven offers a short but sweet 1.5-hour sail on a spacious 60′ catamaran, perfect if you’re pressed for time. It features breathtaking sunset views and the chance to toast with a cold beverage while cruising past Key West landmarks.
Guests mention the breathtaking views and the relaxed atmosphere. It’s priced at $80 per person and suits those wanting a quick but scenic sail.
Bottom Line: Ideal for travelers needing a quick, scenic sunset with drinks on a comfortable catamaran.
12. Key West: Classic Schooner Sail With Boutique Wines
Finally, number twelve offers a 2-hour sail aboard an historic schooner, including boutique wines, beers, and soft drinks. The sail is quiet and uncrowded, with opportunities to help raise the sail or relax and watch the sunset over the Gulf of Mexico.
While reviews are not provided, the experience appeals to those interested in history, maritime charm, and premium drinks. It’s a refined option for those seeking an authentic schooner adventure.
Bottom Line: Perfect for history buffs, sail enthusiasts, and wine connoisseurs wanting an elegant, uncrowded experience.
$81 per person
How to Choose Your Perfect Key West Wine or Sunset Tour
When deciding between these tours, consider your budget, time constraints, and interests. If you want a romantic, upscale experience, the Adults Only Sunset Cruise or the luxury schooner sails are excellent choices. For a more active adventure combined with wildlife, the Sunset Snorkel offers reef exploration plus drinks. Budget travelers might enjoy the shorter Catamaran Champagne Sunset Sail, while history lovers and romantics will appreciate the classic schooner experiences.
Booking early is always wise, especially during peak season (winter months through spring). Think about your group size and preferred atmosphere—small, intimate sails tend to be more relaxed, while larger tours may be livelier.
Final Thoughts
Key West offers a rich variety of wine and sunset sailing experiences that cater to different tastes and budgets. For a romantic, refined evening, the Adults Only Sunset Cruise or Windjammer Champagne Sail are hard to beat. If you want a lively outing that combines dolphin watching and snorkeling, the Dolphin Sail and Reef Snorkel is a good pick.
Whatever your choice, booking in advance ensures you’ll secure a spot for your ideal experience. With so many beautiful sunsets and charming sails available, you’ll find the perfect way to toast your time in Key West.