The 12 Best Wine Tours in Key West
Few places in Florida blend stunning sunsets, vibrant marine life, and laid-back island charm quite like Key West. While it’s famous for its lively nightlife and historic streets, the island also offers a surprisingly diverse selection of wine and sunset cruises. Whether you’re after a romantic evening, dolphin sightings, or a private celebration, there’s a sailing experience waiting for you. From luxury catamarans serving champagne to classic schooners with tapas and premium wines, Key West’s boat tours strike a perfect balance of relaxation, adventure, and indulgence.
In this guide, I’ll walk you through the top 12 wine-related tours on the water, highlighting what makes each stand out. You’ll find options for small, intimate groups, luxury private charters, and family-friendly reef snorkels combined with wine. Expect detailed descriptions, practical insights, and honest analysis to help you choose the right tour for your style and budget.
Quick Overview
The best wine tours in Key West cover a variety of experiences. Some focus on sunset sails with champagne and gourmet cheese, like the Adults-only Sunset Cruise or the Wind and Wine Sunset Sail. Others combine dolphin watching, snorkeling, and tapas, such as the Key West Sunset Sail with Dolphin Watching. You’ll also find private charters perfect for special celebrations, and classic schooner sails with gourmet hors-d’oeuvres. Most tours are around 2 hours to 3 hours, with prices ranging from $70 to over $4,000 for private groups. Whether you want a casual drink, a romantic sunset, or an exclusive experience, this list covers the full spectrum.
1. Adults only Sunset Cruise from Key West with Champagne
The Adults-only Sunset Champagne Cruise offers a peaceful escape into the waters off Key West, perfect for couples or adults seeking a quiet, luxurious hour or two. For $108.91 per person, you get a 2-hour sail on a comfortable catamaran limited to just 14 passengers. The small group makes for an intimate experience, ideal for conversations and enjoying the scenery.
This cruise features sparkling wine, premium red and white wines, and ice-cold beer, all served alongside a gourmet cheese buffet with berries, seafood dip, and fresh-baked bread. You can purchase bottles of Moët & Chandon if you want to elevate the celebration. Reviewers praise the relaxing atmosphere and friendly crew, with one noting it was “one of the best things we did in Key West.”
Bottom Line: Perfect for adults wanting a romantic, relaxed sunset with quality beverages and personalized service. Consider it if you prefer a small, quiet group over large parties.
2. Key West Sunset Sail: Dolphin Watching, Wine, and Tapas
The Key West Sunset Sail with Dolphin Watching, Wine, and Tapas takes you into the water for about 2.5 hours of picturesque sailing. For $89.00, this sail limits to a small group, ensuring a personalized experience with ample opportunities to see dolphins. The sail passes iconic landmarks like Mallory Square and Fort Zachary Taylor, making the scenery just as much a star as the sunset.
Savor shrimp cocktail and other tapas with a glass of wine or champagne, all included in the price. Guests appreciate the friendly crew and the abundance of dolphins — some say, “we saw lots of dolphins and had a great time.” The combination of dolphin sightings and relaxed cruising makes this a favorite for couples and small families.
Bottom Line: An excellent choice if you want a dolphin-focused, scenic sunset with light bites and drinks in a relaxed setting.
3. Champagne Sunset Catamaran Cruise in Key West
The Champagne Sunset Catamaran Cruise offers a 1.5-hour sail in a large, stable catamaran for only $79. This cruise is known for its casual elegance, providing champagne, wine, beer, or sangria included in the ticket, while the captain navigates to the best spots to watch the sunset.
Guests rave about the friendly crew and the spectacular views of Key West from the water. Some mention the casual onboard bar, which is cash-only, but the included drinks and the relaxed atmosphere more than compensate. The short duration makes it ideal for those who want a quick, beautiful sunset without a long commitment.
Bottom Line: Best suited for travelers short on time but wanting a classic Key West sunset with premium drinks and fantastic vistas.
4. Private 2-Hour Wind and Wine Sunset Sail in Key West
At Private 2-Hour Wind and Wine Sunset Sail, the experience is all about exclusivity. For $4,000 per group, you get a private sail on a 65-foot schooner with just your friends or family. It’s perfect for celebrations or a memorable romantic evening.
You’ll enjoy hors d’oeuvres paired with a selection of wines and beers. The ship is your private floating retreat, and reviews highlight how attentive the crew is to all your needs. This tour is highly customizable, making it a top pick for those celebrating special occasions. The luxury feel combined with the private setting makes it a standout.
Bottom Line: Best for groups seeking a private, tailored experience with high-end offerings and privacy.
5. 2-Hour Sunset Sailing With Wine In Stock Island
The Small-Group Sunset Sailing and Wine is a personalized sail for about $133.89 per person. It lasts 2 hours and features a small group setting, ideal for mingling with other wine lovers. The boat offers eight varieties of wine, five beers, and sodas, along with charcuterie boards.
Guests often commend the knowledgeable crew and the beautiful sunset views. One reviewer called it the “best sailing experience ever,” thanks to the wine variety and relaxed atmosphere. It’s a good fit for those who want more than just a sunset — they want tasting options and a convivial vibe.
Bottom Line: Great for wine aficionados looking for variety and intimacy in their sunset sailing.
6. Key West: 2 Reef Snorkel With Sunset Cruise, Includes Drinks
The Key West Reef Snorkel & Sunset Cruise offers a 3-hour adventure combining snorkeling at reef sites with a sunset sail. For $70, you’ll enjoy unlimited drinks after snorkeling, including beer and wine, while the boat sails into the sunset.
Guests love the blend of marine adventure and relaxation on deck. The tour is perfect for those who want underwater exploration coupled with a scenic, drinks-filled cruise. One reviewer praised the unobstructed sunset views and the dolphins seen during the trip.
Bottom Line: Ideal if you want a combination of snorkeling and sunset with drinks, especially for families or groups that enjoy marine life.
7. Key West Wind and Wine Sunset Sail aboard classic Schooner
The Wind and Wine Sunset Sail takes you back in time on a classic schooner. For $134, this 2-hour sail offers premium wines, upscale beers, and hors d’oeuvres in a timeless setting. You’ll help hoist the sails and enjoy the friendly crew’s storytelling.
Guests describe it as a romantic and authentic experience, with some mentioning the beautiful, unobstructed sunset views. The hands-on sailing adds a touch of adventure, making it more than just a cruise. It’s well-suited for couples or anyone wanting an immersive sailing experience.
Bottom Line: Best for travelers wanting authentic sailing with fine wines and a tranquil sunset atmosphere.
8. Champagne Dolphin Sail and Reef Snorkel
The Champagne Dolphin Sail and Reef Snorkel combines snorkeling at reef sites with dolphin watching and champagne service. At $108.91 per person, it’s a 3-hour trip on a luxury sailing catamaran, with up to 17 guests on board.
This tour stands out because of its small group size and the chance to see dolphins in their natural habitat. The professional crew makes sure everyone is comfortable, with reviews emphasizing the friendly service and excellent snorkeling. The highlight is the champagne and snacks after exploring the reefs.
Bottom Line: Perfect for those who want a luxury, dolphin-filled reef adventure with champagne and a small-group touch.
9. Key West Small-Group Sunset Sail with Wine and Hors d’oeuvres
This Small-Group Sunset Sail with Wine and Hors d’Oeuvres is a favorite for its intimate atmosphere. At $120.50 per person, it lasts around 2 hours and features up to eight wines and five beers, paired with gourmet snacks like cheeses, summer sausages, and green apple drizzled with honey.
Guests praise the professional crew and beautiful sunset views, with some noting it as a highlight of their trip. The focus on quality drinks and personalized service makes it suitable for couples or small groups seeking a luxurious yet relaxed experience.
Bottom Line: Ideal if you want a high-end, intimate cruise with a variety of wines and gourmet bites.
10. Key West’s Schooner Appledore Star Champagne Sunset Sail
The Schooner Appledore Star Champagne Sunset Sail offers a romantic 2-hour sail on a spacious, historic schooner. For $110, you get cheers with cold beverages and the chance to help hoist sails or take the wheel.
Guests consistently mention the beautiful, spacious decks and the spectacular sunset as highlights. The chef’s hors d’oeuvres add a gourmet touch, perfect for couples or anyone looking for an authentic sailing experience. The combination of interactive sailing and stunning scenery** makes it a top pick.
Bottom Line: Best for those who want an interactive, picturesque sailing adventure with quality drinks.
11. Stock Island Wind & Wine Sunset Sail aboard classic Schooner
The Stock Island Wind & Wine Sunset Sail offers a romantic journey into the sunset aboard a classic schooner. At $134 per person for about 2 hours, it’s similar to the Wind and Wine sail but from Stock Island. The premium wines, gourmet hors d’oeuvres, and friendly crew ensure a memorable experience.
Guests love the relaxed atmosphere and the beautiful views. The sail provides a peaceful escape, with many mentioning the attentive crew and excellent wine selection.
Bottom Line: A great choice for romantic evenings and those seeking a less crowded sailing experience.
12. Key West: Windjammer Champagne Sunset Sail
The Windjammer Champagne Sunset Sail takes you on a classic 2-masted schooner with snacks and drinks included. For $90, the 2-hour cruise offers spectacular sunset views and a chance to raise the sails in the tradition.
Reviewers appreciate the friendly crew and delicious snacks, with many noting the colorful sunset and the authentic sailing experience. It’s ideal for travelers who want a relaxing, scenic evening with a bit of nautical history.
Bottom Line: Suited for those seeking a traditional sailing trip with good drinks and memorable sunset views.
How to Choose the Right Wine Tour in Key West
Picking the right tour depends on your interests, budget, and the kind of experience you want. If you prefer a romantic, quiet evening, the Adults-only Sunset Cruise or the Wind and Wine sail might be best. For dolphin lovers or snorkelers, the reef and dolphin tours offer added adventure. Those celebrating a special occasion can opt for a private charter, which provides customization and exclusivity.
Consider the group size—small groups tend to be more intimate and personalized, but private charters offer complete control. If time is tight, the shorter cruises give a quick but beautiful experience. Booking early is wise during peak season (winter months) when tours fill quickly.
Final Thoughts
Key West offers a variety of wine-focused sailing experiences that blend stunning sunsets, marine life, and gourmet drinks. Among the standouts are the Adults-only Champagne Sunset Cruise for a peaceful, upscale vibe, and the Private Wind and Wine sail for a truly exclusive celebration. For those wanting adventure, the reef snorkeling combined with open bar tours deliver both underwater excitement and scenic beauty.
Whether you’re after a romantic escape, a fun group outing, or an adventurous day on the water, these tours provide a memorable way to experience Key West’s signature sunsets. Be sure to book early, especially during peak season, so you won’t miss out on these exceptional experiences.
Note: The full list of 12 tours has been included for comprehensive coverage, ensuring you find the perfect match for your Key West visit.