Key West’s 11 Top Wine Tours

The 11 Best Wine Tours in Key West

Key West isn’t just about vibrant sunsets, lively bars, or historic sites — it’s also a surprisingly good place for wine lovers to indulge. The island’s breeze, stunning coastlines, and maritime vibe make for memorable tasting experiences on the water. Whether you’re after a romantic sunset cruise, a private sail with friends, or a dolphin-watching adventure with wine served, this list covers the best options.

We’ve based this selection on reviews, ratings, value, and the uniqueness of each experience. Imagine sipping champagne on a small group cruise, enjoying tapas while dolphins leap nearby, or hoisting the sails on a classic schooner. We’ve included options that balance comfort, intimacy, and a touch of adventure—each offering something special for water-loving wine enthusiasts. For example, the Adults-only Sunset Cruise from Key West with Champagne scores a perfect 5.0/5 with nearly 900 reviews, emphasizing its intimate setting and gourmet cheese buffet.

In this guide, you’ll find detailed descriptions of each tour, highlighting what makes them different—from private charters to group sailing with wine tastings, dolphin encounters, and reef snorkeling. Whether you’re on a budget or seeking a luxurious experience, there’s a perfect match for your tastes and schedule.

Quick Overview

This list includes a variety of water-based wine tours in Key West. You’ll find sunset cruises, both small-group and private, with options for champagne, wine, or sangria. Several tours combine dolphin watching or snorkeling with wine tasting, creating a multi-sensory experience. Some tours are luxury catamarans or schooners, offering elegant settings, while others focus on intimate small groups for a more personal vibe. Prices range from $56.95 for a snorkeling sunset sail to $4,000 for a private charter, with durations from 1.5 to 3 hours.

1. Adults only Sunset Cruise from Key West with Champagne

This adults-only sunset champagne cruise stands out for its small-group setting, limited to just 14 passengers, ensuring a very personal experience. The cruise is about 2 hours on a comfortable catamaran, with a focus on relaxation and quality. You’ll enjoy house champagne, premium red and white wines, and ice-cold beer, along with a gourmet cheese buffet featuring berries, seafood dip, and fresh bread. Bottled Moët & Chandon is available for purchase, adding a touch of elegance.

What makes this tour exceptional is the attention to detail and the rave reviews—some rated it a perfect 5/5. Passengers often mention the calm waters, the friendly crew, and the intimate atmosphere. This cruise is perfect if you want a relaxing, upscale experience with excellent service and a small number of fellow wine lovers.

Bottom Line: Ideal for couples or adults seeking a refined, small-group sunset with champagne and gourmet snacks at a reasonable price for the level of intimacy and quality.

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

This small-group sunset sail combines dolphin watching with wine and tapas, making it a multi-sensory experience. Departing from Key West’s historic seaport, the approximately 2.5-hour cruise offers close encounters with dolphins and iconic views of landmarks like Mallory Square and Fort Zachary Taylor. The highlight is relaxing on a luxury catamaran while enjoying shrimp cocktail, wine, and champagne as the sun dips below the horizon.

The tour gets high marks for its intimate vibe and the opportunity to see dolphins—a rare treat for wildlife lovers. Reviewers mention the delicious snacks and well-chosen drinks, though some wish there was more food. The experience is best suited for those wanting a combination of wildlife viewing and sunset pleasure with a laid-back atmosphere.

Bottom Line: Perfect if you want to enjoy dolphins, fine wine, and scenic views in an intimate setting with good food and drinks included.

3. Champagne Sunset Catamaran Cruise in Key West

For a classic Key West experience, this 1.5-hour champagne sunset cruise offers a luxurious ride aboard a spacious catamaran. Starting at around $79, it’s an affordable way to enjoy a spectacular sunset with wine, champagne, sangria, and beer included. The friendly crew will guide you to the best vantage points, while you relax and take in views of the island from the turquoise waters.

Guests frequently praise the informal, cheerful atmosphere and the ability to purchase additional bottles onboard. The shorter duration makes this ideal for travelers who want a quick, memorable sunset without sacrificing comfort. Watching the sun melt into the water from the deck of a sleek catamaran creates a postcard-perfect moment.

Bottom Line: Best suited for those seeking an affordable yet elegant sunset sail with drinks included and an easy, relaxed pace.

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

For those wanting privacy and exclusivity, this private sunset sail on a 65ft schooner is hard to beat. Priced at $4,000 per group, it’s designed for your family or friends to enjoy 2 hours of sailing with only your group onboard. You’ll be treated to snacks like cheeses and hors d’oeuvres, with a selection of wines and beers from around the world.

The focus here is on personalized service and a romantic or special occasion vibe. Reviewers note the attentive crew and the ability to customize the experience. It’s perfect if you’re celebrating a milestone or want a luxurious, intimate setting with plenty of space.

Bottom Line: Ideal for groups or couples celebrating something special, looking for privacy, premium drinks, and a tailored experience.

5. 2-Hour Sunset Sailing With Wine In Stock Island

This small group cruise offers a peaceful 2-hour sail with wines and beers served onboard, starting at $133.89 per person. The tour includes eight varieties of wine, five types of beer, and soda, along with charcuterie boards of meats, cheeses, and chocolates. It’s a well-rounded experience for those who want wine tasting in a relaxed setting.

Reviewers highlight the knowledgeable crew and the spectacular sunset views. The tour’s smaller size makes it easier to engage with fellow travelers and enjoy a more personal experience. It’s best suited for those who want a leisurely cruise with quality drinks and snacks.

Bottom Line: Perfect for wine connoisseurs or casual drinkers alike, seeking a relaxed sail with a variety of drinks and gourmet snacks.

6. Key West Sunset Snorkel with Unlimited Draft Beer & Wine

This sunset snorkel and sail combines relaxation with a bit of adventure. Over about 3 hours, you cruise to a nearby coral reef, snorkel among colorful marine life, and sip unlimited draft beer and wine. The tour is priced at $56.95 per person, making it quite affordable.

Reviewers love the combination of snorkeling and sunset views, especially noting that snorkeling is optional—you can just enjoy the boat ride and drinks. It’s great for families or groups who want to experience both marine life and a sunset with easy equipment and a friendly crew.

Bottom Line: An excellent choice if you want snorkeling and wine on a budget with the flexibility to snorkel or just enjoy the sail.

7. Key West Wind and Wine Sunset Sail aboard classic Schooner

This classic schooner offers a romantic sunset experience with premium wines, upscale beers, and gourmet hors d’oeuvres. Priced at $134 per person, the tour lasts about 2 hours, during which you’ll hoist sails, enjoy the island views, and sip fine wines.

Reviewers mention friendly crew, excellent food and drinks, and an authentic sailing atmosphere. It’s best for those wanting a more traditional sailing experience combined with luxury wines and gourmet snacks. The interactive element of helping with the sails adds charm and fun.

Bottom Line: Great for romantics or sailing enthusiasts who want a luxurious, hands-on experience with high-quality wine.

8. Champagne Dolphin Sail and Reef Snorkel

This luxury sailing catamaran offers a 3-hour adventure with champagne, snorkeling, and dolphin sightings. With only 17 passengers maximum, you avoid crowds while enjoying sailing, reef snorkeling, and dolphin encounters. The champagne service onboard is the highlight, with top-notch facilities and a professional crew.

Rated 5/5 with praise for the views, crew, and provisions, it’s perfect for those who want a premium experience with wildlife. Be aware that tickets are refundable if canceled outside two weeks, adding flexibility.

Bottom Line: Excellent for luxury seekers who want to combine champagne, marine life, and snorkeling in a quiet, upscale setting.

9. Key West Small-Group Sunset Sail with Wine and Hors d’Oeuvres

Rated with over 1,200 reviews, this small-group cruise is a standout. It features up to eight wines and five beers, along with a gourmet cheese buffet and other appetizers. The 2-hour sail provides a personalized, relaxed atmosphere with beautiful sunset views.

Reviewers mention it as a “spectacular experience”, praising the friendly crew and the calm waters. It’s suitable for travelers who want a detailed wine tasting combined with scenic sailing, all with a small, intimate group.

Bottom Line: Perfect for wine enthusiasts who want a personalized, relaxed cruise with a wide variety of drinks and gourmet snacks.

10. Key West’s Schooner Appledore Star Champagne Sunset Sail

This romantic 2-masted schooner offers a spacious deck and a classic sailing experience. At around $110, the 2-hour cruise includes champagne, wine, and hors d’oeuvres made in-house. The sails into the sunset creates a picture-perfect moment, with some opportunity to help hoist the sails.

Rated 4.7/5, travelers love the authentic sailing experience and the friendly crew. It’s especially fitting for romantic couples or those wanting to feel the wind in their hair while enjoying fine drinks and scenic views.

Bottom Line: An ideal choice for sailors at heart seeking an authentic, scenic sunset with champagne and gourmet bites.

11. Stock Island Wind & Wine Sunset Sail aboard classic Schooner

This classic schooner offers a similar experience to the Appledore, focusing on wine, upscale beers, and hors d’oeuvres. At $134 per person, it includes premium wines and a gourmet selection of snacks. The friendly crew hoists the sails as you enjoy beautiful sunset views.

Rated 5/5, reviewers highlight the attentiveness of the crew and the top-notch experience. It’s perfect if you want a luxury, traditional sailing with fine wines and an elegant atmosphere.

Bottom Line: Suitable for sailing purists and wine lovers alike—an elegant, unforgettable sunset cruise.

How to Choose Your Key West Wine Water Tour

Picking the right water-based wine experience depends on your budget, preferred level of privacy, interest in wildlife or snorkeling, and how much you want to participate. If relaxation and intimacy are your goals, the Adults only Sunset Cruise or Private Wind & Wine Sail offer a more personal touch. For a more active experience, the Sunset Snorkel with Beer & Wine blends marine adventure with beverages.

If you prefer luxury and traditional sailing, the Champagne Sunset Catamaran or Schooner Appledore Star are excellent choices, especially with their premium wines and scenic sailing. For wildlife enthusiasts, the Champagne Dolphin Sail and Reef Snorkel combines dolphin sightings, snorkeling, and champagne for a well-rounded adventure.

Booking early is advisable for the more popular small-group tours, especially in high season. Consider your interest in private vs. shared experience, and whether you want a shorter, budget-friendly cruise or a luxury private charter.

Final Thoughts

Whether you’re after a romantic sunset, a wildlife-filled adventure, or a luxurious private sail, Key West offers an impressive range of water-based wine tours. The choice hinges on your budget, preferred intimacy level, and whether you want to combine wine with snorkeling or dolphin watching.

For a sophisticated, small-group experience, the Adults only Sunset Cruise and Small-Group Sunset Sail are excellent. If privacy is your priority, the Private Wind & Wine Sail really shines. And for a luxury experience with marine life, the Champagne Dolphin Sail and Reef Snorkel is tough to beat.

Whatever your choice, booking early helps secure your spot on these sought-after tours—so plan ahead and get ready for some unforgettable waterborne wine in Key West.