Key West isn’t just about sunbathing and lively bars — it’s a fantastic place to enjoy sailing. Its accessible, warm waters, scenic coastline, and steady breezes make it a prime spot for all sorts of boat trips. Whether you’re after a romantic sunset, a wildlife encounter, or a day exploring offshore reefs, Key West has a lot to offer. We especially like the Champagne Sunset Catamaran Cruise for its relaxed vibe and included drinks, and the Dry Tortugas Day Trip for a mix of history, snorkeling, and remote beaches. These experiences stand out because they combine natural beauty with comfort and a touch of local flavor. If you’re planning your trip, check out this for a memorable sunset sail or this for a full-day adventure exploring one of the most striking parks in the U.S.
Quick Overview
The list below covers a variety of sailing experiences in Key West, ranging from quick sunset cruises to full-day snorkeling trips, private charters, eco-tours, and wildlife encounters. Highlights include romantic sunset sails, family-friendly snorkeling adventures, eco-friendly small boat trips, and private charters perfect for groups. All these tours offer a different way to experience the waters and scenery of Key West, and many come with excellent reviews for their value and memorable moments. For a detailed look at each, keep reading.
1. Champagne Sunset Catamaran Cruise in Key West
At number one, this 2-hour sunset cruise on a 69-foot catamaran offers a relaxing way to end your day. It’s perfect for those who want to unwind with included wine, champagne, sangria, or beer as the sun dips below the horizon. The crew takes you to the best sunset spots, sharing tips on the island’s views from the water. Passengers consistently praise the friendly staff and the positive, laid-back atmosphere, with reviews highlighting “nothing but positive vibes.” The cruise is an ideal choice for couples or small groups looking for a romantic evening or a casual sunset sail. The prize here is the combination of stunning scenery and the all-inclusive drinks, making it great value — especially as cocktails are included in the ticket price. The cash bar offers additional drinks if you want to indulge further.
Bottom Line: Perfect for a quick, romantic, and scenic wrap-up to your day in Key West, with friendly crew and beautiful views.
2. Dry Tortugas National Park Day Trip by Catamaran from Key West
For around $220 per person, this full-day trip offers a rare chance to explore Dry Tortugas National Park, famous for its historic Fort Jefferson, coral reefs, and sparse beaches. The trip onboard the Yankee Freedom III is a highlight, with spacious, modern facilities that make the journey comfortable. The naturalist onboard shares insights about the park’s history and marine life, adding an educational touch. The trip includes snorkeling gear, with many visitors raving about the vibrant reef and sea life like dolphins and sea turtles. While the fort is interesting, most guests agree the snorkeling at the coral reef is the real star. Expect a long but rewarding day, with plenty of time for swimming, relaxing, and exploring.
Bottom Line: An excellent choice for those eager to combine history, snorkeling, and nature in a single trip, with great reviews for the reef experience.
3. 2-Hour Sunset Sailing With Wine In Stock Island
At number three, this intimate sunset sail offers a cozy experience with appetizers and a variety of wines and beers. For $133.89, you get a peaceful two hours on the water, perfect for small groups or couples seeking a relaxed, upscale vibe. The crew is described as knowledgeable and personable, making the experience feel personalized. Reviewers love the snack platter and diverse wine selection, noting that the views of the sunset are spectacular. This tour is best suited for those who want to enjoy the scenery with good company and fine drinks without the rush of larger boats.
Bottom Line: A great option for a romantic or low-key sunset, with thoughtful touches and a small-group atmosphere.
4. Key West: Shark and Wildlife Viewing Catamaran Tour
Next, for wildlife lovers, this 2-hour eco tour promises shark sightings and encounters with dolphins, turtles, and stingrays. The Tigre Cat offers a shaded, comfortable ride where you can relax and learn about marine life from the friendly crew. Rated 4.8/5, this tour stands out for its focused wildlife experience in the backcountry waters of Key West. It’s perfect if your goal is to see sharks in their habitat and observe other sea creatures in their natural environment. The eco-friendly approach appeals to travelers interested in conservation, and the knowledgeable guides keep the experience engaging.
Bottom Line: Ideal for wildlife enthusiasts seeking an informative, comfortable ride that prioritizes marine encounters.
5. Key West Sailing & Snorkeling: A Reef Adventure
This 3-hour trip combines sailing and snorkeling at a beautiful coral reef. For $79 per person, it offers a relaxing sail with included wine, beer, or soft drinks and a snorkeling experience tailored to daily conditions. The captain changes the reef location based on what’s best that day, ensuring a quality experience. Reviewers praise the friendly crew and vibrant marine life, including fish, eels, and sea turtles. It’s perfect for families, first-timers, or anyone wanting a laid-back, eco-friendly trip that blends sailing with underwater exploration.
Bottom Line: A versatile, value-packed tour for snorkeling and sailing lovers wanting a flexible, natural experience.
6. Bimini Charters – Private 3hr Catamaran Charters, Sail & Snorkel
Looking for exclusivity? This private 3-hour charter allows your group of up to six people to enjoy customized sailing and snorkeling. For no set price (up to 6 people, the fee is free), you can bring your own food and drinks, creating a tailored experience. The tour includes snorkeling at West Sambo reef, dolphin spotting, and enjoying the sunset over the Gulf of Mexico. Rated 5 stars by those who’ve booked, this tour offers privacy, flexibility, and a personalized touch, making it a great choice for special occasions or just a quiet escape.
Bottom Line: Best for small groups wanting a private, flexible day on the water with the freedom to bring their own provisions.
7. Private 90-Minute Harbor Sailing Charter in Key West
For those who want a quick but personalized experience, this private 90-minute harbor sail is perfect. Setting sail from 202 William St., the boat heads toward Sunset Key and the Wildlife Refuge, offering a gourmet cheese platter and light refreshments. The reviews are glowing, with one calling it a “great time with an awesome crew.” It’s suitable for small groups or couples wanting an intimate, scenic trip with flexible timing.
Bottom Line: Excellent for a short, private escape with stunning harbor views and a touch of luxury.
8. Key West: Afternoon Catamaran Sail and Dolphin Watch
For a more active afternoon, this 2.5-hour tour takes you along with dolphins in Key West’s waters. At $60 per person, you get a casual cruise on a 60-foot catamaran with chances to see dolphins playing. The crew shares facts about local dolphins, making it both fun and educational. It’s a great option if you want to combine sailing with wildlife spotting in a relaxed atmosphere.
Bottom Line: Perfect for families or those wanting a laid-back dolphin-watching trip with a friendly crew.
9. Day Sailing Adventure in the Florida Marine Sanctuary
This 3-hour sailing on a 50-foot sailboat offers a mix of natural beauty and maritime history. Rated 5 stars, it takes you through Boot Key Harbor, with sightings of dolphins and manatees, plus a visit to the famous Sombrero Lighthouse. The captain’s tales of worldwide sailing add flavor, and the included drinks — soft drinks and water — keep you refreshed. It’s an excellent choice for sailors and nature lovers wanting a peaceful, scenic experience.
Bottom Line: Well-suited for those who want a peaceful, educational sailing trip with wildlife and scenic highlights.
10. 2 Hour Key West Mini Catamaran Eco Tour
If you want adventure on a small scale, this eco tour in a Craigcat boat offers a fast-paced, off-the-beaten-path exploration. For just around $285 for two, you’ll cruise through mangroves, stop at sandbars, and visit secluded islands. The guides highlight wildlife like herons and manatees, and the tour includes wildlife encounters and snorkeling. Reviewers rave about the personalized experience and the chance to see less-visited spots.
Bottom Line: Perfect for eco-minded travelers wanting a fast, fun, and intimate exploration of Key West’s natural surroundings.
11. Key West: Catamaran Snorkel with Seafood Boil and Open Bar
This 4-hour catamaran adventure combines snorkeling, seafood, and open bar in a lively setting. With a Low Country seafood boil and guided snorkel spots, it’s a popular choice for those looking for great food and underwater views. The open bar ensures you can sip on cocktails while enjoying the scenery. The tour’s vibe is festive, making it ideal for groups celebrating or families wanting a lively day on the water.
Bottom Line: Best for travelers who enjoy good food, drinks, and snorkeling in an energetic atmosphere.
12. Key West: Catamaran Champagne Sunset Sail
Rated 4.7/5, this 1.5-hour champagne sunset sail is a classy way to experience Key West’s sunset. The spacious 60-foot catamaran offers unobstructed views, while you toast with champagne or other drinks. It’s ideal for a romantic evening or special occasion, with the captain pointing out local landmarks along the way. The focus here is on relaxation and scenic beauty, making it a top pick for a memorable sunset.
Bottom Line: A refined, scenic way to toast the day’s end in style, perfect for couples or those celebrating.
13. Dock Side Adventure Kayak, Paddle Boarding, Sunfish sailboats
This 8-hour multi-activity trip suits those who want a full day of water fun. It includes kayaking, paddleboarding, and Sunfish sailboats, as well as barbecue and the chance to watch the sunset. Rated 0 reviews so far, it’s an all-day option for active travelers who like variety and family groups. You’ll spend the day on a large floating mat, swimming, and relaxing with plenty of options to keep busy.
Bottom Line: Best for water sports enthusiasts wanting a full day combining several activities in one trip.
$143
How to Choose Your Perfect Sailing Experience
When selecting your ideal Key West sailing adventure, consider your budget, time availability, and interests. For a romantic, short sunset, the Champagne Sunset Catamaran or Champagne Sunset Sail (links) are excellent options. If you want a full-day trip with snorkeling and history, check out the Dry Tortugas Day Trip (link). For a private experience, the Bimini Charters (link) offers tailored sailing with your group.
Fitness level, interest in wildlife, and preference for group size should guide your choice. Book early, especially during peak seasons, to secure your spot on popular tours like the day trip to Dry Tortugas or the private charters.
Final Thoughts
Key West offers a broad selection of sailing trips that cater to different tastes and schedules. For those seeking romance and scenery, the sunset sails are unbeatable. Adventure seekers will enjoy snorkeling, wildlife watching, or private charters that give you flexibility and exclusivity. Whether you prefer a quick, lively outing or a peaceful, scenic cruise, the waters of Key West beckon.
Two or three standout options are the Champagne Sunset Catamaran Cruise for a classic evening, the Dry Tortugas Day Trip for a full-day exploration, or the Bimini Charters private tour for a personalized day on the water. Whatever your choice, booking early helps ensure you get the experience that best fits your trip. Enjoy the sailing — the waters around Key West truly are some of the best in the world.