Key West’s sailing scene delivers practical options for every traveler’s needs. The most worthwhile excursions include the spacious 69-foot catamaran sunset cruise, featuring quality champagne and unobstructed views. The dolphin-watching tours prove consistently reliable, with skilled captains who know exactly where to spot Atlantic bottlenose dolphins. Small-group snorkeling tours stand out for their personal attention and access to less-crowded reef spots. For those seeking a livelier experience, the 65-foot sunset party catamaran hits all the right notes with its combination of live music and included drinks. Private charters offer the best value for families or groups wanting to set their own pace. Let’s look at our favorite sailing tours in Key West.
Key Points
- Champagne Sunset Catamaran Cruise offers an intimate 69-foot catamaran experience with stunning sunset views, wine, beer, and champagne.
- Catamaran Sail & Dolphin Watch provides a 2.5-hour sail with opportunities to spot Atlantic bottlenose dolphins and enjoy unlimited beverages.
- Key West Sailing & Snorkeling allows exploration of vibrant coral reefs and marine life with a small group of up to 24 travelers.
- Private 90-Minute Harbor Charter offers a personalized sailing experience for up to 6 people with hotel pickup and expert crew.
- Sunset Party Cruise on a 65-foot catamaran features a lively 2-hour experience with complimentary drinks, appetizers, and live music.
Champagne Sunset Catamaran Cruise in Key West With Cocktails!
For a truly unforgettable sunset experience in Key West, embark on the Champagne Sunset Catamaran Cruise.
You’ll sail aboard a 69-foot catamaran, sipping on wine, champagne, beer, or sangria as you admire the stunning sunset views.
Keep an eye out for marine life, and enjoy the island’s beauty from the water.
The cruise accommodates up to 86 travelers, ensuring a comfortable and intimate experience.
All taxes, fees, and essential refreshments are included in the starting price of $59 per person.
With a 92% recommendation rate and 4.7-star overall rating, this sunset sail is a must-do activity for your Key West getaway.
Read our full review: Champagne Sunset Catamaran Cruise in Key West With Cocktails! Review
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Key West: Afternoon Catamaran Sail and Dolphin Watch
Set out on a captivating 2.5-hour catamaran sail along the Florida Keys and witness the incredible Atlantic bottlenose dolphins in their natural habitat.
Relax on the deck and enjoy unlimited ice-cold beverages as you watch the dolphins leap and dive around the boat. Knowledgeable crew members provide interesting facts about these magnificent marine creatures.
Capture memorable moments with your camera as you learn about the serene beauty of the Keys.
With a 4.7/5 overall rating and rave reviews, this is an experience not to be missed.
Secure your spot now and pay later, with the option to cancel for a full refund up to 24 hours in advance.
Read our full review: Key West: Afternoon Catamaran Sail and Dolphin Watch Review
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Key West Sailing & Snorkeling: A Reef Adventure
Explore the vibrant underwater world of the Florida Keys with the Key West Sailing & Snorkeling: A Reef Adventure.
You’ll set sail from Key West, snorkel the colorful coral reef, and spot sea turtles, sharks, and tropical fish. The small-group tour (max 24 travelers) includes all necessary equipment, beverages, and snacks.
Relax on the boat as you sail to the reef, then receive expert guidance for your snorkeling adventure. With a 4.8-star rating and 94% traveler recommendation, this excursion promises an unforgettable experience.
The convenient meeting point, flexible booking, and inclusive pricing make this reef adventure a must-do during your time in Key West.
Read our full review: Key West Sailing & Snorkeling: A Reef Adventure Review
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Key West: Catamaran Champagne Sunset Sail
Why not enjoy a romantic sunset sail on a spacious 60-foot catamaran during your time in Key West?
The Key West Catamaran Champagne Sunset Sail offers a 1.5-hour experience that highlights the city’s landmarks and breathtaking sunsets. For $79.95 per person, you’ll embark from the historic seaport, sail with the wind, and sip on unlimited wine, beer, champagne, and more.
The knowledgeable crew will share informative narration about the area. As the sun dips below the horizon, you’ll witness the transition to a starlit sky, creating a truly magical atmosphere.
With free cancellation and the option to reserve now and pay later, this is an excellent way to end your day in Key West.
Read our full review: Key West: Catamaran Champagne Sunset Sail Review
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Private 90-Minute Harbor Sailing Charter in Key West
For those seeking a private and intimate sailing experience in Key West, the 90-Minute Harbor Sailing Charter offered by Sunset Sail Key West is an excellent choice.
Priced from $314.66 per group of up to 6 people, this charter provides a 90-minute sail on the harbor with a private captain and mate. Soft drinks and bottled water are included, and you’re welcome to bring your own alcoholic beverages.
The charter departs from and returns to the Sunset Sail Key West location, with hotel pickup and drop-off available. Past travelers have highly praised the crew’s knowledge and experience, so you can expect a memorable sailing adventure.
Read our full review: Private 90-Minute Harbor Sailing Charter in Key West Review
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Key West: Sunset Sailing Trip With Open Bar, Food and Music
Sailing into the sunset in Key West aboard the Sandie Cat catamaran offers an unparalleled 2-hour experience filled with unobstructed views, an open bar, appetizers, and live music.
For $69.95 per person, you’ll enjoy unlimited rum runners, Champagne, margaritas, and draft beer as you take in the stunning Florida Keys scenery.
Savor a selection of appetizers including Swedish meatballs, veggie treats, and meat and cheese platters.
As you cruise along, you’ll have the opportunity to help raise the sails and even take the helm for a photo op.
With a capacity of up to 149 passengers, this sunset sailing trip is the perfect way to end your day in Key West.
Read our full review: Key West: Sunset Sailing Trip With Open Bar, Food and Music Review
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Luxury Sailing Catamaran – Private Charters, Owner-Operated
Bimini Charters offers a truly exclusive sailing experience in Key West. Their private 3-hour catamaran charters cater to groups of up to six people, providing a personalized and crowd-free adventure.
Recommended by 100% of travelers, the charters are operated by experienced staff and feature complimentary sparkling wine, soda, and water. You can bring your own food and drinks, and enjoy activities like sailing and snorkeling along the scenic Key West coastline.
With a 5.0 rating and rave reviews highlighting the excellent service, relaxing atmosphere, and knowledgeable crew, Bimini Charters delivers a premium sailing experience that’s perfect for small groups looking to avoid the crowded boat tours.
Read our full review: Luxury Sailing Catamaran – Private Charters, Owner-Operated Review
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Key West: Sunset Party Cruise by Catamaran
If you’re looking to experience Key West’s vibrant sunset in a unique and lively setting, the Key West Sunset Party Cruise by Catamaran is a must-try.
For $79.95 per person, you’ll enjoy a 2-hour cruise aboard a 65-foot catamaran, complete with live music, complimentary drinks, and a variety of appetizers.
Soak up the breathtaking views as you sail into the sunset, with the convenience of free cancellation and a reserve now, pay later option.
While not suitable for those prone to seasickness or wheelchair users, this experience promises an unforgettable evening on the water, with high ratings from previous guests.
Read our full review: Key West: Sunset Party Cruise by Catamaran Review
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2-Hour Sunset Sailing With Wine In Stock Island
Set out on a tranquil 2-hour sunset sailing adventure with Danger Charters in the serene waters of Stock Island.
Relax as you sip wine and savor charcuterie while watching the sun dip below the horizon. This highly-rated experience is recommended by 100% of travelers and boasts a Badge of Excellence.
Priced at $133.89 per person, you can cancel or reschedule for free up to 24 hours before the tour.
With a maximum of 20 passengers, you’ll enjoy an intimate setting on this sunset sail.
Don’t miss out – this popular activity is likely to sell out, so book now for an unforgettable evening on the water.
Read our full review: 2-Hour Sunset Sailing With Wine In Stock Island Review
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The Sum Up
Key West offers a variety of sailing experiences, from sunset cruises with cocktails to reef adventures with snorkeling. Whether you’re looking for a group tour or a private charter, there’s an option to suit your interests and budget. With so many tempting choices, you’re sure to find the perfect sailing adventure to make your Key West trip unforgettable.