Sunset Sail Key West: 11 Must-Experience Cruises

Want to experience heaven on earth? Try a sunset sail in Key West. Imagine sailing on crystal clear waters as the sky opens up into a breathtaking canvas of orange, pink, and purple. This is not just another sunset; it’s a Key West sunset—and that makes all the difference.

Whether you’re a visitor soaking up local culture or a resident who knows the island’s best-kept secrets, a sunset cruise here is more than just an activity; it’s a rite of passage. From lavish dinner cruises to lively atmospheres with live music in the middle of the ocean, the options are endless. Here are 10 ways to make your Key West sunset experience unforgettable

1. Sebago Watersports Key West Sail with Full Bar, Live Music & Hors D’oeuvres

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  • Price: $79,95
  • Duration: 2 hours
  • Rating: 4,5 with over 2250 reviews

Embark on the ultimate 2-hour Key West sunset cruise. With a 4.5 rating and over 2,250 glowing reviews, this is no ordinary excursion—it’s an intimate, lively voyage aboard a 70-foot catamaran. Witness the legendary Key West sunset as the sky bursts into color, and indulge in casual hors d’oeuvres, champagne, and a full liquor bar. Elevate the experience with live music from local musicians as you sail to the best spot to view the sunset. Don’t miss out on this quintessential Key West adventure. Reserve your spot now and make your time in Key West unforgettable with this sunset sail!”

So if you’re looking for the ideal way to spend your evening in the Florida Keys, a sunset sail in Key West with full bar, live music, and hors d’oeuvres is an experience you won’t want to miss.

2. Key West Sunset On Historic Schooner When & If

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  • Price: $109.00
  • Duration: 2 hours
  • Rating: 5 with 36 reviews

Set sail into natural splendor with our “2-Hour Key West Sunset Sail on Historic Schooner When And If.” This isn’t just a cruise; it’s a journey back in time aboard a 1939 yacht built for General George Patton. Experience the luxury of teak decks and a seasoned crew as you sip complimentary wine and beer under the Key West skies. Our captain and crew are not only experienced sailors but passionate about sharing the beauty of Key West sunsets. Reserve your spot now to experience natural beauty, history, and the art of sailing all in one unforgettable sunset sail in Key West. Alcoholic beverages included!

3. Key West Sunset Champagne Catamaran Cruise

Catamaran Sunset Sail Key West
  • Price: $59.95
  • Duration: 1 hour 30 minutes
  • Rating: 4,5 with almost 500 reviews

Unlock the magic of a breathtaking evening with our “Sunset Sail Key West Champagne Catamaran Cruise.” This 2-hour adventure aboard a spacious 69-foot catamaran is more than a journey; it’s an experience you’ll treasure. As the sun gracefully descends over the Key West waters, savor your choice of complimentary wine, champagne, beer, or sangria. Our experienced captain knows just the right spots for the most awe-inspiring views of the sunset. Don’t settle for anything less; book now and elevate your Key West getaway with a sunset sail you’ll never forget. All drinks, taxes, and fees included!

4. Key West Dolphin Watch And Snorkel Cruise

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  • Price: $82.46
  • Duration: 3 hours
  • Rating: 4,5 with almost 900 reviews

Elevate your Key West experience with our “Key West Dolphin Watch and Snorkeling Cruise Adventure.” This isn’t just a cruise; it’s a voyage into the heart of the Key West National Wildlife Refuge, where you’ll snorkel in the vibrant shallows and share the waves with playful dolphins. With unlimited soft drinks and complimentary beer and wine post-snorkeling, you’ll stay refreshed as you soak in the panoramic ocean views. Book now to secure your spot on this unforgettable sunset sail in Key West, complete with snorkel gear and a local guide. Make your next Key West visit extraordinary!

5. Adults-only Champagne Celebration Sunset Cruise from Key West

sunset sail in Key West - Adults only Champagne Celebration Sunset Cruise from Key West
  • Price: $81.40
  • Duration: 2 hours
  • Rating: 5 with more than 600 reviews

Unwind in luxury on our “Adults-Only Sunset Sail Key West Champagne Celebration Cruise.” Leave the crowds of Mallory Square behind and embark on an intimate, late afternoon journey limited to just 14 guests. With house champagne, a gourmet cheese buffet, and premium wines and beers, we’ve got everything you need for a sublime evening on the water. As the sun sinks into the horizon, toast to the good life with a complimentary glass of Moët. Seating is limited, so don’t miss out on this personalized Key West sunset experience. Reserve your spot now for a sunset sail that takes Key West elegance to the next level!

6. Small-Group Sunset Sail With Wein

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  • Price: $128,89
  • Duration: 2 hours
  • Rating: 5 with almost 900 reviews

Set sail on a “Sunset Sail Key West Wine Adventure,” limited to a small group for a more intimate experience. As the sun sets over the serene waters of Key West, sip on a selection of up to eight wines and five beers aboard our 65-foot schooner. Relish a gourmet cheese buffet and delectable appetizers as you bask in the golden hues of the sunset. With all-inclusive beer, wine, and light refreshments, this is the ideal way to make your Key West sunset unforgettable. Book now for this exclusive sail!

7. Sunset Sail Cruise in Key West

Sunset Sail Key West
  • Price: $91,38
  • Duration: 2 hours
  • Rating: 5 with almost 100 reviews

“Embark on a ‘Sunset Sail in Key West‘ experience unlike any other aboard the Jolly II Rover, the area’s only square-rigged topsail schooner. Departing from the historic seaport, this cruise takes you to iconic Key West landmarks such as Man O’ War Harbor and Fort Taylor. As the sun sets below the horizon, enjoy snacks and chilled drinks from the onboard cooler. Don’t miss this unique opportunity to see Key West from the water while basking in the glow of a stunning sunset. Book your spot now!”

8. Key West Sushi Sunset Cruise

sunset sail in Key West
  • Price: $75
  • Duration: 2 hours
  • Rating: 5 with almost 60 reviews

Escape the crowds and set sail on a serene Key West sunset cruise. Enjoy the best views of iconic landmarks like the Southernmost Point, all from the comfort of our deck or shaded area. Savor platters of sushi and other snacks, paired with your choice of alcoholic beverages, bottled water, or soda. With a restroom onboard, all your needs are covered. Don’t miss this peaceful way to witness a stunning sunset. Book your Sunset Sail Key West experience now! Included: Alcoholic beverages, bottled water, soda, and snacks.

9. Vitamin Sea Private Charter – Sunset in Key West

sunset sail in Key West
  • Price: $699
  • Duration: 3,5 hours
  • Rating: 5 Stars

Discover paradise your way with a Vitamin Sea Private Charter. In just 3.5 hours, tailor your adventure with options like dolphin watching, snorkeling, or sandbar lounging. Gear is provided, and each 5 p.m. departure includes a breathtaking sunset as you return to the marina. Ideal for families and friends, make this customizable experience your ultimate “I’m in paradise!” moment. Book now!

10. Privat Luxury Charter in Key West/Lower Keys – Full Day

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  • Price: $1.899
  • Duration: 8 hours
  • Rating: 5 with 10 reviews

Embark on a full-day Private Luxury Charter in Key West and the Lower Keys for an experience tailored just for you. Led by a local captain, choose your own adventure—be it snorkeling the coral reef, sipping a drink on a sandbar, or exploring Dry Tortugas National Park. Ideal for special occasions, this exclusive charter accommodates up to 12 people and offers onboard amenities like bathrooms, A/C, and WiFi. Make your day unforgettable; book now!

11. Privat Luxury Sailing Catamaran Sunset Sails in Key West

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  • Price: $800
  • Duration: 3 hours
  • Rating: 5 Stars

Set sail on a private luxury sailing catamaran for an exclusive Key West sunset experience. Avoid the crowds and customize your adventure—watch dolphins, jump off the bow, or sip cocktails while sailing along the coast. The meticulously maintained 44-foot catamaran offers multiple seating areas for your comfort. You can even bring your own food and drinks. Ideal for those looking for a more private, personalized sailing experience. Book your unforgettable sunset sail today!

To sum up, we’ve delved into some of the most sought-after sunset experiences in Key West based on user reviews and popularity. While these offerings represent the best of what Key West has to offer, there are myriad other options available should you wish to explore further. Key West stands distinctively not just as an island, but as a bridge between the cultures of Florida and Cuba, a mere 90 nautical miles or 4-hour sail away from the latter. As you consider your choices, know that the promise of a mesmerizing Key West sunset is a constant, waiting to grace your journey.

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