Top Key West Sunset Cruises

Key West Sunset Sail with Open Bar, Live Music and Hors D'oeuvres

from US$72

4.7

(3,693)

Key West Sunset Cruise: Dinner, Live Music & Drinks Included

from US$79

4.3

(1,794)

from US$93

Sunset Sail in Key West with Beverages Included

(943)

1 hour 30 minutesFree Cancellation

from US$79

Key West Small-Group Sunset Sail with Wine and Hors d'oeuvres

(1,431)

from US$135

Key West Sunset Sail Aboard Legendary Schooner Appledore

(344)

Jam to crowd favorite beats by live musicians, eat, drink, and watch the sunset on this classic party cruise from Key West. Dance the evening away or relax on the sundeck or in shaded areas as you sip on a margarita, beer, or other beverages. Unlimited drinks and light appetizers are included so you don’t need to pay extra. A great standalone evening activity or the start of a night out.

from US$89

Key West Sunset Sail with Live Music, Drinks and Appetizers

4.6

(996)

Key West Cocktail Cruise Adults Only Sunset Cruise with Open Bar

from US$80

4.8

(175)

2 hours

from US$65

Key West Schooner Sunset Sail with Bar & Hors d'oeuvres

(875)

from US$123

Key West Tiki Bar Sunset Cruise (by the seat) BYOB Adventure

4.8

(168)

There's no better way to savor the magic of a Key West sunset than aboard a majestic schooner, complete with a full open bar. This enchanting journey blends the timeless elegance of traditional sailing with the lively spirit of Key West, promising an unforgettable experience for all. As you sail further into the sunset, the full open bar comes to life, offering an enticing array of cocktails, wines, and spirits to complement the evening's splendor. Sip on our signature Schooner Bloody Mary or Dark & Stormy as you watch the sky ignite with color. The skilled bartenders are on hand to craft your favorite drinks, ensuring that your glass is never empty as you drink in the sights and sounds of the sea. As the schooner begins its journey back to Key West, you find yourself lost in the timeless rhythm of the sea, grateful for the opportunity to witness the beauty of a Key West sunset from the deck of a historic schooner.

from US$81

Classic Key West Schooner Sunset Sail with Full Open Bar

(235)

While most boat tours travel on small private vessels or luxury yachts, this sunset cruise takes travelers around Key West on Jolly II Rover, the only square-rigged, topsail schooner in the area. Board your ship at the historic Seaport at the corner of Elizabeth and Greene streets and sail out to see some of Key West’s best sights, including the Man O War Harbor, Christmas Tree Island, Fort Taylor, and others.

from US$109

Sunset Sail Cruise in Key West

(281)

from US$95

Witness a breathtaking Florida Keys sunset aboard Island Girls Excursions. Departing from Skipjack Resort & Marina, this serene cruise includes a complimentary champagne toast and seasonal local seafood appetizers such as fresh Florida stone crab or shrimp (when in season), offering an authentic taste of the region. Our spacious 52’ catamaran provides a smooth, comfortable ride — perfect for couples, families, and small groups seeking relaxation with panoramic ocean views. Enjoy island music, warm breezes, and vibrant sunset colors as the day fades into tropical paradise. Departure times adjust seasonally to align with the actual sunset, ensuring you experience the most spectacular sky colors possible. Your confirmed departure time will be reflected in your booking confirmation.

Florida Keys Sunset Cruise with Champagne Toast and Seafood

(14)

Key West Historic Schooner When And If Sunset Cruise

from US$69

4.8

(134)

from US$109

Private Sunset Cruise around Key West

(66)

from US$400

Key West Glass-Bottom Boat Tour with Sunset Option

3.9

(591)

1 hour 45 minutes to 2 hoursFree Cancellation

from US$70

Cruise into a stunning Florida Keys sunset aboard a comfortable 53’ catamaran. Your crew will guide you through the waters surrounding Marathon, passing local landmarks such as Boot Key Harbor, the Atlantic Ocean, and the historic Seven Mile Bridge. Relax on deck and enjoy the changing colors of the sky while sipping a complimentary champagne toast. The catamaran offers plenty of seating, shaded areas, an onboard restroom, and a cooler stocked with ice, water, and soda. This tour provides a laid-back and memorable way to experience the Keys at golden hour—perfect for couples, families, and anyone who wants to unwind on the water.

Island Sunset Cruise 2 Hour Catamaran Tour in Marathon Florida

(9)

from US$102

Discover the enchanting beauty of the Florida Keys with Island Girls Excursions. This adventure combines relaxing sandbar experiences with stunning sunset cruises. Unwind on your spacious 52’ catamaran, complete with complimentary snacks and drinks while soaking up the sun or exploring the crystal-clear waters. Your experienced crew will ensure a smooth sailing experience, showcasing the best spots in the area. Perfect for groups seeking relaxation, celebration, or exploration, this tour promises unforgettable memories in paradise. - Enjoy a leisurely sandbar trip with paddleboarding and floats - Experience breathtaking sunset views while sipping drinks - Spacious and comfortable 52’ catamaran with Wi-Fi - Friendly and knowledgeable crew dedicated to your safety and enjoyment

Sandbar Adventure Cruise in the Florida Keys

(6)

4 hoursFree Cancellation

from US$85

Cruise alongside Key West’s picturesque waterfront in style during this private sunset tour aboard a charactered tiki bar boat. Enjoy BYOB drinks in a floating, thatched bar, complete with private restroom, bluetooth-equipped television and stereo, and padded bar stools. Head past attractions like Sunset Pier, Mallory Square, Wisteria Island, and Trumbo Point, with cruises timed to capture the coastline’s famous sunsets.

Key West: Private Sunset Cruise on an Authentic Tiki Bar Boat

4.7

(67)

from US$457

Key West Reef Morning Snorkeling with Breakfast and Mimosas

4.5

(625)

3 hoursFree Cancellation

from US$35

This sunset cruise offers a serene escape as you glide across calm turquoise waters during golden hour. Unlike a standard boat ride, you’ll enjoy the perfect blend of sea breeze, gentle music, and breathtaking views of the Florida Keys sky transforming into a vibrant masterpiece. It’s more than transportation—it’s a front-row seat to nature’s nightly show, creating a truly memorable experience.

Sunset Cruise in the Florida Keys

1.0

(1)

from US$65

Private Key West Sunset Sail

4.7

(51)

2 hours

from US$695

Enjoy a Spectacular Key West Sunset Cruise Looking for the perfect way to end your day? Join us on the Seabreeze, your 42-foot Corinthian powercat, and ride in comfort with this relaxing, catered cruise into the horizon on Key West’s gentle seas. Relax in the shade under the bimini or sunbathe on the bow to take in that last bit of sunshine. Sunset Cruises are a Key West luxury with your panoramic views of the sun melting into tropical waters – and the best way to enjoy is with good food and great drinks! Enjoy elevated hors d’oeurvres without the price tag – a typical selection includes fresh sushi, Thai appetizers, charcuterie platter (meats and cheeses), and French desserts catered by locally owned and operated restaurants. Refreshments include your complimentary selection of fine wine, premium beer, Prosecco, and soft drinks. Departure times vary with the seasons, please confirm your departure time when booking this trip.

Key West Sushi and Sunset Cruise

Enjoy a private Sunset Sail on a Classic 60 ft Schooner Serenity and get a front-row seat with just your family and friends to watch Key West's Famous sunsets. View Dolphins, Turtles, and all kinds of Marine Life. Take the helm, learn how to raise and trim the sails, or just sit back and relax. Enjoy a private sunset cruise off the coast of Key West See the sites of Key West from the water Snacks and beverages included Fun for an entire group or family Private guides for a more personalized experience. Enjoy a private sunset sail off the coast of Key West and see the sights of Key West. Bring your favorite alcoholic beverages to enjoy while watching the sunset. Knowledgeable Captains to explain the art of sailing.

from US$90

Private Sunset Sail in Key West Florida

(1)

from US$750

Key West Signature Sunset Sail with Live Music, Open Bar & Food

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Top Attractions in Key West

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Attractions

What are people saying about Key West

ddqualls, May 2026

Amazing sunset!

Great views! Capt Anna and the crew were great! The musician was awesome and played great music. We really enjoyed the tour.The tour was fantastic! We had great views and the captain and crew were incredibly friendly. The musician was also awesome and played some great music. We thoroughly enjoyed the tour.

Classic Key West Schooner Sunset Sail with Full Open Bar

Meriam_T, May 2026

3 chicas

This was a wonderful and fantastic excursion. Went with friends and we had a blast. Kristina and Luana were wonderful. They were professional and just overall gave us the best tour. They were very accommodating and also learned a lot about Key West that we didn’t know. Very informative.

Sunset Sail Cruise in Key West

Pam_M, Apr 2026

Me and my party loved...

Me and my party loved this experience to sail on a real scooter sail boat. Space is limited to a small group. The crew was fun and interactive giving the passengers the oppertunity to hoist the sails and even Captain the boat at the helm. Heart warming was watching a young man with Downs Syndrome at the helm. This young man came aboard with his pirate hat on ready for an adventure and the crew made sure he did. Thank you all for a wonderful sunset sail! We will do it again with your incentives for return guests.

Key West Tiki Bar Sunset Cruise (by the seat) BYOB Adventure

Laura_S, Apr 2026

Beautiful sunset, no crowds.

A great smooth ride and not crowded like other tours. Madison was wonderful and gave us lots of interesting information about the keys. Only thing I would do is make the barstools more comfortable. They are really high and your legs hang, I’m 5’8. They need to add a foot rest on the tiki bar itself or on each stool. Other than that I would highly recommend.

Key West Sunset Sail Aboard Legendary Schooner Appledore

Matt_T, Apr 2026

Surprise Sunset Battle !

We were lucky enough to be part of the reenactment of the Conch Republic Bloody Battle . Thought it was a sunset cruise when we booked, it because of the date - the boat was participating . Turned out to be a blast for the whole family , and we still had an amazing sunset to watch too!

Key West Sunset Sail with Live Music, Drinks and Appetizers

Lisa_C, Apr 2026

Awesome Sunset Cruise!

This excursion was so much fun!!! Great band that played a little bit of everything. Crew was amazing and ready to serve drinks & food the moment we stepped on the boat. Big catamaran, super clean. Had the best time and met so many fun people. I will definitely do this again when I'm back in Key West!

Sunset Sail in Key West with Beverages Included

PATRICIA_S, Apr 2026

Wonderful experience,...

Wonderful experience, very chill crew,, and great boat. I chose this because it was listed on TripAdvisor as "good for solo travelers" - I was visiting the Keys with family and wanted a break for restaurant dinners to do something different - this was perfect! It was a little tricky to find the dock - I ended up calling the number and listening to the recording and then it made perfect sense. Walk through the Hyatt Centric lobby, past the pool, and the dock was right there.

Key West Small-Group Sunset Sail with Wine and Hors d'oeuvres

Mike_Y, Apr 2026

April 2026 Sunset Sail with Danger Charters

Fantastic experience. Sailing on the boat was excellent, the crew was very friendly and fun to chat with, the wines & hors d'oeuvres were tasty, and the views were spectacular! Highly recommend for anyone that is looking for a relaxed and fun sunset cruise!

Key West Sunset Sail with Open Bar, Live Music and Hors D'oeuvres

Robyn_S, Apr 2026

The crew was courteous &...

The crew was courteous & fun - ready to go from the start! Easy to get a drink and plenty of hors d'oeuvres brought around. The performer (Mike's Acoustic Tunes) sounded great and interacted well with everyone on the boat. This sunset experience was well worth it!

Key West Schooner Sunset Sail with Bar & Hors d'oeuvres

Alex_W, Apr 2026

Make sure you go to the...

Make sure you go to the green awning on the left when you arrive. We got caught up in the wrong line to the right and almost missed the cruise. Aside from the arrival confusion all else was truly exceptional. Great crew, beautiful, clean, and comfortable ship, a truly relaxing and enjoyable excursion.

Key West Cocktail Cruise Adults Only Sunset Cruise with Open Bar

Lora_B, Feb 2026

Amazing crew, amazing sunset!

The boat was freshly cleaned and well-stocked. Our captain Steve was friendly and had a bunch of interesting information about the island. He played great music and was always up for suggestions. We had an intimate party of great guests. Sky, the bartender made excellent drinks and had great suggestions. They had about 9 different beers available and a full liquor bar, as well as wine. Both Sky and Steve went out of their way to make sure we were having a great time and had a beautiful view of a beautiful sunset on the water, we even got to see a couple pods of dolphins that they tracked down for a closer view. We enjoyed our experience so much, but what really made it special was the hospitality of Sky and Steve. They made the trip extraordinary, even pointing out different beaches and houses along the way to our sunset view and back. Overall, the trip was about 2.5 hours or so and we will definitely be back the next time we are in Key West to jump aboard “The Good Times”! If you booked through Viator, the details were limited but this is run through Snuba of Key West with a departure time of 5/515pm.

Private Sunset Cruise around Key West

Cindy_C, Feb 2026

Great service with an amazing sunset

This was a great excursion!!! I was a little nervous about getting to the right spot to meet…Don provided easy perfect directions! He was on time taking us out! So nice!! Showed us several landmarks and told us about the area…gave us some good recommendations for food and drinks!! The sunset was gorgeous…so nice seeing it from a different perspective. Can’t wait to go again with Don and try a sandbar excursion with him too!!! He will not disappoint!!