Top Key West Sunset Cruises

4.7

(3,761)

from $79

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

4.3

(1,846)

from $93

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

(1,453)

from $135

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

4.5

(378)

from $72

Sunset Sail in Key West with Beverages Included

1 hour 30 minutesFree Cancellation

(961)

from $79

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

Florida Keys Sunset Cruise with Champagne Toast and Seafood

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.

(21)

from $85

Key West Sunset Sail with Live Music, Drinks and Appetizers

Key West Sunset Sail with Live Music, Drinks and Appetizers

Key West Cocktail Cruise Adults Only Sunset Cruise with Open Bar

4.6

(1,012)

from $80

2 hours

(179)

from $65

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.

Classic Key West Schooner Sunset Sail with Full Open Bar

Classic Key West Schooner Sunset Sail with Full Open Bar

(243)

from $109

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.

Sunset Sail Cruise in Key West

(290)

from $95

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

(172)

from $81

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

Key West Glass-Bottom Boat Tour with Sunset Option

(893)

from $123

1 hour 45 minutes to 2 hoursFree Cancellation

3.9

(608)

from $70

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

Key West Reef Morning Snorkeling with Breakfast and Mimosas

from $90

3 hoursFree Cancellation

4.5

(675)

from $50

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

Sandbar Adventure Cruise in the Florida Keys

4 hoursFree Cancellation

4.6

(10)

from $102

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

Island Sunset Cruise 2 Hour Catamaran Tour in Marathon Florida

(12)

from $102

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

(68)

from $457

Private Key West Sunset Sail

from $695

Key West Historic Schooner When And If Sunset Cruise

(135)

from $109

Private Sunset Cruise around Key West

(66)

from $400

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.

Private Sunset Sail in Key West Florida

(1)

from $750

Drift into tranquility on this private 2-Hour Sunset Tiki Cruise and witness the stunning sunset over the Florida Keys. Glide across crystal-blue waters as the sky transforms into a vibrant canvas of colors, providing an unforgettable backdrop for your evening. Bring your favorite beverages to toast the day's end in a romantic and relaxing atmosphere. Capture unique photo opportunities with breathtaking reflections in the water, making this experience perfect for couples or anyone looking to unwind after a day of exploration. - Enjoy a serene 2-hour cruise on the tranquil waters of the Florida Keys - Front-row seat to a spectacular sunset with unobstructed views - Bring your own beverages for a personal touch during the cruise - Perfect for couples or those seeking a relaxing escape after sightseeing

The Keys at Golden Hour Ultimate Private Sunset Tiki Cruise

The Keys at Golden Hour Ultimate Private Sunset Tiki Cruise

(4)

from $599

Key West Sunset Sail Aboard Legendary Schooner Appledore

Sunset Sail in Key West with Beverages Included

(360)

from $89

Top Attractions in Key West

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Attractions

What are people saying about Key West

Christopher_D, Jun 2026

Magical. Unforgettable.

Magical experience for everyone. Our son’s girlfriend said she had ‘never seen a more beautiful sunset’ (and she is very well travelled)! To top it off, everything was heightened by two great captains, Eric and Ransom, who were kind, attentive, and professional. It was a truly lovely evening, which we will not forget any time soon. Thank you for a fantastic time!

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

Donald_B, Jun 2026

So worth it! - great experience

Upgrade while interesting was really not needed. There was ample room to move around and such fun meeting different groups. Food was great, entertainment was spot on, and the crew was excellent!!! Highly recommend!! Meet several locals on the trip which speaks loudly to the value.

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

Kevin_N, Jun 2026

Great Experience

Great evening sailing trip with captain Tony and the crew. We have been on other sailing trips but this one was great. The crew is very friendly and made sure we had everything we needed for a perfect trip. Had a great time and would highly recommend this charter to anyone. You won’t regret it !! Will return next time in Key West. Thanks for everything.

Key West Sunset Sail with Live Music, Drinks and Appetizers

Morgan_W, Jun 2026

The Raving Reviews are True

If you want to have a good time, book this cruise. We had an absolute blast. Good flowing drinks, food and AWESOME music by the band. We appreciated the awesome staff coming by every so often to top off our drinks. Dance the night away, or relax and enjoy the trip. Great job with everything, would recommend this to anyone!

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

Amy_F, May 2026

Fun excursion!

We had a great time! There is an upper deck that is open and a covered lower deck. There was plenty of food and drinks, full bar. The music is a DJ that played a variety of songs. There are 2 bathrooms. There is not a lot of seating. I would not bring kids since mostly adult atmosphere. For the low price we got our moneys worth!

Key West Reef Morning Snorkeling with Breakfast and Mimosas

Erica_H, May 2026

Told to get there an hour...

Told to get there an hour early. You really only needed to get there about 30 minutes early. You don’t board based on the time you check in so getting there early doesn’t guarantee a seat. Being there extra early was just to give you an opportunity to shop. Otherwise Captain Ana and the rest of the crew were great. Definitely would do it again

Sunset Sail Cruise in Key West

Oksana_M, May 2026

This tour let nature shine!

Amazing, down-to-earth crew, captain, and owner of the ship! Seems they really care about what they do: giving people an authentic sailing experience. What we loved most about this tour is it let nature speak for itself. We witnessed an unforgettable sunset, saw some dolphins, and shot a cannon. Not a party boat. Great for the whole family or a memorable moment with a loved one.

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

Lauren_H, May 2026

Robert was the best! He...

Robert was the best! He kept us entertained with jokes, fun facts, and stories. We felt more than welcome and had a great time. We had a group of 5 which was perfect for the bar with 7 seats. Robert knew so much about the area and boating in general and didn’t hesitate to share some insider knowledge with us. He has fun recs as well!

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

Sandee_B, May 2026

Key West Sunset Sail With Hors d’oeuvres

It was so beautiful! We had the perfect evening weather wise! But what made it even more amazing was the crew! Captain Janet, Mary & Chelsea were so sweet and so knowledgeable! It was so fun watching them put the sails up and take them down! They were also wonderful hostesses! They made sure we always had a fresh drink in our hand. The hor d’oeuvres were fresh and tasty! I highly recommend doing this sail! We will definitely do it again if we come back! One of the highlights of our trip!

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 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.