Top Key West Sunset Cruises

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

4.7

(3,731)

from $79

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

4.5

(374)

from $72

4.3

(1,820)

from $93

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

(16)

from $69

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

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.

(1,439)

from $135

Key West Sunset Sail with Live Music, Drinks and Appetizers

Key West Sunset Sail with Live Music, Drinks and Appetizers

Sunset Sail in Key West with Beverages Included

4.6

(1,006)

from $80

1 hour 30 minutesFree Cancellation

(954)

from $79

Key West Sunset Sail Aboard Legendary Schooner Appledore

Key West Cocktail Cruise Adults Only Sunset Cruise with Open Bar

(359)

from $89

2 hours

(177)

from $65

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

(889)

from $123

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

(240)

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

(285)

from $95

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

(170)

from $81

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

Key West Reef Morning Snorkeling with Breakfast and Mimosas

(8)

from $85

3 hoursFree Cancellation

4.5

(650)

from $35

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

Key West Glass-Bottom Boat Tour with Sunset Option

(11)

from $102

1 hour 45 minutes to 2 hoursFree Cancellation

3.9

(596)

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

from $90

Key West Historic Schooner When And If Sunset Cruise

(135)

from $109

Private Sunset Cruise around Key West

(66)

from $400

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

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

(68)

from $457

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

4.5

from $599

Private Key West Sunset Sail

from $695

Top Attractions in Key West

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Attractions

What are people saying about Key West

Sunset Sail in Key West with Beverages Included

Dean_R, May 2026

Fantastic sunset cruise!

We booked this sunset cruise as it appeared to be smaller and less crowded than others and the reviews were great. Well it did not disappoint! Only 8 guests aboard so it felt like a private charter! Liz and the crew were awesome and very attentive. The sunset itself was spectacular-no surprise for Key West. It was also my wife’s birthday which made it extra special. She had a blast! I would highly recommend this cruise for anyone not looking for the party boat experience. Quiet, low key and just awesome!

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 Signature Sunset Sail with Live Music, Open Bar & Food

Jo_B, May 2026

Worth it!!

We had a great time!! Awesome music, drinks and appetizers!! Sunset was beautiful!!! Don't forget to tip as they mates on the boat definitely will run for you... our girl was up and down the steps many times refilling drinks, she didn't miss a beat!! And tip the dj too... he kept it very lively!!!

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

Karen_D, May 2026

Staff were wonderful....

Staff were wonderful. Plenty of room onboard. There were 90 booked and never felt too crowded. Drinks flowed all night. Never a long line for drinks except when we all boarded at once. Music was great! We sang and danced a bit. Great mix of people too!

Key West Sunset Sail with Live Music, Drinks and Appetizers

Angela_R, May 2026

My partner and I had such...

My partner and I had such a great time on this sunset cruise. We loved the way the band included everyone and the bartenders were all GREAT! I would highly recommend this sunset cruise to anyone looking to have some fun before heading out for the night or just going home to relax. Either way, it’s a great start to your evening!!

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!

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 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.

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!!