Top Key West Sunset Cruises

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

4.7

(3,825)

from $79

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

4.3

(1,917)

from $93

Sunset Sail in Key West with Beverages Included

(1,474)

from $135

1 hour 30 minutesFree Cancellation

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.

(981)

from $79

Classic Key West Schooner Sunset Sail with Full Open Bar

Classic Key West Schooner Sunset Sail with Full Open Bar

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

(263)

from $109

Key West Cocktail Cruise Adults Only Sunset Cruise with Open Bar

4.5

(398)

from $77

2 hours

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.

(183)

from $65

Key West Sunset Sail with Live Music, Drinks and Appetizers

Key West Sunset Sail with Live Music, Drinks and Appetizers

4.6

(1,019)

from $73

Sunset Cruise

Key West Champagne Sunset Catamaran Cruise

(136)

from $89

1 hour 30 minutesFree Cancellation

4.7

(595)

from $59

Key West Glass-Bottom Boat Tour with Sunset Option

1 hour 45 minutes to 2 hoursFree Cancellation

3.9

(611)

from $64

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

Private Sunset Cruise around Key West

(295)

from $95

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.

(66)

from $400

Per group

Likely to Sell Out

Key West Sushi and Sunset Cruise

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.

from $90

Florida Keys Sunset Cruise with Champagne Toast and Seafood

Florida Keys Sunset Cruise with Champagne Toast and Seafood

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.

(26)

from $85

Island Sunset Cruise 2 Hour Catamaran Tour in Marathon Florida

Island Sunset Cruise 2 Hour Catamaran Tour in Marathon Florida

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

(19)

from $102

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

4.8

(175)

from $81

Key West Sunset Sail: Dolphin Watching, Wine, and Tapas

(893)

from $123

2 hours 30 minutesFree Cancellation

4.6

(759)

from $89

Likely to Sell Out

Marathon Seven Mile Bridge Sunset Cruise Tour

Witness the vibrant hues of a Florida Keys sunset on a 90-minute cruise along the stunning Seven Mile Bridge. This intimate experience aboard a 31’ motorized catamaran offers 360-degree views and a shaded seating area, perfect for relaxing with friends and family. Enjoy complimentary soda and water as you soak in the breathtaking scenery, making it a memorable way to end your day in Marathon. With space for just 26 guests, this cruise is a beloved highlight for many visitors to the Florida Keys. - 90-minute sunset cruise with views of the iconic 7-Mile Bridge - Intimate setting with a maximum of 26 guests for a personalized experience - Complimentary drinks: soda and water, with BYOB policy for alcohol - Enjoy 360-degree views on a spacious motorized catamaran with shaded seating

Marathon Seven Mile Bridge Sunset Cruise Tour

1 hour 30 minutesFree Cancellation

from $117

Sandbar Adventure Cruise in the Florida Keys

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

4 hoursFree Cancellation

4.7

(14)

from $102

Key West Sunset Sail Aboard Legendary Schooner Appledore

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.

(363)

from $89

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

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

4.8

(68)

from $457

Per group

The Keys at Golden Hour Ultimate Private Sunset Tiki Cruise

The Keys at Golden Hour Ultimate Private Sunset Tiki Cruise

Sunset Sail in Key West with Beverages Included

(8)

from $599

Per group

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What are people saying about Key West

Mark_L, Aug 2026

Key West sailing

We did the sunset sail in Key West and it was perfect. Great value for the price and an awesome crew (of 2). The captain was great and even positioned the boat perfectly to get the best photo opportunities. Drinks included, so a great time was had by all.

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

Julie_C, Aug 2026

We've been on other...

We've been on other sunset cruises in different areas of the country and this one was one of the better ones! The crew was upbeat, engaging and friendly. The music (an actual musician) kept the crowd on their feet or humming along, as well as took requests when he knew them. The food was some of the best I've had on one of these, and it was a buffet with plenty for everyone. There were quite a few people so they fed us in 2 shifts, but that was well organized and no one seemed to mind the wait. The drinks were good pours and the staff made sure everyone had what they wanted. The captain also made sure to point the boat in the best position for everyone to capture that perfect sunset picture. Great night!

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

Emily_H, Aug 2026

Perfect way to cruise...

Perfect way to cruise around and see the sunset. My only complaint was that it was a bit overcrowded for our trip that was sold out. There was very limited seating (as expected), but also limited areas to be able to stand or grab on to anything for support. But otherwise still think it was a great experience!

Classic Key West Schooner Sunset Sail with Full Open Bar

Kathy_F, Aug 2026

Highly recommend Appledore Schooner

Great experience for our Anniversary! Spectacular views on the Appledore Schooner . Not only are the sunsets gorgeous, you also sail around Sunset Key and see Key West from a different view. FUN Joe & Christina are very experienced sailors with a great sense of humor and making sure everyone had a fantastic time. I loved the small group of 14. The drinks were flowing and our appetizer was shrimp, fish dip with crackers. Not a lot of food but really we were enjoying the Schooner experience! It was windy in some areas and the boat was tilting. My husband gets sea sick but this did NOT faze him one bit. Another fun moment that the other boats can’t do is have a “duel” with another Schooner and “fire the cannon” at each other and also all the people lined up at Mallory Square! Yes, there is a bathroom !

Key West Cocktail Cruise Adults Only Sunset Cruise with Open Bar

ChrisMartinez, Jul 2026

Great Experience!!

The entire trip was well worth it from beginning to end! It was an amazing experience that I would highly recommend for couples. The crew was exceptional—friendly, attentive, and dedicated to making sure every guest was well taken care of. Their outstanding service made the trip even more enjoyable. I would definitely do it again!

Key West Sunset Sail: Dolphin Watching, Wine, and Tapas

Robert_P, Jun 2026

Great and beautiful sunset experience

This was an incredible experience! I would say the trip started with me melting in the hot June sun while walking to the docks. Once there and out to sea, everything changed. The staff were incredible. Old fashioned customer service. Made sure everyone onboard was comfortable, and enjoying the experience. The crew takes care of you. We did see dolphins, and that was excellent. The sunset at the end was stunning. I loved my experience and would highly recommend this.

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!

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 Champagne Sunset Catamaran Cruise

Matthew_P, Jan 2026

Simply Amazing

You may want a sweatshirt or light jacket after the sun sets. The wind is fairly strong and the temperature gets a little cooler. We booked a 1.5 hour champagne cruise but it didn’t sail that evening so we were given a complimentary upgrade to the 2 hour sail with live music and hors d’oeuvres. The crew was amazing and on point attending to any needs we had. Highly recommend this cruise.