Sunset Sails & Cruises


KEY WEST · FLORIDA KEYS

15 Best Sunset Sails & Cruises In Key West

Key West’s best days on the water.

The 15 most popular sunset sails & cruises in Key West. What each trip costs, how long it runs, and who takes you out.

15 Best Sunset Sails & Cruises In Key West

Key West Sunset Sail with Open Bar, Live Music and Hors D'oeuvres - What You Eat and Drink on This Open Bar Sail
Concerts, Cruises & Boat Tours, Drinking Tours, Evening Experiences, Key West, Sunset Sails & Cruises, Tour Reviews

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

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1.Key West Sunset Sail with Open Bar, Live Music and Hors D’oeuvres

Sail Key West at sunset on a large catamaran with an open bar, live local music, and filling hors d’oeuvres. Depart from Elizabeth St.

Most Popular★ 4.5

“The captain and crew were extremely attentive to all of the passengers. They even brought drinks and horsdoeuvres to the passengers hanging out on the main deck who were watching the Amazing sunset. They even mingled with the everyone and helped take pictures when asked. This was a highlight of our time at Key West!!”

3,559 reviews2 hours (approx.)From $79.00by Sebago Key West

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Key West Sunset Cruise: Dinner, Live Music & Drinks Included - Dinner Is a Tropical Buffet (And How to Make It Yours)
Concerts, Cruises & Boat Tours, Dining Experiences, Dinner Experiences, Evening Experiences, Key West, Sunset Sails & Cruises, Tour Reviews

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

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Key West Small-Group Sunset Sail with Wine and Hors d'oeuvres - The on-water timing: check-in, how long you’ll be out, and what to watch for
Cruises & Boat Tours, Evening Experiences, Key West, Sunset Sails & Cruises, Tour Reviews, Wine Tours

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

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3.Key West Small-Group Sunset Sail with Wine and Hors d’oeuvres

Key West small-group sunset sail with up to eight wines, beer, and hors d'oeuvres on a schooner. Intimate, romantic start to night.

★ 5.0

“What an amazing experience! The wine was plentiful, the snacks were delicious, and the view of the water and sunset were unbeatable. Mary, James, and Connor were professional and friendly. All around absolutely worth doing this!”

1,366 reviews2 hours (approx.)From $125.00by Danger Charters

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Key West Sunset Sail with Live Music, Drinks and Appetizers - Live music that turns sunset time into a real event
Concerts, Cruises & Boat Tours, Evening Experiences, Key West, Sunset Sails & Cruises, Tour Reviews

Key West Sunset Sail with Live Music, Drinks and Appetizers

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Sunset Sail in Key West with Beverages Included - Getting There: Hyatt Centric Front St Meeting Point + First Steps
Cruises & Boat Tours, Evening Experiences, Key West, Sunset Sails & Cruises, Tour Reviews

Sunset Sail in Key West with Beverages Included

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Key West Schooner Sunset Sail with Bar & Hors d'oeuvres - Where to Meet at Key West Bight (And How Early Matters)
Cruises & Boat Tours, Drinking Tours, Evening Experiences, Key West, Schooner Sailing, Sunset Sails & Cruises, Tour Reviews

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

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6.Key West Schooner Sunset Sail with Bar & Hors d’oeuvres

Sail on a replica Key West schooner at sunset with open bar and plated hors d’oeuvres, passing Fort Zachary and classic waterfront views.

★ 5.0

“Our captain, Janet was fantastic! She made sure our experience on her ship was perfect including the sunset. Her crew Jade, Milo & Heather were super efficient in not only tending to the ship’s duties but served their guests with a huge smile. Thanks for the great experience!🌞⛵️”

804 reviews2 hours (approx.)From $122.59by Classic Harbor Line

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Key West Sunset Sail: Dolphin Watching, Wine, and Tapas - Getting to the Historic Seaport at 205 Elizabeth St
Cruises & Boat Tours, Dolphin Watching, Dolphin Watching Tours, Evening Experiences, Key West, Sunset Sails & Cruises, Tour Reviews, Wine Tours

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

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Key West Champagne Sunset Catamaran Cruise - Where You Sail: Sebago to Mallory Square to Fort Zachary Taylor
Catamaran Cruises, Cruises & Boat Tours, Evening Experiences, Key West, Sailing, Sunset Sails & Cruises, Tour Reviews, Wine Tours

Key West Champagne Sunset Catamaran Cruise

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8.Key West Champagne Sunset Catamaran Cruise

Sail Key West’s harbor to chase the champagne sunset from a 69-foot catamaran, with included drinks, a restroom, and great photo views.

★ 4.5

“So much fun and the crew is fantastic!! If you do nothing else, DO THIS! I really can’t say enough good things. It’s just a really good time.”

586 reviews1 hour 30 minutes (approx.)From $59.00by Sebago Key West

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Key West: Dolphin Watching and Snorkeling Sunset Cruise - Dolphin watching around Key West National Wildlife Refuge waters
Cruises & Boat Tours, Dolphin Watching, Dolphin Watching Tours, Evening Experiences, Key West, Reef Snorkeling Tours, Snorkeling, Sunset Sails & Cruises, Tour Reviews

Key West: Dolphin Watching and Snorkeling Sunset Cruise

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Key West Rum and Reggae: Reef Snorkel Adventure and Sunset Sail - The Big Idea: Snorkel First, Then Sunset Sail with Reggae
Cruises & Boat Tours, Evening Experiences, Key West, Reef Snorkeling Tours, Sunset Sails & Cruises, Tour Reviews

Key West Rum and Reggae: Reef Snorkel Adventure and Sunset Sail

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Key West Signature Sunset Sail with Live Music, Open Bar & Food - The 2-Stop Route: From Sunset Watersports to Key West Views
Concerts, Cruises & Boat Tours, Drinking Tours, Evening Experiences, Food, Food & Drink, Key West, Sunset Sails & Cruises, Tour Reviews

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

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

Sail Key West at sunset on a modern 3-deck catamaran with live music, unlimited open bar, and light appetizers for about 2 hours.

★ 4.5

“The sunset, the drinks and the music were all great! Snacks were nothing special, but we planned ahead ate dinner. We have done a cruise like this before and it is usually a couple of veggies and maybe rolls or some kind of bite size snack.”

314 reviews2 hours (approx.)From $72.00by Sunset Watersports

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Key West: Sunset Sailing Trip with Open Bar, Food and Music - Open bar and finger foods: the value math at $80
Cruises & Boat Tours, Drinking Tours, Evening Experiences, Food, Food & Drink, Key West, Sailing, Sunset Sails & Cruises, Tour Reviews

Key West: Sunset Sailing Trip with Open Bar, Food and Music

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Sunset Sail Cruise in Key West - Meet the Schooner Jolly II Rover and the Red-Sail Experience
Cruises & Boat Tours, Evening Experiences, Key West, Sunset Sails & Cruises, Tour Reviews

Sunset Sail Cruise in Key West

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14.Sunset Sail Cruise in Key West

Sail Key West at sunset on a vintage topsail schooner with red sails, classic sights from the water, plus snacks and bottled water.

★ 5.0

“Perfect Captain and GIRL POWER CREW! Sweet and attentive to the guests! Highly recommend! Awesomeness beyond believe!”

260 reviews2 hours (approx.)by Schooner Jolly II Rover

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Key West Sunset Sail Aboard Legendary Schooner Appledore - From William Street to the Historic Seaport: where your evening starts
Cruises & Boat Tours, Evening Experiences, Key West, Schooner Sailing, Sunset Sails & Cruises, Tour Reviews

Key West Sunset Sail Aboard Legendary Schooner Appledore

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15.Key West Sunset Sail Aboard Legendary Schooner Appledore

Sail Key West at sunset on a classic wooden schooner with real sail work, small-group calm, and included drinks and hors d’oeuvres.

★ 5.0

“Our experience aboard the Schooner Appledore was fantastic! Crew members Joe, Mary, and Christina were AMAZING; they were prepared with stories and anecdotes of their time at sea, and it was so fun to learn about their adventures. Drinks were great, apps were yummy, and they were appropriately careful of my spouse’s shellfish allergy. We…”

251 reviews2 hours (approx.)by Key West Schooners

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More Sunset Sails & Cruises In Key West

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Every way to get out on the water, and every reason to stay for the sunset.

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