Wedding Cruises


KEY WEST · FLORIDA KEYS

11 Best Wedding Cruises In Key West

Key West’s best days on the water.

The 11 most popular wedding cruises in Key West. What each trip costs, how long it runs, and who takes you out.

11 Best Wedding Cruises In Key West

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, Wedding Cruises, Wine Tours

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

1.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.

Most Popular 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!”

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Small Group Key West Adult Sunset & Moët Sail & Amazing Cheeses - Stop 1 Catamaran Echo: calm sailing, smart positioning, and room to breathe
Bachelorette Party Cruises, Cruises & Boat Tours, Evening Experiences, Key West, Tour Reviews, Wedding Cruises

Small Group Key West Adult Sunset & Moët Sail & Amazing Cheeses

2.Small Group Key West Adult Sunset & Moët Sail & Amazing Cheeses

Adults-only Key West sunset cruise on a small Echo catamaran with champagne-inspired drinks, gourmet cheeses, and Moët upgrades available.

5.0

“This is one of the best experiences of any of our recent trips. JP and Sara made us feel like first class guests! They offered to take our pictures, kept our drinks full, and were engaging and fun. JP frequently changed the ship direction to help us capture the light perfectly. This is a memory…”

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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, Wedding Cruises

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

3.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

“Captain Janet along with her crew of Heather, Jade, and Milo we're so friendly and accommodating and efficient. Good snacks, nice wine, and a beautiful sail into the sunset.”

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

Key West Champagne Sunset Catamaran Cruise

4.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.”

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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, Wedding Cruises

Key West Sunset Sail Aboard Legendary Schooner Appledore

Classic Key West Schooner Sunset Sail with Full Open Bar - The Two-Hour Sail: How You See Key West Without Getting Sand-Heavy
Cruises & Boat Tours, Drinking Tours, Evening Experiences, Key West, Schooner Sailing, Sunset Sails & Cruises, Tour Reviews, Wedding Cruises

Classic Key West Schooner Sunset Sail with Full Open Bar

Key West Sushi Sunset Cruise with Complementary Drinks - Food and drinks: sushi platters, snacks, and what’s actually included
Cruises & Boat Tours, Evening Experiences, Key West, Sunset Sails & Cruises, Tour Reviews, Wedding Cruises

Key West Sushi Sunset Cruise with Complementary Drinks

7.Key West Sushi Sunset Cruise with Complementary Drinks

Key West sunset meets sushi and drinks on a small 2-hour cruise, with calm views of harbors, beaches, and landmarks.

5.0

“Highly recommend this sunset cruise. Great time with plenty of food and drinks. We loved the sushi and snacks! Jason and Charles were excellent hosts. The boat was less than half full, so we had plenty of room to sit and move around to see sights and the sunset.”

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Private 2-Hour Wind and Wine Sunset Sail in Key West - Boarding Just Before Sunset: The “Now We’re Doing This” Moment
2-Hour Experiences, Cruises & Boat Tours, Evening Experiences, Key West, Private, Sunset Sails & Cruises, Tour Reviews, Wedding Cruises, Wine Tours

Private 2-Hour Wind and Wine Sunset Sail in Key West

Private Sunset Cruise around Key West - Getting There at 5950 Peninsular Ave and What to Expect
Cruises & Boat Tours, Evening Experiences, Key West, Private, Sunset Sails & Cruises, Tour Reviews, Wedding Cruises

Private Sunset Cruise around Key West

9.Private Sunset Cruise around Key West

A private 2-hour sunset cruise in Key West with Stock Island Charters. See Sunset Key, Mallory Square, and quiet wildlife spots.

5.0

“This was a great excursion and it was exactly what my family and I wanted when we booked. We were treated very well and learned a few things about Key West. Captain Don was amazing and made sure we were comfortable and able to have an enjoyable experience. He made sure that we had fun…”

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Private Key West Sunset Sail - The 2-Hour Plan: Sailing Past the Sunset Celebration
Cruises & Boat Tours, Evening Experiences, Key West, Private, Sunset Sails & Cruises, Tour Reviews, Wedding Cruises

Private Key West Sunset Sail

10.Private Key West Sunset Sail

Private Key West sunset sail on High Tide with refreshments and BYOB cooler. Depart from 202 William St. About 2 hours.

4.5

“Was excited about the sunset sail but rain caused it to be canceled. Rescheduled for the next morning -11 to 1 which was not the same as a sunset sail. Called company to try to cancel due to wind and cold weather. Told me they had already turned down others - no fool would have…”

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Custom Charters with a Local Captain - Key West Water Options: Sandbars, Dolphins, and Snorkeling
Fishing Charters, Key West, Tour Reviews, Wedding Cruises

Custom Charters with a Local Captain

11.Custom Charters with a Local Captain

A custom half-day private boat charter in Key West for up to six, led by 7th-gen Captain Vaughn, with sandbars, dolphins, and sunsets.

5.0

“Captain Vaughn is awesome! Very knowledgeable and experienced, offering a personalized tour and behind the scenes treats.”

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Explore Key West

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