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 was such a wonderful experience. Having a small group made it even more special. The sunset was beautiful. The captain and crew were knowledgeable and hospitable. If you’re wondering if you should book this trip- you definitely should!”

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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

“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!🌞⛵️”

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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

5.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…”

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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

6.Classic Key West Schooner Sunset Sail with Full Open Bar

Classic Key West schooner sunset sail with a full open bar, cocktails, snacks, and a calm small-boat ride past top waterfront landmarks.

5.0

“Great outing. Service and experience were at the center of everything Captain Josh and Christina did. Safe loading of passengers, a ‘to the point’ safety overview, almost immediate serving of tasty cocktails/water/etc, and tasty treats (shrimp cocktail, key lime tart, smoked fish with crackers). The boat was nice having padded seating, toilet below deck, and…”

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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

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

Private 2-hour Key West sunset sail on a 65-ft schooner with global wines, craft beers, and hors d’oeuvres for your group.

5.0

“The crew was friendly and there was a good variety of wine. The atmosphere was reserved without the obnoxious crowds. One thing to improve upon was the food. There was not many choices and one can only have so many cheeses. Read more”

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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

“Don was amazing! He adjusted the cruise to account for the cooler than normal temperatures, spending more time hunting wildlife in little inlets than offshore waiting for the sunset. We were able to see a manatee and many other animals while learning a lot about what brought him to the Keys. By the end of…”

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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

“We had a nice trip to the sandbar with a friendly captain. Very relaxing and fun to be on the water.”

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Explore Key West

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