Drinking Tours


KEY WEST · FLORIDA KEYS

15 Best Drinking Tours In Key West

Key West’s best days on the water.

The 15 most popular drinking tours in Key West. What each trip costs, how long it runs, and who takes you out.

15 Best Drinking Tours 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

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!!”

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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

2.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 Haunted Pub Crawl and Ghost Tour with Free T-Shirt - What Makes This Tour Worth It: Story, Pace, and Small-Group Energy
Drinking Tours, Ghost & Haunted Tours, Key West, Nightlife, Pub Crawls, Pub Crawls & Bar Tours, Tour Reviews, Tours

Key West Haunted Pub Crawl and Ghost Tour with Free T-Shirt

Key West Afternoon Reef Snorkeling with Open Bar - Snorkeling basics: gear, life vest, and a few tips that save time
Drinking Tours, Key West, Reef Snorkeling Tours, Snorkeling, Tour Reviews

Key West Afternoon Reef Snorkeling with Open Bar

4.Key West Afternoon Reef Snorkeling with Open Bar

Key West afternoon reef snorkeling on the Sandie Cat with gear and an open bar after the swim, built for first-timers and reef lovers.

4.5

“This trip involves a one hour cruise to the reef, an hour to snorkel and an hour back. Snorkel and flippers (if you want them) are provided, and wetsuits can be hired for $20. There are toilets on board and a shower hose for rinsing off after the swim. You are also required to wear…”

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Original Key West Pub Crawl: The Best Bars with Free T-Shirt - Rick’s Key West: comedy, cold drinks, and the Caribbean Breeze
Drinking Tours, Key West, Nightlife, Pub Crawls, Pub Crawls & Bar Tours, Tour Reviews

Original Key West Pub Crawl: The Best Bars with Free T-Shirt

Key West: All-Inclusive Watersports Adventure with Lunch & Beer - Getting to Key West Bight and staying on schedule
Drinking Tours, Food & Drink, Key West, Lunch Experiences, Tour Reviews, Watersports Adventures

Key West: All-Inclusive Watersports Adventure with Lunch & Beer

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

7.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.”

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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

Key West: Sunset Dinner Cruise with Open Bar & Live Music - Dinner Under A/C: How the buffet experience actually works
Concerts, Cruises & Boat Tours, Dining Experiences, Dinner Experiences, Drinking Tours, Evening Experiences, Key West, Sunset Sails & Cruises, Tour Reviews

Key West: Sunset Dinner Cruise with Open Bar & Live Music

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

Classic Key West Schooner Sunset Sail with Full Open Bar

11.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 Cocktail Cruise Adults Only Sunset Cruise with Open Bar - The crew setup: live commentary, music, and a professional photographer guide
Cruises & Boat Tours, Drinking Tours, Evening Experiences, Key West, Sunset Sails & Cruises, Tour Reviews

Key West Cocktail Cruise Adults Only Sunset Cruise with Open Bar

12.Key West Cocktail Cruise Adults Only Sunset Cruise with Open Bar

Adults-only Key West sunset cocktail cruise with an open bar, live narration, and onboard photo help on a smaller boat.

5.0

“Captain Steve and BarTender Sky took care of us. We had a very small crowd so it felt like a very personal experience. We had an added bonus of seeing dolphins playing. They were both very knowledgeable about the area.”

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Key West Tiki Bar Sunset Cruise (by the seat) BYOB Adventure - Meeting at 711 Eisenhower Dr and Getting on the Water
Cruises & Boat Tours, Drinking Tours, Evening Experiences, Key West, Sunset Sails & Cruises, Tiki Boat Cruises, Tour Reviews

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

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

Small-group Key West tiki sunset cruise for up to six. BYOB, ice and cups provided, plus harbor sights and Green Flash chances.

5.0

“The name of the experience, “Key West Tiki Bar Sunset Cruise” suggests this is a traditional booze cruise. Upon arrival, we were informed that only bottled water would be provided however they were happy to dock across the street from a Circle K to allow us to buy alcohol and snacks. The gentleman told us…”

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Key West 2 Reef Snorkel Tour & Sunset Cruise with Beer & Wine - Meeting at 201 William St without the stress spiral
Cruises & Boat Tours, Drinking Tours, Evening Experiences, Food & Drink, Key West, Reef Snorkeling Tours, Sunset Sails & Cruises, Tour Reviews, Tours, Wine Tours

Key West 2 Reef Snorkel Tour & Sunset Cruise with Beer & Wine

Key West Tiki Bar Boat to Popular Sand Bar with Turquoise Waters - Starting Out at Tiki Boat Adventures: Comfort From Minute One
Cruises & Boat Tours, Drinking Tours, Key West, Sandbar Tours, Tiki Boat Cruises, Tour Reviews

Key West Tiki Bar Boat to Popular Sand Bar with Turquoise Waters

15.Key West Tiki Bar Boat to Popular Sand Bar with Turquoise Waters

Private Key West tiki bar boat to a calm sandbar with turquoise water, wildlife spotting, and BYOB fun for up to 6.

5.0

“Our Captain was a joy to hang out with and the sand bar he took us to was perfect. Waist to knee high water level, soft sand for the feet and calm waters. Would totally do it again!”

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More Drinking Tours In Key West

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