Drinking Tours

KEY WEST

Best Drinking Tours In Key West

Ranked by traveller popularity

The 10 most popular drinking tours in Key West. Here's what they actually deliver, who runs them, and what they cost.

10 Best Drinking Tours In Key West

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

Key West Sunset Sail with Open Bar, Live Music and Hors D'oeuvres - Your Route: Mallory Square, Fort Zachary Taylor, and Sunset Key Moments

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

Most Popular★ 4.5

A 2-hour Key West sunset sail on a roomy catamaran with an open bar, sangria, hors d’oeuvres, and live local music.

“Went to the office on the day of the cruise and there was a notice on the door that cruises were cancelled for the day. It was a very windy and cold day. My cruise was a sunset cruise. Weather for the night was no better so it didn’t seem possible that the cruise would…”

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

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

Key West Schooner Sunset Sail with Bar & Hors d'oeuvres - Your Two-Hour Schedule: What Happens From Departure to Sunset

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

★ 5.0

Key West sunset on America 2.0: beer, wine, champagne, and plated hors d’oeuvres as you pass Fort Zachary and Mallory Square.

“The captian and crew showed us the local sites while sailing around. The drinks and hors d'oeuvres were a nice addition to the sailing and sunset views. We even saw dolphins jumping around the bow of a cruise ship as it was departing Key West. The ship had room to move around while enjoying watching…”

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

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

Key West Haunted Pub Crawl and Ghost Tour with Free T-Shirt - Captain Tony’s Saloon and 429 Caroline St: morgue lore and the Porter Mansion photo stop

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

★ 4.5

A 2-hour haunted pub crawl through Key West Old Town with spooky stops, Bone Island lore, and a free T-shirt.

“Gene Beach was an awesome guide! He is passionate about the history of Key West (both haunted and not), and told such interesting stories. My mother and I had a great time, and would absolutely do this tour again!”

549 reviews2 hours (approx.)From $32.20by Key West Promotions

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Key West Afternoon Reef Snorkeling with Open Bar

Key West Afternoon Reef Snorkeling with Open Bar - The 3-hour schedule: what happens when, and why it matters

4.Key West Afternoon Reef Snorkeling with Open Bar

★ 4.5

Key West reef snorkeling on the Sandie Cat with included gear and an open bar on the way back. 3 hours, easy, first-timer friendly.

“The crew were great! The experience felt very safe and professional. They gave clear instructions about the snorkelig experience. Would highly recommend!”

419 reviews3 hours (approx.)From $59.95by Sunset Watersports

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

Original Key West Pub Crawl: The Best Bars with Free T-Shirt - Start time, meeting point, and how the 8 pm plan works

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

★ 4.5

Key West Duval Street pub crawl with 5 included drinks, live music stops, and a free t-shirt. Walk iconic bars in 2.5 hours.

“My wife and I were celebrating my birthday! Our tour guide, Laura was the best and very kind. She was totally knowledgeable about Key West fun facts and showed us a great time. Our group (which included ladies from St Pete) was so much fun!”

356 reviews2 hours 30 minutes (approx.)From $42.95by Key West Promotions

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

Key West: All-Inclusive Watersports Adventure with Lunch & Beer - What 13 Water Sports Means When You’re Managing Your Time

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

Key West Signature Sunset Sail with Live Music, Open Bar & Food - The Two-Stop Sail: How the Water Time Gets Used

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

★ 4.5

Sail the Sandie Cat for Key West sunset with live music, an unlimited open bar, and simple appetizers over two hours.

“I’m not really sure if the vibe was supposed to be a fun party or a romantic sunset experience. The entertainment was a guitarist on the upper deck and his choice of music was something you’d find in a pub. This was not as fun as the others I’ve been on with a DJ &…”

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

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

Key West: Sunset Sailing Trip with Open Bar, Food and Music - Open bar details that actually matter (and what to plan around)

Key West: Afternoon Reef Snorkel Tour with Open Bar

Key West: Afternoon Reef Snorkel Tour with Open Bar - The Catamaran Ride: Roomy, Breezy, and Set Up for Dolphins

9.Key West: Afternoon Reef Snorkel Tour with Open Bar

★ 4.3

Afternoon reef snorkeling from Key West with an easy catamaran ride, guided snorkel instruction, and an open bar for the trip back.

“The snorkel experience was good in general Actually we had just one thing that makes us uncomfortable that nobody from the boat crew went to the water with us or verified the water before we jump in the water. We did a previous snorkel in Brazil and the boat crew jumped in the water first…”

268 reviews3 hoursFrom $59by Sebago Watersports

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

Key West: Sunset Dinner Cruise with Open Bar & Live Music - Dinner in the Air-Conditioned Room: Buffet Choices and Realistic Timing

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

★ 4.5

Key West sunset dinner cruise on The Party Cat with open bar, a tropical buffet, and live music on the upper deck.

“The servers and bartender were incredible. They attended to every request so quickly and efficiently. As soon as we boarded, we were greeted with icy rum punch. The bartender’s (so sorry I forgot his name) specialty was perfect for sipping; his speed filling drink requests was entertaining but astonishing! The food was good, hot, and…”

228 reviews2 hoursFrom $92by Sunset Watersports Key West

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Old Town

After Dark