8 Drinking Tours in Key West to Build a Day Around

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

★★★★★★★★★★4.5 · 3,559 reviews · 2 hours (approx.) · from $79Our pick

Review of Key West’s sunset catamaran sail with an open bar, live music, shrimp, hors d’oeuvres, and views from Mallory Square to Sunset Key.

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

★★★★★★★★★★5.0 · 804 reviews · 2 hours (approx.) · from $122Top rated

Review of Key West’s America 2.0 sunset sail, with sailing views, open beer and wine, plated hors d’oeuvres, tips, and honest value advice.

“Sunset was enchanting and the crew was super accommodating! Captain Dan also added historical tid bits that enhanced the Key west experience. Great trip!”

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

★★★★★★★★★★4.5 · 549 reviews · 2 hours (approx.) · from $32Best value

Review of Key West’s Haunted Pub Crawl: spooky Old Town stories, historic bars, Robert the Doll, a free T-shirt, and practical tips.

“Great and informative! Gene Beach (narrator) was fantastic! Worth it and it’s a must when in Key West!”

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4.Key West Afternoon Reef Snorkeling with Open Bar

★★★★★★★★★★4.5 · 419 reviews · 3 hours (approx.) · from $59

Review of Key West’s Dip & Sip reef snorkel: reef time, boat comfort, open bar, costs, crowd concerns, and practical tips.

“It was an okay experience, we made fun out of it, the waves were rough and the boat was overpacked with too many people, approx 90 people..”

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5.Key West Signature Sunset Cruise with Open Bar, Food & Music

★★★★★★★★★★4.5 · 418 reviews · 2 hours · from $79

Review of Key West’s 2-hour sunset catamaran cruise with open bar, appetizers, live music, dancing, and sunset views for $79.

“Sunset cruise-great music. Wonderful staff. Food and appetizers could have been a little better but open bar. People really enjoyed themselves.”

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

★★★★★★★★★★4.5 · 356 reviews · 2 hours 30 minutes (approx.) · from $42

Review of Key West’s 2.5-hour pub crawl with five drinks, local guides, Duval Street bars, live music, and a free t-shirt.

“Such an amazing time! 5 bars, great service. Amazing tour guide, so much fun! Annndddd a free t-shirt! You have to go!”

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7.All-Inclusive Watersports Adventure with Lunch & Beer

★★★★★★★★★★4.5 · 351 reviews · 6 hours (approx.) · from $179

Review of Key West’s six-hour all-inclusive watersports trip, with jet skis, snorkeling, lunch, drinks, parasailing, and practical booking tips.

“Staff is great and the concept is also great, however there were a few things that took one star off: The jet ski and para sailing are time limited. You get a slot, and based on that slot, all the other activities are decided. Ours were awkwardly apart which did not leave enough time to go kayaking to snorkel for example. We got an estimate that we are up to jet ski in 20 minutes, so we stayed, and ended up waiting an hour, which did not leave enough time when we got back Which brings me to the second issue, when the tour is full, like we had, 105…”

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

★★★★★★★★★★4.5 · 314 reviews · 2 hours (approx.) · from $72

Review of Key West’s two-hour sunset catamaran sail with live music, open bar, appetizers, practical tips, value, and honest drawbacks.

“We really enjoyed being on the water during sunset. The boat had plenty of seating for all the guests and plenty of room to move around to the best areas for views. The live violin duet was a great accompiment to the views. The free pinot grigio and food were what would be expected on this type of tour, acceptable. Great value for the price.”

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