7 Drinking Tours in Key West Worth Booking

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

Spend about two hours sailing from Key West with local musicians, a full liquor bar, champagne, wine, sangria, beer, soft drinks, and hearty hors d’oeuvres. You’ll pass Mallory Square, Fort Zachary Taylor, and Sunset Key before returning to the harbor.

“The staff was excellent as well as the entertainment! They made sure you had a great time and the appetizers were perfect. The captain was skilled and made sure everyone was safe and comfortable.”

Check availability →Read our full review

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

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

Spend about two hours aboard America 2.0, a replica of the 1851 Schooner America. From Key West Bight Marina, sail past Fort Zachary, Sunset Pier, Mallory Square, and Sand Key Lighthouse while the crew serves plated hors d'oeuvres, beer, wine, Champagne, and soda.

“We went out on a cool day with a low cloud bank, so not a great sunset… but they can’t control the weather! The staff did a nice job keeping everything moving smoothly and distributing the hors d’oeuvres, which consisted of vegetable plate with wrench dip, shrimp with cocktail sauce, cheese, and crackers, and a brownie bite for dessert. They had a good offering of different wines and beers and sodas. Sadly, we did not see any wildlife to speak of except birds. It was fun to visit with the people around us, of which there were a lot! It was impressive to see the crew of Milo, Mary, Dan…”

Check availability →Read our full review

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

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

Join Gene Beach, Sarah, or another local storyteller for a two-hour walk through Old Town Key West. Hear tales at Captain Tony’s, the Hard Rock Cafe, Porter Mansion, and Robert the Doll’s home, with time for drinks at your own cost 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!”

Check availability →Read our full review

4.Key West Afternoon Reef Snorkeling with Open Bar

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

Spend about three hours aboard the Sandie Cat with Sunset Watersports, sailing from 201 William Street to Key West’s coral reef. Captain Anna and the crew provide instruction, gear, and safety guidance. After snorkeling, enjoy unlimited beer, wine, champagne, and mixed drinks on the return ride.

“The hard sell to pay tips because the crew works for the service industry and “performs” was followed by seemingly bored crew and captain just doing their job. They seemed bored and ready to be done.”

Check availability →Read our full review

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

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

Sail from Key West’s historic seaport aboard the three-deck Sandie Cat for two hours of sunset views, an open bar, light appetizers, and live music. You can help raise the sails and ask the crew for a photo at the helm. Captain Matthew and crew have earned praise for their friendly service.

“great... would have been better with more people though”

Check availability →Read our full review

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

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

Follow guides such as Sarah, Laurie, Brian, or Garret on a 2.5-hour walk through five Key West bars. You will visit Duval Street, the Historic Seaport, Rick’s, Flying Monkeys, Hard Rock Cafe, Schooner Wharf, and Durty Harry’s, with one included beer or mixed drink at each stop.

“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!”

Check availability →Read our full review

7.All-Inclusive Watersports Adventure with Lunch & Beer

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

From Key West Bight, Sunset Watersports takes you to a floating playground for about six hours. Try jet skiing, parasailing, snorkeling, kayaking, paddleboarding, banana boats, slides, and more, with lunch and post-activity drinks included. Captain Clint, Logan, Dave, and the crew are among the staff praised by past customers.

“Had an amazing experience. The staff were super nice and attentive. They want you to have the best time and do every activity. Great people. Great vibes. Would 100% do it again”

Check availability →Read our full review