Bars & pub crawls · SAILING
This is the shortlist you would send a friend flying in on Friday: 12 sailing tours worth the money, each with its price, its verdict and the one thing to know before you book.
Spend 5 to 6.5 hours sailing from Heraklion to Dia Island on a semi-private catamaran. Swim, snorkel, kayak, use the sea scooter and slide, then enjoy a nutritionist-designed Cretan meal, open bar, and sunset sail back.
“If you are thinking about booking this, DO IT! Everything about this cruise was 100%, you won't regret it.”
Spend four hours aboard Vitamin Sea, a 40-foot former racing catamaran, with a maximum of eight passengers. Sail past Mount Otemanu, snorkel a quiet coral garden, then stop in shallow lagoon water for drinks at a floating bar. Hotel pickup, beverages, and a professional guide are included.
“Terrific experience!!! This was the highlight of our trip to Bora Bora. The all-female crew was amazing. So very nice and informative. Great ride, scenery, snorkeling, and drinking from the floating bar. We even got to drive for a bit and made new friends. Highly, highly recommend so sign up today.”
Sail from Red Hook with a small group of up to 12 people, stopping at Great Harbor and Foxy’s Bar before a long afternoon at White Bay and the Soggy Dollar Bar. Breakfast, mimosas, an open boat bar, snorkeling gear, and BVI customs entry are included. Bring a passport and $85 cash.
“Awesome experience! Sierra and Brandon were the best!! Professional, personal and fun. Would definitely like to do a trip with them again”
Sail from Ornos Bay on a private catamaran with your own group, stopping near Rhenia for swimming and snorkeling before a fresh seafood lunch and open bar. Captains such as Paris, George, and Michael are part of the crew roster, while windy days bring a south-coast Mykonos route.
“Incredible day . Beautiful boat and lovely trip to a secluded bay . The food was the best we had in Mykonos well done George and our captain Pareis were such good fun . Highly recommend to feel spoilt and special For a day”
Join Amir AdvenTours in Bacalar at 2 p.m. for a five-hour sail with guides such as Charlie, Rommel, Omar, and Cesar. Swim at Pirate Canal and Cenote Esmeralda, visit Bird Island, enjoy fresh tacos and fruit, and watch the sunset with an open bar.
“We had the most incredible sailing experience in Bacalar with Amir! The sailboat was beautiful, and the lagoon was absolutely breathtaking, but the best part of the experience was the outstanding service. Amir and Rocio went above and beyond to make sure my family and I had an amazing time. The tacos they served were delicious, and their attention to every detail made the trip unforgettable. We brought our two kids, and they had an absolute blast—it was a perfect family adventure! If you’re planning to visit Bacalar, I highly recommend this sailing tour. Thank you, Amir and Rocio, for such an amazing experience. It’s a memory we’ll cherish forever!”
Set sail from Ornos Bay on a private catamaran for up to 15 people. Swim and snorkel near Rhenia or along Mykonos’s south coast, enjoy an eight-dish meal cooked aboard, and return with beer, wine, and a sunset view. Crew members have included Antony, Costa, Nico, George, and Konstantinos.
“We had the best time on board the catamaran cruise. There was 6 of us in total, and there was plenty of room for everyone on board. The captain and crew of the boat were fantastic- so welcoming and friendly. There was no request too big and we cannot speak highly enough of them! The food was phenomenal and so fresh, and the drinks selection was great. One of our guests had food allergies, and we messaged ahead of time to make sure it was okay for her to attend, and the company were so helpful in sorting that out, along with the crew on the day. You get such…”
Join Georges, Marina, and the captain aboard a luxury catamaran from Heraklion to Dia Island. Swim, snorkel, fish, paddleboard, and enjoy a nutritionist-designed meal with unlimited selected drinks before sailing home at sunset. The small group is capped at 20 people.
“The crew was above and beyond fantastic. Everyone had a wonderful time. The food was excellent and the catamaran was beautiful.”
Book a private 3.5-hour catamaran for up to 10 people from Montego Bay’s Freeport area. Captain CJ and the crew provide snorkeling gear, rum, tequila, vodka, beer, soft drinks, snacks, two hors d’oeuvres, and an onboard DJ, with stops at Montego Bay Marine Park and Doctor’s Cave Beach.
“Our crew from Aristo Kat Tours were phenomenal!!!! We loved every part of our experience. The snorkeling experience was good. The Lifeguard was patient and very helpful. The DJ was a vibe!!!”
Reserve a private 47-foot catamaran from Montego Bay Yacht Club for up to 10 people at $4,300 per group. You’ll get a DJ, bartender, premium cocktails, food, coastal views, swimming, and snorkeling near Doctor’s Cave Beach Club.
“The crew was a blast! Would highly recommend. Please book!! You won’t regret it. Great job to the captain and crew!”
Sail from Cancun to Isla Mujeres on a catamaran with an open bar, snorkeling gear, beach-club buffet, 1.5 hours of free island time, and entry to a minus 18°C ice bar. Certified guides, entertainers, and hotel transfers are available, though an 850 MXN local fee is extra.
“Snorkeling was only for 9 min. My watch recorded the swim time. The motor broke on the boat upon arrival to isla nothing was told to us and we had to sail all the back. Took us almost 2 hours to sail back, we were starving, a lot of people had to use the bathroom that was absolutely disgusting. The sun went down so it got pretty chilly. I felt so bad for the kids that were on there.”
Set sail from Shem Creek at 11 a.m. aboard the Palmetto Breeze for two easygoing hours of Charleston views, mini brunch bites, music, and mimosas available for purchase. Sunshine keeps the mood lively as you pass Fort Sumter, the Ravenel Bridge, and USS Yorktown.
“Palmetto Breeze nailed it! The bartender was fantastic, and Sunshine kept us laughing the entire time—his energy was contagious and the perfect match for the chill, upbeat vibe. The mimosas were flowing, the mini brunch bites were delicious, and the music tied it all together beautifully. The captain was also hilarious and made us feel totally at ease, which added to the laid-back, fun atmosphere. The crew was friendly and attentive, and the views were stunning. Highly recommend for a Sunday well spent!”
Sail privately from Montego Bay Yacht Club for 2.5 hours with up to 10 people. Aristo Kat Tours includes snorkeling gear, rum punch, beer, soft drinks, water, snacks, two light bites, and a stop near Doctor’s Cave Beach.
“Amazing Crew!! It was 18 of us and they made sure we all had a great time! I would recommend this experience to everyone.”
Pick a kind of bar, or a kind of crawl.
