SAILING WORLDWIDE
The best days on the water.
The 15 most popular drinking tours. What each sail costs, how long you are on the water, and which crews run it well.
Premium Santorini catamaran with BBQ, open bar, and multiple swim stops, including hot springs. Includes transfers and small-group comfort.
Most Popular“Great day on the water. Captain Petros,, Helen, Vitos and Ekram were very good!! They made the experience wonderful.”
Santorini luxury catamaran with open bar, volcanic hot springs swim, snorkeling near White and Red Beaches, and a Greek meal.
“This was a beautiful experience I shared with my partner. The whole Catamaran trip had amazing views and the food was delicious!”
Sail Key West at sunset on a spacious catamaran with live music, open bar, and hearty hors d’oeuvres. 2 hours, great views.
“Great time!!! Awesome crew and entertainment!! Snacks were excellent 😊 Drinks, drinks and more drinks! Awesome sunset.”
Half-day Santorini catamaran with hotel pickup, open bar, swims at Red Beach and hot springs, and a BBQ meal on board.
“What a fun day on the water! The staff Bill, Mika and Kostas were very welcoming and knowledgeable! The food was the best that we have ever had on a boat excursion. We had plenty of room to move around and it was not crowded. We had 4 different stops to swim and snorkel. It…”
Cancun to Isla Mujeres by catamaran with an open bar, snorkeling, and Beach Club time at Playa Norte, plus optional lunch.
“Fun vibes! Great atmosphere. Finished around 6:30pm and started at 12:30pm. Not too long and not too short! Food was ok but take some snacks with you :-)”
5-hour Santorini catamaran cruise from Vlychada with Red and White beaches, volcano hot springs, snorkeling, BBQ, and unlimited open bar.
“Excellent day! Amazing hosts, music, food and drink!”
Aruba catamaran snorkel on The Dolphin with 2 stops at Antilla and Boca Catalina, open bar, light lunch, plus slide and rope swing.
“Fun boat trip trip with another couple We had a great time snorkeling, going on the slide and the rope slide Staff was great!”
A romantic Los Cabos sunset sail with a 50-foot sailboat, small group, open bar, and light appetizers near El Arco and Lover’s Beach.
“From start to finish, this was one of the most memorable excursions we’ve ever had. The boat was beautiful, the views were breathtaking, and the overall vibe was relaxing yet fun—but what truly made the evening unforgettable was the incredible crew: Captain Chino, Chava, and Aldo. These guys were phenomenal—engaging, attentive, and genuinely passionate about…”
Barcelona 2-hour sailing from Marina Port Vell with open bar, snacks, and skyline views. Midday or sunset cruises, small-group charm.
“Friendly informative hospitable Beautiful sunset cruise All female crew and passengers in our boat ! Perfect for me booking alone .”
Luxury Aruba catamaran sunset sail with open bar, appetizers, and a lively crew. Cruise along Palm Beach for ~2 hours.
“Very nice and relaxing sunset cruise. The staff made sure we had a good time. Drinks and appetizers were good. Beautiful scenery.”
A 5-hour Santorini catamaran with Greek meal, open-bar drinks, hot springs and Red Beach swims, plus sunset options from the water.
“Absolutely wonderful! The crew was exceptionally friendly and helpful! Service could not have been better!!”
Small catamaran tour from Barbados with turtle snorkel, open bar, snacks, and Bajan buffet lunch, plus hotel pickup and a calmer ride.
“Our 5th trip on the Stiletto and brilliant as ever. Boat is superb and the crew always incredibly friendly. Drinks are always at hand and lunch is fantastic. We have used many of the other local operators and always come back to the Stiletto. Would highly recommend”
Sail from Cancun to Isla Mujeres on a catamaran with guided snorkel at El Meco, open bar, and time to explore downtown.
“Cancelled two days in a row, late message, only talk about new date, not staying anyting about refund or discount”
Small-group Santorini catamaran cruise with BBQ, open bar, hotel transfers, and swimming stops at hot springs and White Beach.
“This tour was amazing. The staff of the Santana was great, they were friendly and extremely helpful as I got sea sick and they came to check in on me and make sure I was okay during the entire ride. The food was also very good and sunset view was beautiful. I definitely recommend this…”
2-hour Barcelona sunset sail with open bar, homemade tapas, and skyline views of Sagrada Família and the W Hotel from Port Olímpic.
“My husband and I ended up being the only ones who showed up because it was a little chilly. With the boat all to ourselves, it was a very personal and very romantic experience. Louigi was an excellent captain. We were able to communicate quite well despite any language bumps. It was a joy to…”
The sailing ports worth the trip, grouped by the sea they sit on.
