Under sail · SAILING TOURS WITH DRINKS
Cava off Barcelona, port wine on the Douro, rum punch off Aruba. These 15 sails come with the bar open, and each one says whether that means one glass or as many as you like.
Board at Lloret de Mar’s beachside promenade for a four-hour Costa Brava cruise with swimming, snorkeling, a floating mattress, BBQ, and drinks. Morning departures suit families, while afternoon and Saturday celebration trips bring a stronger party mood. English, Spanish, and French support is available.
“Absolutely amazing unforgettable You cant go wrong with this purchase”
Spend about two hours sailing from Key West with an open liquor bar, champagne, sangria, wine, premium beer, soft drinks, and chef-prepared hors d’oeuvres. A local musician provides live entertainment while you pass Mallory Square, Fort Zachary Taylor, Sunset Key, and the Key West harbor. Arrive 30 minutes early and bring a sweater.
“Wonderful experience, drinks food and music all terrific and the sunset was breathtaking. Bring a sweater”
Spend two hours aboard a small sailboat with a skipper and guide, passing Belém Tower, the Discoveries Monument, MAAT, Alfama, and Christ the King. Choose daytime, sunset, or night sailing. The crew speaks English, Spanish, and Portuguese, serves one drink, and keeps the group to 10 people.
“Benny & Miguel were wonderful hosts. Benny was very informative and gave excellent information. They were very respectful and we received complimentary drinks. They asked to take photos which was very nice and respectful .”
Join a shared sailing cruise of up to 12 people from Lisbon’s Alcântara marina. Your skipper handles the sailing while you enjoy Portuguese wine, views of Belém Tower, Jerónimos Monastery, the 25 de Abril Bridge, and a sunset over the Tagus. Guides such as Joe, Henry, JP, and Bruno are praised for friendly conversation and local insight.
“It was a great experience. They upgraded us to a luxury boat free of cost. Excellent customer service. Loved the cruise.”
Sail Aruba’s coast aboard *The Dolphin* for two snorkel stops at the Antilla shipwreck and Boca Catalina Bay. Guides such as Frederick, Oscar, Rio, Jay, and Brandon help with the fun, while you get a light wrap-and-fruit lunch, drinks, a rope swing, and a spinning water slide. The three-hour trip leaves from Delphi Watersports near the Hyatt Regency.
“Best snorkeling/catamaran experience we’ve ever been on—and we’ve been on a lot. The vibe was low key and family friendly. Could have had maybe a tad more time at the shipwreck site (that’s where we saw a turtle), but the generous snorkeling time at the next site made up for it. We saw some corals doing a-okay and some unique reef fish. Ending the adventure with the rope swing was awesome! Highly recommend!”
Sail Cabo San Lucas Bay for 2.5 hours aboard a 50-foot vessel with a maximum of 16 people. You’ll pass Lover’s Beach and El Arco, enjoy unlimited drinks and light appetizers, and watch sunset from the water. Crews have included Tito, Chino, Chava, Aldo, and Ronnie, though assignments vary.
“The sailing was awesome! Gorgeous views. Really good appetizers. Staff was fun and entertaining. Got some great pics.”
Join the Hawaii-built Moana Catamaran at Kewalo Basin Harbor for a barefoot sunset sail along Waikiki and past Diamond Head. Your first premium drink is included, with more available for $8. The crew, including staff such as Viv and Eli, serves drinks while you watch for dolphins, humpback whales from November to May, and changing sunset colors.
“Great experience, great crew, very satisfied. The positive attitude of the crew made for a very enjoyable and relaxing trip. They were very attentive, boat is clean and well kept. They went to extra efforts to see a whale off of Diamond Head and we were successful at capturing whale flukes with a gorgeous sunset in the background”
Set out from Marina Port Vell on a two-hour sailing trip with a skipper and crew. Choose midday light or sunset color, share a boat with up to 10 people or book privately, and enjoy cava, wine, beer, soft drinks, snacks, music, and a swim stop when conditions allow. Crew members such as Faith, Vicky, Rodrigo, and Eduardo are known for warm service and clear safety briefings.
“This was so brilliant, Faith & Rodrigo were highlights, looking after my friends and I so well. We swam in the ocean & the drinks were always topped up, I highly recommend this trip!!”
Spend four hours sailing from Pelican Pier with breakfast, mimosas, lunch, an open bar, and three snorkeling stops. You can swim with tropical fish, look for sea turtles and a shipwreck, or try the third-lung air system. The crew, including captains and mates such as Johnny and Andy, keeps the mood lively and safety focused.
“The crew was LITT!! Very professional and super fun!! Looking forward to go for great vibes BOOK THEM”
Spend about two hours aboard Red Sail Sports’ catamaran, sailing along Aruba’s coast near Palm Beach as the sun sets. Junior handles drinks, while crew members such as Brandon, Lizzie, Captain D, Joshua, and William have helped create the lively mix of music, stories, and dancing. Expect appetizers, an open bar, and a return to Piet’s Pier Bar.
“Joshua and his crew were great and accomo on the boat. It started on time and even tho visibility was low during the beginning of Hurricane Melissa, just being in the ocean was a relaxing time.”
Join a small-group or private two-hour cruise from Douro Marina with a welcoming crew such as Miguel, Henrique, Eric, or Francesco. You’ll pass Porto’s bridges, Ribeira, Gaia, and Foz do Douro, hear local stories, enjoy a welcome drink and port wine, and possibly reach the Atlantic. Bring a jacket for the cooler water.
“The captain and crew were wonderful and informative, always communicated on with qhere to meet, etc. The sunset view was the absolute cherry on top of a cruise filled with a few laughs and historical info on Porto. Highly recommend!!”
Sail from Key West’s historic seaport aboard the 69-foot Marquesa to the Florida Reef, about 7.5 miles offshore. The crew provides gear, safety instruction, and time to snorkel in shallow reef water. After swimming, enjoy included beer, wine, soft drinks, and cocktails on the return trip. The boat has restrooms and a freshwater rinse.
“The boat was great as well as the captain and mates! I didn't see a lot of fish that was a bit disappointing. Other than that it was fun!”
Spend about two hours sailing from Palm Beach aboard a 40-foot trimaran with up to 34 people. The crew serves unlimited cocktails, Aruba Ariba drinks, nonalcoholic beverages, and small bites at your seat. Richard, Shaka, Vino, Jose, and Captain Martin have all been part of the welcoming crew, though staffing may vary.
“The sunset cruise was very relaxing and entertaining! Our captain and his assistants were all great. The food and drinks were good. Very intimate small group and we all had such a great time. Thank you Octopus tours.”
You’ll cruise Santorini aboard a luxury catamaran with an English or Greek-speaking crew, stopping at Red Beach, Mesa Pigadia, Palea Kameni, and the hot springs. Expect three swim stops, snorkeling gear, towels, a BBQ, wine, soft drinks, and sunset views. Maria, Neta, and Liz are among the crew members praised for warm, attentive service.
“This was excellent!!!! We wished there was an all day option. The crew on board, our driver, the people answering all my crazy questions on WhatsApp, were fantastic. They were even able accommodate a vegan diet which we were so thankful for as well. This is a top notch company and it shows. For anyone visiting Santorini looking for a great cruise look no further.”
Choose a shared half-day sail to Dia Island, a private yacht trip, or a one-hour coastal cruise from Heraklion. The Dia route includes lunch, unlimited water, soft drinks and local wine, plus snorkeling, paddleboards, and optional fishing. Crew members may include Stavroula, Dennis, Mido, or Miso.
“A very choppy crossing to the island. Very well handled by the skipper though The boat was comfortable and safety was well looked after Food was very good. Would have been nice to have beer as an option perhaps Time went very quickly”
Other ways to get on the water
Pick a boat, a coast or a time of day.
