THE CARIBBEAN · SAILING TRIPS
Trade winds most of the year and flat water on the lee side of every island. These 15 sailing days are priced and timed, with a note on which ones raise a sail and which motor the whole way.
Spend 2.5 hours aboard the 65-foot Arusun from Palm Beach, with snorkeling at the Antilla Shipwreck and Catalina Bay. Captain Amanda, Ronnie, Rashim, or Gabriel may lead your trip. You get gear, snacks, and an open bar, but must reach the pier yourself and board the catamaran by zodiac.
“Had a wonderful experience. We were a small group which was nice. Captian Amanda and 1st mate Ronnie were great.”
Spend three hours aboard The Dolphin catamaran from Noord, with snorkeling at the Antilla shipwreck and Boca Catalina Bay. You get fresh equipment, wraps, fruit, snacks, an open bar, music, and access to a spinning water slide and rope swing. Crew members such as Frederick, Oscar, Rio, Jay, and Brandon are often praised for friendly, attentive service.
“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!”
Join The VI Cat at Marriott Frenchman’s Cove for a three-hour afternoon sail to Turtle Cove at Little Buck Island. Snorkel with green sea turtles, coral, and tropical fish, or stay aboard and swim. Captain Serena, Captain Dave, and crew members such as Isaac, Sam, and Nick are known for friendly service and clear safety guidance.
“Great experience. Very accommodating. Ive been on tours that say they include snacks and drinks but do not. This one really does. The guides were friendly abd helpful, the captain was very skilled. All of them were knowledgeable. You may want to bring a towel. Also, you cannot wear shoes on the deck. My onky regret was not bringing my snorkel and mask from home. We saw about 15 sea turtles, Sgt majors, parroting, blowfish, a school of ballyhoo, sea urchins and more. Well worth the price.”
Spend four hours aboard a spacious catamaran from Pelican Pier, with breakfast, lunch, mimosas, an open bar, and three snorkeling stops. You may visit a shipwreck, Tres Trapi, or Boca Catalina. The crew provides gear, safety help, and, at some stops, a third-lung air system for underwater exploring.
“Great food, great drinks and great snorkeling! Easy location to find. Perfect amount of time for a morning excursion if you are looking for something to do that won't eat up your whole day.”
Sail Aruba’s coast aboard a luxury catamaran from Piet’s Pier Bar at 5:30 pm. Enjoy Palm Beach views, sunset colors, unlimited beer, rum punch, tropical cocktails, appetizers, local music, dancing, and crew storytelling. The crew may include familiar faces such as Junior, Lizzie, Joshua, Brandon, or Captain William, though staff can change.
“Alot of fun, awesome crew and great appetizers and drinks. I highly recommend this for anyone who wants a great time!”
Join Captain Scott, Anna, Jackie, and canine first mate Queenie aboard Random Wind for a relaxed five-hour sail from Simpson Bay. You’ll visit Mullet Bay and Little Bay, snorkel, paddleboard, swim, swing into the sea, and enjoy grilled chicken, Caribbean rice, salad, baguette, snacks, and an open bar.
“Best Experience on the Island. Great Staff. Very Professional. Very clean and well kept vessel. Random Wind is a beautiful ship. Waters were beautiful. The food was great. The drinks were great. The Tarzan swing was amazing. Wasn't crowded like so many other boats offering the same. Saw a plane landing while we were sailing past Maho, amazing experience. Snorkeling at Little Bay was a blast. Tarzan Swing at Simpson Bay was incredible. Would recommend as a must for all visitors. Laid Back and Fun. S2S Reviews”
Board near Palm Beach and ride a short shuttle boat to a 40-foot trimaran for a two-hour sunset sail. Enjoy cushioned seating, an open bar with Aruba Ariba cocktails and spirits, and appetizers served about every 15 minutes. Crew members including Shaka, Jose, Richard, Vino, and Captain Martin keep the mood lively while you watch the coast fade into evening.
“It was so fun! The staff was so engaging and entertaining! The highlights were the beautiful sunset and the wind surfer who entertained. We would highly recommend this experience!”
Sail from Fajardo to Cayo Icacos or Palominitos aboard a catamaran with East Island Excursions. You get snorkeling gear, floating belts, a deli lunch, rum drinks, and time for swimming and beachcombing. Crew members such as Captains Jose and Carlos are known for attentive service, while weather may change the island stop.
“We had a great time on this boat. The crew was absolutely fantastic! Safety and having fun was their priority. I highly recommend this excursion! I plan on another one when I return to Puerto Rico! Have fun!”
Spend four hours aboard a 48-foot catamaran from Grace Bay, with reef snorkeling, a weather-chosen stop at Half Moon Bay or Little Water Cay, lunch, drinks, and beach pickup. Crew members such as Captain Mike, Ross, Reggie, Jay, Willie, and Tye are known for helping beginners and keeping the trip lively.
“We brought 5, 8, 11, and 15 year olds, all ages gave it a 10/10. The 5 year old was a little young for the snorkel but enjoyed watching the others. Reggie and team were fantastic! The food and bev were enjoyed by all. Highly recommend this crew!”
Board the 54-foot VI Cat at Marriott’s Frenchman’s Cove for a two-hour dinner sail toward Little Buck Island and Charlotte Amalie harbor. Enjoy a scratch-made barbecue or Taco Tuesday menu, an open bar, sunset views, and harbor lights. The crew, including captains and hosts such as Mike, Isaac, Anders, Adrian, and Captain Dave on past sailings, keeps the mood friendly and easygoing.
“Nice and relaxing on the water.. Its a must in St Thomas. The crew was nice patient and very informative during this excursion.”
Meet at MooMba Beach at 9 a.m. for a four-hour cruise aboard an 85-foot teak schooner. You’ll snorkel at Malmok, Boca Catalina, and the SS Antilla shipwreck, with gear, barbecue lunch, open bar, restrooms, and a rope swing included. Hotel pickup is not provided.
“We did the early morning pirate sail. It was so much fun! The snorkeling was great, the crew was engaging, and the pirates poison is a must have!”
Spend five hours aboard The Phoenix with Captain Benji and crew, sailing from Bobby’s Marina to Little Bay, Maho Beach, and Mullet Bay. Snorkel with supplied gear, use paddleboards and a floating mat, enjoy cooked lunch and unlimited drinks, then watch aircraft pass over Maho Beach.
“The best experience we had during our stay in St. Maarten, our Captain and Crew were the best, they took amazing care of us! Drinks and Lunch were the perfect treat, wish it was longer we loved it!!”
Sail San Juan Bay aboard a 30-foot J/30 racer-cruiser with a captain such as Ivan, Joe, or Carlos. You’ll pass El Morro, hear local history, enjoy beer, sangria, rum and Coke, and watch the sunset with up to six people. Expect a real sailing trip, not a party boat or dinner cruise.
“What an amazing experience!!!! The sunset was spectacular and the captain was so amazing!! I absolutely recommend this sailing experience!!!”
Join Red Sail Aruba at Piet’s Pier Bar for a four-hour catamaran trip with three snorkel stops, including Catalina Bay and the SS Antilla wreck. You’ll get gear, instruction, snacks, a Caribbean buffet, and an open bar. Crew members such as Captain Dion, Liz, Junior, and Captain Richard have earned praise for safety and fun, though the water time at each stop is limited.
“Snorkeled 3 different places. Had an amazing lunch. Lots of fun!! Tour guides and captain did a great job keeping us safe as well as making us laugh.”
Set sail from Margaritaville at 4:30 pm aboard a new catamaran for about two hours. Enjoy champagne, wine, cocktails, Painkillers, rum punch, soda, and passed appetizers while the crew points out St. Thomas and nearby islands. Captain Big Tuna, Captain Danny Boy, Carolina, Dawn, and other crew members are often praised for attentive service and lively music.
“Very nice and relaxing and great crew - beautiful views. Wish the tour went out a little further instead of going in same circle”
Pick an island, a reef or a road.
