Private Sailing Charters: the 15 Best Whole-Boat Days

2.Los Gigantes Whale Watching Charter by Sail Boat

★★★★★★★★★★5.0 · 608 reviews · 3 hours (approx.) · from $90Best value

Sail Tenerife’s Los Gigantes coast aboard a 45-foot Bavaria Cruiser with a maximum of 10 people. Guides such as Jaime, Eileen, David, and Aileen explain the marine life and cliffs, then serve sandwiches, fruit, snacks, and drinks before a swim and snorkel stop. The trip lasts about three hours and returns to the marina.

“We saw a pod of pilotwhales and dolphins. Had a lovely snorkel, fab views. Crew were excellent, very knowledgeable and helpfull. 😀”

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3.Private Sailboat + Captain for a Day Experience

★★★★★★★★★★5.0 · 582 reviews · 3 hours (approx.) · from $240 whole boat, up to 6

Spend about three hours on a private sailboat for up to six people on Bacalar Lagoon. Your bilingual crew can teach basic sailing or guide you to Cenote Cocalitos, Cenote de la Bruja, quieter swimming spots, birds, and stromatolites. Fruit, natural drinks, three beers per adult, safety gear, and a full-day kayak rental are included.

“My wife and I capped a Bacalar getaway with an incredible private sailboat tour of the lagoon with Captain Abram and Nammi Sparrow. The crew’s sailing expertise was evident throughout the trip, making my wife and me feel safe and comfortable. Captain Abram and Nammi Spareow navigated the lagoon’s stunning waters with ease and provided detailed explanations about the area’s history, natural wonders, and the unique hues of the lagoon at each stop on the tour. Nammi’s passion for the environment and knowledge of Bacalar’s ecosystem made the experience both educational and relaxing. It was the perfect way to explore the lagoon. I cannot recommend this tour higher for anyone…”

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4.Barcelona Private Sailing with Open Bar & Snacks (max 9)

★★★★★★★★★★5.0 · 440 reviews · 1 to 10 hours (approx.) · from $242 whole boat, up to 9

Sail from Port Olimpic on a private yacht for up to nine people, with a skipper such as Daniel, Marie, Luigi, Pau, or Roa. Choose a short coastal outing or a longer trip with time to anchor and swim. Beer, water, sodas, and light snacks are included, but bring a towel and eat beforehand.

“Pol the captain was very nice! The sailboat interior could have been cleaner and safety instructions could be informative… over all it was a beautiful sunset sailing…”

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5.Private sailing tour of Bacalar Lagoon

★★★★★★★★★★5.0 · 403 reviews · 3 hours (approx.) · from $215 whole boat, up to 7

Meet Captain Flor, Leandro, or another Wild Wave crew member at Casa Sirena dock for a private three-hour sail across Bacalar Lagoon. You’ll see Cenote Negro, swim near Pirate Canal and Bird Island, and share seasonal fruit, beer, and water aboard a small sailboat. The private format suits couples and families who want a calm, flexible outing.

“A fantastic ride across one of the most beautiful places in the world. The Lagoon of Bacalar is a sight to behold and there is no better (and eco friendlier) way than by sailing.”

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6.Private Full-Day Luxury Sailing Catamaran Charter in Sint Maarten

★★★★★★★★★★5.0 · 402 reviews · from $1,700 whole boat, up to 8

Captain Mike and Elmira host a private seven-hour catamaran charter for up to eight people from AzianaBobby’s Marina. Expect snorkeling, swimming, paddleboarding, beach time, a charcoal BBQ lunch, snacks, and an open bar. Stops can change with weather, so bring a towel and non-spray sunscreen.

“Captain Mike and Elmira were nothing short of AMAZING! My eight year old son has not stopped talking about getting to drive/steer the boat with Captain Mike!! My 5 year old daughter has not stopped talking about how wonderful, “My Love,Read more”

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7.Barcelona Private Sailing Tour with Drinks for Family and Friends

★★★★★★★★★★5.0 · 389 reviews · 2 hours (approx.) · from $151

Spend two private hours off Barcelona’s coast with a captain such as Fiona, Marc, Alessio, or David. Expect drinks, snacks, music, skyline views, and time to swim when sea conditions allow. Port Olímpic makes the start easy, while the boat offers a relaxed setting for families, friends, birthdays, and sunset outings.

“Marcos was amazing! He was very kind, patient and understanding with kids. His attention made a huge difference. The boat was wonderful: clean and beautiful.”

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8.Fort Lauderdale Sailing Charter

★★★★★★★★★★5.0 · 387 reviews · 4 hours (approx.) · from $150

Captain Dan takes your private group of up to six from a Fort Lauderdale residence through the New River, past yachts and waterfront homes, then toward the Atlantic. Bring your own food and drinks, learn basic sailing, swim when conditions allow, or simply stretch out on the bow of the Wind Pirate.

“10/10 recommend!!!! It was the most wonderful and relaxing day !!!!! Captain Dan was so nice and friendly !!!! Def worth it”

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9.Private Luxury Catamaran Yacht. Full or Half Day Charter – Sail, Beach, Snorkel.

★★★★★★★★★★5.0 · 386 reviews · from $1,495 whole boat, up to 12

Sail aboard S/Y Pisces, a 47-foot Leopard catamaran, with your own captain and mate from Havensight. Build a half or full-day plan around snorkeling, turtles, beaches, Water Island, Buck Island, and quiet coves. Snorkel gear, floats, water, soda, beer, and rum punch are included for groups of up to 12.

“Such a relaxing and wonderful way to spend the day! Loved snorkeling in areas that we've never gone to. Honeymoon beach is our new favorite spot!”

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10.4-Hour Fort Lauderdale Sailing Charter

★★★★★★★★★★5.0 · 311 reviews · 4 hours (approx.) · from $148

Spend four hours aboard Daffy, a private Fort Lauderdale sailing charter led by Captain Charlie. Cruise the New River, Port Everglades, the Intracoastal Waterway, and the Atlantic, or remain docked. Bring your own food and drinks, take the wheel with instruction, and watch for dolphins, manatees, turtles, and porpoises.

“We booked this for a bachelorette party (5) and had a blast—even with choppy water out at sea and one of us getting seasick. Captain Charlie was a unique character but knew how to operate the sailboat with ease. He took amazing photos of our group in the canal and of the bride driving the boat, which became the perfect memory saver for the excursion. If you are sensitive to bolder personalities and don’t have a wide sense of humor, I would recommend a different experience.”

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11.Afternoon Luxury Catamaran Sailing and Charter Cruise from Bridgetown

★★★★★★★★★★5.0 · 269 reviews · from $175

Set sail from Bridgetown at 2:45 p.m. for a 3.5-hour Calabaza cruise with turtle snorkeling, a reef or shipwreck stop, canapes, and a premium bar. The crew, which may include captains such as Chad or Danny, provides gear, lessons, and water help. Hotel pickup covers Speightstown to Oistins.

“Excellent small group experience. The crew was friendly and exceptional in interacting with the group, and very knowledgeable.”

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12.Ibiza & Formentera Private Catamaran Full-Day Sailing Tour

★★★★★★★★★★5.0 · 242 reviews · 8 hours (approx.) · from $1,610 whole boat, up to 10

Spend about eight hours on a private catamaran for up to 10 people, sailing from Cala Jondal past Ibiza’s coves to Espalmador and Ses Illetes. You get snorkeling gear, two paddleboards, Wi-Fi, and a restroom. Lunch and drinks cost extra, and a friendly 10-year-old Border Collie lives aboard.

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13.2 Hours Private Sailing Tour in Lisbon

★★★★★★★★★★5.0 · 242 reviews · 2 hours (approx.) · from $363 whole boat, up to 12

Set sail from Doca do Bom Sucesso with your own group of up to 12. A skipper guides the boat past Belém Tower, the Discoveries Monument, the 25th of April Bridge, Cristo Rei, and Terreiro do Paço. Expect crackers, one beer or soft drink per person, and a relaxed private setting. Sunset departures cost an extra €50.

“We had an unforgettable sunset sailboat ride in Lisbon! The views were stunning but what really made the experience stand out was the incredible staff. They were friendly, welcoming, and clearly passionate about what they do — they made us feel safe, relaxed, and completely taken care of the entire time. They answered all our questions, and even let our daughter get involved a bit. By the end of the trip, she was absolutely captivated — I think she may have found a new passion for sailing! It was peaceful, beautiful, and truly memorable. We’d recommend this experience to anyone visiting Lisbon.”

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14.Private Sailing City & Sunset Tour

★★★★★★★★★★5.0 · 238 reviews · 2 hours · from $106

Join Paulo for a private two-hour sailing trip from Doca de Santo Amaro. You’ll pass under the 25 de Abril Bridge, sail to Belém Tower, then return east past Praça do Comércio, Alfama, the cathedral, and São Vicente. A white or rosé wine is served, and stories about Lisbon come with the views.

“We had an amazing experience on this boat trip! paulo was incredibly friendly, welcoming, and made sure we felt comfortable throughout the journey. The atmosphere on board was relaxed and enjoyable, with beautiful views that made the ride truly special. It felt both private and personal, which made the whole experience even more memorable. I would definitely recommend this trip to anyone looking for a unique and fun way to enjoy a private Lisbon from the water.”

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15.Private Catamaran Swim sail snorkel cliff jumping SUP

★★★★★★★★★★5.0 · 232 reviews · from $1,175 whole boat, up to 15

Spend three hours aboard a private Bermuda catamaran with Captain Mark, Alex, Georgia, or another Island Time crew member. You can sail, snorkel, cliff jump, swim, paddleboard, or use the crystal kayak, with stops adjusted to your group and the weather. The boat has a restroom, cooler, grill, Bluetooth audio, and room for 15.

“Great experience for our group of 10.... Both the captain and crew were amazing. The boat was amazing to be on (just the right size for our group). Water was a little choppy but the captain took us to a calm cove were we cliff jumped and snorkeled. Highly recommended”

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