12 Two-Day Sailing Trips, Coast by Coast

1.Whitsunday Islands 2-Day Sailing Tour

★★★★★★★★★★4.5 · 452 reviews · 2 days · from $350Our pick

Spend two days and one night sailing from Airlie Beach aboard Matador, a racing yacht with an English-speaking crew. You will snorkel coral reefs, reach Whitehaven Beach early, eat fresh meals, watch the sunset, and sleep onboard beneath the stars. Crew members such as Tony, Chris, Dave, Ruby, and Fi have earned praise for their friendly care and local knowledge.

“I had an amazing time on the Matador with Kate, Ash and Arron!! Literally would not change a thing. The boat was really nice and I slept pretty well. I usually get sea sick but didn't feel sick at all on this trip. We were the first on Whitehaven Beach which was really nice before all the other tour companies came in. We saw sharks, sting rays, turtles and dolphins, went snorkelling twice and swimming which was so much fun. We event we on a little sunset walk which was so pretty. Everything is exactly like the pictures so would definitely recommend.”

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2.2-Day Oriental Sails Junk Cruise of Halong Bay

★★★★★★★★★★4.5 · 399 reviews · from $349

You’ll sail Halong Bay aboard an 18-cabin Oriental Sails junk, with a guide such as Tommy, Tom, Jackie, or Peter leading cave, island, and kayaking visits. The trip includes a deluxe twin or double cabin, meals, tai chi, cooking, and Hanoi transfers for an extra fee. Expect beautiful scenery, a busy schedule, and a boat that may show its age.

“Yes this is a tourist desire but well worth it to soak in the beauty of this unique place. If you're lucky enough to get Tom as a tour guide, he made the trip. He's so informative and just Awesome to be with. The food on the boat was delicious. Modest accommodations with a comfortable bed.”

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3.Paradise Sails Cruise 2 days 1 night Halong Bay Tour

★★★★★★★★★★5.0 · 306 reviews · from $527 whole boat, up to 2Top rated

Spend two days and one night aboard Paradise Sails in Halong Bay, with Hanoi transfers, an onboard lunch, dinner, breakfast, cave and island visits, and time for optional kayaking or spa treatments. Staff members such as Blue, Kaye, Mikha, Korina, and Ms Ly are praised for attentive service. Confirm the exact sailing schedule before booking.

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4.2 Day & 2 Night Whitsunday Islands Sailing Adventure on Condor

★★★★★★★★★★5.0 · 302 reviews · from $501

Set sail from Coral Sea Marina at 2pm for two nights aboard Condor. You’ll sleep onboard, eat all meals, snorkel with supplied gear, walk to Hill Inlet Lookout, and return to Airlie Beach around 11am on day three. The social, active format suits adults aged 18 to 45, solo adventurers, couples, and friends.

“The passengers and crew were amazing and as a solo traveler I felt so embraced and comfortable sooner than I would’ve ever expected. I had a lovely time even though we didn’t catch the best conditions. Everyone’s attitude and williRead more”

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5.2-Day Whitsunday Islands Sailing Snorkel Tour

★★★★★★★★★★4.4 · 215 reviews · 60 hours · from $488

Join OzSail Whitsunday aboard Avatar, a fast trimaran sailing from Coral Sea Marina. Over about 60 hours, you’ll snorkel reef sites, visit Whitehaven Beach and Hill Inlet, watch for turtles and rays, sleep under the stars, and share fresh meals with the crew. Guides vary, with Max, Meg, Hannah, and others regularly leading trips.

“Awesome experience and great way to visit Whitsunday! The OZ Sail crew (Max, Meg and Hannah) made it a safe, enjoyable and fun experience. It was a pretty chill atmosphere on the boat, good meals and great activities with snorkeling and island experiences. We also got to see an amazing sunrise and it was possible to sleep outside on the boat falling asleep while looking at the stars on a clear sky. All in all really great value and would recommend this to everyone else looking to experience Whitsunday in the best possible way!”

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6.2 Day & 2 Night Whitsundays Sailing Adventure on Broomstick

★★★★★★★★★★5.0 · 207 reviews · from $501

Join Prosail Whitsundays at Coral Sea Marina for a 2-day, 2-night sailing trip on maxi yacht Broomstick. You’ll visit Whitehaven Beach, walk to Hill Inlet Lookout, snorkel coral reefs, eat crew-prepared meals, and sail with a social group of up to 25 people. The usual crowd is aged 18 to 39, though younger-at-heart adults are welcome.

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7.2 Day & 2 Night Whitsunday Sailing Adventure on Hammer

★★★★★★★★★★5.0 · 163 reviews · from $501

Sail from Airlie Beach aboard Hammer for three days and two nights, with snorkelling, island walks, meals, and a bed on board. The crew may include experienced skippers such as Gabe, Thomas, Hugo, Bam, Miabi, or Donald. Expect a social, active trip with limited personal space below deck and plans shaped by weather and tides.

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8.Siska – 2 day 1 Night – Maxi Sailing Tour of the Whitsundays

★★★★★★★★★★4.5 · 155 reviews · from $351

Spend two days and one night sailing aboard Siska from Airlie Beach. You’ll help raise the sails, visit Whitehaven Beach and Hill Inlet, snorkel coral reefs, and sleep aboard with meals, bedding, gear, and stinger suits included. The crew has included Jess, Laila, Matty, Isaac, Zack, and Rysh.

“such a great experience traveling with siska! was definitely a good decision. the crew were really nice, friendly and helpful with everything i needed. i would say that the meals weren’t enough and i would recommend to bring some snacks with you! but other than that i’ve had a wonderful time!”

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9.Great Barrier Reef 2-Day, 2-Night Sailing Tour

★★★★★★★★★★5.0 · 4 reviews · 3 days · from $460

Sail for two days and two nights aboard Mandrake, a small 12-passenger yacht with two crew. Kate, Kayla, or Kianna may guide reef visits, where you can snorkel, learn about marine life, and help record species and coral health. Meals, snorkel gear, and stinger suits are included.

“Our trip on the Mandrake was unforgettable! With just 12 guests, it felt personal and friendly from the start. Snorkeling at the Great Barrier Reef was incredible – colorful fish, rays, beautiful coral – and Kate and Kayla took the time to explain everything, making it fun and educational. We learned a lot and even felt like we contributed to protecting the reef. Amazing sailing, stunning beaches, delicious food, and a super warm, fun crew. Highly recommended! 🌊⛵”

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10.2-Day Combo: Isla Mujeres Sailing And Tulum Mayan Ruins

★★★★★★★★★★4.0 · 4 reviews · 2 days (approx.) · from $79Best value

Spend one day at Tulum with a guide and cenote swim, then sail to Isla Mujeres for MUSA, snorkeling, Playa Norte, buffet lunch, drinks, and open bar. Jacqueline guides Tulum and Alex brings energy to the boat trip. Hotel pickup is available as an upgrade, but MX$750 in Tulum fees and a $20 marine fee are extra.

“The first day was Tulum and Jacqueline was our tour guide and she was fabulous. The second day was Islam had us and Alex was our entertainment and he was great and all of the staff on the boat were wonderful. Also, the transportation to and from the hotel was great. We were very far because we were in Tulum and they picked us up and we very timely and brought us back both times, it was a great experience. I highly recommend them.”

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11.Sea trip in a fast and comfortable sailboat in Leucate: privatization 1/2d

★★★★★★★★★★5.0 · 4 reviews · from $648 whole boat, up to 9

Spend four hours aboard Cap’One, a fast and comfortable Kaïdoz 31 sailboat, with Captain Fabrice at the helm. Your private group of up to nine can learn basic sailing, take the wheel, swim near the cliffs, use snorkeling gear and a stand-up paddleboard, or enjoy a sunset aperitif. Routes depend on weather.

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12.2-Day Halkidiki Sailing Cruise

★★★★★★★★★★5.0 · 4 reviews · from $954

Spend two days aboard a private sailing yacht from Miraggio Thermal Spa Resort, with a skipper, co-skipper, fuel, snorkeling gear, music, and port fees included. You will explore Sithonia’s hard-to-reach beaches, stop for swims and lunch, and sleep aboard. Marcos, Simon, Dimitrios, and Simoes are among the crew members connected with this experience.

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