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Where to Sail: the 7 Best Crewed Sailings Worldwide

7 sailing trips  ·  from $35 a head

The good crewed sailings fill up weeks ahead and the small boats go first. Below: the 7 to book early, what each includes and how they differ.

Moana’s Waikīkī Grand Guided Turtle Snorkel & Sailing Adventure - A catamaran built for comfort, not just transport
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Moana’s Waikīkī Grand Guided Turtle Snorkel & Sailing Adventure

Lisbon: Sailboat Tour w/ Local Guide and Open Bar Green Wine - What the Eight-Person Boat Feels Like
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Lisbon: Sailboat Tour w/ Local Guide and Open Bar Green Wine

2.Sailboat Tour w/ Local Guide and Open Bar Green Wine

★★★★★★★★★★4.9 · 625 reviews · 2 hours · from $35Best value

Sail Lisbon’s Tagus River on a small-group sunset cruise with local guides, Vinho Verde, music, and views of Belém Tower and Alfama.

“This trip was the highlight of my Lisbon vacation. Francisco did an excellent job explaining the history behind each site. He struck the perfect balance—knowing when to give us space, when to engage, and when to top up our wine. The wine itself was wonderful; I especially loved the Green wine, which felt perfect for the occasion. While on the boat, we passed by other party and sailing boats, but honestly, this one was the most relaxing I saw and experienced. If you want to enjoy the natural breeze, the sound of the waves, and the beautiful scenery without distractions, this is the tour to take.”

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Mykonos Sail Cruise to Rhenia, Guided Tour of Delos, Lunch&Drinks - Starting at the Yacht in Mykonos
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Mykonos Sail Cruise to Rhenia, Guided Tour of Delos, Lunch&Drinks

3.Mykonos Sail Cruise to Rhenia, Guided Tour of Delos, Lunch&Drinks

★★★★★★★★★★4.5 · 608 reviews · 6 hours (approx.) · from $145

Sail from Mykonos to Rhenia and Delos for swimming, lunch, Greek ruins, wine, and a guided island tour in six hours.

“The experience was incredible and genuinely memorable. The onboard crew were excellent, attentive, and responsive to our needs. Communication before the trip was clear, especially when they let us know our morning cruise was moved to the afternoon due to wind conditions. The food was a bit too carb-heavy for my preference. It included pasta, salad, bread, and cheese, served family style with other passengers. Drinks were complimentary but needed to be requested directly from the crew. The biggest issue was time management, or more accurately, the lack of clarity around how long we had at each stop. We spent a lot of time at Rhenia, which was enjoyable, but…”

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Abel Tasman National Park: Sailing and Self-Guided Walk - Getting the morning right in Marahau
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Abel Tasman National Park: Sailing and Self-Guided Walk

2.5-hour Guided Sailboat Tour - Sailing Toward One World Trade Center
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2.5-hour Guided Sailboat Tour

5.2.5-hour Guided Sailboat Tour

★★★★★★★★★★5.0 · 181 reviews · 2 hours to 2 hours 30 minutes (approx.) · from $118Top rated

Review of Brooklyn Sail’s 2.5-hour small-group sail, with Statue of Liberty views, Brooklyn Bridge, pricing, tips, and practical details.

“Best way to see New York, hands down. Captain was knowledgeable and very skilled. We went out just as described and docking was expert level.”

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Kayak + Guided Snorkel & Morning Sail hosted by Honest Eco - Through the mangroves by tandem kayak
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Kayak + Guided Snorkel & Morning Sail hosted by Honest Eco

6.Kayak + Guided Snorkel & Morning Sail hosted by Honest Eco

★★★★★★★★★★5.0 · 177 reviews · 4 hours 30 minutes (approx.) · from $156

Review of Honest Eco’s Key West kayak, guided snorkel, and morning sail, with wildlife, mangroves, snacks, pricing, and practical tips.

“It was a very well put together tour, very enjoyable with activity but also some time to just relax and cruise. Libby and Angela were super friendly and clearly know their stuff, but also were just fun to chat with. Lunch was great as well!”

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Catania: Guided Sunset Sailing Trip with Aperitif & Prosecco - Watching Catania change from the water
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Catania: Guided Sunset Sailing Trip with Aperitif & Prosecco

7.Guided Sunset Sailing Trip with Aperitif & Prosecco

★★★★★★★★★★4.7 · 67 reviews

Review a Catania sunset sailing trip with Etna Coast views, Ulysses Caves, swimming, prosecco, local appetizers, and practical tips.

“Elsa and I had an amazing time. Sergio and Carlo were great company, and taught us a lot about Sicily and the local customs. The views were beautiful and the trip was so peaceful. The appetisers that Carlo prepared were brilliant, and we had more than we could ever ask for. Sergio and Carlo looked after us so well, and treated us like kings! We cannot recommend highly enough! Thank you guys for a great evening !”

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