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Where to Sail: the 15 Best Crewed Sailings Worldwide

21 sailing trips  ·  from $21 a head

The good crewed sailings fill up weeks ahead and the small boats go first. Below: the 15 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
Guided, Oahu Sailing Tours, Sailing and Snorkeling Trips, Sailing and Snorkeling Trips in Oahu, Sailing and Snorkeling Trips in the USA, Sailing Tours, Tour Reviews, USA Sailing Tours, Whale and Dolphin Watching Sails, Whale and Dolphin Watching Sails in Oahu, Whale and Dolphin Watching Sails in the USA

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 $35

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
Greece Sailing Tours, Guided, Lunch Experiences, Mykonos Sailing Tours, Sailing Tours, Sailing Tours with an Open Bar, Sailing Tours with an Open Bar in Greece, Tour Reviews, Tours

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
Guided, National Parks, New Zealand Sailing Tours, Sailing Tours, Self-Guided Tours, Tour Reviews, Walking Tours

Abel Tasman National Park: Sailing and Self-Guided Walk

2.5-hour Guided Sailboat Tour - Sailing Toward One World Trade Center
Guided, New York City Sailing Tours, Sailing Tours, Tour Reviews, Tours, USA Sailing Tours

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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Mexico Rocks Day Sail Shared Guided Tour - A shallow natural pool and Belizean lunch
Guided, Sailing Tours, Tour Reviews, Tours

Mexico Rocks Day Sail Shared Guided Tour

7.Mexico Rocks Day Sail Shared Guided Tour

★★★★★★★★★★5.0 · 69 reviews · 6 hours (approx.) · from $134

Review of the Mexico Rocks day sail from San Pedro, with snorkeling, Belizean lunch, open bar, shallow-water swimming, and practical tips.

“Staff was wicked great! Very nice and helpful. Food was good and rum punch had lots of rum and was delicious!!”

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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

8.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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Bacalar: Group Sailing Tour with Guide - Meeting the captain and choosing your boat
Guided, Mexico Sailing Tours, Sailing Tours, Tour Reviews, Tours

Bacalar: Group Sailing Tour with Guide

9.Group Sailing Tour with Guide

★★★★★★★★★★4.7 · 66 reviews · 3 hours · from $43

Sail Bacalar’s warm lagoon to Black Cenote, Birds Island, and Pirates Channel with a guide, drinks, wildlife, and easy three-hour pacing.

“Brilliant trip. Super relaxing and the lagoon was lovely and warm. Our guides were great. Gave us lots of information about the surrounding area. Lovely to have free time to relax and enjoy a beer at sunset. The fruit plate at the end was a lovely touch.”

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Lisbon: 2-Hour Sailing Yacht Cruise & Guided Tour w/2 drinks - Meeting beside the Discoveries Monument
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Lisbon: 2-Hour Sailing Yacht Cruise & Guided Tour w/2 drinks

Mantua: Guided sailing from the Park to the Port with the water elevator - Boarding at Red Pier B beside Castle of San Giorgio
Guided, Italy Sailing Tours, Sailing Tours, Tour Reviews

Mantua: Guided sailing from the Park to the Port with the water elevator

11.Mantua: Guided sailing from the Park to the Port with the water elevator

★★★★★★★★★★4.5 · 50 reviews · 1h 45m · from $21Best value

Sail Mantua’s lakes, Vallazza wetlands, and Leonardo-inspired water elevator on a 105-minute guided boat tour for $21.

“The trip gave us another perspective on Mantua. It was amazing to experience technology that has been working for hundreds of years and to see the wildlife. We throughly enjoyed our hour and a half voyage. Although the guide spoke in Italian we received a nice paper with translation to English. In addition we had a conversation with the guide at the conclusion of the trip. In spite of the rainy day we were very glad that we went.”

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Barcelona Guided Sagrada Familia Tour & Sailing Experience - Meeting the guide outside the shop
Barcelona Sailing Tours, Guided, Sailing Tours, Spain Sailing Tours, Tour Reviews, Tours

Barcelona Guided Sagrada Familia Tour & Sailing Experience

14.Barcelona Guided Sagrada Familia Tour & Sailing Experience

★★★★★★★★★★4.9 · 25 reviews · 3.5 hours · from $187

Review of Barcelona's Sagrada Familia and sailing tour, with skip-the-line entry, expert guides, sunset options, costs, and practical tips.

“At besøge sagrada familie og en sejltur Hang slet ikke sammen. Hver for sig var det fint. vi skulle selv transportere os fra katedralen til havnen. En gåtur på 1. time og lost presset på toden, var vi nødt til at tage en taxa. Guide roger var meget engageret og kaptajn på båden var meget kompetent. Vi var 6 gæster på båden”

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Guided Sailing Yacht Trip in Corfu Island - The first swim at Barbati
Corfu Sailing Tours, Greece Sailing Tours, Guided, Island Hopping Sailing Trips, Island Hopping Sailing Trips in Greece, Sailing Tours, Sailing Yacht Charters, Tour Reviews

Guided Sailing Yacht Trip in Corfu Island

15.Guided Sailing Yacht Trip in Corfu Island

★★★★★★★★★★4.5 · 21 reviews · 5 hours (approx.) · from $82

Review of Corfu’s five-hour sailing trip, with Barbati, Gialiskari, Nisaki Blue Cave, swimming stops, snacks, and practical booking advice.

“Amazing time! I didn't want it to end. The captain was so fun and easy-going. And the vibe was so wholesome and fun the whole time! The sites were amazing. especially the blue caves experience. I was even given a life vest as i wasn't as good a swimmer. 10/10 experince. We swam in the deep ocean.”

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