Under sail · GUIDED

Top 4 Guided Sails Worldwide

4 sailing trips  ·  seats from $35 each

The good guided sails fill their decks early in the season. Here are the 4 to book first, what each includes and how they differ.

Moana’s Waikīkī Grand Guided Turtle Snorkel & Sailing Adventure - Why this works for first-time snorkelers
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Moana’s Waikīkī Grand Guided Turtle Snorkel & Sailing Adventure

1.Moana’s Waikīkī Grand Guided Turtle Snorkel & Sailing Adventure

★★★★★★★★★★4.5 · 936 reviews · 2 hours 30 minutes (approx.) · from $76Top of the fleet

Sail from Kewalo Basin Harbor to Turtle Canyon for a guided snorkel with provided gear, lifeguards, and a secured raft for beginners and children. You may see turtles, tropical fish, octopuses, starfish, dolphins, or even a monk seal. The 2.5-hour trip ends with a complimentary first drink from the full bar.

“We had a great time. The staff was very nice and courteous. Water was beautiful, so relaxing so worth it.”

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Lisbon: Sailboat Tour w/ Local Guide and Open Bar Green Wine - Meeting the boat beneath the 25 de Abril Bridge
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Lisbon: Sailboat Tour w/ Local Guide and Open Bar Green Wine

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

★★★★★★★★★★4.9 · 625 reviews · 2 hours · from $35Lowest fare aboard

Sail the Tagus for two hours aboard a 33-foot boat with up to eight people, local guides such as Andre, Mariana, Francisco, and Felipe, and an open bar of Portuguese Vinho Verde. You’ll pass Belém Tower, the Monument to the Discoveries, Alfama, Almada, and Commerce Square. Sunset departures offer the best light, but bring warm layers.

“Amazing tour with great wine and a great guide, would recommend ☺️”

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Mykonos Sail Cruise to Rhenia, Guided Tour of Delos, Lunch&Drinks - Rhenia: clear water, a golden beach, and a yacht ladder
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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

Spend about six hours sailing from Mykonos to Rhenia and Delos. Swim from the yacht in clear Aegean water, use the free snorkel gear, eat lunch with wine and soft drinks, then tour Delos with a licensed English-speaking guide. The group can reach 35 people, though yacht size and numbers vary.

“Thld was the highlight of our trip--swimming in the Mediterranean Sea with my son. The crew of Chris, Thanos and The Captain (I don't want to butcher his name) was incredibly hospitable with our 3 yr old. The only very minor complaint was the extended 2 hrs stay on Delos given the heat, but that's just Greece. The whine was minor, and my child just hung at the boat. Hopefully you are as lucky as us and we were with 2 other amazing families that we really enjoyed sharing the boat with......the other boat looked miserable based on the demanding and rude guests at check-in (lol & dodged that boat).…”

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Catania: Guided Sunset Sailing Trip with Aperitif & Prosecco - Sailing beside Sicily’s volcanic coast
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Catania: Guided Sunset Sailing Trip with Aperitif & Prosecco

4.Catania: Guided Sunset Sailing Trip with Aperitif & Prosecco

★★★★★★★★★★4.7 · 67 reviews

Set sail from Catania Nautical Club for three hours along Sicily’s volcanic coast. Your skipper and host, possibly Giulia, Sergio, Carlo, Benjamin, or Ivan, guide you toward Ulysses Caves for a short swim, followed by local appetizers and prosecco as the sky changes color. English and Italian tours are available.

“It was AWESOME. Julia rocks :) Could be improved: Better appetizers!”

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Other ways to get on the water

Sunset Sailing CruisesCatamaran Sailing TripsSailing and Snorkeling TripsPrivate Sailing ChartersIsland Hopping Sailing TripsTall Ship and Schooner Sailing
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