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Find Sailing Charters Near You

5.0
(270 Reviews)

Page 1 of 112 listings

Luxury Sailing Charters at Navy Pier Marina
Sailing in Chicago · 10 guests

Luxury Sailing Charters at Navy Pier Marina

5.0
Superowner
$300/hour
Instant Book
#1 Manhattan Sailboat! Champagne & Catering & Special Occasion Packages
Sailing in Manhattan · 6 guests

#1 Manhattan Sailboat! Champagne & Catering & Special Occasion Packages

5.0
Superowner
$300/hour
Instant Book
The Gallivanders Ultimate Sailing Adventure
Sailing in Nassau · 12 guests

The Gallivanders Ultimate Sailing Adventure

New
$435/hour
Instant Book
The Wanderlust Ultimate Catamaran Adventure
Sailing in Nassau · 13 guests

The Wanderlust Ultimate Catamaran Adventure

5.0
$638/hour
Instant Book
Cancun PARTY YACHT 46ft flybridge
Tours in Cancún · 15 guests

Cancun PARTY YACHT 46ft flybridge

5.0
$260/hour
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YACHT PARTY 42FT FREE pick up transportation Hotel Marina one way
Events in Cancún · 8 guests

YACHT PARTY 42FT FREE pick up transportation Hotel Marina one way

5.0
$180/hour
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SUNSEEKER 60FT, free pick up transportation HOTEL MARINA one way
Events in Cancún · 20 guests

SUNSEEKER 60FT, free pick up transportation HOTEL MARINA one way

5.0
$330/hour
Instant Book
Private Boat Rental Turks & Caicos | Drive Yourself | No Captain
Powerboats in Long Bay Hills · 8 guests

Private Boat Rental Turks & Caicos | Drive Yourself | No Captain

5.0
$200/hour
Instant Book
Sail Away Private Day Trip with Snorkelling and Island Hop!
Sailing in San Pedro · 10 guests

Sail Away Private Day Trip with Snorkelling and Island Hop!

4.9
$275+/hour
Instant Book
Private Charter Adventure to Palomino or Icacos, Fajardo PR - 26' Hydra Sports
Powerboats in Fajardo · 6 guests

Private Charter Adventure to Palomino or Icacos, Fajardo PR - 26' Hydra Sports

New
$650/day
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All inclusive sailing charters, half day full day fishing week long sunset sail
Sailing in Charlotte Amalie · 12 guests

All inclusive sailing charters, half day full day fishing week long sunset sail

5.0
$250/hour
Instant Book
Luxury Sailing Catamaran for up to 12
Sailing in Cruz Bay · 12 guests

Luxury Sailing Catamaran for up to 12

5.0
$350/hour
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Local Sailing Reviews

  1. SS

    Simon

    Luxury Sailing Catamaran for up to 12

    Unforgettable Post-Wedding Sail!! We spent a half-day with Aaron on the Catamaran Quest right after our wedding in St. Thomas, and it was easily one of the highlights of our entire trip. From the moment we stepped on board, Aaron made us feel incredibly special. He was super attentive and helpful, ensuring we had everything we needed to just relax and soak in the "just married" bliss. The food and drinks he served were fantastic—well-prepared and exactly what we needed for a day on the water. The boat itself is awesome and very well-equipped with everything you’d want for a comfortable excursion. We did encounter some minor technical issues with the engines during our trip, but Aaron handled it with total professionalism and didn't let it dampen the experience at all. If you are looking for a captain who truly cares about his guests' experience, book with Aaron. Thank you for making our celebration so memorable! PS: Aaron’s mango salsa is to die for - awesome stuff!!

  2. ST

    Stephanie

    Sail Away Private Day Trip with Snorkelling and Island Hop!

    We had a fantastic time with the Ambergris guys. They were flexible, informative, kind, and great with my teenagers. Can’t wait to come back and see them.

  3. ek

    elizabeth

    Luxury Sailing Catamaran for up to 12

    Our family of 5 had an amazing day with Aaron! He had great communication leading up to our day. Everything about the day was great! He made us feel very at home on his beautiful boat and our day was so much fun! He was a great host!

  4. Eric

    Eric

    The Wanderlust Ultimate Catamaran Adventure

    Great day on the boat with David & Z! They were great host who made us feel welcome. We snorkel’d twice where we saw turtles & a reef teaming with fish. If we ever come back we’ll definitely do this again. Our only regret is that we didn’t book an entire day!

  5. MT

    Mikyla

    Sail Away Private Day Trip with Snorkelling and Island Hop!

    Booking the trip was so smooth and Karen was extremely helpful when we were concerned about weather issues. Our boat captain and crew were phenomenal. The boat was well maintained and clean. I will be booking again when I return.

  6. cf

    carolynn

    Luxury Sailing Charters at Navy Pier Marina

    This is an iconic trip in Chicago. I have always been on the river walk or on a kayak looking at people boats and thought "Those lucky kids." So this time I rented a sailboat to go out on the lake- even luckier! The operators are very organized and helpful. Everything was as expected from the site. Communication throughout was excellent. Thanks for lovely and memorable sail. I'm coming back to jump in the lake when the water temperature is a bit warmer :)