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All listings near me

Find Sailing Charters Near You

4.9
(3,782 Reviews)

Page 1 of 10240 listings

32ft Sailboat for Beautiful Sail on Lake Erie (Cleveland area)
Sailing in Cleveland · 6 guests

32ft Sailboat for Beautiful Sail on Lake Erie (Cleveland area)

5.0
$325+/hour
20ft Bayliner VR5 Boat in Rockville, IN
Powerboats in Indiana · 8 guests

20ft Bayliner VR5 Boat in Rockville, IN

5.0
$510/day
2hr Day Sail from the port of South Haven Mi. on a Catalina 36
Sailing in South Haven · 6 guests

2hr Day Sail from the port of South Haven Mi. on a Catalina 36

5.0
$175/hour
2hr Sunset Sail from the port of South Haven Mi. on a Catalina 36
Sailing in South Haven · 6 guests

2hr Sunset Sail from the port of South Haven Mi. on a Catalina 36

5.0
$200/hour
Sail Lake Macatawa and cruise past the lighthouse, Big Red onto Lake Michigan
Sailing in Holland · 6 guests

Sail Lake Macatawa and cruise past the lighthouse, Big Red onto Lake Michigan

New
$150/hour
1986 22ft Catalina Sailboat in Holland, Michigan
Sailing in Holland · 6 guests

1986 22ft Catalina Sailboat in Holland, Michigan

New
$75+/hour
Ask about our SPECIAL end of season Sunday Savings! Captain included.
Sailing in Chicago · 6 guests

Ask about our SPECIAL end of season Sunday Savings! Captain included.

5.0
$450/hour
Special End of Season Sunday pricing for 8 to 13 passengers
Sailing in Chicago · 13 guests

Special End of Season Sunday pricing for 8 to 13 passengers

5.0
$550/hour
Set Sail with 36' Sailing Boat in Downtown, Chicago
Sailing in Chicago · 6 guests

Set Sail with 36' Sailing Boat in Downtown, Chicago

5.0
$225/hour
Sailing Lessons with Chicago's #1 Rated Sailing School
Tours in Chicago · 6 guests

Sailing Lessons with Chicago's #1 Rated Sailing School

New
Best of 2025
$175+/hour
Catamaran Sailing Lessons Chicago
Tours in Chicago · 6 guests

Catamaran Sailing Lessons Chicago

New
Best of 2025
$350+/hour
Private Cruise onboard Hunter Legend Sailboat in Chicago
Sailing in Chicago · 6 guests

Private Cruise onboard Hunter Legend Sailboat in Chicago

5.0
Best of 2025
$200/hour
Chicago's Largest Chartered Catamaran!
Sailing in Chicago · 13 guests

Chicago's Largest Chartered Catamaran!

5.0
Best of 2025
$375+/hour
Oceanis 393 Beneteau Sailing Yacht Rental in Chicago
Sailing in Chicago · 10 guests

Oceanis 393 Beneteau Sailing Yacht Rental in Chicago

New
$275/hour
41' Morgan Classic Sloop in Muskegon, Michigan!!!
Sailing in Muskegon · 6 guests

41' Morgan Classic Sloop in Muskegon, Michigan!!!

5.0
$100/hour
41ft Sailing Crusing Monohull Charter on ''White Lake'' Michigan, USA.
Sailing in Whitehall · 6 guests

41ft Sailing Crusing Monohull Charter on ''White Lake'' Michigan, USA.

5.0
$140/hour
Affordable Yacht 27' Doral in Toronto
Events in Etobicoke · 10 guests

Affordable Yacht 27' Doral in Toronto

5.0
$107+/hour
Instant Book
Sail Lake Michigan from Racine, WI
Sailing in Racine · 6 guests

Sail Lake Michigan from Racine, WI

5.0
$75/hour
Sail in downtown Toronto
Sailing in Toronto · 6 guests

Sail in downtown Toronto

5.0
Snoozed - Active 17 Apr 2026
28' Sailboat for 5 guests in Toronto
Sailing in Toronto · 5 guests

28' Sailboat for 5 guests in Toronto

New
$300/hour
38' Sailing Yacht in Toronto, Ontario
Sailing in Toronto · 8 guests

38' Sailing Yacht in Toronto, Ontario

New
$450/hour
Discover Sailing 3hr Introductory Sail
Sailing in Toronto · 4 guests

Discover Sailing 3hr Introductory Sail

4.5
$69/hour
2hr Shared Champagne Sail
Sailing in Toronto · 12 guests

2hr Shared Champagne Sail

New
$85/hour
41' Beneteau Oceanis Sailing Yacht in Toronto for 12 Guests
Sailing in Toronto · 12 guests

41' Beneteau Oceanis Sailing Yacht in Toronto for 12 Guests

New
$45/hour

Local Sailing Reviews

  1. NB

    Nicole

    20ft Bayliner VR5 Boat in Rockville, IN

    First time renting a boat through this platform - would definitely do it again. HIGHLY recommend Peter. Communication was excellent from the get go... easy to schedule, easy to pick up/meet, boat and equipment was in great condition...we had everything we needed for a great day on the lake. Would DEFINITELY rent from him again. As we stopped past the marina to fill up, the worker said, "nice boat." When we told him it was a rental he was shocked and said it was way nicer than anything they rented out. Highly recommend!

  2. Cindy

    Cindy

    2hr Sunset Sail from the port of South Haven Mi. on a Catalina 36

    Took our three grandchildren on a sailboat excursion with Captain Andy. Such a great, peaceful experience. Let the waves and breeze carry your troubles away. We’ve spent a good bit of time on the water but never in a sailboat and had me wanting to learn more. Such great hospitality, beautiful day, and magnificent lake. Dreading returning to the heat!

  3. M

    Mark

    Ask about our SPECIAL end of season Sunday Savings! Captain included.

    Another Great Day on the Water This was my second trip with Captain Russell, and it won’t be my last. The boat is better than advertised — super clean and comfortable. Captain Russell just makes it easy. He knows what he’s doing, keeps everything relaxed, and makes you feel like you’ve got your own personal captain for the day. Always a great time out on the lake with him.

  4. S

    Sandra

    Ask about our SPECIAL end of season Sunday Savings! Captain included.

    Captain Russell was incredibly hospitable and entertaining, making this Afternoon Delight even more special. On the yacht was pure bless -- sunshine, bevies, great music and stunning Lake Michigan views. Plus there's a huge Yeti Tundra hard cooler onboard with ice... just bring your fav adult beverages. Highly recommend for a fun, luxe day with your besties.

  5. J

    Jeff

    Ask about our SPECIAL end of season Sunday Savings! Captain included.

    What a WONDERFUL experience!! Capt. Russell was truly amazing, our 2 hour cruise Friday could not have been better! His attention to detail, coupled with a strong focus on safety didn't go unnoticed. We had 1 person in our party that was a little nervous about being on the open water. The Capt. was able to sooth their apprehension with his vast knowledge of sailing, peppered with humor...it was the needed medicine. We will be back soon, next time we'll book a 4 hour cruise, 2 hours was clearly not enough time. 5 star recommendation, only because 6 stars was not an option.

  6. SB

    Susan

    Special End of Season Sunday pricing for 8 to 13 passengers

    I would absolutely recommend everything about this experience. The boat was beautiful and very spacious. Captain Russell was wonderful to work with, very professional and a great communicator. Captain Brian was excellent at navigating wind and choppy water and was so much fun to have aboard with our group. Thank you again for a wonderful time!