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All listings near me

Find Sailing Charters Near You

4.9
(4,577 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
$300+/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

New
$200/hour
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
Instant Book
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
Sailing Catamaran along Chicago's Lakefront 6ppl $300hr. Captain included.
Sailing in Chicago · 6 guests

Sailing Catamaran along Chicago's Lakefront 6ppl $300hr. Captain included.

5.0
Snoozed - Active 02 Jan 2026
$450hr up to 13 passenger sailing charter! Must hire Captain from list.
Sailing in Chicago · 13 guests

$450hr up to 13 passenger sailing charter! Must hire Captain from list.

5.0
Snoozed - Active 02 Jan 2026
Sail & Swim from a Luxury Sailing Yacht
Sailing in Chicago · 7 guests

Sail & Swim from a Luxury Sailing Yacht

5.0
Superowner
$200+/hour
Instant Book
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
Superowner
$225/hour
Instant Book
Come Sailing at Navy Pier Marina, Chicago - Beautiful 36' Catalina Sailboat
Sailing in Chicago · 6 guests

Come Sailing at Navy Pier Marina, Chicago - Beautiful 36' Catalina Sailboat

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

Catamaran Sailing Lessons Chicago

New
Superowner
Best of 2025
$350+/hour
Charter a 31' Pearson Cruising Sloop, Chicago
Sailing in Chicago · 6 guests

Charter a 31' Pearson Cruising Sloop, Chicago

4.5
Superowner
$200+/hour
Captained Charter this 36' C & C Cruising Monohull in Chicago, Illinois
Sailing in Chicago · 6 guests

Captained Charter this 36' C & C Cruising Monohull in Chicago, Illinois

5.0
Superowner
$220/hour
Chicago's Largest Chartered Catamaran!
Sailing in Chicago · 13 guests

Chicago's Largest Chartered Catamaran!

5.0
Superowner
Best of 2025
$375+/hour
Private Cruise onboard Hunter Legend Sailboat in Chicago
Sailing in Chicago · 6 guests

Private Cruise onboard Hunter Legend Sailboat in Chicago

5.0
Superowner
Best of 2025
$200/hour
No tie-ups: 39' Sailboat, Catalina 380 with huge cockpit
Sailing in Chicago · 12 guests

No tie-ups: 39' Sailboat, Catalina 380 with huge cockpit

New
$245/hour
Instant Book
41' Morgan Classic Sloop in Muskegon, Michigan!!!
Sailing in Muskegon · 6 guests

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

5.0
$100/hour
Instant Book
Hunter 43 Sailing Yacht in Oakville, Ontario
Sailing in Oakville · 5 guests

Hunter 43 Sailing Yacht in Oakville, Ontario

5.0
$270/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
Instant Book
Fully Licensed Sailboat Charter | Jeanneau Sun Odyssey 39i Performance
Sailing in St. Catharines · 8 guests

Fully Licensed Sailboat Charter | Jeanneau Sun Odyssey 39i Performance

New
$432/hour
35ft C&C 35 Sailboat in Toronto
Sailing in Etobicoke · 6 guests

35ft C&C 35 Sailboat in Toronto

5.0
$180/hour
Sail Lake Michigan Racine, WI
Sailing in Racine · 6 guests

Sail Lake Michigan Racine, WI

5.0
$199/hour
Sail in downtown Toronto
Sailing in Toronto · 6 guests

Sail in downtown Toronto

5.0
$147/hour

Local Sailing Reviews

  1. J

    Jeff

    Sailing Catamaran along Chicago's Lakefront 6ppl $300hr. 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.

  2. SB

    Susan

    $450hr up to 13 passenger sailing charter! Must hire Captain from list.

    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!

  3. MD

    Morgan

    $450hr up to 13 passenger sailing charter! Must hire Captain from list.

    Captain Russell was fantastic! When the weather for our original charter date didn't work out, he was extremely proactive in reaching out and getting ti rescheduled asap. On the day of the charter itself, the whole experience was seamless and the group had a fantastic time. They would definitely do it again!

  4. Josh

    Josh

    $450hr up to 13 passenger sailing charter! Must hire Captain from list.

    My friends and I have chartered a few boats here in Chicago, but this was by far the best experience we have had. We actually had to reschedule our initial cruise last minute due to bad weather. The boat owner, Russel, was very communicative and made the best of the not-so-great situation. He graciously offered to allow for our group to enjoy the boat for a lesser amount of time and stay at the dock. We were also able to reschedule for the following week and go out with Captain Brian at that time. Our group had such an amazing time during both sessions. We certainly had some strong personalities in the bunch (myself included) and Captain Brian was such a great sport. He was very professional but also blended in so well with our group that he was like another guest. We will without a doubt be reaching out to Russel & Captain Brian again for future events. Thank you both for making this such an unforgettable experience for us and our guests.

  5. AC

    Alicia

    Sail & Swim from a Luxury Sailing Yacht

    When I say I celebrated my 36th birthday on this beautiful boat, it was AMAZING!! Cait was so incredibly helpful and prompt with any questions I had. Her husband Greg was the coolest captain you could possibly meet. I wish I could rate this 10 stars, for it was truly a wonderful experience! You can’t go wrong if you book with them!! Thank you again!!

  6. RM

    Raymond

    Sail & Swim from a Luxury Sailing Yacht

    Cait was a lifesaver! Another captain canceled on me less than 40 hours from a booking on a Saturday! The horror of potentially having 10 guest in my crew with that time of letdown was so disappointing. Luckily Cait answered my bat signal and things happen for a reason because we got her amazing sailing yacht and awesome husband, captain Greg, to take care of us which was such a great upgrade! Thank you for taking such good care of us! We will be back and recommending you to all our friends!