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All listings near me

Find Sailing Charters Near You

4.9
(976 Reviews)

Page 1 of 371 listings

Sailing on Eagle Creek with Hunter 240 Sailboat
Sailing in Indianapolis · 4 guests

Sailing on Eagle Creek with Hunter 240 Sailboat

New
$150+/hour
Instant Book
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 & 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
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
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
Sail on the Potomac in Washington, DC aboard the 28ft Hunter Sailboat
Sailing in Washington · 6 guests

Sail on the Potomac in Washington, DC aboard the 28ft Hunter Sailboat

New
$280/hour
Instant Book
Fun time Jet Ski Rental at Lake Norman near Charlotte, NC
Water Sports in Cornelius · 8 guests

Fun time Jet Ski Rental at Lake Norman near Charlotte, NC

4.9
$84+/hour
Instant Book
Fun family time Jet Ski Rentals at Lake Norman, NC
Water Sports in Cornelius · 8 guests

Fun family time Jet Ski Rentals at Lake Norman, NC

5.0
$85/hour
Instant Book
SEARAY SLX400 | $750hr | 13 People
Events in Washington · 13 guests

SEARAY SLX400 | $750hr | 13 People

5.0
Superowner
Best of 2025
$800/hour
Instant Book
Captained Charter 30' Sailboat in Milwaukee, Wisconsin
Sailing in Milwaukee · 6 guests

Captained Charter 30' Sailboat in Milwaukee, Wisconsin

5.0
Snoozed - Active 02 Jan 2026
Charter 44' Orana Cruising Catamaran In Deale, Maryland
Sailing in Deale · 10 guests

Charter 44' Orana Cruising Catamaran In Deale, Maryland

5.0
$450/hour
Instant Book
38-ft Hunter 376 Sailing Adventure in Annapolis
Sailing in Annapolis · 6 guests

38-ft Hunter 376 Sailing Adventure in Annapolis

5.0
Superowner
$138+/hour
Instant Book
Chesapeake Bay Sailing Charter - 33' Cape Dory Sailing from Kilmarnock, Virginia
Sailing in Kilmarnock · 6 guests

Chesapeake Bay Sailing Charter - 33' Cape Dory Sailing from Kilmarnock, Virginia

5.0
$73+/hour
Instant Book
Charter 32' Modern Hunter Sailboat In Gloucester, Point Virginia
Sailing in Gloucester Point · 6 guests

Charter 32' Modern Hunter Sailboat In Gloucester, Point Virginia

5.0
Superowner
$125/hour
Instant Book
Private Sailing Charters Aboard a 40ft Trimaran – Explore PEC by Wind
Sailing in Prince Edward · 12 guests

Private Sailing Charters Aboard a 40ft Trimaran – Explore PEC by Wind

4.9
$324/hour
Instant Book
Melges 24 - One Design Racing Experience
Sailing in Hampton · 5 guests

Melges 24 - One Design Racing Experience

5.0
Superowner
$100/hour
Instant Book
Classic Sparkman & Stevens Sailboat: Choose Leisure Sailing or Hands-On Lessons
Sailing in Lacey Township · 6 guests

Classic Sparkman & Stevens Sailboat: Choose Leisure Sailing or Hands-On Lessons

5.0
Snoozed - Active 02 Jan 2026
Hinckley Pilot 35 Classic Sailboat in the Heart of NYC
Sailing in Manhattan · 6 guests

Hinckley Pilot 35 Classic Sailboat in the Heart of NYC

5.0
$330/hour
Instant Book
Private Sailing Charters - 37ft Sailboat in New York
Sailing in Manhattan · 6 guests

Private Sailing Charters - 37ft Sailboat in New York

5.0
$325/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 Only 40ft Hinckley Sailboat in Manhattan
Sailing in Manhattan · 6 guests

The Only 40ft Hinckley Sailboat in Manhattan

5.0
$300/hour
Instant Book
Enjoy Spacious Sailing with our Large Catamaran on the Beautiful Hudson River!
Sailing in New York · 12 guests

Enjoy Spacious Sailing with our Large Catamaran on the Beautiful Hudson River!

5.0
$624+/hour
Instant Book

Local Sailing Reviews

  1. Abhishek

    Abhishek

    The Only 40ft Hinckley Sailboat in Manhattan

    Captain Andy is one of the best hosts and extremely skilled at what he does. I was planning a proposal for my girlfriend and he went above in beyond in helping us out. He gets back quickly regarding any queries and makes sure you have a memorable experience. I have nothing but good this to say about our experience. Definitely recommend Captain Andy if you are looking for a good time on a sail boat.

  2. ST

    Sherzod

    38-ft Hunter 376 Sailing Adventure in Annapolis

    Great experience, it was my first time boat sailing and Alberto and his wife were great. My fiance and I had a great time. Highly recommend!

  3. UU

    Uche

    Fun family time Jet Ski Rentals at Lake Norman, NC

    Breyanna was very good with communicating instructions and prioritizing safety. She was also flexible with scheduling and wanted us to have the best experience by providing alternative times when weather proved unstable.

  4. 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!!

  5. 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!

  6. rb

    ryan

    Sail & Swim from a Luxury Sailing Yacht

    Booked this as a last night surprise for my family and friends. On the day, it ended up being super cloudy and rainy but Cait was so great at letting us reschedule. Her communication was excellent throughout. We ended up pushing by a few days and got perfect weather. We had an amazing sunset sail. The boat was clean and comfortable. We sailed and stopped to swim as well. Captain Greg (Cait’s husband) was super friendly and knowledgeable. He was a pleasure to be around. I would highly recommend booking this trip. For us, it was a life changing experience.