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All listings near me

Find Sailing Charters Near You

4.9
(755 Reviews)

Page 1 of 368 listings

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
SEARAY SLX400 | $800hr | 13 People
Events in Washington · 13 guests

SEARAY SLX400 | $800hr | 13 People

5.0
Superowner
Best of 2025
$800/hour
Instant Book
Charter 44' Orana Cruising Catamaran In Deale, Maryland
Sailing in Deale · 10 guests

Charter 44' Orana Cruising Catamaran In Deale, Maryland

5.0
$250+/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
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
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
Sail Long Island's Gold Coast on this beautiful 36' Jeanneau!
Sailing in Oyster Bay · 6 guests

Sail Long Island's Gold Coast on this beautiful 36' Jeanneau!

5.0
$200+/hour
Instant Book
Luxury Stylish Poontoon
Powerboats in Cornelius · 8 guests

Luxury Stylish Poontoon

New
$150/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
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
Affordable Yacht 27' Doral in Toronto
Events in Etobicoke · 10 guests

Affordable Yacht 27' Doral in Toronto

New
$110+/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
$330/hour
Instant Book
Custom Sailing Charter - Newport/ Block Island
Sailing in Newport · 6 guests

Custom Sailing Charter - Newport/ Block Island

5.0
$290/hour
Instant Book
Private Charters on Classic 80' Sailing Schooner in Salem, Massachusetts
Sailing in Salem · 6 guests

Private Charters on Classic 80' Sailing Schooner in Salem, Massachusetts

5.0
$550/hour
Instant Book
Luxury BYOB Sailing in the Charleston Harbor
Sailing in Charleston · 6 guests

Luxury BYOB Sailing in the Charleston Harbor

5.0
Superowner
$220/hour
Instant Book
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
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
Enjoy beautiful Maine at Damariscotta Lake with Mariah SX19 Bowrider!
Powerboats in Nobleboro · 8 guests

Enjoy beautiful Maine at Damariscotta Lake with Mariah SX19 Bowrider!

New
$260+/day
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

Local Sailing Reviews

  1. TA

    Tanisha

    Fun family time Jet Ski Rentals at Lake Norman, NC

    Breyanna was amazing , she made sure to throughly go over all rules and regulations before we hit the water to make sure we were comfortable and have the best experience. We have already planned to rent through her again before the summer is over and in the future.

  2. Marie

    Marie

    38-ft Hunter 376 Sailing Adventure in Annapolis

    We thoroughly enjoyed our time with Alberto and his wife, Grace. Alberto is a delight to sail with - we learned so much from him. Grace is so lovely and gracious. We sailed around Annapolis during Memorial Day weekend and the weather was perfect. Alberto was very accommodating and friendly. We hope to see you again soon!

  3. Sam

    Sam

    38-ft Hunter 376 Sailing Adventure in Annapolis

    Captain Alberto is a wonderful Captain. Handles the boat with an expert confidence and was also a willing and kind teacher to my two kids who had millions of questions.

  4. DeWitt

    DeWitt

    38-ft Hunter 376 Sailing Adventure in Annapolis

    We had a great afternoon with wonderful hosts. They were great company, so friendly and went out of their way to help make a terrific time.

  5. 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.

  6. BD

    Beyonce

    The Only 40ft Hinckley Sailboat in Manhattan

    The scenery and the whole experience were great!!! Loved everything about it.