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All listings near me

Find Sailing Charters Near You

4.9
(4,731 Reviews)

Page 3 of 10240 listings

41’ Bristol Sailboat Charter in Solomons Island, MD
Sailing in Solomons · 6 guests

41’ Bristol Sailboat Charter in Solomons Island, MD

New
$90/hour
Private Sail Up to 13 Guests | 44ft Leopard Catamaran
Sailing in Saint Michaels · 13 guests

Private Sail Up to 13 Guests | 44ft Leopard Catamaran

New
$580/hour
Private Historic 1935 Ketch Sail | 13 People | Gratuity & Tax Included
Sailing in Saint Michaels · 13 guests

Private Historic 1935 Ketch Sail | 13 People | Gratuity & Tax Included

New
$645/hour
Private Sail on 44ft Leopard Catamaran | 6 People | Gratuity & Tax Included
Sailing in Saint Michaels · 6 guests

Private Sail on 44ft Leopard Catamaran | 6 People | Gratuity & Tax Included

New
$585/hour
Sunset Sail or Daytime Cruise on 33' Endeavour Yacht - Chesapeake Bay, MD
Sailing in Maryland · 6 guests

Sunset Sail or Daytime Cruise on 33' Endeavour Yacht - Chesapeake Bay, MD

New
$85/hour
Sailing Adventures on the Choptank River
Sailing in Cambridge · 6 guests

Sailing Adventures on the Choptank River

New
$100/hour
Catamaran |15 People |Choptank River
Sailing in Maryland · 15 guests

Catamaran |15 People |Choptank River

New
Superowner
$700/hour
Chesapeake Bay Sailing (w/ Captain) - 33' Cape Dory - Kilmarnock, Virginia
Sailing in Kilmarnock · 4 guests

Chesapeake Bay Sailing (w/ Captain) - 33' Cape Dory - Kilmarnock, Virginia

5.0
$15+/hour
Let's Go Sail in Gloucester Point, Virginia
Sailing in Gloucester Point · 6 guests

Let's Go Sail in Gloucester Point, Virginia

5.0
Superowner
$117+/hour
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
Sail the Chesapeake Bay, Atlantic Coast or the Caribbean Islands in style! Charter this Jeanneau Sun Odyssey 509
Sailing in Deltaville · 8 guests

Sail the Chesapeake Bay, Atlantic Coast or the Caribbean Islands in style! Charter this Jeanneau Sun Odyssey 509

New
$524+/day
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
$326/hour
Melges 24 - One Design Racing Experience
Sailing in Hampton · 5 guests

Melges 24 - One Design Racing Experience

5.0
Superowner
$100/hour
Bayliner Deck Boat Rental at Lake wallenpaupack!
Powerboats in Pennsylvania · 6 guests

Bayliner Deck Boat Rental at Lake wallenpaupack!

New
$115/hour
Sunset Sail - Philadelphia Waterfront with O'Day 322 Sailing Yacht
Sailing in Philadelphia · 6 guests

Sunset Sail - Philadelphia Waterfront with O'Day 322 Sailing Yacht

5.0
$350/hour
 Come Play and Sail Away Barnegat Bay!
Sailing in Lacey Township · 6 guests

Come Play and Sail Away Barnegat Bay!

5.0
$150/hour
2006 Hunter 44’ Sloop Sailing Charter In Island Heights, New Jersey
Sailing in Island Heights · 6 guests

2006 Hunter 44’ Sloop Sailing Charter In Island Heights, New Jersey

5.0
$120/hour
Relax, feel free & sail into a nautical world of Wonder - Hunter 36 Sailboat
Sailing in Berkeley Township · 6 guests

Relax, feel free & sail into a nautical world of Wonder - Hunter 36 Sailboat

New
$125/hour
Charter our J-35 Sailboat, Blue Mind @ Northwest Creek Marina in New Bern NC
Sailing in Morehead City · 6 guests

Charter our J-35 Sailboat, Blue Mind @ Northwest Creek Marina in New Bern NC

New
$100/hour
Cruise on the Blue Mind J35 Sailboat for 6 guests
Sailing in Morehead City · 6 guests

Cruise on the Blue Mind J35 Sailboat for 6 guests

New
$90/hour
Chaparral 256 Family Cabin Cruiser
Powerboats in Jersey City · 9 guests

Chaparral 256 Family Cabin Cruiser

5.0
$275/hour
Sail New York's historic waterways aboard Water Music, a classic 40 foot yacht.
Sailing in Brooklyn · 6 guests

Sail New York's historic waterways aboard Water Music, a classic 40 foot yacht.

5.0
Snoozed - Active 02 Jan 2027
Private Sail Charter of NYC Skyline and Statue of Liberty
Sailing in Manhattan · 6 guests

Private Sail Charter of NYC Skyline and Statue of Liberty

New
$250+/hour
ASA Practice Sailing Exercises | 30ft C&C
Tours in Manhattan · 6 guests

ASA Practice Sailing Exercises | 30ft C&C

New
$150/hour

Local Sailing Reviews

  1. JF

    Joshua

    Chaparral 256 Family Cabin Cruiser

    we highly recommend eli as a captain - he was very accommodating & easy communication, great boat and enjoyable experience! 5+ star!

  2. EM

    Erin

    Chesapeake Bay Sailing (w/ Captain) - 33' Cape Dory - Kilmarnock, Virginia

    Our trip was just perfect. We were looking for a true sailing experience, and Captain Russ gave us that. My husband was at the wheel almost the entire trip, talking all things sailing Capt Russ. Meanwhile I enjoyed the sun and sounds of the water against the boat and the wind in the sails from up front. It was a peaceful and enjoyable trip, despite the wind giving out on us towards the end. We'd book with Captain Russ again in a heartbeat!

  3. Thomas

    Thomas

    Chesapeake Bay Sailing (w/ Captain) - 33' Cape Dory - Kilmarnock, Virginia

    Captain Russ was just ideal for our half day on the bay! Super pleasant and communicative; completely adaptive to whatever we were up for. The Joie de Vie is ship-shape and the perfect vessel for the Chesapeake Bay. I’ll go ahead and credit him with steady 5-6k winds All day also- just a perfect day. No doubt we will be back for more- thanks again, Captain Russ!

  4. JP

    John

    Let's Go Sail in Gloucester Point, Virginia

    Captain Bill was a fantastic host for our inaugural sailing adventure in the York River out of Gloucester Point, VA. We booked him for a Saturday afternoon in June for a 2:30 to 5:30 cruise and it was everything we could have asked for and more. He explained the region's waters and relation to the Chesapeake Bay as well as the naval and nautical history of the area in addition to teaching us about his boat and how to sail it properly. We wanted to be immersed in the experience and he let us be very hands on, giving direction for assisting with deploying the sails, commanding the helm, reading the wind and performing the tacking maneuvers while being at the helm. We also had a chance to relax on the forward section of the deck as Bill took over, he passed our libations to us and helped us enjoy the experience of sailing while soft music played that even invited an interaction with one of the regions local dolphin who accompanied and entertained us for well over a half an hour on our return up the river. What an awesome way to spend an afternoon.

  5. DH

    Dan

    Let's Go Sail in Gloucester Point, Virginia

    Bill was awesome. Very communicative leading up to the sail with weather, directions, and other logistical specifics. The trip left and returned on time, Bill was very knowledgeable about the boat and the area, let my wife and I take the helm several times and the boat was in great condition. Would totally sail with Cpt Bill again.

  6. BS

    Bill

    Charter 32' Modern Hunter Sailboat In Gloucester, Point Virginia

    I highly recommend a sail with Captain Bill. The entire experience was exciting and relaxing at the same time. Whether an experienced sailor or a novice with boats, just being on the open water will refresh and invigorate. 5 ⭐️⭐️⭐️⭐️⭐️