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Find Sailing Charters Near You

4.9
(4,263 Reviews)

Page 3 of 10240 listings

34ft Sailing Yacht in Annapolis, Maryland
Sailing in Annapolis · 4 guests

34ft Sailing Yacht in Annapolis, Maryland

New
$250hour
Beneteau Oceanis 50 Cruising Yacht in Rock Hall, Maryland
Sailing in Rock Hall · 6 guests

Beneteau Oceanis 50 Cruising Yacht in Rock Hall, Maryland

5.0
Superowner
$150hour
Fully Crewed Sailing Cruises Aboard 41' Sailboat in Rock Hall, MD
Sailing in Rock Hall · 4 guests

Fully Crewed Sailing Cruises Aboard 41' Sailboat in Rock Hall, MD

5.0
$150hour
34' Hunter Cruising Monohull In Rock Hall, Maryland United States
Sailing in Rock Hall · 4 guests

34' Hunter Cruising Monohull In Rock Hall, Maryland United States

4.5
$275-$375night
Starratt & Jenks Morgan 45ft Sailing Charter in Havre de Grace, MD - USCG Licensed Captain
Sailing in Havre de Grace · 6 guests

Starratt & Jenks Morgan 45ft Sailing Charter in Havre de Grace, MD - USCG Licensed Captain

New
$200hour
Learn to Sail in Havre de Grace, MD (Minutes off of I95 in Historic Havre de Grace, MD)
Tours in Havre de Grace · 2 guests

Learn to Sail in Havre de Grace, MD (Minutes off of I95 in Historic Havre de Grace, MD)

New
$200person
41’ Bristol Sailboat Charter in Solomons Island, MD
Sailing in Solomons · 6 guests

41’ Bristol Sailboat Charter in Solomons Island, MD

New
$90hour
Charter 41ft S/Y Selina II Sloop in St. Michaels, Maryland
Sailing in Saint Michaels · 6 guests

Charter 41ft S/Y Selina II Sloop in St. Michaels, Maryland

5.0
$250-$349hour
Sunset Champagne Cruise on the Chesapeake Bay
Sailing in Saint Michaels · 6 guests

Sunset Champagne Cruise on the Chesapeake Bay

New
$55person
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-$112hour
Bayliner Deck Boat Rental at Beltzville Lake!
Powerboats in Pennsylvania · 6 guests

Bayliner Deck Boat Rental at Beltzville Lake!

New
$115hour
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-$125hour
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
$125hour
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-$1,240day
Melges 24 - One Design Racing Experience Or Charter
Sailing in Hampton · 8 guests

Melges 24 - One Design Racing Experience Or Charter

5.0
Superowner
$200hour
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
$350hour
Fish On! Rent Your 38ft Dawson Sportfish in Norfolk, VA
Sailing in Norfolk · 6 guests

Fish On! Rent Your 38ft Dawson Sportfish in Norfolk, VA

New
$725day
2019 HOBIE MIRAGE ADVENTURE ISLAND SAILBOAT IN GREENSBORO
Sailing in Georgia · 2 guests

2019 HOBIE MIRAGE ADVENTURE ISLAND SAILBOAT IN GREENSBORO

New
$40hour
Captained Sailing Adventure in Lacey Township, New Jersey
Sailing in Lacey Township · 6 guests

Captained Sailing Adventure in Lacey Township, New Jersey

New
$119hour
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

New
$99hour
 Come Play and Sail Away Barnegat Bay!
Sailing in Lacey Township · 6 guests

Come Play and Sail Away Barnegat Bay!

5.0
$150hour
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
$120hour
Sail from Atlantic Highlands, NJ - $265/Hour - $44/Person
Sailing in Atlantic Highlands · 6 guests

Sail from Atlantic Highlands, NJ - $265/Hour - $44/Person

4.0
Superowner
Best of 2023
$265hour
Sail New York's historic waterways aboard Water Music, a classic, semi-custom 40 foot Passport yacht.
Sailing in Brooklyn · 6 guests

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

5.0
Snoozed - Active 02 Jul 2024

Local Sailing Reviews

  1. LR

    Loretta

    Beneteau Oceanis 50 Cruising Yacht in Rock Hall, Maryland

    What a gorgeous day on the water aboard Sol Searcher! Captain Joe was an awesome host for our day! Peaceful, serene and exactly what we were hoping for to bring the summer to a close. What a lovely world we have to enjoy when we step away from the hustle of life and take the opportunity to take in all that it has to offer. Thank you Capt’n Joe for a wonderful sailing experience. Until we meet again, Loretta and Greg

  2. CR

    Chad

    Beneteau Oceanis 50 Cruising Yacht in Rock Hall, Maryland

    For our wedding anniversary, I wanted to try to do something that we'd never done before. Getting a chartered boat for a day cruise along the Chesapeake Bay was certainly a memorable way to spend the day, in no small part due to the efforts of Cap'n Joe. The weather was wonderful, which he had nothing to do with, but he took us on a wonderful round trip on the Bay so we could get back to our son on-time in the evening. The vessel was magnificent! It was well worth the expense and was honestly impressive. I'd definitely do this again with friends. Simply outstanding.

  3. WD

    William

    Beneteau Oceanis 50 Cruising Yacht in Rock Hall, Maryland

    Sailing with Captain Joe was like spending an afternoon sailing with your buddy Joe. Friendly, gracious, knowledgeable, and highly skilled Joe made for a relaxing and enjoyable sail. The Beneteau is a very comfortable and roomy boat and we would definitely book another sail with him!

  4. IW

    Ian

    Beneteau Oceanis 50 Cruising Yacht in Rock Hall, Maryland

    We had a great afternoon sail with Captain Joe, followed by some swimming off the boat at the end of the day. Our three kids had a great time, from some time at the helm, hanging out on the bow, and swimming at the end of the day, we all enjoyed every moment. Captain Joe was attentive, a great communicator, and flexible in figuring out the itinerary. I highly recommend a sail on the bay with Captain Joe!

  5. Tatsiana

    Tatsiana

    Beneteau Oceanis 50 Cruising Yacht in Rock Hall, Maryland

    We can't wait to come back and experience new marine adventures with Captain Joe and his Sol Searcher again. According to my 13 y.o. kid, it was one of the best birthdays she has ever had. The sailboat is so beautiful, spacious, and comfortable. Captain Joe was very hospitable, friendly, and considerate. He told us a lot about sailing and made my daughter's dream come true - we saw a rare and hardly accessible caisson structure Baltimore Harbor Lighthouse. It was amazing! Upon return we had some delicious brownies baked by Joe's wife. Always appreciate a personal touch. We felt very welcome and had a great time! Highly recommend this captain and his gorgeous sailboat!

  6. Kyle

    Kyle

    Beneteau Oceanis 50 Cruising Yacht in Rock Hall, Maryland

    Captain Joe is an excellent sailor and has great communication. When I booked the private charter I reached out to let Joe know that I would be proposing on his vessel, we had a few date changes that joe worked through with me flawlessly. The pictures on the listing do not do this boat and captain justice! 10/10 would recommend!