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Find Sailing Charters Near You

4.9
(4,499 Reviews)

Page 2 of 10240 listings

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
$150/hour
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
$150/hour
Relaxing historic sailing experience in St. Michaels, Maryland - Half Day Sail
Sailing in Saint Michaels · 6 guests

Relaxing historic sailing experience in St. Michaels, Maryland - Half Day Sail

5.0
$325/hour
Romantic Sunset Champagne Cruise on the Chesapeake Bay - 2 Hours
Sailing in Saint Michaels · 6 guests

Romantic Sunset Champagne Cruise on the Chesapeake Bay - 2 Hours

New
$400/hour
50ft Catamaran Charter with Water Toys in St. Michaels, MD
Sailing in Saint Michaels · 12 guests

50ft Catamaran Charter with Water Toys in St. Michaels, MD

New
$525/hour
Experience the Charm of St. Michaels Aboard the 41ft Sail Selina 2hr Boat Tour
Sailing in Saint Michaels · 6 guests

Experience the Charm of St. Michaels Aboard the 41ft Sail Selina 2hr Boat Tour

New
$350/hour
41’ Bristol Sailboat Charter in Solomons Island, MD
Sailing in Solomons · 6 guests

41’ Bristol Sailboat Charter in Solomons Island, MD

New
$90/hour
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
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
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
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
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
Melges 24 - One Design Racing Experience
Sailing in Hampton · 8 guests

Melges 24 - One Design Racing Experience

5.0
Superowner
$100/hour
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
$725/day
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
$149/hour
Instant Book
 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
56' SeaRay Yacht in New York!
Events in New York · 12 guests

56' SeaRay Yacht in New York!

4.7
$475/hour
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
$265/hour
Family fun Bayliner boat NJ/NYC
Powerboats in Jersey City · 9 guests

Family fun Bayliner boat NJ/NYC

5.0
Snoozed - Active 03 Apr 2025
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
$225+/hour
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
Sail from Jersey City, NJ - $265/Hour - $44/Person
Sailing in Manhattan · 6 guests

Sail from Jersey City, NJ - $265/Hour - $44/Person

5.0
Superowner
$265/hour
Set sail on NY Harbor aboard this beautiful and luxurious Ericson sloop!
Sailing in Manhattan · 6 guests

Set sail on NY Harbor aboard this beautiful and luxurious Ericson sloop!

5.0
Snoozed - Active 04 May 2025

Local Sailing Reviews

  1. George

    George

    Beneteau Oceanis 50 Cruising Yacht in Rock Hall, Maryland

    HIGHLY recommend Capt Joe for a fantastic sailing experience out of Rock Hall. Joe worked with us to get a last-minute booking when another booking fell through. He and his crew are experts and you will not be disappointed. He let us take the helm and participate as much or as little as we wanted to. Sol Searcher is a beautiful, well-equipped boat - plenty of comfort and speed (wind dependent of course.)

  2. 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

  3. 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.

  4. 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!

  5. 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!

  6. 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!