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Find Sailing Charters Near You

4.9
(4,783 Reviews)

Page 2 of 10240 listings

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
Woman-owned luxury with transparent pricing - read our 5-star reviews!
Sailing in Manhattan · 6 guests

Woman-owned luxury with transparent pricing - read our 5-star reviews!

5.0
$285/hour
Classic Yacht Charter in New York, New York
Sailing in Manhattan · 30 guests

Classic Yacht Charter in New York, New York

5.0
$1,800/hour
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

Local Sailing Reviews

  1. EM

    Erin

    Chesapeake Bay Sailing Charter - 33' Cape Dory Sailing from 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!

  2. Thomas

    Thomas

    Chesapeake Bay Sailing Charter - 33' Cape Dory Sailing from 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!

  3. CH

    Cyndi

    Charter 32' Modern Hunter Sailboat In Gloucester, Point Virginia

    My family of 5 had a wonderful day sailing with Bill to celebrate my husband's 40th birthday. Bill was very knowledgeable and excellent at explaining things to my children, even letting them each take the helm. We felt very at ease and safe our entire trip. I am already recommending him to friends.

  4. LN

    Linda

    Charter 32' Modern Hunter Sailboat In Gloucester, Point Virginia

    Mom, Dad, & three GROWN children went out on a wonderful outing with Captain Bill. He was a gracious host & his beautiful sailboat was spectacular! Enjoyed the experience immensely & seriously considering sailing lessons next spring. His boat was not only in immaculate condition but very comfortable for all five adults (plus the amiable captain). We were thrilled to see dolphins and hear about the area's history. We sailed 14.9 memorable miles. I gave a 5 star rating because the ratings don't go to 10. Honestly, how does one rate a great memory that lasts a lifetime? We weren't sure if the weather was going to be a wash out for a few days out, but Captain Bill kept in contact via email with weather updates and was extremely accommodating to what would work best for us. The weather wasn't what one would call picture perfect but I thought it was awesome having so much of the water to ourselves. We only saw one other sailboat. This was an exhilarating experience with a knowledgeable captain and I can't recommend him enough!

  5. JM

    Josh

    Charter 32' Modern Hunter Sailboat In Gloucester, Point Virginia

    I had my four children with me ages 5 to 12 the captain was very kind and understanding to them teaching them new things my son it was comfortable taking the helm and the captain enjoy teaching him the other kids not so much but that was okay however not to be prejudiced because they are my children but they are exceptionally good kids my youngest commented that she was upset she would not be seeing Captain bill the next day and on how much she liked him. we will be back to sail in August we learned about the wind the ocean and how to read it wheeler and practical knowledge and history of the area The boat was beautiful the captain was awesome it was a great day my kids will remember forever I am not one to give A+ review without truly meaning it

  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 ⭐️⭐️⭐️⭐️⭐️