We use cookies to improve your browsing experience.

And dolphins make us happy. Find out more about our cookies policy here.

All listings near me

Find Sailing Charters Near You

4.9(Average of 4,265 reviews in this area)
Page 2 of 10 (240 listings)
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
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
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
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
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
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
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
Bayliner Deck Boat Rental at Beltzville Lake!
Powerboats in Pennsylvania · 6 guests

Bayliner Deck Boat Rental at Beltzville Lake!

New
$115hour
38ft Dawson Sportfish in Norfolk Virginia
Sailing in Norfolk · 6 guests

38ft Dawson Sportfish in Norfolk Virginia

New
$725day
2018 Chaparral 21 H2O Sport ,tow tube available
Powerboats in Virginia Beach · 8 guests

2018 Chaparral 21 H2O Sport ,tow tube available

5.0
$100hour
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
Captained Sailing Adventure in Lacey Township, New Jersey
Sailing in Lacey Township · 6 guests

Captained Sailing Adventure in Lacey Township, New Jersey

New
$119hour
 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
$210-$250hour
Caribbean Vibez SPECIAL $220 x 2 hrs August 16th , 17th and 18th on a Brooklyn Sailboat
Sailing in Brooklyn · 4 guests

Caribbean Vibez SPECIAL $220 x 2 hrs August 16th , 17th and 18th on a Brooklyn Sailboat

5.0
Superowner
$191hour
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
$210-$250hour
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
Best of 2023
$265hour
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
$224-$298hour
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
Snoozed - Active 03 Apr 2024
Learn To Sail On The Moose with Pearson Ensign Sailing Yacht!
Sailing in Brooklyn · 4 guests

Learn To Sail On The Moose with Pearson Ensign Sailing Yacht!

5.0
$180hour
Classic Yacht Charter in New York, New York
Sailing in Manhattan · 30 guests

Classic Yacht Charter in New York, New York

5.0
$1,600hour

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. 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.