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All listings near me

Find Sailing Charters Near You

4.8
(5,236 Reviews)

Page 5 of 10 • 240 listings

Charter 38' Pearson Cruising Monohull in Mamaroneck, New York
Sailing in Mamaroneck · 10 guests

Charter 38' Pearson Cruising Monohull in Mamaroneck, New York

5.0
$50/hour
Sailing Long Island Sound with Captain Steve onboard 34ft Beneteau Oceanis
Sailing in Port Washington · 6 guests

Sailing Long Island Sound with Captain Steve onboard 34ft Beneteau Oceanis

5.0
$169+/hour
Sail From Port Washington, NY with Hunter Passage 456 Sailing Yacht
Sailing in Port Washington · 12 guests

Sail From Port Washington, NY with Hunter Passage 456 Sailing Yacht

4.8
Superowner
$219/hour
Sail Long Island's Gold Coast on this beautiful 36' Jeanneau!
Sailing in Oyster Bay · 6 guests

Sail Long Island's Gold Coast on this beautiful 36' Jeanneau!

5.0
$225+/hour
Charter Sailboat Cruiser Motorsail Yacht, in Stamford, Connecticut
Tours in Stamford · 6 guests

Charter Sailboat Cruiser Motorsail Yacht, in Stamford, Connecticut

4.9
Superowner
$225+/hour
Sail From Northport or Huntington, NY
Sailing in Huntington · 12 guests

Sail From Northport or Huntington, NY

4.8
Superowner
$150/hour
Hunter Marine Passage 450 - Sail from Norwalk/Westport, CT
Sailing in Westport · 12 guests

Hunter Marine Passage 450 - Sail from Norwalk/Westport, CT

4.7
Superowner
$200/hour
Captained Charter 21ft Sailboat in Salisbury 2 person charter 2 hrs.
Sailing in Salisbury · 2 guests

Captained Charter 21ft Sailboat in Salisbury 2 person charter 2 hrs.

5.0
$85/hour
Captained Sailboat Charter in Salisbury 2 hr sails 4 persons
Sailing in Salisbury · 4 guests

Captained Sailboat Charter in Salisbury 2 hr sails 4 persons

5.0
$160/hour
Private Luxury Sailing in the Charleston Harbor — Captain Included, BYOB
Sailing in Charleston · 6 guests

Private Luxury Sailing in the Charleston Harbor — Captain Included, BYOB

5.0
Superowner
$240/hour
Luxury BYOB Sailing in the Charleston Harbor
Sailing in Charleston · 6 guests

Luxury BYOB Sailing in the Charleston Harbor

5.0
Superowner
$240/hour
Glastron GX185 Bowrider Rental in Saint Germain, Wisconsin
Powerboats in Wisconsin · 8 guests

Glastron GX185 Bowrider Rental in Saint Germain, Wisconsin

New
$449/day
Sunset Sail | Private 50ft Luxury Sailing Yacht in Charleston
Sailing in Mount Pleasant · 12 guests

Sunset Sail | Private 50ft Luxury Sailing Yacht in Charleston

5.0
$250/hour
Afternoon Sail | Private 50ft Jeanneau Sun Odyssey Sailing Yacht in Charleston
Sailing in Mount Pleasant · 12 guests

Afternoon Sail | Private 50ft Jeanneau Sun Odyssey Sailing Yacht in Charleston

New
$250/hour
3-Hour Morning Sail | Private 50ft Luxury Sailing Yacht in Charleston
Sailing in Mount Pleasant · 12 guests

3-Hour Morning Sail | Private 50ft Luxury Sailing Yacht in Charleston

New
$250/hour
Luxury 42ft Catamaran Sailing Charter in Charleston Harbor
Sailing in Mount Pleasant · 6 guests

Luxury 42ft Catamaran Sailing Charter in Charleston Harbor

5.0
Superowner
$235+/hour
Sunday Mimosa Brunch Sail: Shared Sail with Brunch Bites Included
Sailing in Mount Pleasant · 100 guests

Sunday Mimosa Brunch Sail: Shared Sail with Brunch Bites Included

New
$375/hour
Limited Availability
Shared Charleston Harbor Sunset Sail - 50ft Catamaran with Bar Onboard
Sailing in Mount Pleasant · 100 guests

Shared Charleston Harbor Sunset Sail - 50ft Catamaran with Bar Onboard

New
$375/hour
Limited Availability
Shared Party Boat Sail w/Bar: Charleston Harbor - Perfect for Bach or Birthday
Sailing in Mount Pleasant · 100 guests

Shared Party Boat Sail w/Bar: Charleston Harbor - Perfect for Bach or Birthday

5.0
$375/hour
Private Charter Charleston Harbor Sail - 55ft Catamaran with Bar Onboard
Sailing in Mount Pleasant · 100 guests

Private Charter Charleston Harbor Sail - 55ft Catamaran with Bar Onboard

New
$1,625+/hour
FOLLY BEACH CATAMARAN SUNSET SAIL, departing Folly River boat landing 190/hr
Sailing in Folly Beach · 6 guests

FOLLY BEACH CATAMARAN SUNSET SAIL, departing Folly River boat landing 190/hr

5.0
$200/hour
 CATAMARAN/DOLPHIN SAIL  FOLLY BEACH SC
Sailing in Folly Beach · 6 guests

CATAMARAN/DOLPHIN SAIL FOLLY BEACH SC

5.0
$190/hour
Sailing The Edge of America - Folly Beach
Sailing in Folly Beach · 6 guests

Sailing The Edge of America - Folly Beach

5.0
$200/hour
Tiki Bar, Hoppin, Sandbars, Down Island Vibes with Barrier island views
Powerboats in Folly Beach · 6 guests

Tiki Bar, Hoppin, Sandbars, Down Island Vibes with Barrier island views

New
Superowner
$150/hour

Local Sailing Reviews

  1. KM

    Kimberly

    Sunset Sail | Private 50ft Luxury Sailing Yacht in Charleston

    This boat was seriously so amazing and was the highlight of our trip to Charleston! The boat is fully stocked with ice, cups, and non alcoholic drinks. The inside area was super comfy and a great place to get some shade. The outside area of the boat was super spacious and had plenty of room. Highlight was seeing so many dolphins!

  2. MC

    Mia

    Sail From Northport or Huntington, NY

    Captain Mark hosted us for my boyfriend’s surprise birthday party. Mark was extremely easy to plan with, accommodatingly sailed out of a more convenient port for us, and took us to two swim spots! The day was described as “the best outing ever” by many of our friends.

  3. JP

    Jenny

    Charter 38' Pearson Cruising Monohull in Mamaroneck, New York

    I can’t say enough about how great this experience was! I celebrated my birthday, and it will definitely be one of the most memorable ones. The boat was beautiful, clean, and spacious. The best part was having Captain Rick on board. He was knowledgeable, kind, and made us feel very comfortable the entire time. He showed us around, shared interesting information, and made sure we had a smooth and relaxing sailing trip. Truly an unforgettable experience!

  4. PC

    Peter

    Charter 38' Pearson Cruising Monohull in Mamaroneck, New York

    Had a GREAT day on the sound with Captain Rick. His boat is in excellent condition clean comfortable and so well maintained. Rick is a very experienced sailor with whom we always felt safe. He showed us all over Long Island Sound, which he knows so well. I highly recommend Rick for a great day on the water!!

  5. PP

    PARNAZ

    Charter 38' Pearson Cruising Monohull in Mamaroneck, New York

    Captan Rick's boat trip was an incredible experience that I highly recommend ! The planning was flawless, offering a perfect blend of activities. Captan Rick excellent communication and warm demeanor made the journey even more enjoyable. This boat trip is a must-do for anyone looking for an unforgettable day on the water!

  6. KB

    Keisha

    Charter 38' Pearson Cruising Monohull in Mamaroneck, New York

    The boat is large enough to comfortably fit a group of 10. We learned some new terms and had a sailing lesson. Capt Rick is a great vibe and fits right in with the group from kids to adult, the experience was one of a kind. Boat is very well kept and has lots of lounging areas inside and outside.