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All listings near me

Find Sailing Charters Near You

4.9
(5,112 Reviews)

Page 5 of 10240 listings

Sailboat on the Hudson
Sailing in Ossining · 6 guests

Sailboat on the Hudson

New
$120+/hour
Sail NYC in Style: Luxury Private Charter Aboard the Sleek NEEL 47 Trimaran
Sailing in Bronx · 12 guests

Sail NYC in Style: Luxury Private Charter Aboard the Sleek NEEL 47 Trimaran

New
$813+/hour
Cruising Monohull Rental in Kingston
Sailing in Kingston · 6 guests

Cruising Monohull Rental in Kingston

5.0
$125/hour
2 Hour Sunset Sail in Wrightsville Beach
Sailing in Wrightsville Beach · 6 guests

2 Hour Sunset Sail in Wrightsville Beach

New
$175/hour
Sunset C&C Sailboat cruise outside of NYC: the beauty of Long Island!
Sailing in Bronx · 6 guests

Sunset C&C Sailboat cruise outside of NYC: the beauty of Long Island!

New
$150/hour
ASA practice sailing exercizes
Tours in Bronx · 6 guests

ASA practice sailing exercizes

New
$150/hour
Fun in the Sun with Manhattan skyline in the background
Sailing in Bronx · 6 guests

Fun in the Sun with Manhattan skyline in the background

New
$150/hour
Shamrock-Classic 42 foot Allied XL Yawl Wilmington, NC
Sailing in Wilmington · 6 guests

Shamrock-Classic 42 foot Allied XL Yawl Wilmington, NC

5.0
$350/hour
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 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
$190+/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
Sailing JOURNEY on the Sound
Sailing in Stamford · 6 guests

Sailing JOURNEY on the Sound

New
$262/hour
Sail From Northport or Huntington, NY
Sailing in Huntington · 12 guests

Sail From Northport or Huntington, NY

4.8
Superowner
$150/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
Glastron GX185 Bowrider Rental in Saint Germain, Wisconsin
Powerboats in Wisconsin · 8 guests

Glastron GX185 Bowrider Rental in Saint Germain, Wisconsin

New
$449/day
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
$220/hour
Luxury BYOB Sailing in the Charleston Harbor
Sailing in Charleston · 6 guests

Luxury BYOB Sailing in the Charleston Harbor

5.0
Superowner
$220/hour
The Rainbow Boat: 23ft Catboat with Captain Ryan
Sailing in Charleston · 6 guests

The Rainbow Boat: 23ft Catboat with Captain Ryan

New
$174/hour
Pearson 42ft Sailboat | Charleston Sailing Trip
Sailing in Charleston · 6 guests

Pearson 42ft Sailboat | Charleston Sailing Trip

New
Superowner
$250/hour
Charleston's Largest Private Luxury Sailing Yacht 50ft Windchaser Custom Cruises
Sailing in Mount Pleasant · 12 guests

Charleston's Largest Private Luxury Sailing Yacht 50ft Windchaser Custom Cruises

New
$250/hour
40 ft Luxury Catamaran Sailing Yacht in Charleston
Sailing in Mount Pleasant · 6 guests

40 ft Luxury Catamaran Sailing Yacht in Charleston

5.0
Superowner
$225+/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
$135/hour

Local Sailing Reviews

  1. dh

    deborah

    Cruising Monohull Rental in Kingston

    We had a wonderful time sailing with Karins family! They were very friendly, easygoing and so knowledgeable, made us very comfortable and they were great about social distancing/COVID conscious. We were able to relax and enjoy the ride at the bow with comfy seats provided and we brought our own snacks. The weather was beautiful and the whole experience couldn’t have been better. Definitely a highlight of our stay in Kingston. We can’t wait to be back for another sail! Many thanks :)

  2. MA

    Megan

    Shamrock-Classic 42 foot Allied XL Yawl Wilmington, NC

    James was so accommodating for our elopement on his sailboat. He was always quick to respond and great at communicating with us. We really enjoyed our trip on the water and James made it easy for us to be comfortable and sit and relax. It was perfect!

  3. 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!

  4. 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.

  5. DE

    Desireé

    Charter 38' Pearson Cruising Monohull in Mamaroneck, New York

    Captain Rick was excellent!!! He is a skilled and patient captain. We had so much fun on the trip. Lots of laughs and great conversations. This day could not get any better. The boat and amenities were as advertised. I will definitely book this trip again with Captain Rick!

  6. Brooke

    Brooke

    Charter 38' Pearson Cruising Monohull in Mamaroneck, New York

    Capt. Rick was so fun! His knowledge of sailing and expertise made him a wonderful guide. Plus he is so personable! You can tell he really enjoys the water and loves to share the joys of being on the water with his guests! The boat was great and well outfitted! Such a wonderful experience!! I highly recommend! The trip on Capt. Ricks boat was so memorable and special! It made my 40th birthday an event to remember!