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All listings near me

Find Sailing Charters Near You

4.9
(4,197 Reviews)

Page 5 of 10240 listings

27 Foot Sailboat for a Day of Fun in the Sun in Toronto
Sailing in Toronto · 6 guests

27 Foot Sailboat for a Day of Fun in the Sun in Toronto

5.0
$55person
41' Beneteau Oceanis Sailing Yacht in Toronto for 12 Guests
Sailing in Toronto · 12 guests

41' Beneteau Oceanis Sailing Yacht in Toronto for 12 Guests

New
$435hour
28' Sailboat for 5 guests in Toronto
Sailing in Toronto · 5 guests

28' Sailboat for 5 guests in Toronto

New
$235hour
Fountain Pajot Astrea Luxury 42' Catamaran for Charter
Sailing in Toronto · 18 guests

Fountain Pajot Astrea Luxury 42' Catamaran for Charter

5.0
$1,000-$1,300hour
38' Sailing Yacht in Toronto, Ontario
Sailing in Toronto · 8 guests

38' Sailing Yacht in Toronto, Ontario

New
$400hour
Sailing Charter in Toronto
Sailing in Toronto · 6 guests

Sailing Charter in Toronto

5.0
Snoozed - Active 17 Apr 2024
35ft C&C 35 Sailboat in Toronto
Sailing in Etobicoke · 6 guests

35ft C&C 35 Sailboat in Toronto

5.0
$185hour
Sailing Charters in Wilmington NC
Sailing in Wilmington · 6 guests

Sailing Charters in Wilmington NC

5.0
$89person
Discover the Magic of Sailing: Private Tours for Every Occasion
Sailing in Scarborough · 4 guests

Discover the Magic of Sailing: Private Tours for Every Occasion

5.0
$74hour
Able Custom 42' Chartered Sailing Experience in Stonington, CT
Sailing in Stonington · 3 guests

Able Custom 42' Chartered Sailing Experience in Stonington, CT

New
$200-$215hour
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
$1,500day
4 or 8 Hour Sails on Narragansett Bay on Seafarer Swiftsure Yacht!
Sailing in North Kingstown · 6 guests

4 or 8 Hour Sails on Narragansett Bay on Seafarer Swiftsure Yacht!

5.0
$150hour
Sailing Lesson in Little River, South Carolina
Tours in Little River · 1 guest

Sailing Lesson in Little River, South Carolina

New
$360hour
Sunset Cruise in Myrtle Beach, South Carolina
Sailing in Little River · 6 guests

Sunset Cruise in Myrtle Beach, South Carolina

5.0
$450hour
Ocean Inlet Captained Charter onboard Beneteau 39 Sailboat in Little River, South Carolina
Sailing in Little River · 6 guests

Ocean Inlet Captained Charter onboard Beneteau 39 Sailboat in Little River, South Carolina

5.0
$150hour
Sailing in Newport- Catalina 320 Sailboat with Captain Kenneth & Captain Perrin
Sailing in Newport · 6 guests

Sailing in Newport- Catalina 320 Sailboat with Captain Kenneth & Captain Perrin

5.0
$200hour
Custom Sailing Charter - Newport/ Block Island
Sailing in Newport · 6 guests

Custom Sailing Charter - Newport/ Block Island

5.0
$290hour
42ft J Boat Sailing Yacht in Newport, Rhode Island
Sailing in Newport · 4 guests

42ft J Boat Sailing Yacht in Newport, Rhode Island

5.0
$260hour
Private Sailing Charter Newport, Bristol RI | Captain and Crew
Sailing in Newport · 6 guests

Private Sailing Charter Newport, Bristol RI | Captain and Crew

New
$120-$175hour
Instant Book
41' Catana Cruising Catamaran for Charter in Newport, RI
Sailing in Newport · 6 guests

41' Catana Cruising Catamaran for Charter in Newport, RI

5.0
$290hour
Spectacular Sailing in Newport, RI Aboard our 36' Catalina Sailing Yacht
Sailing in Newport · 6 guests

Spectacular Sailing in Newport, RI Aboard our 36' Catalina Sailing Yacht

5.0
$200hour
Enjoy Lake Simcoe on Lowe Cruise 1600 Pontoon!
Powerboats in Georgina · 7 guests

Enjoy Lake Simcoe on Lowe Cruise 1600 Pontoon!

5.0
Snoozed - Active 02 May 2024
Sail World-Famous Newport & Narragansett Bay Aboard Tartan 34 Classic
Sailing in East Providence · 6 guests

Sail World-Famous Newport & Narragansett Bay Aboard Tartan 34 Classic

4.0
$200hour
43' Sailboat, Bristol RI & Beyond
Sailing in Bristol · 6 guests

43' Sailboat, Bristol RI & Beyond

New
$199hour

Local Sailing Reviews

  1. ES

    Emily

    Sailing Charter in Toronto

    We had an incredible trip on Dom's boat! We went out for my partner's birthday (2 of us). Dom is an amazing host and made us feel welcome from the start. He let us help with the sails and asked our input on where to go based on the wind. We had such a great experience and would recommend him to anyone!

  2. ZF

    Zachary

    Sailing Charter in Toronto

    Captain Dom was an incredible host! If I could give 6/5 stars I would. He communication was excellent, he was welcoming, kind, safe and wanted to ensure we all got we needed when on board. His boat is excellent quality and we definitely got more than we asked for. 100% would recommend to anyone, and definitely will do again. Cheers!

  3. James

    James

    35ft C&C 35 Sailboat in Toronto

    Peter is a great skipper and host. We thoroughly enjoyed the trip. His boat was spotless and well maintained. He was very knowledgeable about the area and his sailing skills were superb. Certainly would recommend this to anyone especially people never having sailed before.

  4. BS

    Brooke

    Sailing Charters in Wilmington NC

    Oliver is an amazing captain! My husband and I celebrated our anniversary aboard Oliver’s sailboat and it was an amazing experience. He’s extremely personable, knowledgeable, and safe! We loved having the opportunity to help steer, put sails up, and dock the boat. We also loved the relaxing moments where we could soak up the sun and the view! We will definitely be booking other Oliver again and highly suggest him for anyone looking to do a boat ride in Wilmington. This is a must do!!

  5. JK

    Jorn

    Sailing Charters in Wilmington NC

    I would recommend this to anyone that would like the experience and feeling of being on a sailboat in a safe and peaceful manner. Captain Oliver was knowledgeable and a very pleasant person. More wind would have been appreciated but who’s in control of that.

  6. 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!