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All listings near me

Find Sailing Charters Near You

4.9
(4,886 Reviews)

Page 2 of 10240 listings

Affordable Yacht 27' Doral in Toronto
Events in Etobicoke · 10 guests

Affordable Yacht 27' Doral in Toronto

5.0
$158+/hour
Sail Lake Michigan from Racine, WI
Sailing in Racine · 6 guests

Sail Lake Michigan from Racine, WI

5.0
$75/hour
Sail in downtown Toronto
Sailing in Toronto · 6 guests

Sail in downtown Toronto

5.0
Snoozed - Active 17 Apr 2026
28' Sailboat for 5 guests in Toronto
Sailing in Toronto · 5 guests

28' Sailboat for 5 guests in Toronto

New
$300/hour
Discover Sailing 3hr Introductory Sail
Sailing in Toronto · 4 guests

Discover Sailing 3hr Introductory Sail

4.5
$69/hour
90min Champagne Sail
Sailing in Toronto · 12 guests

90min Champagne Sail

New
$75/hour
38' Sailing Yacht in Toronto, Ontario
Sailing in Toronto · 8 guests

38' Sailing Yacht in Toronto, Ontario

New
$450/hour
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
$50/hour
Come Experience the ambient waters of the Potomac on the Sylvan MIRAGE Pontoon!
Powerboats in Washington · 6 guests

Come Experience the ambient waters of the Potomac on the Sylvan MIRAGE Pontoon!

5.0
$185/hour
Sail on the Potomac in Washington, DC aboard the 28ft Hunter Sailboat
Sailing in Washington · 6 guests

Sail on the Potomac in Washington, DC aboard the 28ft Hunter Sailboat

New
$280/hour
Fun time Jet Ski Rental at Lake Norman, NC near Charlotte
Water Sports in Cornelius · 8 guests

Fun time Jet Ski Rental at Lake Norman, NC near Charlotte

4.9
$90/hour
SEARAY SLX400 | $650hr | 13 People
Events in Washington · 13 guests

SEARAY SLX400 | $650hr | 13 People

5.0
Superowner
$650/hour
Captained Charter 30' Sailboat in Milwaukee, Wisconsin
Sailing in Milwaukee · 6 guests

Captained Charter 30' Sailboat in Milwaukee, Wisconsin

5.0
$150/hour
Hunter 216 Sailboat for rent in McKinley Marina, Milwaukee WI
Sailing in Milwaukee · 6 guests

Hunter 216 Sailboat for rent in McKinley Marina, Milwaukee WI

New
$120/hour
Charter this beautiful Catalina from Milwaukee, WI - Captain Included
Sailing in Milwaukee · 6 guests

Charter this beautiful Catalina from Milwaukee, WI - Captain Included

4.8
$150/hour
2022 Chaparral 23' SSI  - Get up to 6 captained up and down the Potomac River
Powerboats in Fort Washington · 6 guests

2022 Chaparral 23' SSI - Get up to 6 captained up and down the Potomac River

5.0
$150+/hour
Charter 42' Lagoon Catamaran in Annapolis, MD
Sailing in Arnold · 12 guests

Charter 42' Lagoon Catamaran in Annapolis, MD

5.0
$425/hour
Come Aboard and Sail Optimystic-Experience the breeze w/Lunch, Wine and Cheese
Sailing in Essex · 6 guests

Come Aboard and Sail Optimystic-Experience the breeze w/Lunch, Wine and Cheese

5.0
$150/hour
VIKO 30 Premium Sailing Yacht In Deale, MD
Sailing in Deale · 5 guests

VIKO 30 Premium Sailing Yacht In Deale, MD

New
$925/day
Hunter Passage 42' Sailboat - Take your Dream Sailing Lessons on Chesapeake Bay
Sailing in Mayo · 6 guests

Hunter Passage 42' Sailboat - Take your Dream Sailing Lessons on Chesapeake Bay

5.0
$150+/hour
Charter 44' Orana Cruising Catamaran In Deale, Maryland
Sailing in Deale · 10 guests

Charter 44' Orana Cruising Catamaran In Deale, Maryland

5.0
$250+/hour
 VIKO S 35 Sailboat in Deale
Sailing in Deale · 6 guests

VIKO S 35 Sailboat in Deale

New
$298/hour
New Yacht Charter Bali 5.4 Sailing Catamaran in Annapolis Maryland
Sailing in Annapolis · 13 guests

New Yacht Charter Bali 5.4 Sailing Catamaran in Annapolis Maryland

5.0
$1,100/hour
38-ft Hunter 376 Sailing Adventure in Annapolis
Sailing in Annapolis · 6 guests

38-ft Hunter 376 Sailing Adventure in Annapolis

5.0
Superowner
$100+/hour

Local Sailing Reviews

  1. BG

    Ben

    Affordable Yacht 27' Doral in Toronto

    Gino and his dad took us out on their boat to the island off the city, where they anchored and we could swim into the beach. We got amazing views of the skyline on the way, and then on the way back they took us even closer to the city before looping back to the dock. Great experience!

  2. ES

    Emily

    Sail in downtown 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!

  3. ZF

    Zachary

    Sail in downtown 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!

  4. Clinton

    Clinton

    Fun time Jet Ski Rental at Lake Norman, NC near Charlotte

    Breyanna was AWESOME! Very accommodating! She went above, and beyond to ensure that our party had everything they needed for a great experience. I Look forward to working with her again. Next time we rent JetSki’s! Thank you Breyanna for making my birthday with my friends one to remember!

  5. Brandon

    Brandon

    Fun time Jet Ski Rental at Lake Norman, NC near Charlotte

    Good time on the lake with two jet ski's. Drove around for awhile, hopped in the lake to cool off, jumped back on and explored the lake. Good summer day with the family. Read up on boating and lake rules and water safety before you go to keep yourself safe and the ski's in good shape. Stay in the open water, as Beyanna says

  6. JW

    Jessica

    Captained Charter 30' Sailboat in Milwaukee, Wisconsin

    Our group of six women celebrating girl's weekend had the most memorable and special outting on Scott's boat. He is very friendly, accomodating, generous, and easy going. His background as a Navy search and rescue swimmer coupled with his confident sailing abilites assured the group that safety was never an issue. He perfectly integrated into or out of our conversations, highlighting is flexible nature. We all highly recommend!