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All listings near me

Find Sailing Charters Near You

4.9
(4,625 Reviews)

Page 2 of 10240 listings

28' Sailboat for 5 guests in Toronto
Sailing in Toronto · 5 guests

28' Sailboat for 5 guests in Toronto

New
$235hour
38' Sailing Yacht in Toronto, Ontario
Sailing in Toronto · 8 guests

38' Sailing Yacht in Toronto, Ontario

New
$400hour
Fountain Pajot Astrea Luxury 42' Catamaran for Charter
Sailing in Toronto · 18 guests

Fountain Pajot Astrea Luxury 42' Catamaran for Charter

5.0
$1,100-$1,250hour
Stylish & Spacious‼️ Enjoy Toronto's One of a Kind 44ft Bayliner!
Events in Toronto · 15 guests

Stylish & Spacious‼️ Enjoy Toronto's One of a Kind 44ft Bayliner!

5.0
$362hour
Beautiful Trimaran for 10 People in Toronto
Sailing in Toronto · 12 guests

Beautiful Trimaran for 10 People in Toronto

5.0
$289hour
A Tropical Experience on a Massive Sailing Trimaran
Sailing in Toronto · 12 guests

A Tropical Experience on a Massive Sailing Trimaran

4.9
$325hour
The Twilight Tour on 35ft Hughes Sailboat
Sailing in Toronto · 2 guests

The Twilight Tour on 35ft Hughes Sailboat

New
$108hour
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
$72hour
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
$150hour
Sail on the Potomac in Washington, DC
Sailing in Washington · 6 guests

Sail on the Potomac in Washington, DC

New
$280hour
$275 HR | 8 people | Sea Ray 330 Sundancer Yacht
Events in Washington · 8 guests

$275 HR | 8 people | Sea Ray 330 Sundancer Yacht

5.0
Superowner
$275hour
$400 M-Th | $600 F-Su | 13 ppl | Luxury Yacht SLX 400
Events in Washington · 13 guests

$400 M-Th | $600 F-Su | 13 ppl | Luxury Yacht SLX 400

5.0
Superowner
$400hour
Sailing Catamaran, National Harbor Ready for Sunrise, Sunset or Any Time Cruise
Sailing in Oxon Hill · 6 guests

Sailing Catamaran, National Harbor Ready for Sunrise, Sunset or Any Time Cruise

New
$200hour
Captained Charter 30' Sailboat in Milwaukee, Wisconsin
Sailing in Milwaukee · 6 guests

Captained Charter 30' Sailboat in Milwaukee, Wisconsin

5.0
$150hour
Charter this beautiful Catalina from Milwaukee, WI - Captain Included
Sailing in Milwaukee · 6 guests

Charter this beautiful Catalina from Milwaukee, WI - Captain Included

5.0
$150hour
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-$190hour
Luxury Sailing Catamaran ⭐️⭐️⭐️⭐️⭐️
Events in Baltimore · 12 guests

Luxury Sailing Catamaran ⭐️⭐️⭐️⭐️⭐️

5.0
Superowner
Best of 2023
$399-$499hour
30 ft sailboat with highly experienced Captain in Baltimore Inner Harbor
Sailing in Baltimore · 5 guests

30 ft sailboat with highly experienced Captain in Baltimore Inner Harbor

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

Charter 42' Lagoon Catamaran in Annapolis, MD

5.0
$425hour
Sail out of Middle River onboard Hunter 41 AC Sailboat!!
Sailing in Essex · 6 guests

Sail out of Middle River onboard Hunter 41 AC Sailboat!!

5.0
$175hour
Captain Bill invites you to find your Sailing Dream on Chesapeake Bay.
Sailing in Mayo · 6 guests

Captain Bill invites you to find your Sailing Dream on Chesapeake Bay.

5.0
$150-$200hour
Instant Book
Experience the Serenity of Sailing SV Magic
Sailing in Mayo · 6 guests

Experience the Serenity of Sailing SV Magic

4.9
$165hour
Charter 44' Orana Cruising Catamaran In Deale, Maryland
Sailing in Deale · 10 guests

Charter 44' Orana Cruising Catamaran In Deale, Maryland

5.0
$2,600day
Catamaran in Maryland
Sailing in Annapolis · 12 guests

Catamaran in Maryland

5.0
Superowner
Best of 2023
$390hour

Local Sailing Reviews

  1. 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!

  2. DZ

    Dunja

    Luxury Sailing Catamaran ⭐️⭐️⭐️⭐️⭐️

    Captain Shane and Captain Andy were extremely communicative and helpful throughout the entire process from booking all the way through the excursion. The catamaran was clean, beautiful, and the entire charter was a great experience! I would strongly recommend S&S and if I ever host another boating event, I know who to go to!

  3. AN

    Ashley

    Experience the Serenity of Sailing SV Magic

    We rented Josh’s boat to do our engagement pictures! He was helpful with timing to catch the best sunset and navigated the boat so our photographer could get the best shots. There was room below for outfit changes and speakers on board to enjoy our time!

  4. RZ

    Rachel

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

    David was communicative and professional during the booking process. He was easy to reach and very responsive. Leading up to the trip, he communicated everything we needed to know. Our boat ride was smooth sailing and relaxing. It was a nice Father’s Day trip for the family. We hope to book again soon!

  5. EL

    Elford

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

    This is A Comfortable Pontoon, An easy going Captain, and a REALLY RELAXING way to Enjoy the Water! We had a Wonderful Day! Celebrating a 24 year anniversary. Make an inquiry, hit the “Book Now” button, have a good time!

  6. CB

    Caprice

    Catamaran in Maryland

    This was one of the best rides I’ve had in a while. Captain Jess is communicative, helpful and kind. We went out for 4 hours and had great weather. The boat is clean, he had 2 fridges for our food and drinks, it was nice and spacious, and there were floaties to get out on the water. It was a very enjoyable day.