We use cookies to improve your browsing experience.

And dolphins make us happy. Find out more about our cookies policy here.

All listings near me

Find Sailing Charters Near You

4.9
(4,283 Reviews)

Page 2 of 10240 listings

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
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
$361hour
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
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
36ft Regal Luxury Yacht | $350 | 7 people
Events in Washington · 7 guests

36ft Regal Luxury Yacht | $350 | 7 people

New
Superowner
$350hour
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
$175hour
ATX 24 Type S Bowrider Rental on Mountain Island Lake, North Carolina
Powerboats in Charlotte · 18 guests

ATX 24 Type S Bowrider Rental on Mountain Island Lake, North Carolina

New
Superowner
$160hour
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
Luxury Sailing Catamaran ⭐️⭐️⭐️⭐️⭐️
Events in Baltimore · 12 guests

Luxury Sailing Catamaran ⭐️⭐️⭐️⭐️⭐️

5.0
Superowner
Best of 2023
$389-$459hour
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

New
$400hour
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
The Licensed Captain of this 42ft Sailboat, provides charters on Chesapeake Bay.
Sailing in Mayo · 6 guests

The Licensed Captain of this 42ft Sailboat, provides charters on Chesapeake Bay.

5.0
$175hour
Experience the Serenity of Sailing SV Magic
Sailing in Mayo · 6 guests

Experience the Serenity of Sailing SV Magic

4.8
$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
50ft Catamaran Charter with Water Toys - Annapolis, MD
Sailing in Annapolis · 12 guests

50ft Catamaran Charter with Water Toys - Annapolis, MD

New
$425hour
41' Lagoon Catamaran in Maryland
Sailing in Annapolis · 12 guests

41' Lagoon Catamaran in Maryland

5.0
Superowner
Best of 2023
$390hour
 VIKO S 35 Sailboat in Deale
Sailing in Deale · 6 guests

VIKO S 35 Sailboat in Deale

New
$298hour
Sailing Adventure in Chesapeake Bay with 28ft Tartan Sailing Yacht!
Sailing in Annapolis · 4 guests

Sailing Adventure in Chesapeake Bay with 28ft Tartan Sailing Yacht!

5.0
$150hour
38' Hunter 376 Cruising Monohull in Annapolis, Maryland
Sailing in Annapolis · 6 guests

38' Hunter 376 Cruising Monohull in Annapolis, Maryland

5.0
Superowner
Best of 2023
$138-$150hour
Sail the Sea on the Pintita
Sailing in Annapolis · 20 guests

Sail the Sea on the Pintita

New
$500-$750hour

Local Sailing Reviews

  1. NS

    Nitya

    Beautiful Trimaran for 10 People in Toronto

    Chris and Rob are simply amazing ! They showed us the best time on the boat. They had all services available on board to heat food and store our stuff. The boat was clean, spacious and both, Chris and Rob, were very attentive to make sure we had everything we needed to enjoy our experience. I'm coming back to these guys each time i want a sailing experience ! Highly recommend these guys

  2. JB

    Janis

    Beautiful Trimaran for 10 People in Toronto

    Many thanks to Chris and Rob for an amazing, chill adventure. We had to book this last minute but they were very accommodating and even went above and beyond all expectations. My only regret was not booking this experience sooner with your boat and crew. Thanks again! All the best, JB

  3. Emma

    Emma

    Beautiful Trimaran for 10 People in Toronto

    We had a lovely evening on the catamaran with Captain Chris and the crew! I was a bit chaotic with organizing with Chris for confirming dates/times/number of people joining as it was for a bachelorette. Chris was extremely patient and accommodating throughout the whole experience. The boat was beautiful and we were taken to lovely locations for beautiful views. I have already recommended this experience to many people!

  4. SS

    Srijanani

    Beautiful Trimaran for 10 People in Toronto

    We had a great time with Chris and his crew. Really appreciated the relaxed and friendly approach and communication.The boat is big enough to hold 12 ppl comfortably. The hammock is a great way to relax and take in the views. Chris took us out to a warm calm swimming spot and provided floaties and pool noodles too! The views, chats with captain and crew all added to the wonderful experience. Bluetooth speaker is provided with the boat to enhance the vibe. Amazing time spent out on the water!!

  5. LM

    Liadha

    Beautiful Trimaran for 10 People in Toronto

    Myself and 9 friends had an absolute blast on Chris' boat! The booking and communication all went smoothly, even when we asked to push the booking out by a day due to weather. It was more affordable than other options and there were no hidden costs/fees. Chris and Rob let us decide where we wanted to go and were very generous with their time, they didn't rush us back. They were also great fun! The bluetooth speaker is a great addition. Highly recommend.

  6. BB

    Barbara

    A Tropical Experience on a Massive Sailing Trimaran

    David was a most excellent captain. We were having a special send off for someone extremely important to us and David went above and beyond to make sure we all had a great time. He even got out his accordion and sang a song for the woman of the evening which was very funny and very special. We will absolutely book again. Thanks David and Sara!