Sail The World

Imagine staying in a beautiful hotel with an uninterrupted ocean view and waking to the sounds of the sea. We will pour excitement into your vacation making the journey a memory of a lifetime.

🍂 The Journey of a Season

As summer fades, we set our sails south on a voyage that blends exploration, seamanship, and adventure. The Fall Cruise & Passage Making transit offers hands-on experience, coastal discovery, and the unmatched beauty of navigating through inland waterways and open sea.

Leg 1 –  Toronto, ON – Hudson, NY
            9 days Oct 5 – 13
            Lake Ontario Crossing / Locks & Rivers
 
Leg 2 – Hudson, NY – Hampton Roads, VA
            12 days Oct 15 – Oct 26
            Hudson River / Coastal / Chesapeake Bay
 
Leg 3 – Hampton Roads, VA – Marsh Harbor, Abacos Bahamas
           12 days Oct 30 – Nov 10
           Ocean Passage / Bahamas Reefs
 

Spend the Best Vacation of your Life Sailing with Cap't Howie

From the Caribbean to the Mediterranean to the South Pacific, Gone Sailing Adventures can take you there. We are connected to the world’s best charter companies offering Bareboat, Crewed and Flotilla Charters Check with us for the best pricing on your destination sailing. We have catamarans, mono-hulls and power boats available and the ability to meet any budget. If it’s on the water, we can make it happen!

Choose from a 7 or 10 day itinerary

$ All prices are in US dollars
Testimonials
What Our Guests Say

Sail The world

YOUR SAFETY IS AT RISK

When considering chartering a yacht in Canada, we know you have many options. Some of these options look super exciting and at ridiculously great prices. Recent trends in the industry have opened the door for many unqualified individuals to purchase boats and offer charter services to the unsuspecting public. It’s easy to create a website and even easier to just list a boat on sites such as Facebook Marketplace, Kijiji, Getmyboat, Boat Setter and many others.

Unfortunately, many of these operators are NOT licensed, insured or qualified to accept your trust on the water.

In order to be licensed and insured a number of items MUST be in place. Listed are just a few.

  • The operator must be licensed by Transport Canada with a commercial license known as either:
    – Limited Master under 60tonne.
    – Small Vessel Operators Permit (SVOP).
  • The name of the vessel must be visible on the stern (back) or the registration number beginning with the letter “C” must be visible on the side of the vessel near the front. Boats with a registration number beginning with “ON” are not licensed for passengers.
  • If the vessel is under 12m (40’) it should participate in the Transport Canada Small Vessel Compliance Program and display a “Blue Decal” and have corresponding certificate.
  • If the vessel is over 12m (40’) or carries more than 12 passengers, it MUST BE INSPECTED by Transport Canada and have an inspection certificate on board.
  • All vessels must have commercial liability insurance and coverage specifically for the number of passengers approved to be carried on board.
  • The vessel must comply with commercial safety requirements beyond recreational standards. Many of these illegal operators do not have the proper training, carry proper safety equipment, nor do their recreational boats meet the design/construction requirements of a commercial, passenger carrying vessel. These illegal operators try to stay under the radar of Police/OPP/RCMP/Transport Canada by:
  • hiding the name of their vessel by hanging items over the stern
  • not letting you know where they will have you board until just before the start of your charter.
  • pick you up at a public park (where docking is not permitted).
  • suggest to you that you are friends of the owner/operator out for a ride and not a paying customer.
  • allow you to drink alcohol while the boat is underway (illegal-same as a car) but tell you to hide your bottles etc.
  • insist on a cash transaction or part of it as a way of defrauding the internet listing company.
  • Make you sign a “Charter Agreement” just before you board without giving you details of the document beforehand.

    Over the last few years there have been a number of deaths and even more accidents resulting from these types of operators. Be safe and know who you are getting on a boat with. All licensed operators should willingly display their credentials, and most are members of the Passenger & Commercial Vessel Association (PCVA).

    Link to Global News Report on Charter Accidents

Check before you book
&
Know before you Go!

Oct 4th & 5th

Experience Toronto's Water/Fall Festival on the Water

Choose a 60 or 90 min sailing experience from 54.99pp