Toronto Islands Private Sailing Charter

Charter your private yacht and invite your family, friends or colleagues to enjoy a relaxing sail around Toronto Harbour, the Toronto Islands and Lake Ontario. A Private Sailing Charter for up to 10 people is perfect for couples, more intimate groups, families, bachelorette parties, bachelor parties and engagements.
Where: Toronto, Ontario
Price for: Up To 10 Participants
Picture of Private Sailing Charter
Private Sailing Charter
The price is for up to 10 people.
$1,195.00
Picture of Private Sailing Charter with Wine & Cheese
Private Sailing Charter with Wine & Cheese
Your sail includes a variety of premiere Wines with specially selected Cheeses to tantalize your taste buds. Of course the sail ends with a decadent tray of sweets. The price is for up to 10 people.
$1,945.00
$1,850.00

Sail Toronto Harbour, the Toronto Islands and Lake Ontario on a private sailing charter.

Sailing is an exceptional experience, a true getaway.  Private sailing means you have the whole boat to yourself and your professional crew will do everything and beyond to make this cruise memorable.

No sailing experience is required and you won't need to lift a finger, unless you want to.


A Private Sailing Charter is the perfect way to  celebrate your birthday, engagement, bachelor, bachelorette party or a family reunion.

Most of the excursions start as a three sail circumnavigating the Toronto Islands. You can customize your event with a cruise through the Toronto Island channels and then head out to the lake for a sail. Stop for a swim in the fresh clean waters south of Gibraltar Point. Anchor at sunset and watch the sun drop over Toronto at dusk. The choices are almost endless.  As Toronto adventures go, this Toronto Islands cruise is the way to go!

Hold your next sales conference in comfort and luxury. There is plenty of space and opportunity to think outside the box. Break for a BBQ lunch or stop at one of the yacht clubs along the waterfront.   

Team building: Plan great team building events where everyone participates in hands-on sailing, challenging each other.  

Boats can be anchored for swimming, sunbathing and barbeque.

Capacity: A private sailing charter for up to 10 people

Duration: 3 hours

Need to know:

  • Sailing season runs from May to September.
  • Please book well in advance.
  • Gratuities not included.
  • All participants must sign a waiver.
  • All bookings are final once confirmed subject to our severe weather rescheduling and minimum participation. (Sailing occurs rain or shine subject to dangerous conditions.)

What to wear:  We recommend wearing sunscreen, hat and non-marking, rubber soled shoes, layered clothing (a base cool layer, warmer middle layer and waterproof outer layer) The temperature can be much cooler during a breeze and when the sun goes down.

Can you swim:  During the hot summer days you can swim in the fresh Lake Ontario water. The boats have noodles and other flotation devices and provide towel service.

This Toronto Harbour and Toronto Islands sailing experience takes place at Toronto, Ontario.   VIEW MAP

How To Book Your Experience