Daydream Sailing


Customizable packages up to maximum 4 adults. Larger groups may be accommodated with multi-session reservations. Light snacks and non-alcoholic beverages included at no additional charge. Our guests are welcome to bring aboard their favorite adult beverages or snacks.
NOTE: Package prices are for 1-2 guests, each additional guest is $40.  All sessions by advance reservation, and weather permitting.

daydream sailing canandaigua Brenda daughter grandson

Starter Package

This sailing session is great for squeezing a bit more fun in your weekend plans or a weekday getaway that fits right in between,  for a much needed break from all the business of life. This is also a great option for folks new to sailing; that may wish to take smaller sessions at time. We try to coordinate best sailing times to forecasted predictions to optimize our experience together.

1.5 hours / $180

daydream sailing canandaigua customer 8

Premier Package

This sailing session allows more time for taking in the majestic views along the lake. We welcome active participation, as desired, or just relax and enjoy the ride. We aim to educate as well as provide a great experience.

2.5 hours / $280

daydream sailing canandaigua sunset sail

Sunset Package

One of our most popular sessions for couples, wanting to experience a fabulous Date night. Times for these sails will vary with the calendar through the season. Typically boarding times between 5:30-7:00.

1.5 hours / $180

daydream sailing canandaigua customer 5

Individual Lessons

For individuals wishing to enhance their previous sailing instruction, or for those who would like to begin to learn to sail. These lessons are for one person, at either a beginning or intermediate level.

1.5 hours / $150

Daydream Sailing View of Canandaigua Lake from Canandaigua City Pier in New York

Sailboat Rental Only (Bareboat)

This option is for experienced qualified skippers only. By advanced reservation and pre-sail meeting for details of lake soundings and equipment onboard. Dinghy with oars provided for access to mooring.

Waiver and confirmation of credentials required. No smoking or pets allowed.

daily / $475   deposit $500    multi-day discount TBD

daydream sailing canandaigua Santa on boat

Gift Certificate | Pre-Season Sales

Gift certificates available for purchase for any amount each season and make a great gift idea for special occasion celebrations, birthdays, anniversaries, engagements and retirements. All certificates expire at end of September each year for sailing season. They do not carry over to the following year. These can be mailed directly to the recipient with a gift message.

to purchase a Gift Certificate or for Pre-Season Sales