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 / $150

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 / $250

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 / $150

daydream sailing canandaigua moonlight at pier

Moonlight Package

This session is a rare opportunity for a night-time sailing experience, with a limited number of dates available. All weather permitting only. This is NOT recommended for children under 13 years of age.

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 / $425 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