On South Main Street in Canandaigua, Freedom Boat Club offers a unique membership-based boating experience. With a history spanning over 35 years, this international boat club has established a presence in the area, providing access to a diverse fleet of premium boats suited to various preferences. The club's location on Canandaigua's waterfront allows members to enjoy the scenic beauty of the Finger Lakes region. As part of a larger network, members can also access over 400 locations across North America, Europe, and Australia. The club's fleet is maintained with concierge-level support, handling tasks such as maintenance, cleaning, repairs, insurance, and storage, allowing members to focus on their boating experience. Freedom Boat Club also provides unlimited, free training to ensure members feel confident and comfortable at the helm, regardless of their prior experience. This comprehensive approach to boat club membership has established Freedom Boat Club as a notable presence in Canandaigua's maritime community. Local Finger Lakes locations include : Canandaigua Lake , Port of Rochester, Sodus Point, Keuka Lakes.

On South Main Street in Canandaigua, the Fleet Boat Club offers an alternative to traditional boat ownership or rental. This boat club provides its members with access to a variety of late-model boats, suited for activities such as waterskiing, wakeboarding, tubing, or simply relaxing on the water. The club's concept is designed for those who want to enjoy boating without the associated expenses and hassles. By offering multiple locations, including Canandaigua Lake, members can experience different boating settings without the need for trailering. The Fleet Boat Club's approach allows members to choose the right boat for their planned activities, providing flexibility and convenience. With locations across the Finger Lakes region, including Irondequoit Bay, Sodus Bay, and Seneca Lake, members can enjoy a diverse range of boating experiences. The club's presence in the area provides an opportunity for people to appreciate the region's waterways without the long-term commitment of boat ownership.

On the west side of Canandaigua, the Yacht Club Cove Association is a member-owned sailing club with a rich presence in the community. Situated in a scenic location, the club offers a unique setting for its members to enjoy sailing and social activities. As a community association and boat club, it provides a space for like-minded individuals to come together and share their passion for sailing. The club's location on the water's edge allows for stunning views and easy access to the lake. The Yacht Club Cove Association has a strong focus on community, with members actively involved in various sailing and social events throughout the year. The club's facilities cater to the needs of its members, providing a comfortable and welcoming environment for relaxation and recreation. With its beautiful location and strong sense of community, the Yacht Club Cove Association is an integral part of the Canandaigua community, serving as a hub for sailing enthusiasts and social gatherings in the area.

On South Main Street in Canandaigua, Sutter's Canandaigua Marina has been serving the Greater Rochester boating community since 1993. The marina's team brings over 50 years of professional experience in boat sales, service, rentals, and storage. Sutter's is conveniently located on the Canandaigua city pier, near Inn on the Lake and the New York Wine and Culinary Center. The marina offers a range of services, including boat sales from leading brands like Regal and Bennington, as well as boat repairs and maintenance for Mercruiser, Yamaha, and Volvo-Penta engines. Sutter's Canandaigua Marina also provides boat rentals, with half and full-day options available, and has over 190 boat slips to accommodate vessels up to 34 feet with power and water available. Additionally, the marina offers winter storage services, including professional shrink wrap and regular inspections, to give boat owners peace of mind during the off-season. With its comprehensive services and experienced team, Sutter's has established itself as a key part of the Canandaigua boating community.

On Lakeshore Drive in Canandaigua, The Canandaigua Lady offers a unique experience on Canandaigua Lake. This 19th-century steamboat replica is an authentic double-decker paddle wheeler, providing a relaxing cruise experience while serving meals and offering captivating narration. The boat operates from May to October, hosting lunch, dinner, and excursion cruises, as well as themed and tasting cruises throughout the season. Its sixty-five ton Mississippi-style paddle wheel boat is a notable feature of the vessel. The Canandaigua Lady's cruises offer a chance to enjoy the scenery of Canandaigua Lake while learning about its history and significance. The boat's public and private cruises cater to various groups, including special events and charters, making it a popular destination in the Finger Lakes region. With its distinctive paddle wheel and double-decker design, The Canandaigua Lady is a recognizable presence on the lake, providing a memorable experience for those on board.

Located on the west side of Canandaigua Lake, the Canandaigua Yacht Club is a member-owned sailing club in the Finger Lakes region of upstate New York. This family-friendly club offers its members a range of sailing and social experiences, including sailboat racing and cruising. The club's facilities include waterfront camping, catering services, and meeting spaces for members and their guests. Situated about 28 miles from Rochester, the club provides a scenic backdrop for its members to enjoy their love of sailing. The Canandaigua Yacht Club features a variety of sailing fleets, including Sunfish, Ensign, and J 24 fleets, as well as a power boat fleet and opportunities for crewing and racing. The club also offers lessons and hosts several regattas throughout the year, such as the J-DAZE Regatta and the Sunfish Regional Championship Regatta. With its strong focus on community and sailing, the Canandaigua Yacht Club has become a staple in the Finger Lakes region, providing a welcoming environment for members to socialize and enjoy their passion for sailing.

On Lakeshore Drive in Canandaigua, The Showroom by Canandaigua Sailboard serves as a hub for water sports and activities in the Finger Lakes region. This sporting goods store and boat club combination offers a range of equipment for rent, including kayaks, standup paddleboards, and windsurfers. The location is situated on the north end of Canandaigua Lake, providing easy access to the water. The business is part of the local community, with a focus on connecting people to nature through various experiences. The Showroom by Canandaigua Sailboard features a variety of activities, such as yoga classes, wakefoil lessons, and kayak trips to Skenoh Island. They also offer private and community lessons, as well as customized experiences for events and parties. The store is stocked with high-end gear from brands like Patagonia, Oakley, and Werner, and the staff is available to provide assistance and coaching to customers. With its unique location and range of activities, The Showroom by Canandaigua Sailboard is a key part of the local water sports scene in the Finger Lakes region.