Set Sail on Muskoka's Legendary Lakes
From a 130-year-old steamship gliding past millionaire's row to an intimate supply boat threading the locks of Port Carling — Muskoka's boat cruises are among the most unforgettable experiences in cottage country. All you need is a dock nearby to call home.
Browse CottagesMuskoka Lakes Classics
Muskoka Steamships — R.M.S. Segwun & Wenonah II
North America's oldest operating steamship has been gracing Lake Muskoka since 1887 — and a cruise aboard her remains the most storied way to experience the water. The 97-passenger Segwun and the grand 216-passenger Wenonah II depart from Gravenhurst's Muskoka Wharf with options ranging from one-hour sightseeing runs to four-hour dinner and High Tea sailings. The signature Millionaire's Row cruise, a designated Canadian Signature Experience, drifts past palatial summer estates that have stood for five generations. And the newly restored Wanda III — once owned by Mrs. Timothy Eaton — adds a private-yacht chapter to this legendary fleet.
Book a Cruise →Sunset Cruises — The Peerless II
The Peerless II spent fifty years delivering fuel and heating oil to cottages across the Muskoka Lakes — and in 2003, Captain Randy Potts gave it a gloriously different second act. Smaller, more intimate, and able to navigate waters that larger vessels simply can't reach, the Peerless II departs Port Carling daily for the Lake Rosseau Circle Tour and Millionaire's Row route, with sunset cruises running on select evenings. Captain Randy's live commentary — steeped in local lore and genuine passion — is the kind of narration you'd pay handsomely for and can't find anywhere else. A local favourite, and for good reason. Season runs May to September; advance booking required at 705-645-2462.
Learn More →Muskoka Cruises — The Lady Rosseau
Since 1966, Muskoka Cruises has been ferrying guests across the pristine lakes that earned this region its reputation as cottage country royalty. Aboard the sleek, modern Lady Rosseau — equipped with panoramic windows, an upper deck, and a fully licensed bar — you'll glide through Lake Rosseau and Lake Joseph past multi-million-dollar architecture and unspoiled Canadian Shield shoreline. Whether you're joining a guided sightseeing tour or chartering the vessel for something more private, this is the kind of experience that leaves you searching the property listings on the way home.
Learn More →Lake of Bays Heritage Sailing
S.S. Bigwin — A Living Legend on Lake of Bays
Built in 1910 and once the private ferry to the illustrious Bigwin Inn, the S.S. Bigwin has carried some remarkable passengers — Clark Gable, Louis Armstrong, Winston Churchill, and Greta Garbo among them. After decades of neglect, a passionate coalition of cottagers returned this piece of Lake of Bays heritage to its former glory. Today, one-hour public cruises depart the Dorset town docks from June through October, tracing the shoreline past forest-clad cliffs and the storied islands of Trading Bay. Cruise tickets include admission to the adjacent Lake of Bays Marine Museum — an understated gem that tells the full story of this remarkable vessel. A cruise that connects you to something much older than any cottage on the water.
Book a Cruise →Georgian Bay: The 30,000 Islands
30,000 Island Cruise Line — Island Queen & The Islander
Georgian Bay is home to the largest concentration of freshwater islands on earth — and the Island Queen gives you a front-row seat to all of it. The 500-passenger vessel runs two- and three-hour sightseeing tours from the Parry Sound town dock, threading past granite shoals, windswept pines, and the rugged charm of remote summer cottages. Highlights include the Hole in the Wall, the Rose Point Swing Bridge, and multiple Provincial Parks. For something more intimate, the Islander — a 40-passenger zodiac-style vessel — runs tours to Frying Pan Island for lunch at Henry's World Famous Fish Restaurant, and eco-tours of Huckleberry Island led by the Georgian Bay Biosphere Reserve. Utterly unforgettable.
Book a Cruise →Beausoleil Island & National Park Adventures
DayTripper — Gateway to Beausoleil Island
Fifteen minutes across sparkling Georgian Bay water and you're standing on Beausoleil Island — the centrepiece of Georgian Bay Islands National Park and one of Ontario's most singular day-trip destinations. The DayTripper vessel operates five days a week (Friday to Tuesday) from the Victoria Day long weekend through to Thanksgiving, giving cottage guests an effortless half-day escape into the Canadian Shield wilderness. Hike the cedar ridges, find a secluded swim spot, or simply spread out a picnic and let the island work its magic. No crowds, no cars — just the kind of quiet that reminds you why you came to cottage country in the first place.
Plan Your Island Day →Miss Midland — Lunch & Dinner on the 30,000 Islands
The 300-passenger Miss Midland has been a beloved Georgian Bay tradition for decades — and her lunch and dinner cruise packages remain among the finest ways to combine extraordinary scenery with a proper sit-down meal on the water. Departing from Midland, the vessel traces the shimmering channels of the famous 30,000 Islands, giving guests an unhurried window onto the windswept pines and weathered granite that defines the bay's rugged character. Lunch and dinner cruises run weekends and select weekdays well into the autumn season — a wonderful pairing with a weekend at a Homeseeker cottage along the Georgian Bay shoreline.
Book a Cruise →Ready to find your cottage on the water?
Wake up to the lake, spend your days exploring Muskoka's legendary waterways, and return to your own dock as the sun goes down. cottage memories. together.
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