Start early with a classic Toronto peameal sandwich at Carousel Bakery in St. Lawrence Market (or grab a to-go breakfast nearby). It’s a fast, tasty start for the drive; the bakery typically opens around 7:00am but check current hours.
Head east on Hwy 401 then County Rd 49 toward Picton — expect about 2.5–3 hours driving depending on traffic; this sets you up for a beach/wine afternoon.
Enjoy the famous sandy beaches and massive dunes at Sandbanks — a scenic spot for swimming, beach walking, and photos. Day-use areas typically open 8:00am–sunset; parking/day fees apply and can vary by season.
Relax with a locally sourced lunch in Picton—many cafes and casual restaurants serve farm-to-table salads, sandwiches and pies. Most Picton lunch spots are open by 11:30am–12:00pm; check specific restaurant hours.
Sample local wines at one of Prince Edward County’s approachable wineries; tastings are usually available from ~11:00am–5:00pm. It’s a great way to experience the County’s terroir before driving on.
Walk the vibrant downtown waterfront and Market Square to see limestone architecture and lakeside views; shops and public spaces are lively in the early evening.
Dine at a popular Kingston restaurant — Chez Piggy (bistro feel) or Dianne’s Fish Shack for local seafood. Most sit-down dinner spots open by 5:00pm–5:30pm; reservations recommended in the summer.
Fuel up at Pan Chancho or another beloved Kingston bakery for pastries, coffee, or a hearty breakfast sandwich. Typical bakery hours start around 8:00am, but check specific times.
Visit Fort Henry for guided tours, demonstrations, and excellent views of Lake Ontario; site hours usually run ~9:00am–4:00pm with tours in season. It’s an informative, photogenic slice of Canadian military history.
Have a waterfront lunch in Gananoque before the cruise; many cafes and pubs open for midday service. Plan for a relaxed quick meal to make the afternoon boat.
Take a classic 1–2 hour sightseeing cruise through the Thousand Islands to see island cottages, Boldt-style views and the St. Lawrence River. Cruises operate seasonally (typically 10:00am–5:00pm) — book ahead for summer weekends.
Stop in Brockville to visit the Aquatarium (interactive freshwater centre) or enjoy the riverside promenade; Aquatarium hours often ~10:00am–5:00pm. It’s a family-friendly, quick educational stop.
If you want a short cultural break, drive through Cornwall for a quick look at the waterfront and the Cornwall Canal; many museums have limited hours so check before planning a long stop.
Final leg to Montreal on Hwy 401 then A-20 (approx 2–2.5 hours from Brockville/Cornwall depending on traffic). Aim to arrive early evening for dinner in the city.
Celebrate arrival with Montreal smoked meat at Schwartz’s (open until about 10:00pm) or poutine at La Banquise (open late) — both are iconic and a great introduction to the city’s food scene.
Take a relaxed walk through Old Montreal if you have energy, or check into your downtown hotel and rest; many attractions and shops in Old Montreal close by early evening, though restaurants remain open late.