Ontario and Canada’s East offer an easy mix of big-city culture, lakeside beaches, and vineyard-dotted countryside. Toronto grew from a British colonial town to Canada’s largest city; Niagara Falls has lured travelers for centuries; and Montreal blends French heritage with cutting-edge food and arts. This 21-day itinerary strings them together at a gentle pace—ideal for a relaxing road trip.

Expect world-class museums, old markets, island beaches, and scenic drives framed by the Great Lakes and the St. Lawrence River. You’ll base in three hubs to minimize hotel hopping, with optional day trips that keep daily driving near 400 km. Winery patios, riverside promenades, and leafy parks ensure you’re never far from a slow moment.

Practical notes: Driving in Ontario and Quebec is straightforward; highways are well signed. The 407 ETR (near Toronto) is a toll road billed to your rental car—stick to Highway 401/403 if you want to avoid fees. Niagara City Cruises typically runs April–Nov; Journey Behind the Falls operates year-round. For lodging, filter “Breakfast included” on Hotels.com or choose VRBO apartments with kitchenettes to stretch your budget.

Toronto

Toronto is Canada’s cultural engine: museums (ROM, AGO), sports, theater, and neighborhoods that read like a world atlas. Between glass towers you’ll find indie coffee bars, vintage shops, and the restored red-brick lanes of the Distillery District. Ferries whisk you to the Toronto Islands for beaches and skyline views.

Getting there: Fly into Toronto Pearson (YYZ) or Billy Bishop (YTZ). Compare fares on Trip.com and Kiwi.com; typical nonstop flights from major North American hubs take 1–6 hours and run about $120–$450 one-way depending on season.

Days 1–3: Downtown icons, museums, markets

• CN Tower views, then stroll to the Harbourfront boardwalk. Pop into the Art Gallery of Ontario (AGO) for Canadian art and the Gehry-renovated wing, or the Royal Ontario Museum (ROM) for dinosaurs to design.
• Wander the Distillery Historic District for boutiques, galleries, and patios. Hit St. Lawrence Market—try Carousel Bakery’s peameal bacon sandwich and Buster’s Sea Cove for fish tacos.
• Explore Toronto’s underground city with a guided walk:
  Discover Toronto's Underground - PATH walking tour

  

• See the city your way on a hop-on, hop-off loop:
  City Sightseeing Toronto Hop-On Hop-Off Bus Tour

  

• Evening on the water: skyline sunset with dinner and a DJ:
  Toronto Premier Dinner Cruise on Odyssey in Toronto Harbour

  

Where to eat and sip: Breakfast at Saving Grace (tiny, creative plates) or Bonjour Brioche (buttery pastries). Coffee at Sam James Coffee Bar or HotBlack Coffee. Lunch at St. Lawrence Market (Carousel Bakery, Uno Mustachio, Kozlik’s mustards). Dinner ideas: Pai (bold northern Thai), Bar Isabel (Spanish tapas, charcuterie), Seven Lives (Baja-style tacos in Kensington Market), or Rasa (share plates).

Days 4–5: Islands and beaches (relaxing days)

Pack a beach day: ferry to the Toronto Islands for soft-sand stretches at Centre Island and Gibraltar Point, with skyline views along the boardwalk. Alternatively, unwind at Woodbine Beach in the Beaches neighborhood—boardwalk strolls, volleyball, and ice cream stands set a summery mood.

Light extras: quick fun at the Museum of Illusions (Toronto) for mind-bending photo ops.

Days 6–7: Neighborhoods, shopping, day-trip options

Shop the CF Toronto Eaton Centre, indie boutiques along Queen West, or galleries and cafes on Ossington. Yorkville offers designer storefronts and polished cafes, a good foil to Kensington’s street art and vintage racks.

Optional day trip: Wasaga Beach, the world’s longest freshwater beach (~2 h each way), for gentle swimming and sandy walks. Or explore Hamilton’s waterfalls (Albion Falls, Tiffany Falls) with easy trails and picnic spots.

Toronto stays (breakfast-friendly & value): Use filters for “Breakfast included” or kitchens on Hotels.com (Toronto) or browse apartments on VRBO (Toronto). For budget-friendly breakfast and parking, look at reliable brands like Hampton Inn, Fairfield Inn & Suites, or Holiday Inn Express.

Drive to Niagara Falls (morning of Day 8): ~130 km, 1.5–2 h via QEW. To avoid tolls, skip the 407 ETR. Aim to arrive before lunchtime to check in and stroll Queen Victoria Park’s viewpoints.

Niagara Falls & Niagara-on-the-Lake

Few sights stir the soul like Niagara Falls—thunder, mist, and rainbows over the gorge. The Canadian side pairs classic attractions with leafy trails, a revitalized downtown, and the historic wine village of Niagara-on-the-Lake just 25 minutes away.

Days 8–10: Falls highlights at an easy pace

• Feel the mist up close with boat and tunnel access:
  Niagara Falls Tour With Journey Behind the Falls & Boat Cruise

  

• Panoramic views from above:
  Skylon Tower Observation Deck Admission

  

• Adventure option: soar past the American Falls on a guided zipline:
  Zipline To The Falls in Niagara Falls, Canada

  

Eat & drink: Breakfast at Blue Line Diner (hearty plates, local hockey lore). Lunch at Tide & Vine Oyster House (seafood rolls, chowder). Dinner at Weinkeller (house wines, seasonal menus) or AG Inspired Cuisine (regional tasting menus). For a casual evening, stroll Clifton Hill lights, then return to the river park for fireworks in summer.

Days 11–12: Niagara-on-the-Lake wineries and heritage

Base in storybook Niagara-on-the-Lake (NOTL) for vineyards, boutiques, and verandas. Sample cool-climate whites and icewine, or settle into a fireside tasting when the air turns crisp.

• Guided tastings minus the driving:
  Niagara Wine Tour and Tastings with Transportation

  

• Cozy seasonal option (winter/shoulder seasons):
  Fireside Flights Outdoor Tasting Experience

  

NOTL eats: Treadwell Cuisine (farm-to-table), Farmhouse Café at Caroline Cellars (comfort classics on a vineyard), and Butler’s Sports Bar for a laid-back night. Coffee at Balzac’s and baked goods at Niagara Home Bakery.

Days 13–14: Beach and canal day

Unwind at Port Dalhousie beach (St. Catharines) or Crystal Beach (Fort Erie) for soft sand and shallow swimming. Then watch freighters navigate the Welland Canal at Lock 3 with a lakeside promenade.

Niagara stays (breakfast-friendly): For Niagara Falls, compare on Hotels.com (Niagara Falls) or browse apartments on VRBO (Niagara Falls). Good value options with breakfast include many Days Inn, Hampton Inn, and Country Inn & Suites. Consider:
- Marriott Fallsview Hotel & Spa (best views, spa)
- Days Inn by Wyndham Niagara Falls Near The Falls (budget-friendly)
- Great Wolf Lodge Niagara Falls (family-friendly waterpark)

For Niagara-on-the-Lake, search Hotels.com (Niagara-on-the-Lake) or VRBO (Niagara-on-the-Lake). Classics:
- Prince of Wales Hotel
- The Olde Angel Inn (historic pub rooms)
- Pillar and Post Inn & Spa

Drive to Montreal (morning of Day 15): ~670 km, ~7 h. To keep under ~400 km, break the drive with a lunch/leg-stretch in Kingston (historic waterfront) or Gananoque (1000 Islands), then continue to Montreal the next morning. Alternatively, if you’d rather fly, check Trip.com for 1h20 nonstop YYZ–YUL fares often $80–$180 one-way.

Montreal

Montreal melds French charm with North American energy—cobblestone lanes in Old Montreal, bagel bakeries in Mile End, and a festival calendar that barely pauses. It’s excellent for museums, food markets, and leisurely park time along Mount Royal.

Days 15–17: Old Montreal, museums, and markets

• Stroll Old Montreal from Place d’Armes to the waterfront, admiring 18th–19th century facades. Don’t miss the Montreal Museum of Fine Arts and Pointe-à-Callière (archaeology/history) for a deep dive into the city’s past.
• Snack your way through Marché Jean-Talon, then wander Mile End for indie shops and record stores.
• Get oriented with a narrated city tour:
  Montreal City Sightseeing Tour with Live Commentary

  

Eat & drink: Breakfast bites at St-Viateur Bagel (sesame bagels from a wood-fired oven) or Olive et Gourmando (legendary sandwiches, pastries). Coffee at Café Olimpico. Lunch at Schwartz’s (smoked meat) or La Banquise (poutine variations). Dinner at L’Express (classic bistro), Vin Papillon (seasonal small plates, veg-forward), or Le Passé Composé (creative brunch-for-dinner).

Days 18–19: Food tour and city beaches

• Taste Mile End with a local guide:
  Montreal Mile End or Jean Talon Market Food Tour with 8 Tastings

  

• Relax at urban beaches: Clock Tower Beach (Old Port; seasonal, lounge chairs) or Jean-Doré Beach at Parc Jean-Drapeau for calm swimming and paddle rentals.
• Sunset walk on Mount Royal to the Kondiaronk Belvedere for the classic skyline panorama.

Day 20 (optional full-day): Quebec City & Montmorency Falls

• Day trip from Montreal to Old Quebec’s fortified streets and the dramatic Montmorency Falls:
  From Montreal: Quebec City & Montmorency Falls Full Day Trip

  

• If you extend in Quebec City, deepen the visit with a guided walk:
  Old Quebec Classique Walking Tour with Funicular

  

Day 21: Slow morning and departure

Enjoy a final café au lait and almond croissant, then drive back to Toronto (~540 km, ~5.5–6 h) for flights, or fly out of Montreal. Compare fares on Trip.com or Kiwi.com. If driving to Toronto, consider a lunch stop in Cornwall or Kingston to keep the day easy.

Montreal stays (breakfast-friendly & value): Use Hotels.com (Montreal) to filter “Breakfast included” (look at Hampton Inn, Holiday Inn Express, Best Western Plus), or search apartments on VRBO (Montreal) for kitchenettes near Jean-Talon Market or the Plateau.

How the 21 days break down (relaxing pace)

• Toronto: Days 1–7
• Niagara Falls & Niagara-on-the-Lake: Days 8–14
• Montreal (with optional Quebec City day trip): Days 15–21

Driving notes: We’ve kept travel days to ~130 km (Toronto→Niagara) and ~540–670 km (Niagara→Montreal / Montreal→Toronto). If you prefer sub-400 km segments, split the longer legs with an overnight stop in Kingston/1000 Islands—historic walks, river views, and excellent bakeries make it a restful break.

Overall, this route blends Canada’s headline sights with beaches, markets, and winery patios—unhurried days, scenic drives, and plenty of good coffee. You’ll return home with skyline photos, vineyard notes, and a little mist still clinging to your jacket from the Falls.