Itinerary Toronto - Maine - New York

Question

Hi guys we are looking to head over around the 8th of September coming back around the 23rd.

Our thoughts are to fly into Toronto and fly back from New York spending a few nights in a both cities. We can also fly into/out of Boston or Montreal.

It’s the bit in between we are struggling with. Niagra Falls seems an obvious stop. We love the Sea and Seafood so a long sea road trip appeals staying at Coastal towns along the way maybe dropping the car in Boston before heading to NY by train.

Is this feasible in 2 weeks? What modes of transport are recommended? Is it car all the way or should we use Amtrak to get from Niagra to the Coaat.

We literally have no ties or must sees apart from Niagra so your thoughts are very much appreciated.

Thank you

Answer

A two-week itinerary from Toronto to New York with a focus on coastal towns and seafood is definitely feasible, but it will require careful planning to balance driving, sightseeing, and relaxation. With September weather generally mild and the tourist season winding down, this is a great time to explore the Great Lakes, New England coast, and New York City.

Suggested Itinerary Flow:

Toronto (2–3 nights): Explore the city, Niagara Falls day trip, and enjoy local dining and waterfront areas. Flying into Toronto makes sense if you want to start in a vibrant city.
Niagara Falls (1 night or day trip): You can either stay near the Falls for a night or do a day trip from Toronto. Evening illumination and optional boat tours (Maid of the Mist) are highlights.
Drive to Maine via Upstate New York and Vermont/New Hampshire (5–6 nights): A coastal road trip can include stops in:
- Portland, ME – great seafood, Old Port district.
- Camden – scenic harbor, hiking nearby.
- Bar Harbor / Acadia National Park – classic Maine coastline, lobster, hiking.
- Boothbay Harbor – charming small coastal town with excellent seafood.
Drop car in Boston (1–2 nights): Explore Boston’s historic districts, waterfront, and food scene. This can be your transition from a road trip to a more urban experience.
Train to New York City (2–3 nights): Amtrak from Boston to NYC is convenient, avoiding driving into the city. Focus on sightseeing, cultural attractions, and local dining.

Modes of Transport:

Car: Essential for the coastal and rural sections of the trip (Toronto to Maine). Provides flexibility for scenic stops, small towns, and Acadia National Park. Rental car drop in Boston is feasible.
Amtrak: Ideal for Boston to New York City. Avoids city driving, parking, and traffic headaches. Comfortable and scenic along the Northeast Corridor.
Flights: Flying in and out (Toronto in, New York out) is the most time-efficient for your itinerary. Flying into/out of Boston is an alternative but slightly limits flexibility if you want to maximize Maine stops.

Feasibility Tips:

Two weeks gives roughly 12–13 days of travel, which allows for 2–3 nights in major cities (Toronto, Boston, NYC) and 5–6 nights along the Maine coast, with 1–2 nights for travel and transitional stops.
Be selective with coastal stops; while Maine has many charming towns, focusing on 3–4 key locations keeps driving manageable and allows you to enjoy seafood and scenic areas without rush.
Use Google Maps or a GPS-enabled app to plan driving segments; some stretches along Maine’s coast can be slower than expected due to scenic roads and small-town traffic.
Book accommodations in advance, especially Bar Harbor and Portland, as even in mid-September these towns are popular.

In summary, a car is essential for the road trip portion along the coast for maximum flexibility and enjoyment. Amtrak or trains are recommended from Boston to New York City to avoid urban driving stress. With careful planning, two weeks is sufficient to enjoy Toronto, Niagara Falls, the Maine coast, Boston, and New York City at a comfortable pace while indulging in seafood and scenic drives.

Itinerary Toronto - Maine - New York

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