Make tracks from Chicago to New York with Boston and Toronto in between.
Canada and America. Both big places with big reputations, so take your time soaking it all in on this tour from Chicago to Toronto and New York City. Criss-cross the country and enjoy the sights of the Midwest and the North as you drive through scenic countryside and towns. Feel the fine spray on your face at the thundering Niagara Falls, look out over the city and beyond from the CN Tower in Toronto, enjoy a Chicago-style hotdog in the Windy City and chat with an Amish Bishop in Berlin, Ohio. Walk the Freedom Trail in Boston, and then head on out to New York, New York for a stroll around Times Square, taking in the Empire State Building, the Rockefeller Center and the Statue of Liberty.
Learn about another way of life over a home cooked meal, in the company of an Amish Bishop and his family
With an overnight stay at Niagara Falls, you'll be able to see this spectacular sight in the day, at night, up close and from afar. The scenes are unique from both the Canadian and American sides
As an extremely popular activity, the Kensington Market Urban Adventure is a great way to get under the skin of Toronto in a short period of time
Stroll galleries, walk out to a lighthouse or spot harbor seals in the water. Cape Cod is a picturesque retreat away from the big city
The Freedom Trail in Boston is one of the best free ways to learn about America's history. Taking you indoors and out, this living museum is made up of at least 16 sites across the city
You'll be travelling in a van with a group of travellers on long journeys, so conditions may feel a little cramped. This is all part of the adventure though and you might even make some long-term friends.
As this trip includes a visit to Amish country, we ask you to dress respectfully and please don't take photos without asking.
This part of the country can experience extremes of weather. Summer can be very hot and humid on the east coast of the USA, whereas shoulder seasons can be chilly around Chicago and Niagara Falls. Bring layers regardless of the season.
Traffic in/out of the cities of New York, Toronto and Boston can be quite hectic and busy, especially during the holiday period. There may be delays, so be prepared to take part in car games to keep you entertained.
This itinerary includes a walking tour of Toronto and free time in Montreal and Boston, which are best explored by foot. You'll get the most out of your trip if you're reasonably fit and able to walk moderate-to-long distances. However, public transportation in these cities is modern and reliable.
This itinerary is valid for departures from 01 January 2018 to 03 November 2018. View the itinerary for departures between 01 January 2019 - 31 December 2019
1. A single supplement is available on this trip.
Our US & Canada Discovery trips score an average of 4.63 out of 5 based on 27 reviews in the last year.
This fabulous trip took us from Chicago to Amish country, Niagara Falls, the contrasting Canadian cities of Toronto and Montreal, the serenity of Vermont, historic Boston and the excitement of New York City. We loved all of it!
Review submitted 07 Sep 2018