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. Dine at a historic restaurant in Boston and walk the Freedom Trail, and then head on out to New York, New York for a stroll around Times Square, taking in the Empire State Building, the Rockefeller Centre and the Statue of Liberty.

Chicago, United States
New York, United States
United States
Physical rating
Cultural rating
Min 15
Group size
Min 1 Max 13
Carbon offset
621kg pp per trip


  • 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
  • Learn about immigrant history and culture through the food of New York City. Lower East Side, Chinatown and Little Italy are individual pocket-stops on your Urban Adventure
  • Stroll galleries, walk out to a lighthouse or take a dolphin and whale-watching trip in season. 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


This itinerary is valid for departures from 01 January 2016 to 31 December 2016. View the itinerary for departures between 01 January 2017 - 31 December 2017

Welcome to Chicago, USA. Your adventure begins with a welcome meeting at 6 pm. Please look for a note in the hotel lobby or ask the hotel reception where it will take place. If you're going to be late, please inform the hotel reception. We'll be collecting your insurance details and next of kin information at this meeting, so please ensure you have all these details to provide to your leader. If you have time during the day, perhaps explore the lake front paths that Chicago is famous for or take a cruise down the river and into Lake Michigan. In the evening, settle into your hotel in downtown Chicago.
Special Information
Notes: If you can't arrange a flight that will arrive in time for the meeting, you may wish to arrive a day early so you're able to attend. We'll be happy to book additional accommodation for you (subject to availability).

This trip doesn't spend much time in Chicago. We highly recommend you arrive early and spend a couple of extra days.
In the morning the trip starts with a long drive to Berlin, Ohio, which usually takes around seven hours. As part of the largest Amish settlement in the world, Berlin is at the heart of Amish country in Ohio. After checking in to the hotel in the evening, the group will visit a local's house for dinner tonight. The menu consists of homemade bread, baked chicken, vegetables, salad, pie beverages and more. This is a unique chance to learn about the hosts, who will also be sat at the table with you.
Special Information
Notes: The Amish are quite conservative and we recommend you dress modestly for dinner, with shoulders and knees covered, so as not to cause offence.
Today the group will make the five hour journey to Niagara Falls. Once there, take a tour of the falls before putting on a raincoat and heading out on the 'Maid of the Mist' boat ride. There are numerous viewpoints from which you can appreciate the power of this amazing set of falls, but there's no better way than to approach them from the water.
Special Information
Notes: The Maid of the Mist boat tour is subject to weather conditions. While this activity is scheduled to run from 01 April to 30 October, there is a chance that it will be unavailable (especially at the start and end of this period). If unavailable, your leader will organise a replacement activity for the group.
This morning take a short drive to Toronto. This afternoon, join a local guide on an Urban Adventure tour through Kensington Market and Chinatown. Explore two of the city’s most colourful and multicultural neighbourhoods. On the walking tour you'll experience the history, culture and individuality of both of these areas - your guide will also enlighten you with some local stories and intriguing history surrounding Toronto’s Chinatown. As one of Canada's most thriving and cleanest cities, there's a lot to explore. Either side of your Urban Adventure, perhaps take in the views from the CN Tower, catch a Blue Jays baseball game (in season), visit the Hockey Hall of Fame or go shopping in the PATH underground market.
Today it will take around six hours to drive to Montreal. Once there, the rest of the afternoon and evening are free. This is a compact island city, which is great for walking around and exploring the neighbourhoods on foot. Maybe head to Old Montreal and visit the famous Notre-Dame Basilica. Montreal is also home to more than 80 ethnic communities and enjoys an outstanding reputation for gourmet dining. Perhaps head to one of the many restaurants for dinner in the evening.
Today is a free day in Montreal. The old town is a must-see and rambling the cobblestone streets is a great way to spend a couple of hours. For lunch perhaps try the famous pastrami sandwiches at Schwarz's Deli, or relax over a long brunch at Beauty's Luncheonette. If you're feeling active, hike up Mont Royal and capture the cityscape from the Kondiaronk Lookout. Tonight, possibly head to O. Noir restaurant for dinner. Staffed by blind waiters, diners eat in complete darkness and part of the profits from the restaurant goes to support local associations.
In the morning, head south and back across the border into the USA on your way to Boston (approximately five hours drive in total). En route, stop at the picturesque Lake Champlain to stretch your legs. A bit further down the road is the Ben and Jerry's Factory, where you'll take a tour and try some ice-cream. Depending on time and traffic, you may also stop at a chocolate factory, cheese-maker's or a maple syrup farm. Arriving into Boston late in the afternoon, your evening is then free to explore.
Special Information
Note: Intrepid's aims when researching and contracting accommodation is to find properties that are well maintained, clean and as centrally located as possible. In an expensive destination such as Boston there is a balance to be reached in choosing a centrally located, clean property and still maintaining a value priced trip. Because Boston is such a great city for walking, in this case we have elected to go with a slightly lower standard hotel, but in a more central location. The hotel will still be clean and comfortable, but may not be up to the level expected on a Comfort trip.
Today is a free day to explore Boston, and it's highly recommended you walk the Freedom Trail. Start at the beginning, middle or end and wind your way through the streets of this very modern city and its historic paths. This is Boston’s indoor/outdoor history museum, with 16 'official' sites to explore. Afterwards, possibly go on a free student-led tour of Harvard University. Tonight, perhaps go for an optional dinner at Union Oyster House, which is reputedly the oldest restaurant in the United States.
Take a short drive from Boston to Provincetown, on the tip of Cape Cod (approximately two hours). Along the way stop at Plymouth Rock, which was apparently the disembarkation point for the Mayflower pilgrims who founded the first colony at Plymouth. Continue onto Provincetown, a charming town full of art galleries and beaches. Perhaps take a whale or dolphin watching tour, stroll the dunes or explore the trails along the seashore on a bike.
In the morning, drive through Rhode Island and along the Connecticut coastline to New York (approximately 5-6 hours). On arrival in the afternoon, head out on an Urban Adventure through the East Village area, and learn about the history of the craft cocktail movement, including tastings of course! The evening is then free to do as you wish. Perhaps take a walk around Times Square and grab yourself a slice a pizza, New York style.
Special Information
Notes: Please note that the legal drinking age in New York is 21. If you are under 21 we will aim to organise non-alcoholic mocktails for you to try during the Urban Adventure.

If you have any dietary requirements, please let your leader know in advance so they can pass this information on to your Urban Adventures guide.
Your US and Canada Discovery adventure has come to an end. There are no activities planned for the final day and you're able to depart the accommodation at any time. As there's a great deal to do in New York City, we recommend staying a few extra days to make the most of this exciting city. If you need help booking extra accommodation (subject to availability), our reservations team will be happy to assist. You should also consider doing our one-day sightseeing tour of New York (
View trip notes to read full itinerary


5 breakfasts, 1 dinner
Private vehicle
Hotel (10 nights)
Included activities
  • Dinner with an Amish family
  • Maid of the Mist boat tour
  • Kensington Market Urban Adventure
  • Ben and Jerry's Factory Tour
  • Plymouth Rock


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Important notes

1. A single supplement is available on this trip.

Trip notes

Want an in-depth insight into this trip? Your trip notes provide a detailed itinerary, visa info, how to get to your hotel, what’s included - pretty much everything you need to know about this adventure and more.

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Our US & Canada Discovery trips score an average of 4.56 out of 5 based on 9 reviews in the last year.

US & Canada Discovery , September 2016

US & Canada Discovery , September 2016