Get amongst the winter festivities of Canada and USA

Canada and America are big places with big reputations, and their larger-than-life personalities are all the more impressive in the snow. Check out the Windy City, see a completely different side of American life in small-town Ohio, experience the misty magic of Niagara Falls, attend an exhilarating ice hockey match in Toronto, be charmed by stately downtown Ottawa, explore eclectic and French-infused Montreal, get behind the scenes of American food production en route to Stowe, walk the Freedom Trail in Boston, and finish up among the snow-dusted icons and skyscrapers of New York. Along the way, there’s a slew of winter festivals and Christmas markets to explore.

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Terms & Conditions

Start
Chicago, United States
Finish
New York, United States
Countries
Canada, United States
Style
Comfort
Theme
Explorer
Code
SSKS
Physical rating
Ages
Min 15
Group size
Min 1, Max 13

Why we love this trip

  • Winter is a great time to travel the States and Canada – it’s less crowded and the snow and Christmas decorations can be magical. This flexible itinerary is specially designed to show you not only the highlights but also the added bonus of some seasonal treats

  • Enjoy a home cooked meal with an Amish bishop and his family and learn about another way of life

  • Attend an ice-hockey match in Toronto to learn all about this national pastime from a local’s perspective – not without a cold beer and some tasty Canadian snacks of course

  • This is our only trip that goes to Ottawa, a beautiful city full of grand Victorian architecture and fascinating museums

  • Canadians love a winter festival, and depending on when you visit there's always something going on – like December Christmas markets, festivals of lights in Toronto and Montreal, and Ottawa’s Winterlude

  • Visit the Von Trapp Family Lodge in Stowe to learn the truth behind the Sound of Music, and strap on some snowshoes for a walk through the mountains

  • 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 spans at least 16 sites across the city

Is this trip right for you?

  • 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.

  • Traffic in/out of the cities of New York, Toronto and Boston can be quite hectic and busy, especially during holiday periods. There may be delays, so be prepared to take part in car games to keep you entertained. 

  • Some of the cities on this itinerary 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.

  • It will be cold. Very cold. You'll need to make sure you have appropriate gear such as a pair of warm winter boots. See our packing list (http://www.intrepidtravel.com/au/packing-list) for a full suggestion of what to take.

  • Highways are generally well-maintained in this part of the world and ploughed regularly, however there can occasionally be disruptions to transport due to storms or heavy snow. Winter is a great time to travel but it does require some flexibility.

Itinerary

Welcome to Chicago, USA. Your adventure begins with a welcome meeting at 6 pm. Please 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 arrive early and have time, why not go ice skating in Millenium Park, check out Winter Wonderfest in (December and January), or find a little blues club or comedy club to curl up and have a drink in. If it's the season, perhaps visit the Christkindlmarket, an excellent traditional German-American Christmas market which runs in November and December. In the evening, settle into your hotel in downtown Chicago.
Accommodation
  • Hotel (1 night)
Optional Activities
  • Chicago - History Museum - USD14
  • Chicago - Boat Cruise - USD18
  • Chicago - Field Museum - USD15
  • Chicago - Navy Pier - USD16
  • Chicago - Museum of Science and Industry - USD27
  • Chicago - Bobby's bike hike - USD35
  • Chicago - Willis Tower Skydeck - USD18
  • Chicago - Adler Planetarium - USD12
  • Chicago - Museum of Contemporary Art - USD12
  • Chicago - Art Institute of Chicago - USD23
  • Chicago - Buddy Guy's Legends - USD55
  • Chicago - Architecture Boat Tours - USD50
Meals Included
There are no meals included on this day.
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.
Accommodation
  • Hotel (1 night)
Included Activities
  • Berlin - Dinner with an Amish family
Meals Included
  • Breakfast
  • Dinner
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 six hour journey to Niagara Falls. Once there, take a walk around town, and stop at a couple of different viewpoints to see the falls in action. Winter is a lovely time to see the falls, as the mist and spray blows in the wind and settle to create oddly shaped ice sculptures here and there. Afterwards, enjoy a free evening in Toronto. Perhaps explore dining options in and around Yonge-Dundas square, or check out what's playing at the Bell Lightbox cinema in the entertainment district.
Accommodation
  • Hotel (1 night)
Included Activities
  • Toronto - Kensington Market Urban Adventure
Optional Activities
  • Toronto - CN Tower - USD28
  • Toronto - Blue Jays baseball game (in season) - CAD40
  • Toronto - Hockey Hall of Fame - CAD18
Meals Included
  • Breakfast
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. With your time in Toronto otherwise free, there are plenty of other activities to enjoy. Maybe visit the Hockey Hall of Fame or go shopping in the PATH underground market. For a bite to eat, check out the essential Toronto food event Winterlicious (January and February), or the Winter Village at Evergreen Brick Works and its new street food market (December to March). 
Accommodation
  • Hotel (1 night)
Meals Included
There are no meals included on this day.
Drive to Ottawa, the capital city of Canada (approximately 5 hours). In the afternoon, perhaps check out the awesome Gothic parliament building, or visit the National Gallery of Canada or the Canadian Museum of History. Byward Market Square is great for a meal, with quality cuisine from all over the world (don't miss the beaver-tails – an Ottawa trademark a delicious winter snack). In early February, the Winterlude Festival is fun to explore. And from December to February, Rideau Canal turns into a 'skateway'.
Accommodation
  • Hotel (1 night)
Included Activities
  • Canadian Museum of Nature
  • Royal Canadian Mint
  • National Gallery of Canada
  • Canadian Museum of History
Meals Included
There are no meals included on this day.
Drive to Montreal (approximately 2.5–3 hours). Once there, the rest of your day 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.
Accommodation
  • Hotel (1 night)
Meals Included
  • Breakfast
Today is a free day in Montreal. For lunch perhaps try the famous pastrami sandwiches at Schwarz's Deli, or relax over a long brunch at Beauty's Luncheonette. The winter activities on offer are many: Fete des Neiges de Montreal festival (January), Igloofest music festival (January), Montrel en Lumiere festival (late February and March), the Old Port of Montreal Skating Rink, or Mont Royal for some snowshoeing. For dinner, the unique O Noir restaurant is a fine choice – it's a social enterprise with blind waiters in which you eat in the dark, and proceeds go to good local causes.
Accommodation
  • Hotel (1 night)
Optional Activities
  • Montreal - Jet Boat ride - CAD67
  • Montreal - Biodome - CAD19
  • Montreal - Olympic Park - Free
  • Montreal - Montreal Tower - CAD23
  • Montreal - Dinner at O'Noir - CAD50
Meals Included
There are no meals included on this day.
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.
In the morning, head south and back across the border into the USA on your way to Stowe (approximately 3 hours). 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 season, you may also stop at a chocolate factory, cheese-maker's or a maple syrup farm. There's a lot to do in Stowe once you arrive: perhaps visit the Von Trapp Family Lodge (this is the family from the Sound of Music); ride the Mount Mansfield gondola; or try some winter activities like sleigh riding or snowshoeing.
Accommodation
  • Hotel (1 night)
Optional Activities
  • Stowe - Ice skating (winter only) - USD20
  • Stowe - Snowshoeing (winter only) - USD20
Meals Included
There are no meals included on this day.
Drive to Boston (approximately 4 hours). Enjoy a free afternoon to explore. Perhaps visit the Harvard Campus or take a tour of the Samuel Adams brewery and sample a warming ale. Alternatively, take a stroll around Copley Square for its beautiful historic buildings, such as the French-Romanesque Trinity Church.
Accommodation
  • Hotel (1 night)
Included Activities
  • Waterbury - Ben and Jerry's Factory Tour
Meals Included
  • Breakfast
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.
Accommodation
  • Hotel (1 night)
Optional Activities
  • Boston - Cheers Bar - Free
  • Boston - Freedom Trail - Free
  • Boston - USS Constitution Boat Tour - Free
  • Boston - USS Constitution Museum - USD5
  • Boston - Samuel Adams Brewery - USD5
  • Boston - Harvard Campus - Free
  • Boston - Celtics basketball game at TD Garden (in season) 2 - USD75
  • Boston - Red Sox baseball game at Fenway Park (in season) - USD50
Meals Included
There are no meals included on this day.
In the morning, drive through Rhode Island and along the Connecticut coastline to New York (approximately 5 hours). Arrive late in the afternoon. On arrival your leader will take you for a quick orientation walk, showing you how to get around. You will have a 24 hour metro card provided to you so you can ride the subway. 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 or head to the Rockefeller Center for a skate on the famous ice rink.
Included Activities
  • New York - Metrocard
Meals Included
There are no meals included on this day.
Your US and Canada Discovery adventure comes to an end today. 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 (urbanadventures.com).
Optional Activities
  • New York - American Museum of Natural History - USD22
  • New York - Empire State Building - USD27
  • New York - Guggenheim Museum - USD22
  • New York - Metropolitan Museum of Art - USD25
  • New York - Museum of Modern Art - USD25
Meals Included
There are no meals included on this day.

Meals

4 breakfasts, 1 dinner

Transport

Private vehicle

Accommodation

Hotel (11 nights)

Included activities

  • Berlin - Dinner with an Amish family
  • Toronto - Kensington Market Urban Adventure
  • Canadian Museum of Nature
  • Royal Canadian Mint
  • National Gallery of Canada
  • Canadian Museum of History
  • Waterbury - Ben and Jerry's Factory Tour
  • New York - Metrocard

Dates & availability

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Important notes

1. A single supplement is available on this trip.

Essential trip information

Want an in-depth insight into this trip? Essential Trip Information provides 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.