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Eastern USA

Cities and mountains of North East USA

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Group Size: Max 25

Trip code: CTEU

Duration: 7 days

7 day group experience
Chicago to New York
Twin-share accommodation

Experience the modern vibes of Chicago with soaring skyscrapers and its deep dish pizza, then head over to the riveting Catskills for a chance to reconnect with nature in a surreal mountain setting, where you’ll get to swim, bike or just gaze at the stars by the fire. Top it all off with a stop in Boston, for a chance to discover the magnificence of this revolutionary city, with famous landmarks and delicious cuisine.

Trip highlights

  • Feel the student spirit on a Harvard tour
  • See Lake Michigan, Buckingham Fountain, the Navy Pier & Chicago River
  • Travel to 3 amazing USA cities - Chicago, Boston and New York
  • Toast s'mores and star gaze in the Catskill Mountains
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What's included
  • 6 nights accommodation
  • 6 breakfasts, 1 lunch and 4 dinners
  • Internal flight from Chicago to New York
  • On trip transport
  • Trip leader and driver 
  • See Soldier Field home to "The Bears" American Football
  • See Guaranteed Rate Stadium, home to the Chicago White Sox baseball club
  • See Lake Michigan, Buckingham Fountain, the Navy Pier & Chicago River
  • See the Hancock Building, Willis Tower & the Magnificent Mile
  • Go local at a pizza dinner in Chicago
  • Time Out Market Dinner in Boston
  • Harvard tour
  • 24 hour emergency support
What's not included
  • International flights
  • Optional activities
  • Some meals and drinks 
  • Airport transfers
  • Visas
  • Insurance
Further trip information

Day 1 - Chicago

Welcome to Chicago! This city of contrasts has pretty much everything you could possibly want in a great travel experience: stunning skyscrapers, world-class museums, delicious food, and enough entertainment to keep you on your toes. There is plenty to do, so we'll start off with a guided tour hitting all the major sights.

Day 2 - Chicago

Rise and shine! You've got a free day to explore the Windy City all on your own. Whether you want to bike around town for a street level perspective, jump on an architectural cruise or even see the White Sox or the Cubs play in a huge stadium game, the choice is yours. Nevertheless, you can't leave Chi -town without trying their signature deep-dish pizza, a perfect blend of American and Italian traditions.

Day 3 - Catskill Mountains (via NYC)

It's time to wave goodbye to the Windy City. We hop a flight across to NYC where our private coach will chauffeur us out of the mayhem and into the mountains. It's time to get back to nature and the Catskills is unmatched for beauty, location and its ability to make you feel remote without having to drive for days. 

Day 4 - Catskill Mountains

Today is all about YOU. Hike, swim, hire a bike or just be at one with the absence of traffic noise and exhaust fumes. Light a fire and toast s'mores and gaze at the stars above. This is living.

Day 5 - Catskill Mountains to Boston

Ready to venture back into the big city lights? Today we've got Boston in our sights. This forward-thinking city, also nicknamed Beantown, is one of the most popular tourist destinations in the U.S. Known for its iconic historical sights, great food spots and famous sports teams, this city will definitely tempt you to stay a bit longer. We'll get a taste of the local culinary scene with an included dinner at the famous TimeOut market. Lobster roll anyone?

Day 6 - Boston

We'll start the day at Harvard University and get a tour with one of the students. This hilarious look at student life will bring out all the LOLs. Take a coffee break at one of the many local cafes, go for a walk through the Emerald Necklace, then top it all off with some delicious seafood. Maybe opt to walk the Freedom Trail and stop at locally owned small restaurants to support the Shop Small, Shop Local movement here in the US. To add to this experience, pizza will be on the menu but not like the Deep Dish you had in Chicago.

Day 7 - Boston to New York City

Sadly, this is where our trip ends. You can check out in Boston or take the complimentary transfer to NYC with a drop at the Moxy Times Square....just in time to rest up and join the New York Uncovered or New York to Miami trip tomorrow!

Booking options

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Email us at: [email protected]
Arrival information

Your trip starts in Chicago on day 1. As there are planned activities for day 1, we recommend you arrive into Chicago at least 1 day in advance of your trip. If you need help arranging pre-tour accommodation please let us know.

Your trip ends in Boston on day 7, however we include a transfer to New York City where you will be dropped near Times Square. If you want to take some independent travel time in NYC, let us know and we can recommend some accommodation options.

Airport transfers are not included, and you will need to meet your group at the starting hotel on day 1. Once your trip is confirmed, we will advise on the best way to get from the airport to the starting hotel.

Accommodation & meals

6 nights of hotel accommodation are included in this trip. All nights are twin-share rooms. 

6 breakfasts, 1 lunch and 4 dinners are included.

Minimum age & eligibility

You’ll need to be a minimum of 18 years old to participate in this trip. This trip is designed for 18-35 year olds.

British passport holders can enter the USA for up to 90 days without a visa. You’ll need to apply online for an Electronic System for Travel Authorisation (ESTA) though. Your passport should be valid for the proposed duration of your stay.

If you’re under 21, you won’t be able to enter bars, clubs or other establishments where alcohol is served. It’s recommended that even if you are over 21, you always carry a valid form of ID.

Please note, this trip requires you to show evidence that you have been fulled vaccinated against covid-19 (final dose administered a minimum of 14 days prior to the start of the trip).

Please note: Visa, passport and entry restrictions can be subject to change. Always check foreign travel advice before your trip. 

Covid safety

This trip is designed with your safety and wellbeing in mind. As a result of Covid-19, many of our suppliers and partners around the world are introducing new policies and procedures surrounding health and safety in response to the Coronavirus outbreak. As the state of travel is evolving these new safety measures will adapt over time, and will be different for each trip. Here are some of the changes you may see on your trip:

Arrival safety meetings
Most trips have an arrival meeting on the first day where the guide or local team will run through the trip, the safety protocols, and to answer any questions you may have. Now more than ever it is important you arrive in time for these meetings.

Proof of vaccination or negative covid test
For the safety of all travellers, at the start of some trips you may be required to show evidence that you are fully vaccinated (14 days after your second dose) and/or show evidence of a negative PCR test taken within 72 hours of the tour start date in order to join the programme.

Updated hygiene and safety procedures
Our suppliers and partners have health and safety procedures in place on all of our trips. These protocols will be updated and adapted as a response to the Coronavirus outbreak, dependent on local restrictions and laws.

Transport and accommodation choices
Our suppliers and partners choose the accommodation and transport on our trips very carefully, and you may see a change to what would normally be used as a response to the outbreak. This may involve such changes as enhanced use of private transport or quieter accommodation.

Trained and knowledgeable staff
Our staff in the UK are trained to help you with your trip before you depart and answer any questions you may have. In addition, the local team and guides on our trips are there to help with any health and safety concerns and to ensure our trips run safely and smoothly.

Reduced group sizes
Some trips will run with reduced group sizes to start with. You may find that trips are more intimate and chilled, whilst still being packed with fun and adventure.

Your guide or the local team will be on hand to help you seek medical attention should you require it during your trip. As medical facilities and standards can vary around the world, you should ensure you have adequate travel insurance in place before you depart to cover you for any medical emergencies.

24/7 emergency support
We operate an emergency phone line for our travellers abroad. This is operated by a UK based member of staff 24/7 if you have a genuine emergency or urgent matter that you need attending.

It is important that you take measures to make travelling safer for yourself and others around you. Ensure you frequently wash your hands, cover your face when you sneeze and cough, bring and use your own hand sanitiser and facial coverings/masks, and enable social distancing where necessary. You should also ensure you listen to the instructions and guidance of the local team at all times, and follow all local laws and restrictions.

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