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North East Highlights

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The one that brings you the best of Northeastern USA, from Chicago to the Catskills, and Boston.

Travel Style

In-Depth Explorer

Take your time and explore in-detail each destination on this trip.

  • Duration

    7 days

  • Places

    4 places

  • Meals

    6 Breakfasts, 1 Lunch, 4 Dinners

  • Transport Style

    Coach & Internal Flight

  • Group Size

    Maximum 25 people

  • Team

    Expert Trip Manager and Driver team

Chicago, The Catskills, Boston, New York City

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    STEP 2

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    STEP 2

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    Everything has been sorted for you. Cool, convenient accom, smooth transport from place to place - plus a bunch of meals and travel experiences all locked in.

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    STEP 3

    Have the time of your life

    Your Trip Host has designed every trip to be packed with incredible, local experiences, made even more amazing as you share it with other incredible travellers.

North East Highlights

7 Inclusions

Experiences that are included with your trip

  • 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
  • Ciao Bella! Go local at a pizza dinner in Chicago
  • Time Out Market Dinner in Boston
  • Feel the student spirit on a 'Hahvahd' (Harvard) tour

4 Free Time Add-Ons

Optional experiences that you can choose from and pay for on your trip

  • Architectural Cruise in Chicago USD $32.00
  • Bike and Roll Chicago (seasonal) USD $35.00
  • 360 Observation Deck in Chicago
  • Freedom Trail and Food Tour

Where You'll Stay

Learn more about the accommodation available on this trip

  • 6 nights

    All accommodation is included on this trip

    6 nights in Hotel

About this trip

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.

Buy With Confidence

  • Only $99 deposit to book*

    For a limited time, reserve your space now with a deposit of only $99, pay the rest 45 days before departure

  • Pay over time, interest free

    Can't pay in full? We've got you covered with our Part Pay Program

  • No booking fee, no change fees

    Change your travel dates or even your trip for free

  • Financing available with UpLift

    Book now, pay later when you're eligible for Uplift

Map & Itinerary

  • Start location
  • End location
  • Trip day
  • Via location
  • River route
  • Plane route

Nights spent per location

  1. 2 2 nights

    Chicago

  2. via via

    New York City

  3. 2 2 nights

    The Catskills

  4. 2 2 nights

    Boston

  5. New York City

DAY 1 - Arrive Chicago

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.

INCLUDED EXPERIENCES

  • 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

  • Ciao Bella! Go local at a pizza dinner in Chicago

DAY 2 - Chicago

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.

FREE TIME ADD-ONS

  • Architectural Cruise in Chicago

    USD $32.00

  • Bike and Roll Chicago (seasonal)

    USD $35.00

  • 360 Observation Deck in Chicago

DAY 3 - Chicago to The Catskills via New York City

Chicago

It's time to wave goodbye to the Windy City.

New York City

We hop a flight across to NYC where our private coach will chauffeur us out of the mayhem and into the mountains.

The Catskills

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 - The Catskills

The Catskills

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 - The Catskills to Boston

The Catskills

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?

Boston

Stay

The Revolution

INCLUDED EXPERIENCES

  • Time Out Market Dinner in Boston

DAY 6 - Boston

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.

Stay

The Revolution

INCLUDED EXPERIENCES

  • Feel the student spirit on a 'Hahvahd' (Harvard) tour

FREE TIME ADD-ONS

  • Freedom Trail and Food Tour

DAY 7 - Boston to New York City

Boston

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!

New York City

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