Boston NYC Cycle

The Challenge

This spectacular 320 mile bike ride takes us not only on a geographical but also a historical journey, following America’s journey to independence. Starting in Boston, one of America’s oldest cities, our journey then takes us through quaint communities, untouched coast, colonial villages, rolling hills and seaside towns running along the Atlantic Coast. An unforgettable last leg of the trip is the ride over Brooklyn Bridge into the heart of Manhattan Island for a victorious bite of the Big Apple!


Day 1 (Weds 4th October 2017): London – Boston
Depart London on flight to Boston. On arrival transfer to hotel for dinner and a two night stay. Overnight: Hotel

Day 2 (Thurs 5th October 2017): Boston
Free time to explore Boston today, before a trip briefing and dinner before our cycling commences tomorrow. Overnight: Hotel

Day 3 (Fri 6th October 2017): Boston Harbour – Plymouth
After breakfast and bike fittings we are ready to start the challenge. We make our way through the city traffic to the quieter roads of our mostly flat route. Today is about getting used to the bikes as we cycle through the towns of Weymouth and Kingston, with lunch en route, finally reaching Plymouth (famous for Plymouth Rock, the site of the landing of the Pilgrim Fathers on the Mayflower, in 1620). Dinner and overnight at our hotel. Riding: 45 miles (72km), Elevation: +2018 ft. (615m)

Day 4 (Sat 7th October 2017): Plymouth – Narragansett, Rhode Island
An early start today for one of our longest days of cycling, but it is also one of the most scenic, full of coast and forest routes, as we follow the coast before heading inland to quiet tree-lined roads before our lunch stop in Providence (capital of Rhode Island). Some busy city roads then lead us to Scenic Route 1, where we enjoy the amazing coastal ecosystem with rich bird-life, arriving finally at the small summer beach town of Narragansett. Dinner and overnight at our hotel. Riding: 88 miles (143 km), Elevation +3837 ft. (1170m).

Day 5 (Sun 8th October 2017): Narragansett – New London, Connecticut
After a morning ride to a lighthouse and through a beautiful park, we enter Connecticut, the third of the four states covered on this challenge. Our ride includes some challenging hills today, but ice cream awaits in the historic seaport town of Mystic! Continuing to New London, we stop for dinner and overnight at our hotel near the port. Riding: 58 miles (93km), Elevation: +3046 ft. (928m)

Day 6 (Mon 9th October 2017): New London (Ferry to Long Island) – Woodbury, New York
The final state of our journey, New York State, lies ahead today! This, the longest day of our challenge, includes a 1 ½ hour ferry crossing to Long Island, New York. We ride 35 miles along a vineyard-dotted route to today’s first hill at Port Jefferson, then spend the afternoon winding through quaint, wooded residential areas until we arrive in Woodbury, our overnight stop. Dinner and overnight at our hotel. Riding: 90 miles (145km), Elevation: +3315 ft. (1010m)

Day 7 (Tues 10th October 2017): Woodbury – New York City
The final day of cycling, we follow a series of local bike paths and routes through New York City, enjoying stunning views of Manhattan and the Statue of Liberty, and finally ride over the Brooklyn Bridge to our finish line where we have time to celebrate with team photos. This evening we have a special celebratory dinner. Overnight: Hotel. Riding: 40 miles (64km), Elevation: +1647 ft. (502m)

Day 8 (Weds 11th October 2017): New York
Today is free for you to explore the incredible city of New York. With the largest population of any US city, and stark contrast between wealth displayed in the skyscrapers of Manhattan and poverty of the urban ghettos, New York is one of the world’s great cities and its location, attractions and the diversity of its neighbourhoods makes it unlike any other. You might choose to spend your time sight-seeing and take in famous sights including the Empire State Building, Central Park, the Statue of Liberty and Times Square to name just a few, or prioritise spending time in some of New York’s galleries and exhibitions, or alternatively hit the shops for an unrivalled shopping experience on Madison Avenue or Fifth Avenue – the choice is yours! Overnight: Hotel

Day 9 (Thurs 12th October 2017): New York*
Depending on our flight schedules there may be some more time this morning to enjoy some more of New York before our transfer to JFK Airport for our flight to London. *NB: Depending on flight schedules you may arrive back in London the following day

Day 10 (Fri 13th October 2017)
Arrive back into London (depending on flight times)

N.B. This itinerary may change due to unusual weather patterns, the ability of the group and so on. We will do our best to keep to the set itinerary however we cannot be held responsible for changes that might occur outside of our control. In all such circumstances your guide and tour leader will have the final say in the interest of the health and safety of the group.

What is included
  • Return flights from the UK
  • Airport taxes and charges
  • Local transfers and transport
  • 3* hotels throughout
  • Cycling guides
  • Trek hybrid touring bikes
  • Bike support vehicle
  • Different Travel UK tour manager
  • All meals as per itinerary
What is not included
  • USA ESTA (if required)
  • Any necessary vaccinations
  • Travel insurance
  • Spending money (tips, drinks, souvenirs)
  • Transport to/from UK airports
  • Personal biking kit
  • Carbon emission offsetting

Want to hear what other people thought of this tour? Click here for testimonials.

Trip Dates

4th - 12th October 2017

Tour Price


£520 plus £4950 sponsorship for any UK charity

Which payment option?

This option is for those who wish to raise sponsorship to cover both the costs of the trip (flights, accommodation, food, guides etc) and a donation to their chosen charity. There is a minimum sponsorship amount for each tour that you are required to raise in order to participate.

  • There is a registration fee payable at the time of booking.
  • The minimum sponsorship must be paid to the charity 12 weeks prior to departure.

This option is for those who choose to pay the tour costs (flights, accommodation, food, guides etc) themselves. There is no sponsorship required although if you wish to raise sponsorship for a charity you are welcome to do so.

  • A registration fee is payable at the time of booking.
  • Tour cost balance is payable to Different Travel eight weeks prior to departure.
The prices vary - please refer to individual tour pages for exact pricing.
Trip Difficulty

Moderate to Challenging

This trip is graded as Moderate to Challenging


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