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Boston & New England

Adventure, City Break, Cruise, Culinary, Cultural, Escape to the Country, Featured Destination
United States
Won't break the bank
Age range
35-44, 45-54, 55-64, 65 and above

Spend about a week in Boston starting 05/09/2018, then train up to Portland Maine, spend a few days there then hire a car to see the nearby country side, including historic Train journeys in / near Mount Washington.

I'm planning a trip covering Boston and New England from 05 Sept 2018 until about 18 September 2018. It will be in two halves so looking for 1-3 travel buddies to either join me for both halves or one half.

Section 1 - 05/09/18 -about 11/09/18

Start in Boston, my flight will arrive around 8pm local time. Stay in Boston for about 5 days and see what we can. On my list is (in no special order):

  • Martha's Vineyard
  • Salem
  • Isabella Stewart Gardner Museum
  • River Cruise
  • Boston Tea party Tour
  • Freedom Trail Walking Tour

​My usual preference is for a mix of cultural, and standard tourist things with some good food along the way. Pretty scenery and views are always a biggie for me. I expect this part will be a public transport adventure.

I am fine if my travel buddy only wants to do some or even no actual activities with me during the day. What I am looking for is someone who will join me some evenings for a meal and is ok to share a room, (or an affordable multi bedroom apartment if we can find one). Accommodation costs are quite high for central hotels and B&Bs in Boston and close surrounds.

Section 2 - 11/09/18 -about 18/09/18

Train up to Portland. There is the opportunity (if we time the journey right) to get the train with the glass dome ceiling for this. It will be early Fall and the area is renowned for amazing Fall scenery (from my research I have learnt they call the enthusiasts 'Leaf Peepers'). Plan is to spend 1-2 nights in Portland and then hire a car to go to Mount Washington and particularly to ride the heritage railways there. There is a Cog one that goes to the weather observatory and another couple which wind through the Forrest / Parkland. Probably involve 1-2 nights in Conway. If there's time a trip up the coast from Portland to see the sights there could be included.

My plan is to then train back down the coast from Portland to Boston or NY to head home to the UK.

I am really looking for a travel buddy (or three) to share accommodation and driving for this section. Though in Portland single accommodation is more affordable so not so essential to room share. What is most important is that you share the driving and cost of same. I do like driving, but don't want to be stuck doing all of it and missing the views. Also, you have to be OK about driving an automatic as although I have a manual DL I struggle with them - height issue, nothing else.

Interested in going?

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