Honeymoon · Travel

New England road trip: decisions, decisions, decisions…

On our honeymoon with the pumpkin display at the Town Hall in Stowe, Vt
On our honeymoon with the pumpkin display at the Town Hall in Stowe, VT

This post is the first in a series of weekly blogs about our October 2014 honeymoon to New England and New York City. See all New England road trip posts.

It was the trip of a lifetime for us and even months after we’ve got back I still think our time in New England everyday. When I was researching our trip I found some interesting blogs from people who had done similar trips but nowhere near as many as I had expected. So I thought, why don’t I blog about it? As well as being fun for me, I hope it is helpful for some of you out there who might be planning a similar trip.

This post will mainly be about booking the trip, the next one will be about researching things to do including useful websites and apps then we’ll be onto the trip itself. Exciting! I hope you enjoy them.

Deciding where to go

On the road in New England
On the road in New England

A road trip around New England had been on my bucket list for years and years and with the realisation that our October wedding would provide the perfect timing to see the region in autumn (sorry, Fall!) with the leaves changing colour and Halloween, my mind was set and I began my campaign to convince my husband-to-be that New England was the way to go. Bombarding him with pictures of covered bridges, coastal resorts, beautiful leaves in autumnal colours and intricately carved pumpkins it didn’t take long to persuade him!

Sadly we quickly had to come to terms with the fact that it wouldn’t be possible for us to be out there for Halloween (as we wanted to leave pretty much straight after the wedding and our annual leave and budget would run out too early) but consoled ourselves with knowing that we would get the best of the autumn colours and with the realisation that we could sneak a little city break to New York onto the end of our stay instead. Silver lining!

I’ve been to New York a few times but my husband-to-be hadn’t and he was instantly sold on the opportunity to visit New York whilst we were so close. It seemed rude not to!

Deciding on an itinerary

Researching our upcoming honeymoon in our local American-style diner in Swadlincote, Derbyshire, England
Researching our upcoming honeymoon in our local American-style diner

Once settled on the idea, we started doing research into itineraries, travel companies and getting quotes. We considered booking it all ourselves initially but knowing that we would be very busy with work and the wedding we decided to look into travel companies instead. I’m really glad we did because whilst the trip was costly I think we got good value for money and I was pleased not to have the additional pressure of making sure I got the perfect accommodation in the perfect location for a perfect price as well as booking flights, hire cars and Amtrak tickets. Instead I could focus on the fun aspects like where to go for cocktails and good beer!

We noticed that most travel agencies offer pretty much a standard two weeks in New England itinerary with just minor differences to hotels/number of days in places/the direction of the trip.

We talked it over and decided that our ‘musts’ were to:

  • start in Boston and work anti-clockwise round the region ending up in Cape Cod
  • visit all the New England states
  • visit Kennebunkport, ME
  • visit Bar Harbor, ME (some itineraries sacrificed the trip up to Bar Harbor for extra time in other places)
  • add three nights in New York onto the end of the trip. A lot of itineraries suggest you start in New York but we thought having this to look forward to at the end would prevent us from feeling too sad at the end of our time in New England and so we weren’t exhausted/out of money for the rest of the trip!

Booking the trip

Kennebunkport Inn
Kennebunkport Inn

We spoke to loads of travel companies but in the end we booked with the online-only American Sky. They offered a very good price and itinerary which we amended slightly to change our stay in mid-coast Maine to Kennebunkport from Freeport and to add our days in New York on at the end.

They offered two levels of accommodation – Standard and Select. We wanted to make sure we had nice hotels but that were still in our budget so upgrading to Select was perfect. We added a second driver onto our car hire package too as both of us wanted the chance to drive around New England and I’m so glad we did because the drives were long!

They also offered a reasonable rate for upgrading our British Airways flights to Premium Economy. We realised that if you upgrade your flights on the outward bound leg of your journey you get the additional baggage allowance (2 x 23kg per person) on both the outward and inbound flights even if you’re returning in Standard Economy. We’re really glad we upgraded for this reason as it meant we could pack all the layers we wanted and buy treats for ourselves and friends and family without worrying about the luggage allowance.

We found American Sky to offer good value for money and good customer service and didn’t regret our decision to book our trip with them. We had some minor issues whilst we were out in New England but we received quick replies and resolutions to these.

The decision to specify Kennebunkport for our stay in Mid-Coast Maine was because of some wonderful pictures we’d seen of the place. From those images I was sold and had to visit. Thankfully American Sky were happy to arrange this change for us and suggested the Kennebunkport Inn which I’d read about and thought it sounded wonderful. It ended up being our favourite hotel on the trip.


Welcome to Heathrow Terminal 5
Welcome to Heathrow Terminal 5

So after all the research and quotes, here’s the 17 nights itinerary of wonder we booked:

Fly from Heathrow, London to Logan Airport, Boston (Premium Economy)

Boston, 2 nights at the Hilton Back Bay

Pick up intermediate car from Dollar Car Hire, Boston

Kennebunkport, ME, 1 night at the Kennebunkport Inn

Bar Harbor, ME, 2 nights at the Bluenose Inn

Jackson, NH, 2 nights at the Lodge at Jackson. We were originally due to stay in North Conway but this was changed by American Sky a couple of months before departure.

Stowe, VT, 2 nights at the Golden Eagle Resort

Great Barrington, MA, 1 night at the Comfort Inn & Suites Berkshires

Newport, RI, 2 nights at the Hotel Viking

Hyannis, MA, 2 nights at the Cape Cod Resort and Conference Centre

Amtrak from Boston to New York

New York, 3 nights at Row NYC

Fly back from JFK (Economy)

In next week’s post I indulge my geeky hobby of holiday planning and research. Apologies in advance!

See all New England road trip posts

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