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3 stops on a road trip from Boston to NYC

Early October is a great time for a trip to Boston, Cape Cod, Rhode Island and New York.  The weather is likely to be all over the place – so it isn’t a busy time of year for tourists.  We had half our trip high 20s and above, a hurricane, some cooler days and then more hot weather in New York.  We flew BA and the flight times work quite nicely to and from Heathrow.  The Newark lounge is thankfully now much improved – flew through there in February this year and the former McDonalds-esque space is now happily replaced with the Galleries brand!  Proper pre-flight dining is handy as that means on the plane, glass of fizz and straight to sleep – next stop London! Boston I would suggest you go to Boston first – I think if you went to New York and up then Boston probably doesn’t have such a wow factor.  Notwithstanding they are very different cities –  plenty to enjoy in them both.  We went low(er)-budget for our nights in Boston – Hotel 140.  We were there with jet lag and didn’t plan to be at the hotel much so this worked fine; it is strange in that it is connected to the YMCA, but it is also 50 yards from an Avis depot so easy to get your car from later on. Things to do in Boston: have a good mooch and lunch at Quincy Market, Boston Common is lovely and its worth the stroll out to the Reflecting Pool and the church with fancy maps on the ceiling.  We saw the rest of the city on a pre-booked Duck Tour – a tad touristy, but to be honest we wanted to see the city and head to the Cape ASAP so this was the easy way!  It’s worth getting the ferry over to see the USS Constitution and also to look back at the city skyline that is very pretty.  Seeing Boston in the fall was stunning – if you are a runner then it is perfectly flat around the river basin and very popular for jogging! On to Cape Cod – an easy drive We stopped to enjoy the beach and lighthouses in Hull and then to see a bit of Plimoth (CabbyShack was a good priced diner) history. We often mix up our accommodation a little and avoid hotels for too much of a holiday.  A friend had suggested Wellfleet as being a good choice of place to stay and we found Oyster Cove Bed and Breakfast.  The room is large and airy and comfortable – it’s all in one room, but it is so big that it feels more like a mini open-plan apartment.  Breakfast is lovely and you have your own entrance round the side of the owners house.  There is also a microwave and fridge and balcony as well as plenty of sofa space.  It was a good choice between a hotel (far nicer than a hotel as personal service) and self-catering because we had breakfast provided but also had space to cater for ourselves simply (and there’s a little store in the village that makes that easy).  Plenty of nice walks nearby to see the sunset from different beaches – our favourite was Duck Harbour.  It felt like a very privileged area and largely undiscovered by tourists so it was very quiet and relaxing.  There are some lovely jewellery shops in the village.  I think it closes down for the winter, we were there just in time. Nearby, Cahoon Hollow was a lovely beach – but to be honest the whole area is rather spoilt for lovely beaches!  Chatham beach is pretty and the town is quite quaint – lunch at the Impudent Oyster is recommended.  Provincetown is certainly an interesting place to visit, and the Pilgrims monument gives a stunning view on a clear day.  There are a few vineyards around – we went to Truro, not the best wine but the tasting session is very well delivered and it’s on a lovely spot. Rhode Island was our next stop We did this in 2 pieces – first a couple of nights at a little cottage in Bristol right on the waterfront with its own pontoon (just like the Dawson’s Creek setting but not in the Carolina’s!!)  This place fits 4 single beds into a very diddy but idyllic wooden hut with a great family story behind it (the proprietor leaves her memoirs for you to enjoy whilst sitting on a rocking chair on the porch). You have to be a bit into quirky accommodation to stay here – but then I did type ‘quirky’ into Google to find it and we loved it!  There doesn’t seem to be a great deal to do in Bristol (friends that stayed their recently pointed this out); however if you want to put your nose in a good book and enjoy the view away from the hum drum then this is nice.  I wouldn’t call this luxury but neither would I say basic – I’ve never stayed anywhere like it and would love to go back in the height of Summer! From Bristol we went on to Newport My husband was given the task of booking one night’s accommodation on the trip and he smashed it here, in terms of just how wonderful it was but also in terms of the budget (of course)!  We had a wonderful stay at the Vanderbilt Grace.  This is our kind of hotel:  no front desk but welcoming staff, staff that know your name as they wander round the hotel, fizz on arrival, splendid breakfast, Molton Brown goodies, rooftop terrace, etc.  It’s a good base to explore the historic town.  We were there during a seafood festival and there was a real buzz to the place.  We had a mooch around ocean drive and looked at the outside of some of the other mansions.  We were also lucky my husband had a meeting at the New York Yacht Club and I very much enjoyed that as a location to take in the atmosphere and read more of my book!  For any yotties, then you need the obligatory photo next to the ‘America’s Cup Avenue’ road sign – it is in the middle of a busy carriageway so pick your time! If you are then going on to New York – dump the car en route – we got the train in from Stamford which reduced the hassle factor of arriving in the city.  Our stay in NYC was in Hotel Wales – boutiquey upper east side spot. Impossible to choose  hotels in NY but we figured that given our main aim for NYC was to walk for miles each day then high end wasn’t needed and this was the best price we could find at the time.  We got the New York city card which meant we’d pre-paid for lots of different tourist venues which reduced the outlay during our time here. New York Top tips: – see the view from the Rockefeller and Empire State at different times – i.e. dawn and dusk; – enjoy the High Line parkway for a nice stroll – quirky and lovely; – stroll around central park Jackie O lake with a morning coffee then have breakfast on the upper east side (we watched on with interest at how the school run works here – it really does seem to be like gossip girl!!); – cocktails on the roof terrace of the Met Gallery (I remember my husband yawning at the idea of a gallery until he realised where I was headed in it); – and take a river cruise – hop-on hop-off ones are good – we didn’t have the energy to walk back into the city over the Brooklyn Bridge but the view is supposed to be worth the effort. Continuing the theme of yacht clubs we then dined at the city venue of the NYYC and that was just amazing.  It is also situated on a road full of this type of old-skool club, quite something in US history and lovely to see. The 9/11 memorial shouldn’t become a “tourist attraction” per se but it is a place to visit and remember and reflect on the scale of what happened and also see the size of the new building which is a triumph and the pools that are built in the space of the twin towers.  It’s a very peaceful part of the downtown area and I hope it stays that way. We didn’t use this holiday to splurge on fancy food.  To be honest after a couple of days we’d realised we barely needed more than a lunch out and a salad from a a corner shop to eat in our hotel.  Our favourite place for a prosecco and vino tinto in New York we found when we were killing a little bit of time waiting to go to the airport – just across the road from Hotel Wales is a sweet little place called Pascalou.  We’d have happily found that place earlier but it did reassure us NYC is just like anywhere else and little gems are there to be found if you look off the beaten track!

Anna Parker

I am happiest when travelling in style with my husband, enjoying the outdoors and taking photos to keep the memories! On the lookout for luxury and unique stays. Based in the UK. Find me on twitter @aeparker81 or at www.travelwithpenelopeandparker.com

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  1. Some great tips, thanks for sharing! Boston has to be one of my favorite American cities. It’s deceptively large but still seems to retain that village feel.

  2. Boston is one of the most favorite city for me. I always love to visit Boston again and again and specially after reading this post i am thinking to do a road trip to Boston.Thank you for sharing.

  3. Thank you for all the tips. How long did you take to do this trip? Is 2weeks enough?

    Many thanks Sophie

  4. Hi Sophie – we did it in around 10 days. It didn’t feel rushed, but we have since been back to Boston for a day or so before heading in to Maine instead. On the trip above – we had 2 days in Boston, 4 in Cape Cod, 1 in Newport and 2 in New York. Enjoy!

  5. Hi, thank you for your lovely blog. I am wanting to do this exact routing but nervous of where to drop off the car and finding my way around on the train into NYC. Did you buy the ticket before or just drop car at station and catch train? Is it pretty simple to get to your hotel once in the city? (Am used to the London underground) Thanks again!

  6. Hi Tracy – we got a taxi into Boston from the airport and picked up a car on the day we left the city. With 3G google maps it was easy getting out of the city. I’ve picked up from 2 of the Boston Avis depots now with no issue. Coming into NYC – I hear you – terrifying to drive there. We dropped the car back at an Avis place in Stamford and got the train into NYC from there. I pre booked the train tickets. I think once in NYC we got a cab to the hotel as we had a lot of luggage but the underground in NYC is easy enough, there just isn’t as much as in London so it was a long walk to our hotel from the nearest stop. You could get the train all the way down from Providence? If you time your trip well it might clash with a fire and light show in Providence which sounds great – our timing didn’t work so we didn’t do that option.

  7. Thank you SO MUCH for this. We are booking into Hotel 140 for one night, Oyster Cove for 3 nights and the Grace Vanderbilt for 2 nights then our fave place in NYC THE LUDLOW.
    Thanks for all these great tips, I needed to pick up my teen in Boston and then work out a holiday and all your wonderful research is being harvested by me. Thank you!!

  8. Planning on travelling to Boston for the first time, from Hollywood, FL. Please forward some tips of where to stay and what to do. Thanks.

  9. This is a great blog post! I’m planning a road trip from Boston to NYC and this post has given me some great ideas for stops along the way. Thanks for sharing your experience!

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