Travel tips required! Boston/Cape Cod

We are very soon leaving for a family holiday, with a little trepidation I must admit as it’s the first looooong flight we have subjected Bea to since she was mobile. We are doing a road trip I’ve long wanted to check off the bucket list – New England in the fall. Our route takes us to Boston, then Cape Cod, back inland to do some real ‘leaf peeping’ and finally 5 days in New York for a bit of fun before flying home. I absolutely can’t wait.

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We have both been to New York before so have places we want to revisit and new sights to see, but I’d love to hear any tips you have on Boston particularly or Cape Cod if you have been.

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We plan to do the Freedom trail in Boston but are pretty open other than that as I don’t know much about the city. In Cape Cod we will mostly be enjoying playing on the beaches, cycle rides and some mooching around the towns but if there’s anything you recommend please let me know. I know there is a Dr Seuss museum and and Eric Carle (of The Very Hungry Caterpiller) museum on our route as both Authors originate from Massachusetts.

Thanks in advance for your tips! (Bonus points if you know of any quick pit stop places where we can let Bea loose to play for a break during all the sight seeing!)


PS Our first trip with Bea – Flying with a baby

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10 thoughts on “Travel tips required! Boston/Cape Cod

  1. Not 100% sure whether it is still the right season or not, but you can go whale watching off the coast in Boston. The trips only take a few hours and are amazing, we were lucky enough to see a couple of species on our trip and I can imagine this would be quite a spectacular sight for a little one! The top of the Prudential Tower ha a lovely bar and restaurant for stunning views over the whole city and towards the ocean..Enjoy your trip!

  2. I’ve spent a lot of time in Boston and New England this year with work, and it is definitely one of my favourite places in the US. Boston especially is beautiful and has a very historic and ‘European’ feel about it compared with NYC.
    I second the whale watching, I went with Boston Harbor Cruises and it was brilliant, they have zoologists on board from the aquarium explaining everything that you’re seeing, and in the 45minutes we were out on the sandbanks we saw whales constantly, right next to the boat.
    After the freedom trail, walking along the waterfront is beautiful, and also Beacon Hill. You’ll pass Faneuill Hall and Quincy markets on the freedom trail and it’s well worth stopping off here for a mooch around the food and nick nack stalls.
    I also visited the Boston tea party museum on a ship in the harbour, good, and interesting, but probably better for older children as there is lots of participation.
    Food wise, we literally ate our way around the city – the choices are incredible! Mikes diner in the south end ( is second to none if you like a full on heart attack inducing American brunch! Their full breakfasts are named ‘Emergency room’ and ‘Intensive care’ …..says it all!! At the other end of the scale, Atlantic Fish Co on Boylston has amazing fresh fish and seafood of all sorts, and it was exceptionally well prepared.
    We stayed in Loews and the Omni Parker on separate trips and would highly recommend both if you haven’t got accommodation yet – both beautiful old historic hotels in great locations.
    Finally (!), head to Plymouth for a traditional seaside town and great fish restaurants. It’s where the Mayflower landed with the first pioneers, and full of lovely old white clapboard houses to admire when wandering around.
    Hope you have a fantastic trip! xx

  3. Sounds like a fantastic trip. We toured Boston and New England for our honeymoon 4 years ago. We loved it, such a beautiful part of the world. In Boston we loved the Beacon Hill area, lots of quirky shops and delis and cafes to explore. The Freedom Trail was great, the perfect way to see most of the city. I also remember a lovely paddling pool and fountain in Boston Common that children we splashing around in. We went to watch the Red Sox too, which was so much fun. Have fun planning your trip. X

  4. Great trip. We did it a few years ago and “the Cape” is one of my favourite places in the world.

    We flew into Boston. We ate at a tourist hot spot as we were there for so little time and I wanted the experience (plus the views of the Boston sky line). If Bea is anything like LMJ, she loves just sitting and people watching so I would recommend the Barking Crab. Its centrally located, the food is OK but its the atmostphere that really swings it. And the cocktails and views are awesome.

    Activity wise, we did a tour of the Boston Red Sox Stadium (also download Moneyball and also that film with Ben Affleck in – the Game/the Town – to watch when Bea is in bed on your ITunes as both are set/filmed in Boston) and the Freedom Trail. We didn’t see a game as we saw one in New York on the same trip but if you can get tickets, I would.

    The Freedom Trail is OK but, like all things Boston, it was a bit ummm…pointless. I think Boston sells itself on being “the historical heartland of the USA” but some of the stops on the Freedom Trail are things like “Gravestone from 1900” and its like, I can see ones older than that in our local cemetery! I would spend less time in Boston and more time at the Cape / around Boston.

    Cape Cod wise, we stayed around Eastham which is half way up the Cape and close to the protected national seashore. A few tips:

    1. When you drive to the Cape, there is a scenic route which runs alongside the faster route – take that and stop A LOT – we found lots of small beaches to stop at, all completely quiet. We only took the faster route back to Boston when we were running out of time.

    2. We did a whale tour which was BRILLIANT. We got the boat from Provincetown at the top of the Cape – about half an hour drive. I wouldn’t stay in Provincetown itself – its very busy and quite Brighton-ey in its feel.

    3. The sun sets on Western side of the cape and all the locals and a few tourists took blankets down and roasted smores and had fire pits etc. It was like Dawsons Creek. Do it. Our B & B told us to go down an hour before which was a great shout as we had some gorgeous late afternoon sun too.

    The best, and the protected beaches, are those just North of Eastham on the Eastern shore.

    4. We had a really lovely meal at Wellfleet which is between Eastham and Provincetown – its famous for its Oysters.

    5. Chatham is well worth a visit – its often the place you see in postcards. The white clapperboard church against the cloudless blue sky. Lots of nice places to eat around here.

    6.Anything on the bottom half of the Cape, around Dennis/Barnstable/Yarmouth is good for a trip to Martha’s Vineyard but not for staying in – very touristy / Skegness-esque / tacky.

    There are some photos on my facebook page if you fancy a nosey.

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