We have been incredibly fortunate to travel much of the US every summer for the past 14 years. You can find all my itineraries on Jetlag & Mayhem from New Mexico to Hawaii to Wisconsin and Florida. What’s interesting is that as the years progress (Jetlag & Mayhem are now 14 and 12), these trips become more challening to plan. In the old days they would do as they were told with minimal moaning, whether that’s visiting a museum or hiking a national park. Now they are much more opinionated with their top itinerary votes either going to sunbathing or Sephora. So I try to build a trip where everyone has a say in what we do. I ask them to find amazing eateries and exhibitions on Tiktok (it’s actually a treasure trove of information). Then I combine that with an itinerary to suit us all.
In the past, Mr Jetlag and I would choose the state. When we lived in Asia, we tended to travel to the West Coast and South West as it was a much shorter flying time. Now we have access to the East coast, we can tick off much more of the country! In 2022 we visited Pennsylvania. This was a fantastic trip but I didn’t factor in much time for relaxation. So when we were picking our state for 2023, I promised Jetlag & Mayhem that we would spend time at the beach. With more than 1500 miles of coastline, Massachusetts looked like a winner. Combined with the fact I’d never been to Boston, this was clinched by the lure of beach, culture and plentiful shopping.
You’ll know I’m a complete Excel nerd. I keep track of what we’re doing every day, opening hours, driving distance and any booking confirmations.
Planning our stops
Research takes some time and a route takes a while to materialise. But once I have it, the excitement builds on my Excel spreadsheet. I start with the flights and managed to find some decent priced British Airways flights from London Heathrow to Boston. Bear in mind I tend to book nearly a year in advance so that is why it is always a good price!
With Boston as my starting point, I scoured the blogs for itinerary ideas. I stumbled across Rockport, a quaint little seaside spot north of Boston and thought this could be a cute place to head after a few days in the city. It would also mean we could drive via the famed witch town of Salem enroute. From here we travelled inland West towards the Berkshires, a highland region in Massachusetts and part of Connecticut. Whilst we like to try and just focus on one state, I couldnt head to Cape Cod without dipping into Newport, Rhode Island. Rhode Island is the smallest US State by area and probably won’t get its own roadtrip! Our last stop on the roadtrip was beach time in Cape Cod. A peninsula, extending into the Atlantic Ocean from the bottom of MA, I hadn’t realised how big the area was. I chose to base ourselves in Dennis as it had decently priced accommodation options. Our final itinerary looked like this:
Boston (4 nights), Rockport (2 nights), Great Barrington (3 nights), Newport (2 nights) and Cape Cod (4 nights).
There’s a really great resource called Wanderlog where you can input your stops and see what there is to visit in between. I also love reading a good old fashioned guidebook, shout out to Lonely Planet who make the best in class.
Booking Our Accommodation
When you have young children it’s easy to pile into one room. With teens, they really don’t want to share a bedroom with us and the most cost effective way to book accommodation is Airbnb. I am a big fan of the site and always choose places with plentiful top reviews. You can really mix it up and stay in all kinds of unique properties. For Boston we ended up in a lovely suburban house with easy access to the tram. In Rockport we stayed in a cute little apartment above a restaurant and in Great Barrington we were in a beautiful log house.
For the hotels at the end of our trip, we ended up sharing one room as it was just so expensive but there was a lot of moaning about privacy from Jetlag & Mayhem.
Car Hire
If you’re starting off in a big city, you might want to consider delaying your car rental until you really need it. In 2022 we started our trip in Philadelphia and our car was a nightmare. We could never find anywhere to park it and the streets around our airbnb were very narrow and one way. If the city has good public transport then you really don’t need a car (you can also uber around). For Boston, we decided to pick up a car on the day we were departing Boston. You can often find inner city car rentals but as we weren’t far from the airport, Mr Jetlag headed off to pick up the car from the Avis there, whilst I packed up.
Try to sign up for the preferred club of your chosen car rental (e.g. Avis Preferred) as this will save you time (and it’s usually free). Unfortunately the cars are often dirty so I always pack wipes to give everything a rub down.
Activities
I try to roughly plan what we do each day (yes very little spontaneity). This way I can keep track of opening hours and book restaurants, activities etc that need some pre planning. For this trip I pre-booked our tickets to the Boston Tea Party Museum, Fenway Park Tour, Tanglewood Concert and one dinner in Cape Cod. Depending on where you go, you might not need to be so detailed but I’ve been burned in the past!
Unfortunately you can’t plan for weather. Whilst August should have been guaranteed sunshine, we were met with a few days of unseasonable cold weather whilst in Rockport so had to turn our beach days into hiking instead.
