I’ve been MIA from the blog the past few months due to various things happening in my personal life including starting a new job. I also took a trip to the USA for 3 weeks to see the autumn leaves and do some planner shopping!

USA Itinerary: Dallas, Chicago, Boston, New England, Pennsylvania and Washington DC (3 weeks)

Here’s an overview of the trip:

• Dallas including visiting Fort Worth
• Boston to join a Trafalgar ‘Autumn Colors’ bus tour with stops in Massachusetts, Vermont, New Hampshire and Maine
• Boston for a few days, including a day trip to Martha’s Vineyard
• Philadelphia including a day trip to visit the Amish
• Washington DC
• Chicago

I’ll be posting an in depth review of the Trafalgar Autumn colors tour soon.

If you’d like to download a copy of the itinerary, I’ve uploaded it to the free printables library here (my other itineraries from past trips are in there too). If you’d like an editable version of the itinerary that you can customise however you please, see here.

What I liked about this itinerary

Start in Dallas, end in Chicago. By ordering the start and end cities with the shortest long haul flight routes to / from Australia, it made the journey more bearable.

The departure flight route – I had a 14 hour flight home from Vancouver a few years ago, that turned into 16 hours as we sat on a tarmac while they did maintenance on the plane and didn’t bother making up the time in the air. So this time I decided to try a 15 hour direct flight from Sydney to Dallas. It was great! It didn’t feel much longer than Brisbane to Dubai, you can bypass LAX and land just about in the middle of the USA. The transfer in Sydney was straightforward and we didn’t have to collect luggage, re-check bags or re-go through security. I would definitely do that route again!

The return flight routes – better to exit the USA via transiting through LAX, rather than enter the USA via LAX, having to clear customs in LAX etc.

We felt we had the right amount of time in Dallas, Chicago, Philadelphia and Washington DC (maximum 2 days in each city).

No driving – I would love the control and flexibility of having a hire car but driving in the USA would be too stressful for me (I hate driving in general and don’t own a car). Parking was also hard to find and expensive in many places on this itinerary.

Timed the autumn colors in New England! I created a spreadsheet and cross checked so many fall foliage predictor websites, blogs etc. to try and pinpoint dates that would have a high chance of seeing peak fall foliage and it worked out well. We timed peak in Massachusetts (outside of Boston, not in the city itself), Vermont, New Hampshire and Maine. Sadly we were too early to see peak autumn colors in Philadelphia, Washington DC or Chicago (can’t be everywhere at once and when online says end of October, it must literally mean the very end of the month – the last week. We flew home on the 26th October and Chicago hadn’t reached peak yet). But then the colors can be unpredictable so who really knows, if you really want to see peak, I’d just block out the entire month of October.

Green Mountain Girls farm in Vermont

Download a copy of the itinerary from the free printables library here. If you’d like an editable version of the itinerary that you can customise however you please, see here.

What I would change about the itinerary

A bit too long in Boston. The last day probably could’ve been a half or 3/4 day. I had originally planned on visiting Plymouth or somewhere else on Cape Cod, but the logistics to get there proved too difficult without a car. The only day trip option I could find from Boston via a bus / ferry was to Martha’s Vineyard (which was already on the itinerary).

Boston is quite spread out and the metro is very old, the stations are not quite in the right areas to pop out right where you need to go, there was often 10 – 15 minutes walking just to get to / from the station so sometimes it ended up being only sightly longer to just walk between places. I was trying to time good weather at viewpoints so ad-hoc changed the order of a few things. Getting between places took up a bit of time.

I did this trip with my Mum who had already been to Boston in 2016 including Martha’s Vineyard, Salem and just about everything else already on the Boston itinerary. I would’ve liked to add a day trip to The Breakers Mansions but she didn’t want to do it again (fair enough). Boston accommodation is limited and extremely expensive – it’s not an affordable city to visit solo. So even though it’s not on mine, consider adding The Breakers if you’re going to use my Boston itinerary.

If I’d had more time, I would’ve added a few days in New York between Boston and Philadelphia, then take the train all the way to Philadelphia and Washington DC instead of flying.

I only visited Chicago 360 at night, I wish I had gone at sunset so I could see the skyline during daytime, sunset and at night.

What about the Trafalgar tour?

I’ll be doing a detailed review of the Trafalgar tour (similar to the one I did for the Globus tour a few years back) in another post. I didn’t mind the tour but I’m so used to being in total control of the itinerary these days, that the pace and some of stops I would’ve skipped or made shorter.

On the flip side, some of the visits to key destinations were extremely short. We only had 45 minutes in the cute town of Stowe, yet we would have 30 minute pee stops at random visitor information centres where there was nothing to do. The main reason I chose Trafalgar over other tour companies running similar tours was that it stopped in Stowe, so I was quite disappointed / frustrated by that.

Acadia National Park

Unfortunately the best places in the USA for fall foliage are car destinations. I considered flying into Burlington and attempting to drive around Vermont, but then how do you get to Conway and Acadia national park? There are no commercial airports nearby, and very few bus or train routes (and they had weird timetables) to and from Boston. The best autumn colors were in New Hampshire and there’s not much public transport there. A lot of places were too far for day trips from Boston (and you’d still need a car), so the itinerary is best done in a one way circuit.

If you’d like to download a copy of the itinerary, I’ve uploaded it to the free printables library here (my other itineraries from past trips are in there too). If you’d like an editable version of the itinerary that you can customise however you please, see here.

More travel itineraries

• USA itinerary: west coast cities and national parks of Utah and Arizona (3 weeks) 
• Globus Enchanting Canyonlands Tour Review (Arizona, Utah & Nevada)
• 4 Week Paris and London Itinerary (plus thoughts from my first time trying slow
• How I Planned a 6 week European Holiday (Plus download my detailed Itinerary)

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