2 Week Itinerary: New England and Canada

This was our first international trip with Kiddo! It was also the first trip we were to embark upon with him where we were not completely visiting friends/family or taking family with us. We were a bit nervous, but ultimately, it worked out really well!

At this point in time, Kiddo was still taking two naps per day – though to be fair, he mostly didn’t need them both. We were holding on to the 2nd nap because we liked it for ourselves! However, it did give us an outline for how we would plan this trip. Initially, we decided to fly to Boston because there was a direct flight on Southwest. (We currently hold a companion pass!) We knew we had a few friends scattered throughout New England that it would be fun to see. We also each had a few states up there that we had not been to. In addition, we saw that you could easily drive up to Canada, and in particular, to Prince Edward Island (PEI). We were excited that Kiddo could cross an international border and Della has been a fan of Anne of Green Gables so has always wanted to get to PEI. We decided to plan around those locations. We knew that Kiddo would nap in the car in the morning but then need something to interest and excite him in the afternoon before he would sleep in the car again in the afternoon. So, our goal was to never drive more than about 3 hours at a time and to always pick somewhere interesting to be in the middle of the day.

The 2 week itinerary was as follows:

Day 1: Arrive Boston
Day 2-3: Explore Boston
Day 4: Boston to Portland, Maine. We spent the middle of the day visiting a friend who we had experienced the Nepal Earthquake with us in Kennebunk, ME.
Day 5: Portland to St. Andrews, New Brunswick (Canada). We spent the middle of the day in Bangor, ME.
Day 6: St. Andrews to Summerside, PEI. We spent the middle of the day exploring Fundy National Park.
Day 7-8: PEI: one day exploring Charlottetown and one day exploring Cavendish
Day 9: PEI to Halifax, Nova Scotia. This was only a 3 hour drive.
Day 10: Halifax to Saint John, NB. We spent the middle of the day exploring Hopewell Rocks along the Bay of Fundy.
Day 11: Saint John to Northport, ME where we met a good friend of Della’s. We stopped for lunch in Machias, ME and then we explored Wild Blueberry Land near Columbia Falls, ME.
Day 12: Northport, ME
Day 13: Explored Acadia National Park
Day 14: Northport, ME to North Conway, New Hampshire. We stopped for lunch and a playground in Bridgeport.
Day 15: North Conway back to Boston via the scenic Kancamagus Highway.
Day 16: Boston with an evening flight home!

We really enjoyed the trip and our strategy of having Kiddo nap twice a day in the car worked almost flawlessly!

5 thoughts on “2 Week Itinerary: New England and Canada

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