In May my husband Jason graduated medical school and all our parents came in to town for the ceremony. Afterwards, since everyone was already in town, we decided to take a trip together. None of us had ever been to Boston so we thought, why not! We were going to be moving further South in a few weeks, so we wanted to take advantage of our time off and travel up North.
Our first day we went to Martha’s Vineyard. It was stormy with a little rain, but we still had a good time. We got up early and drove to where the ferry picked up passengers. Decide ahead of time where on the island you’d like to be dropped of at because the ferries don’t come very often and they all go to different locations. We took the Ferry to Vineyard Haven then road the bus to Oak Bluffs where all the Gingerbread Cottages were.
*Dog Tip- Boris was allowed to ride the ferry and the buses which made transportation with a dog super easy.
We walked around the neighborhoods and the coast, then took the bus to different areas of the island for shopping and eating. Such a fun day!
On day 2 we went into the city of Boston! We drove in and parked our car near the Boston Common (a big park in the city). Most of the day was spent touring, eating, and more touring. We started our guided tour of the Freedom Trail at Boston Common and I highly recommend it! Our guide dressed up and taught us so much about the history of the city.
*Dog Tip- Boris was allowed on the tour! 100% of the tour was walking around the city and Boris is very well behaved so it wasn’t a problem having him. I will say we brought a huge jug of water for him to drink in between stops because it was pretty hot out (and it was only May!). If it’s in the middle of the summer, maybe leave your pup at home because they might overheat.
After the tour, we found ourselves at the Quincy Market which was the perfect location to grab an outdoor table and eat some food from one of the varies restaurants. We sat with our gyros and let other tourists come over and pet Boris. Many people took photos with him too! He’s like his own little attraction.
The rest of the afternoon was spent doing the last few stops of the Freedom Trail. Most guides only take you on the first half because the other half is on the other side of town. So we walked and visited the last locations on our own.
For dinner, we left Boris at the Airbnb and ate at Union Oyster House which is Boston’s oldest standing restaurant established in 1826. Make a reservation days in advance because this place doesn’t allow walk-ins. The food was delicious and the original architecture inside was incredible. So worth it!
#Dog Tip- We love getting Airbnb’s when we travel with Boris because we can find something close that allows us to drop Boris off when he’s getting tired. Which then gives us flexibility to keep exploring while he takes a nap :)
Last day we visited the battle sites of Lexington and Concord to explore the grounds. Very relaxing day to end on before our drive home to Pennsylvania the next day. And yes, Boris did jump in that river for a swim and we didn’t care one bit! Boris is actually a really good swimmer!
We ate lunch at the cutest little place in Concord called Main Streets Market and Cafe. We sat at a table outside with Boris in the beautiful weather and the waiter took good care of us.
We love traveling with Boris and look forward to doing so a lot more in the future!
