Lets jet set off to Boston from Los Angeles. First things first, we have to book our flights. You know me and my love of a good deal, and we found exactly that on Frontier https://www.flyfrontier.com/ . We chose Frontier due to their promotion of KIDS FLY FREE (up to 16 years) on some roundtrip flights (if you are a part of the Discount Den, $59.99/annually). This promotion worked perfect for our situation, as we were gifting this trip to my mom as a retirement present, so we had three adults and three kids flying and only paid for three round trip tickets. As a note for Frontier, you can find some amazing deals. I once flew from Los Angeles to Denver for $7.00!
So, back to the trip… Our flights had us arriving relatively late, so we stayed near the airport prior to heading to Chatham the next day. For hotels near the airport I recommend Courtyard Boston Logan Airport https://www.marriott.com/en-us/hotels/bosla-courtyard-boston-logan-airport/rooms/ if you are using points or The Westin Boston Seaport District https://www.marriott.com/en-us/hotels/bosow-the-westin-boston-seaport-district/overview/ for a good rate and I love how Westin hotels smell.
On the drive to Chatham, we stopped at Pilgrim Memorial State Park for some slushies and to get a first hand look at Plymouth Rock. It is an actual rock you can view. It does have a fence around it so you are not able to touch it. Plymouth Rock is located next to a gorgeous harbor with boats and a river running near the town in the Brewster Gardens area. If we had more time, I think this adorable spot would be a wonderful place to spend the day.
We arrived to our Airbnb http://www.airbnb.com at grabbed some coffee at Monomoy Coffee Company, which is now called Chatham Perk https://www.chathamperk.com/ The entire downtown area is adorable in Chatham and had some cute shops and restaurants.
The next day we walked around fabulous homes in South Chatham and played “if we won the lottery…” and visited a beach with a library style shovel and bucket wall to share. The beaches have “Be Shark Smart” signs all over, which was a bit intimidating, but the water was amazing and we felt safe, even in the water close to the shore.
After our morning at the We ate lunch at Sandi’s Diner, where the motto is “Sandi’s Diner, Nothing is Finer”…however it too has now been sold and it now called Lily’s diner https://lilysdiner.wordpress.com/everday-menu/
After lunch we walked down to the beach near the U.S. Coast Guard Chatham. We found a spot at Chatham Lighthouse Beach and relaxed for the afternoon, building sandcastles, playing in the water and taking pictures with the lifeguards. Being from the west coast, the east coast ocean always feels so warm and refreshing.
That evening we went to Chatham Bars Inn https://www.chathambarsinn.com/ for Happy Hour and to take in the view. This is an absolute must see and was gorgeous! We sat in adirondack chairs, on a hill overlooking the ocean and then ended the day with ice cream and grabbed the http://vineyardferries.com map to plan the rest of our adventures. We would be leaving from Woods Hole, MA to Martha’s Vineyard, with a stop in Hyannis Port along the way.
The next afternoon we drove to Hyannis Port. I have a slight obsession with the Kennedy Family and wanted to see the Kennedy Compound. We were able to drive to the block on Marchant Avenue where the homes are located. Three homes make up the Kennedy compound and Ethel Kennedy still lives in 20 Marchant Avenue; however the “big house” located at 50 Marchant Avenue was donated to the Edward M. Kennedy Institute for the US Senate in 2013.
In Hyannis Port, we found shells, walked on the beach and headed to Woods Hole to catch the ferry. The ferry was an easy trip to Oak Bluffs where we sat on the top level to breathe in the ocean air and feel the wind in our hair as we made our way to Martha’s Vineyard. Once we arrived, we ate lunch at Fishbones Bar and Grille https://fishbones-mv.com/, walked around Edgartown, of course had to visit Lily Pulitzer and Vineyard Vines and made our way back to South Boston after our day trip. I have visited Martha’s Vineyard twice on day trips and would love to stay the night next time. My recommendation is for the Harbor View Hotel & Resort and Kelley House in Edgartown https://harborviewhotel.com/ I worked with the previous general manager at this resort and was able to visit and enjoy some wine and lobster rolls on the wrap around porch and would love to come back to stay. The resort was stunning and the food and beverage experience was first class. I can just imagine the rooms and service would be just as pristine.
Once back in the city, our Airbnb was on Atlantic Street in the Boston neighborhood of Dorchester Heights. We were able to walk over to the location of the American Redoubts from our home, which compelled the evacuation of Boston by the British army. The area is close to public transportation and worked well for our large group. We also walked through Thomas Park and onto Carson Beach from our house, which is perfect if you have young kids that love the sand.
While in Boston we visited the Paul Revere House, walked along the Freedom Trail, caught a Red Sox game at Fenway Park, where the kids were able to run the bases and we all joined in singing “Sweet Caroline” for the seventh inning stretch. At Fenway, there is a bar (Bleacher Bar https://www.bleacherbarboston.com/ )that opens up to the field before and after the game that was fun to visit.
One of my favorite things to do in places with a lot of history in the hop on/hop off tour bus. We took it all over Boston, to MIT, Cambridge, walked around Harvard and had lunch at Cheers https://www.cheersboston.com/; which is also a family friendly restaurant. We visited the location of the Boston Tea Party, ate lobster rolls and found a rooftop bar on the water to have some drinks to complete our trip. This is my son on the steps of Harvard, on what should have been his first day of Kindergarten. Flights were best the next day and he is our third kid, so his “first day” of Kindergarten was everyone else’s second day. Life of a third child-ha! I absolutely recommend this area for a family vacation, couples trip or even to explore solo. It is a gorgeous part of the US filled with history and beauty. Safe Travels!
Trip Trek Go 