New England Itinerary

New England Itinerary – Jen

10 Days

Arrive: Boston Massachusetts

Stayed at the:
Royal Sonesta Boston (rooms were clean and comfortable, but very small)

*duck tour in the morning:

Boston Duck Tours
Overview of the City and a splash through the Charles River

    • We departed from the Museum of Science that was walking distance to our hotel.
    • Tickets at that time were $39.50 for Adult, and $27.00 for kid

After the duck tour we drove to Freeport Maine:
Stayed at the:
Brewster House B&B (

*day 1
Charted a Fishing Boat in Saco Maine.
Trina Lyn Fishing Charter: The Captain was great, promised fish and lobsters and
delivered. My 8 year old was in heaven.

*day 2
Bath Country Club for so family Golfing and a drive through the beautiful area

*day 3
Explored some areas at the recommendation of Dave, the B&B owner. Found Robinhood Cove and had lunch. It was a beautiful, perfect day.

*day 4
Relaxed and Explored Freeport. LL Bean has an amazing store, there are so many cute boutiques, great food, and ice cream, and a Starbucks!

Traveled back to Boston:
Stayed: Boston Marriott Cambridge on Points 🙂

*Picked up Brooklyn from Harvard
Drove to Newport Rhode Island

*went to a polo match, An experience I am so glad had!
(I purchased tickets ahead of time, and bought in the Alex and Ani seating pavilion. Nice to have reserved seating, but there was no shade. If I went back, I would bring a blanket, umbrellas to shade the sun, a picnic lunch, and a football to throw before and after, I also would let my husband wear shorts! I thought we had to be fancy but nope, super casual)

Drove to Cape Cod Massachusetts
Stayed at the Red Jacket Beach Resort and Spa
(old, our room configuration was not the best, I should have booked 2 bedroom, and very outdated, BUT…. you cannot beat the charm and the association with families who are the parents, bringing their children, bringing their children. These Families have been returning for 20 + years. I grew to understand Cape Cod is old, and outdated but full of history and long standing family traditions that will make you want to come back again and again)

*day 1
Stayed at the resort, fished, laid in the sun, read a book. Nice day to relax.

*day 2
Took the ferry to Martha’s Vineyard (book ferry tickets a head of time to guarantee passage)
Rented a jeep from a company right off the ferry dock
Drove the island, took pictures of the houses, ate yummy food at The Black Dog Tavern, and ate more ice cream!
Took the Afternoon Ferry back to Cape Cod.

Drove back to Boston:
Stayed at the Boston Cambridge Marriott on Points:)
Went to the Freedom Trail and walked Downtown Boston to take in Historical Sites
Went to Wahlburgers for lunch, DELICIOUS!!
Went to a Red Sox Game!

Flew Home the Following Morning.

This trip involved planning around, picking up Brooklyn at Harvard 1/2 way through, and making a Red Sox Game. Due to the schedules of both we ended up in Boston a few more times than I would have otherwise scheduled, but nothing was to far of a drive so it worked out just fine. This trip was perfect for the schedule it met.

Travel Notes:

  • Don’t be afraid to stray from your plan! Some of our best experiences were ones that we hadn’t prepared for!!
  • When booking Tours read reviews! I cannot say enough about how important it is to research a tour and a guide. The better guides make all the work so worth it!!
  • There is an App for everything. On this trip, I had 2 new Gluten Free Kids. We utilized the GF app on my phone to eat on the road. It was great to be able to see what food was offered and read a few reviews along the way! I would search the area we were in and headed towards and plan our food that way. It really was a huge blessing and kept us from going hungry!
  • I am a people person so making friends comes easy to me, but I promise if you are not, step outside your comfort zone and talk to the people you meet. Some of the best stories can come from perfect Strangers.
  • Look for activities unique to the area you are in. The Polo Match in Newport was a fun way to experience a little of what the area has to offer!