8-Day New England Itinerary

On our first adventure as a family of 4 we traveled from Boston to Maine, then down to New York City.  Cadyn was 7 years old and Jolene was 6 Months old at the time.  We are sharing our exact itinerary with you.  Watch the video of our trip below!

New England Road Trip Video

Instagram: @coco.flowerss

Itinerary:

Day 1

    • Fly to Providence
    • Trillium Brewery
    • Check in the Sheraton Back Bay
    • Boston Red Sox game
    • Dinner at the game
  • Drive time for the day: 1 ½ hours

Day 2

    • Breakfast at Flour (across the street from hotel)
    • Walked the Freedom Trail
    • Lunch at Panza in the North End
    • Cannolis at Mike’s Pastry
    • Lawn on the D
  • Dinner: Dumpling Palace

Day 3

    • Leave Boston and head up the coast to Maine
    • Stop in Salem Massachusetts
    • Stop at Portsmouth Harbor Lighthouse
    • Stop at Ogunquit – Lobster Roll at Footbridge Lobster
    • Stop in Kennebunkport – Lobster roll at Clam Shack
    • Portland Head Light
    • Check in Airbnb
  • Drive time for the day: about 2 ½ hours

Day 4

    • Donuts at The Holy Donut
    • Stop at LL bean store
  • Drive time for the day: about 3 ½ hours

Day 5

    • Sand Beach
    • Drive to Cadillac Mountain Summit
    • Camp

Day 6

    • Drive to New York City
    • Checked into Hotel Hayden-Priceline Hotel
    • Walked to Times Square
    • Dinner Joe’s Pizza
  • Drive time for the day: 7 ½ hours

Day 7

    • Ferry to the Statue of Liberty
    • 911 Memorial
    • Lunch: Spicy Village and Easy Dumpling
    • City parks
    • Hotel for the night

Day 8

    • The Central Park Mall
    • H&H Bagels
    • Drive back to Providence
    • Late night flight home
  • Drive time for the day: 4 hours

Boston, New England Road Trip

Day 1

We took an early morning flight from New Orleans.  We always fly Southwest right now because we have a lot of baggage and it all flies for free.  We flew into Providence instead of Boston because flights were cheaper and the car rental was way cheaper.  This ended up being a great decision because there was no one at this airport.  We had our rental car within 30 minutes of landing.  I don’t think this has ever happened before.  We once stood in line for 4 hours in LA trying to get a rental car.  This was a huge relief not having to wait with 2 kids.  Our first stop was to Trillium brewery in Canton.  My husband loves fancy, hazy beer and they are amazing.  Next we headed for Boston.  When we can’t find a decent priced Airbnb we usually use Priceline Express Deals.  Our hotel was the Sheraton in Back Bay.  It was a nice hotel but we ended up in a 1-bed queen room.  Luckily we were camping prepared so Cadyn had to sleep on a camping pad pallet next to the bed.  This is the only time we have ever had this issue with a Priceline room. After checking in we headed to the Red Sox game.  We bought tickets on Stub Hub.  We ate dinner at the game.  The game was amazing.  Everyone should definitely put this on their bucket list.  FYI on parking in Boston, in the 2 hour parking you have to physically move your car every 2 hours.  We got 2 parking tickets the first day because we just kept feeding the meter and not actually moving the car.  Fenway Park, New England Road Trip

Day 2

Flour is a great breakfast spot.  It is across the street from the Sheraton.  They had amazing pastries and fresh squeezed orange juice.  We started at Bodega, a hidden shoe/clothing store. We then headed to the Freedom Trail.  The Freedom Trail is a great fun and free activity.  We started at Boston Common and ended at the bridge. It was full of beautiful buildings and amazing history.  Our 7 year old even loved it.  We ate lunch at Panza in the North End.  The food was amazing.  We ordered the fried calamari, chicken Parmesan, and lobster ravioli.  We chose to eat our fancy Italian meal for lunch rather than dinner to save money.  We ordered a cannoli at Mike’s pastry, which lives up to the hype and is delicious.  Next we headed to a park across the city called Lawn on the D.  It was the cutest park ever.  It had light up swings, giant Jenga, corn hole, a bar, and a live band.  We were there on a Wednesday evening.  There were a lot of locals there in their business attire ending the day.  For dinner the girls were exhausted so we picked up dumplings from Dumpling Palace about a block from our hotel.

Boston, New England Road Trip
Lawn on the D

Day 3

We left Boston and headed up the coast to Portland, Maine.  For this drive we found multiple stops so the kids did not go crazy in the car. First stop was Salem, Massachusetts.  This was a really fun stop.  It can be a little cheesy but we are glad we stopped.  The houses were so cute and the town embraces the history.  Next stop was at the Portsmouth Harbor Lighthouse.  This was a convenient and quick stop.  The lighthouse and views were beautiful. Next stop was Ogunquit, Maine.  This was the cutest coastal town.  This is also where we ate our first lobster roll and it was amazing.  It was from Footbridge Lobster.  We were hooked and wanted to try every lobster roll in Maine after that.  This is impossible because they cost $20 a piece, but they are delicious.   Next stop was Kennenbunkport, Maine.  We stopped at the Clam Shack.  We ordered 1 lobster roll and 1 fresh lobster.  The first one was better but this one was still really good and fresh.  Last we stopped at the Portland Head Light.  This was a beautiful light house.  There were picnic tables set up everywhere.  We watched the sunset here then headed to our Airbnb for the night.

Portland Head Light, New England Road Trip
Portland Head Light

Day 4

Breakfast at Holy Donut was perfect.  This is sadly the only thing we did in the city of Portland.  It took us longer to get to Portland than we thought.  It is one of my favorite cities.  We have actually been back since this trip and love it. We stopped in Freeport at the LL bean store.  It was a fun little store.  My daughter loved the giant book bag and boot outside. We stood in the super long line at Red’s Eats for lobster rolls.  We ordered 2 lobster rolls and fried scallops and they all were delicious.  This was our favorite lobster roll of the trip.  We waited about 45 minutes and it was worth it. We headed to Bar Harbor where we set up camp for 2 nights at the Bar Harbor KOA Oceanside.  This was a great campsite.  There was a small waterfront area.  The bathrooms were clean.  We stopped at a grocery store and bought food for the 2 camping nights.  Our favorite camp meal is of course hot dogs and chili with s’mores for dessert.  Camping with a 6 month old went surprisingly well. A pack and play was key so we could put her down at the campsite because she was mobile at this point.

Lobster Roll, New England Road Trip
Red’s Eats Lobster Roll

Day 5

The Ocean Path Trail was a great family friendly hike.  After we headed to Sand Beach for most of the day.  This is one of the most beautiful beaches I have ever been to.  The water was crystal clear but freezing cold. We dipped our toes into the water but that was about it.  Some people were actually swimming in the water.  We drove to the summit of Cadillac Mountain.   There is a hike to the summit but it was too far to go with a 6 month old.  The views from the top were amazing.  We ended the day with the sunset by our campsite and cooking burgers over the fire pit.

Sand Beach, New England Road Trip
Sand Beach

Day 6

We were only planning on going to Massachusetts and Maine but our 7 year old had been begging to go to New York City for a while, so adding the city to the itinerary was her birthday present.  It took about 9 hours with stops to get to NYC.  We got the hotel with Priceline express deals.  We stayed at Hotel Hayden.  We had 2 queen beds this time.  This was a great central location for us.  We ate dinner at Joe’s Pizza.  We ordered 1 pepperoni pizza and it was amazing.  We stopped in Times Square and of course the M&M store, every 7 year old’s dream.

New York City, Ultimate Road Trip

Day 7

We walked from the hotel to They Battery Park to catch the ferry to Liberty Island.  We bought tickets prior to the trip.  I really don’t recommend this.  I would have much rather taken the free Staten Island Ferry, but our daughter wanted to be on the island so we did it.  You have go through 2 checkpoints to get onto the boat.  There were a ton of people and huge lines throughout the whole process.  It was not very fun.  Our tickets included going to the pedestal.  There were great views from there but definitely not worth all the hassle to get to the island and back.  We only had time to walk through the 9/11 Memorial.  I would love to go back and visit the museum.  We then headed to Chinatown for the chicken hot pot at SpicyVillage.  Beware, it is hot but it was delicious.  We also had like a million dumplings from East Dumpling for like $3 and they were amazing.  There was a park right by the restaurants so we let our daughter burn energy before heading back to the hotel.  We were exhausted so we stayed the rest of the night at the hotel to prepare for our long travel day the next day.

Statue of Liberty, Awesome Road Trip

Day 8

Bagels from H&H Bagels are a must.  We made quick stop to walk through the Central Park Mall before leaving the city.  We drove about 4 hours back to Providence for an evening flight home.

Bar Harbor, camping, New England Road Trip
Bar Harbor Oceanside KOA

Both the girls did great on this trip.  We have gone on a couple long weekend trips but this was our first trip over 1 week.  Camping was great with both of the girls.  We have traveled to Boston and Portland again since this trip and we love both cities.  Click here for all of our favorites in Boston.

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