During our first full summer in SW Florida, we needed a break from the heat and humidity so we booked an 11-night junket north, using Boston as our start and end point. Since neither of us had spent much (or in my case, any) time in this region, we decided to use this trip as a “scouting mission” for future travel planning. We mapped a course from Boston to Bar Harbor, including two nights in Martha’s Vineyard and Nantucket. Apart from Bar Harbor, we only stayed one night in each destination. We added a second night in Bar Harbor so we could spend a day at Acadia National Park.

Itinerary

	Destination	Accommodations	Food
Day 1	Boston	Family Stay	NA
Day 2	Martha’s Vineyard	Morgan’s Hotel	Pawnee House, 19 Raw
Day 3	Nantucket	Jared Coffin House	The Charlie Nobel, Brotherhood of Thieves
Day 4	Boston (Red Sox game)	Arcadian Hotel Brookline	NA
Day 5	Kennebunkport	Breakwater Inn & Spa	The Clam Shack
Day 6	Camden	Lord Camden Inn	Barren’s Distillery, Marriner’s
Day 7	Bar Harbor	Mira Monte Inn	Project Social
Day 8	Bar Harbor	Mira Monte Inn	Havana
Day 9	Portland	Hilton Garden Inn	The Honey Paw
Day 10	Boston	Hilton Boston Logan	NA

We arrived in Boston in time to have dinner with family in Medfield, and got a good night’s sleep before the start of our trip the next morning. After breakfast we headed to the Hy-Line ferry for the boat to Martha’s Vineyard. We purchased our ferry tickets online for our Hyannis port-Oak Bluffs-Nantucket-Hyannis port journey. We opted to purchase reserved parking through Hy-Line, which you must call to reserve. In hindsight it was an excellent decision…parking was close to the port and the lot felt safe.

We walked with our bags to the port where there is a café serving light fare and drinks. We enjoyed a bloody mary while waiting for boarding time. As soon as people started queuing we closed our tab and joined the line. If you have large luggage, you will be asked to check-it with a porter before boarding. In no time we were leaving the harbor; I knew it was going to be a great trip when I saw a boat with my daughter’s name!

The ferry to Oak Bluffs was a fast hour. Our hotel was an easy walk from the ferry dock, but there are plenty of taxis waiting to shuttle passengers. We arrived too early to check in to our room, so we stowed our luggage and set out to explore the area. Directly across the street was a nice pub called The Alley so we stopped for a pint and made a game plan. We had a few hours until dinner so we walked up and down Kennebec and Circuit avenues, checked out the famous gingerbread cottages, explored the dock, had a drink at Nancy’s and walked along the ocean before settling on Pawnee House for dinner (definitely recommended!).

The next day we were taking the ferry to Nantucket, but we had time to Uber to Edgartown for lunch at 19 Raw, which was a great experience. The ride takes you across the “Jaws” bridge, where there were many people swimming and jumping from the bridge. We spent a few hours walking all over Edgartown, and were enamored with its charm. We felt that Oak Bluffs offered a family-style beach vacation vibe, whereas Edgartown was posh and refined elegance. When we return to MV we want to spend at least one night in Edgartown. On our trip back to Oak Bluffs, we took the local bus, which was cheap and fairly quick.

There are numerous beaches and water excursions available for exploration in MV, and having a car on the island would be ideal. If you don’t want to get a car rental, there are copious scooter rental options, and as mentioned, the local bus and Uber are also options.

The ferry to Nantucket was an hour and 20 minutes, and we arrived just in time for dinner. After an incredible lunch in Edgartown, we were not at all hungry for dinner, so upon checking in to the hotel, we decided on drinks and appetizers at The Charlie Nobel. Afterward we took a twilight stroll around town exploring cobblestoned streets, gorgeous homes both quaint and grand, and fantasizing about where we would want to live if Nantucket was our home. The streets are lined with boutique shops of drool-worthy clothes, art, décor and souvenirs. Only having one day, we kept our on-foot exploration to the area between Center St and the water. On the day of our departure, we had a lunch reservation at Brotherhood of Thieves, so to kill some time, we walked to the White Elephant resort for a look around and a cocktail. Afterward we walked to lunch and noticed the many cottages belonging to the White Elephant resort, which would be a nice change of pace from a hotel. Next time we come we will look in to a stay there.

We were sad to leave Nantucket, but we still had a week ahead of us and four towns to explore. Before making our way to Kennebunkport, we returned to Boston to catch a Red Sox game with some friends and our Boston family. The next morning, we were back on our way, making a detour through Salem to get a dose of witches and history.

Salem is infamous for the witch trials of 1692, so there are lots of occult and witch-themed activities for those interested. But Salem also has some remarkable architecture and the McIntire Historic District makes a great walking tour. The entirety of Chestnut Street is a Registered National Historic Landmark, showcasing Federal-style mansions and magnificent homes, including Stephen Phillips Memorial Trust House and Hamilton Hall, named in honor of Alexander Hamilton. Other things to see in Salem are the House of the Seven Gables, The Witch House, the Salem Witch Trials Memorial, the Old Burying Point cemetery, and the Witch Museum. Word to the wise: if you plan to visit Salem during Halloween, make reservations early!

We said goodbye to Salem and in no time we were arriving in Kennebunkport, and the first thing on our to-do list was to try the clams and lobster roll at the Clam Shack. I’m not sure what I expected, but I never knew a clam could taste so good. And despite the high price tag ($19 for a small plate of clams), we got seconds. The lobster roll was also amazing, but those delicious clams will haunt my dreams!

We checked in to our hotel for the night, and despite a beautiful location, the Breakwater Inn was a disappointment. Old, broken and worn out furniture, and a vintage bathroom from the 70s did not justify the rate of the room, but when you’re traveling through New England in the summer, expect very high prices. The glorious weather is in high demand! We had a nice walk through town and picked up some souvenirs, then ventured beyond the hotel to St. Ann’s by-the-Sea Episcopal Church to take in the views at sunset and admire the grounds where the rich and privileged worship.

In the morning we took the 2.5 hour drive to Camden, where we arrived in the midst of a storm and the power was out in the whole town. The front desk at the Lord Camden hotel allowed us to stow our bag in our room and we decided to drive around town in the rain to find some lunch. We drove up route 1 to the High Street Historic District then back down towards the docks for a late lunch at Barren’s Distillery. The power finally came back on so we returned to our hotel to dry out and relax.

In the morning we headed across the street from the hotel for a great, affordable breakfast at Marriners, where we sat outside on the deck overlooking the Megunticook Falls and the sailboats moving about in the harbor. The sun was shining so we took the car to Camden Hills State Park and drove to Mt. Battie Tower for a look over the city and its beautiful harbor before making our way further north.

Our next stop was Bar Harbor, the furthest point north on our New England trip. We stayed at the Mira Monte Inn for two nights. Our room was comfortable and the bathroom had been recently upgraded. Everyone at the Inn was pleasant and the breakfast was delicious. The Inn is an easy walk in to town and it was nice to have a free place to park for two nights. We spent our short stay in Bar Harbor walking and eating; we had amazing meals at Project Social and Havana. When we weren’t eating, we were exploring the water front. The historic Shore Path was created around 1880, begins near the town pier and Agamont Park, and continues for about 1/2 a mile along the eastern shore of town. Off shore to the east are the four Porcupine Islands which are especially beautiful at sunrise. Directly north of the town pier is Bar Island, which is where Bar Harbor gets its name. The island is accessible by foot at low tide and provides a spectacular view of the town with the mountains behind it. But be sure to venture back to the mainland before the tide comes in or you’ll be stranded!

On our second day in Bar Harbor we drove to the nearby Acadia National Park (our 5^th national park in 2023!), where we headed directly to Cadillac Mountain to take in the endless views of the harbor and many islands dotting the coast. Afterwards we drove along the coast to the Northeast Harbor for some refreshment, then made the short drive back to Bar Harbor in time for dinner.

The next morning we departed after breakfast to make our way to Yarmouth to meet some old friends of ours from Atlanta who we hadn’t seen in 5+ years. We ended the day in Portland, and after a walk around town and the docks, we found ourselves at the Honey Paw for dinner, tucking in to spicy and delicious noodles and fried chicken. The next morning it was back to Boston for our last night, and we were fortunate to catch up with more friends who are currently studying at MIT.

Although the trip was fast and furious, we enjoyed the cooler weather and seeing new places. It also gave us an idea of where we would like to spend an extended stay on a return visit. Looking forward to it!