This past fall Shawn and I took our first trip ever to the East Coast. I had been daydreaming of staying on Martha’s Vineyard, taking in the sights of Maine, and seeing what Boston is all about for years but had never sat down and put pen to paper [and a lot of google searches] for what the best plan to travel the Northeast would be.
It turns out, I should have done this years ago because wow, it did not disappoint.
A few things to note in regards to our itinerary:
- We traveled in late September [September 20 – 28th to be exact] which proved to be an amazing time to travel out East! The weather was still warm, but not too warm [think low 70’s] and while we were a week or two early for the leaves to turn, we were able to see early signs of the colors they were about to get and I can assure you, fall in the Northeast is beautiful!
- We felt like 8 days was an adequate amount of time to do everything that we did. We wouldn’t have wanted it to be shorter, but also felt like we wouldn’t have wanted it longer. We were able to do everything we wanted and still had time to simply relax!
- We flew in and out of Boston Logan International for our vacation!
- We did rent a car for the entire length of our trip, even though we didn’t use it the entire time [we didn’t take it over to Martha’s Vineyard / Nantucket]. While we could have tried to Uber from the Boston airport to the ferry landing we departed from, we didn’t want to have to rely on finding an Uber and figured by the time we paid for two hours and a half Uber rides it would cost more than paying for the rental car for those days we didn’t use it!
- As you go through our itinerary below, I put in bold all of the names of the hotels and restaurants we stayed at for easy navigation!
DAY 1: Travel to Martha’s Vineyard
We flew from our local airport to Boston International airport and arrived sometime in the afternoon. After picking up our rental car from the airport, we made the 90-minute drive to the ferry landing at Woods Hole to abord the Steamship Authority ferry to take us to Martha’s Vineyard. They have ferries that run continually throughout the day and you don’t need to buy tickets ahead of time is what I was told. Note: You can take a car on this ferry, but you have to have your spot rented ahead of time! I loved that they served beer and wine [and snacks] and you could just sit and enjoy the scenery for the 45-minute ride!
Once we arrived at Martha’s Vineyard, we got an Uber to take us to our hotel, Harbor View Hotel, where we stayed for 3 nights! We loved the hotel and would recommend it 100%! It is located in Edgartown on Martha’s Vineyard where so many of the restaurants and shopping are. We were within walking distance to most things we wanted to do on the island [and for when we couldn’t walk, they did offer complimentary bicycles and had 3 Mercedes-Benz vehicles you could use for a couple of hours at a time!] There was a great pool area and a delicious restaurant on site! The night we arrived we decide to stay put and eat at their restaurant, Bettini, which we loved!
DAY 2: Martha’s Vineyard
We walked to breakfast [which would be where we would end up walking every day because we loved it so much] to Among The Flowers Cafe. It’s a cute little cafe literally nestled in with flowers all around and had a great variety of breakfast options!
We then spent the morning and afternoon walking around town taking in the scenes of Edgartown which is such a charming town on the water. We ate lunch at The Seafood Shanty for a place with a view of the water!
We definitely took advantage of shopping at Vineyard Vines, which was originated on the island.
After shopping, eating lunch, and lounging at the hotel pool, we decided to take one of the hotel’s complimentary cars and make the drive to Aquinnah, which is on the other side of the island and absolutely worth seeing! It’s a beautiful place to see a lighthouse, walk on a trail down to the beach, and snap some photos!
On the way back from Aquinnah to the hotel, we stopped at Nancy’s for their famous Dirty Bananas, which hello delicious [and strong]. They are a Martha’s Vineyard must!
While on the subject of food [let’s be real, what else do you do on vacation?] we had our best meal of the trip at 19 Raw Oyster Bar. Note to self: order every side possible [including the gnocchi and Au gratin potatoes] and prepare to be delighted.
DAY 3: Nantucket
On our second full day on Martha’s Vineyard, we decided to take a ferry [we used Hy-Line Cruises] over to Nantucket to explore and spend the day! It’s an hour and a half ferry ride and I would say is absolutely worth doing while you are on Martha’s Vineyard to see Nantucket! The minute we arrived on Nantucket I knew I was going to love it [so much so I wish we would have booked a night or two here!] Between the incredible yachts, brick streets, restaurant after restaurant, and all of the charm that there is to take in, it’s a must-do while on the east coast!
First stop – lunch at Town, which hands down had the best truffle fries I’ve ever had and I’m still dreaming about them to this day.
After a cocktail, I was convinced that we absolutely must rent scooters to ride around the island which was equally horrifying and amazing at the same time. Being that I’ve never driven a scooter [or any motorized thing with less than 4 wheels] there was definitely a learning curve, but I survived and riding through the roads of Nantucket with my little turtle head looking helmet gave me the exact feeling of being in Dumb and Dumber which was worth every moment of near death.
After Shawn couldn’t take the anxiety of me nearly killing myself, he decided we had to be done with the scooters so we returned them a few hours early [there goes that money] and wound up at a less anxious place, The Juice Bar, for ice cream.
While I wish we could have stayed and had dinner at Nantucket, we had to catch the ferry back to Martha’s Vineyard so we ended up eating at The Lookout back at MV for a very casual dinner!
DAY 4: Boston
It was a sad morning to say goodbye to Martha’s Vineyard, but we were ready to keep the trip moving along and take in new to us, never seen before scenery! We loaded up on The Steamship Authority ferry to head back to where our car was parked at the Wood’s Hole to get in our rental car and head to Boston for the day and night!
We first checked into our hotel, The Langham, which was located in a great spot to walk all around town [and close to our evening plans which consisted of eating in the North End]!
For our day of exploring, we ate lunch at Florina Pizzeria [just a small little spot to sit down and get a slice or two of some delicious pizza!] From there we walked around and made our way to The Seaport District, which is such a cool neighborhood and area of Boston. We hit up The Lookout Rooftop Bar on top of the Hotel Envoy for a cocktail [or three] and simply enjoyed the views and conversation for quite a while.
That evening, we went to the neighborhood of the North End, which is one of the main reasons I wanted to travel to Boston! I am a sucker for all things Italian food and WHOA, does this place have Italian food. It is literally just street after street lined with old-fashioned Italian-looking buildings and restaurants. The area was hoppin’ and I felt like I’ve never been happier eating somewhere. We opted for Giacamo’s [tip: it is a cash-only restaurant so come prepared!] and enjoyed one of the better Italian meals I’ve ever had. From there we made our way to Modern Pastry where we filled up a box of insane-looking desserts to enjoy in our room and yes, it was by this time I couldn’t button my pants anymore.
DAY 5: Rockport, Massachusetts
Because we apparently didn’t eat enough the night before, we ventured off to Cafe Bonjour for breakfast in Boston before heading out which hi, you must eat here. It was absolutely wonderful!
After eating enough to ensure we couldn’t button our pants, we took off from Boston and made our way to Rockport, MA which was less than an hour’s drive from the city. Rockport is the cutest fishing village with such a vintage and rustic charm to it. From the old painted houses to all of the little boats floating around, this is a must-stop! There are several shops + restaurants to walk around and enjoy. We ate at Roy Moore’s Fish Shack Restaurant which was a great spot!
After spending a few hours in Rockport, we made our way to our final destination and hotel stay for the trip, Cliff House Maine Hotel, located in Cape Neddick, Maine. While it was a splurge [it was our 15 wedding anniversary so we sprung for an oceanfront suite], it was hands down the most beautiful hotel I’ve ever stayed in. From the ocean views to the perfectly cozy nautical decorated rooms, the live music in the lobby, options of several on-site restaurants, and very friendly and accomodating staff, it was a hotel stay I will never forget!
That evening we ate at Nubbs Lobster Shack which is at the hotel for a casual dinner, listened to live music in the lobby, and ended the evening in the hot tub overlooking the ocean.
DAY 6: Cliff House Main + Oguinquit
If you stay at Cliff House Maine, do yourself a favor and make the short drive to walk The Marginal Way in the nearby town of Oguinquit. It’s such a beautiful way to start your day and get some fresh ocean air.
After walking, we spent most of the day hanging by the pool, in the hot tub, enjoying cocktails, and relaxing the day away!
That evening we ventured back to the town of Oguinquit to walk around the shops, have a drink at The Front Porch Piano Bar, and ate dinner at The Maine Catch [which Shawn loved!]
DAY 7: Kennebunkport
One week in and we were still going strong. Only 30 minutes away from the hotel is the town of Kennebunkport which is an absolute must if you are staying at Cliff House Maine [or if you’re in the general area at all!] It is such a beautiful town that sits right on the water with so many charming shops and restaurants to enjoy. We ate lunch at The Boathouse which was a great atmosphere right on the water.
After making our way back to the hotel, we ate at their fancy dinner spot, The Tiller, which sits right over the ocean. Both the view and the food got 5 stars!
DAY 8: Portsmouth, New Hampshire
For our last full day on the East Coast, we took a little mid-day jaunt over to Portsmouth, New Hampshire to take in the city and all it had to offer. There are so many fun spots in Portsmouth, from shopping to restaurants, bars, coffee shops, etc! While we didn’t eat a full meal while there, we did stop in at Barrio for beers and chips & salsa! It was fun to simply walk around and take in the city on foot, although a boat ride would have been fun too!
That evening I did what I do best, threw on the hotel’s robe and swimsuit [seriously, do yourself a favor and stay at this hotel simply for the robes], got a glass of wine from the hotel bar and made my way to the hot tub for the remainder of our night.
DAY 9: Travel Home
And on our final morning, I enjoyed one last Mimosa poolside before making our way back to Boston Logan International Airport to fly home!
All in all, our trip couldn’t have been better and I would recommend the East Coast to anybody and everybody. There is so much to do, to see, and to eat 😉 Our 8-day trip length was perfect for covering all of the things we wanted to do and gave us such a great taste of what the East Coast is all about!
Founder and creator of LIY, Erin turned her dream of a hobby blog into a full-time career which she now runs alongside the LIY team! When not in front of her computer screen [with a La Croix or wine in hand] or in front of a mirror taking mirror selfies, you can find Erin spending time on the water, cuddled up with her two pups and husband most likely watching the latest Shark Tank episode, or getting lost in an easy beach read.