October 26, 2023

Our 7 Day New England Itinerary

I can’t believe it’s been almost 2 months since our beautiful New England trip, but it has been. It was such an incredible experience to visit several states I had never even been to. If you’re anything like me, being from the South, I was completely at a loss of where to even start when planning a trip to New England. Luckily for me, Mary Kate was an expert in the area!

When planning we first started with how many days we wanted to travel. We decided on 7 days, which really just leaves 5 full days after spending 2 days traveling at the beginning and end of the trip. We didn’t want to rush our trip, but we also wanted to get in as much has we ideally could while still really getting to take in the scenery and experiences. Also, we decided to stay in 3 different locations in 3 different states, all within pretty close proximity to drive to every couple days. Keep reading for our full itinerary below.

Kennebunkport, Maine

We flew into Portland, Maine, and immediately started off our trip in Kennebunkport. It was only about a 5 minute drive from the airport, so it was relatively close by. We had a late afternoon arrival, and then we rented a vehicle from the airport. The day we landed, there were tons of people traveling to and from Portland, so we had a 2 hour wait at the rental car location. Keep that in mind if it is during the busy season.

After arriving in Kennebunkport, we stayed at Kennebunkport Inn. This hotel was a favorite of mine! It was so quaint with its perfect location right off the square, cozy rooms and pretty nautical theme throughout the hotel. The hotel has a cute little restaurant and you can sit indoors or out depending on the time of year. Everyone at the hotel was so friendly and helpful, and honestly we just loved the entire vibe of the hotel and the adorable rooms.

It was such a quick, short walk right across the street to see the water and to do all the shopping your heart desires at Dock Square! There is so much great shopping on the square in Kennebunkport. I bought some pretty decor for the house, and Matt bought some whiskey glasses he loves. There are also the Shops at Morning Walk that I loved! There is so many incredible restaurants to eat at in and near Kennebunkport, and you can definitely get your fill of lobster and clams too! Read more about our time in Kennebunkport, Maine here.

Bar Harbor, Maine

Our next morning, we got up and early and drove to visit Acadia National Park. It is approximately a 3.5 hour drive. It is a busy park, and especially during the summer months. You will definitely want to plan for an entire day here just to be safe. Parking can be tricky during summer too. But it is worth visiting for yourself. It is the highest point on the east coast, and there are so many beautiful sights to see at this national park. You can also hike or cycle here. We spent most of our morning and afternoon here, and we made a reservation to go to Cadillac Summit. Read more about our day in Acadia National Park here.

Ogonquit, Maine

After visiting Acadia National Park, we drove over to Ogonquit for dinner at Cliff House at the Tiller Restaurant. It is a stunning resort that has an amazing restaurant. And named after its landscape, it is situated on the edge of the water with views of the rocky cliff surrounding the hotel. It is definitely worth the drive to head over and eat and see the views. We loved it so much there that we stopped by the next morning for coffee and pretty views too. It was almost a 4 hour drive from Acadia National Park to Ogonquit. It is only about a 30 minute drive from Kennebunkport though.

York, Maine

After breakfast in Ogonquit the next morning, we headed over to York to see Nubble Lighthouse. New England is definitely known for its lighthouses, and this one is unique as it sits on an island. This lighthouse is now automated, but it is a very popular one to visit. It is so pretty seeing it across the water. To read more about the lighthouses we visited in New England, read this post here.

Nubble Lighthouse (also known as the Cape Neddick Light) sits right there next to some great places to visit, like Fox’s Lobster House. Matt had lobster here, and I had their lobster roll. They were both so good! Afterwards we grabbed ice cream from Dunne’s Ice Cream. Yum!

Cape Cod, Massachusetts

After we left York, we drove over to Cape Cod to check into Autocamp. it was almost a 3 hour drive from York to Autocamp. It is actually situated in Falmouth, Massachusetts, so we made our way over to our second state on our trip. While we didn’t get to explore Cape Cod itself much, I absolutely loved Autocamp so much! Matt and I stayed in an airstream, and Mary Kate and Ben stayed in a cabin. We loved our little airstream so much! It was plenty roomy, and we loved how modern and updated it was. We loved it so much that we will be visiting 2 other Autocamp locations next year. Read more about our stay with Autocamp Cape Cod here.

Nantucket, Massachusetts

Our very next morning after getting to Cape Cod, we drove over to take the ferry to Nantucket. It was about 45 minutes to get from Autocamp to the ferry. They recommend getting there early. It is just like checking in for a flight. We bought our parking in advance, so we had to go park, get our luggage, walk to the checkin point at the ferry and then line up and wait in line until they started boarding.

After we started boarding, we found a seat and grabbed some coffee and a bite to eat on board. The ferry ride itself was about an hour. Quickly after we docked in Nantucket, we all deboarded, grabbed our luggage and then picked up our rental car on the island. You don’t have to get a rental car in Nantucket, but I highly recommend it! It will get you around the island so much faster, especially if you are only in Nantucket for a day!

There is no way I can fit into one post how gorgeous and unique Nantucket is, but trust me, you will want to include Nantucket in your New England itinerary! From the moment you step off the ferry, you are greeted with the iconic Nantucket architecture on the homes and businesses, especially in the historic district. You will also see so many gorgeous florals cascading over doorways, windows and along trellises. The hydrangeas and roses are just stunning.

After walking around and viewing all the signs including the homes and the water, we did some shopping. There are so many great shops and places to grab a bite to eat that are within walking distance when you get off the ferry. We then drove over to Siasconset to see Sankaty Head Lighthouse. This was one of my top 2 favorite lighthouses we visited while in New England. The views around it with the tall grass blowing in the breeze was just jaw dropping!

We then visited Brant Point Lighthouse. From there, it was just a short walk to White Elephant. It is a beautiful hotel on the island. They also have a restaurant there, and we had dinner. I got the lobster this time, and it was 100% worth it! We all loved the food, and Matt said it was his favorite dinner of the entire trip. It was so peaceful sitting outdoors and overlooking the water too. It was the perfect ending to our day spent in Nantucket.

Newport, Rhode Island

After making our way back to Cape Cod after Nantucket, we got on the road the next morning to make our way to our 3rd and final state on our trip, Rhode Island. It was a 1.5 hour drive from Cape Cod to Newport, Rhode Island. Newport actually ended up being Matt’s favorite spot of all that we visited on this trip. We stayed in an airbnb downtown, and we loved the location.

There are also some great hotels downtown you can stay at like Hotel Viking. We didn’t stay here on this trip, but we plant to visit next time. Downtown Newport is so walkable. From coffee shops to restaurants to shopping to iews of the water, there is so much to do in downtown Newport. We spent both days walking around and exploring and shopping. And I even stopped by The Black Pearl both days to get a lobster salad sandwich (it was my favorite version of the lobster roll!) It was so good!

After shopping, we drove over to Castle Hill Inn. It is a hotel with amazing dining options too. They also have a lighthouse on property that happened to be my favorite lighthouse of the trip. We ate dinner at the bar, and everything was so good! This was one of my favorite hotels that we visited on our trip and ate at. And the next day, we got to see the hotel and the lighthouse from a different vantage point – from the water while sailing. For more about Castle Hill Inn, check out this blog post.

The next day we went sailing with On Watch Sailing. It was such an incredible experience, and it definitely won’t be our last time going sailing. WE did the 2 hour sail, and we should have done longer! It was so beautiful, peaceful and just plain fun! Matt loved helping to steer the boat, and we loved seeing the views of lighthouses from the water. All we needed this day was a little more of a breeze, but either way, you cannot have anything other than a good time sailing here! Check out more about our sailing here.

Westerly, Rhode Island

On our last night, we drove over to Westerly for dinner at Ocean House. It was about an hour drive. Ocean House was definitely an incredible experience unlike anything else! The hotel was stunning. They had just finished having a wedding there outdoors, and the grounds were so pretty. The hotel overlooked the water, and the dining overlooked the water too. We had dinner at their indoor restaurant, and their tasting menu was so good. Matt did the wine pairing too, and we absolutely loved it all. It was a wonderful experience and really stood out as one of our favorite fine dining experiences.

After dinner, we drove back to our bnb over in Newport. And the next morning, we hit the road for a 3 hour drive back to Portland, Maine’s airport. This marked the end of our New England trip. Though it was quick, we feel like we really did a good job of squeezing in a lot of amazing experiences and locations. I honestly loved every single area we visited. Newport, Rhode Island was Matt’s favorite area. Maine was my favorite for the food and shopping. And Nantucket was a favorite as far as beautiful scenery and picturesque locations go. We cannot wait to plan another trip in the future to New England. If you’ve been before, what are your favorite spots to visit?


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