First Trip to Nantucket

I made my first trip to Nantucket for 4th of July Weekend in 2017. My boyfriend and his family have a house there and had been spending summers there for most of his life. His living room in his apartment is decorated in a Nantucket theme, so it was quite a treat for me to finally be able to visit the beautiful island.

As far as transportation to Nantucket, getting to the island is not as simple as you would think. In our case, we flew from Pittsburgh to Boston, took a bus from Boston to Hyannis, and then took a ferry from Hyannis to Nantucket.
Since it was my first ferry ride to Nantucket, we decided to sit on the upper deck of the boat- super windy + super misty = messy hair.


Once we got to Nantucket, we went to the house, unloaded our things, and then went straight to the beach. As I quickly learned, Nantucket is significantly cooler than mainland in the summer. Even though it was 4th of July weekend, I ended up wearing a sweatshirt for most of the time I spent on the beach.

Since this trip happened a week or so after my birthday, My boyfriend’s parents took us to dinner to have a belated celebration. We went to Cru for dinner. Cru is awesome because it’s right on the waterfront near the ferry dock. We all shared a few appetizers, and then my boyfriend and I split a lobster roll. At dinner time, Cru serves a warm lobster roll which is buttered instead of the traditional lobster salad style. It was divine. Between the buttered lobster and the buttered roll, we were in butter heaven. After that meal and our day of traveling, we called it an early night.

The next day, we toured around the island a bit. Since this was my first trip there, I fully intended on making it a touristy trip. Which worked out because it is probably the place that my boyfriend loves more than anywhere else in the world, so he very much enjoyed playing tour guide. We drove around the island in his family’s jeep, visited Bartlett’s farm, stopped by Cisco Brewery, and did a quick overview of some of the shops in town.  We stopped at Straigh Wharf, grabbed a lobster roll and some clam chowder and enjoyed both outside.

After lunch, we walked around and peeked into some of the shops. I loved the selection at Skinny Dip and made a big long list of things to come back and buy later. We finished our afternoon with THE BEST chocolate chip cookie dough ice cream I have EVER had from the Juice Bar. Seriously, this stuff was heavenly.

It was a pretty great day and it kept getting better. Coincidentally, a friend from home, Chelsea, was traveling through New England during this weekend and we asked her to come out and spend a couple of nights with us. We picked her up from the ferry and then we got back together with the rest of our group. Chelsea had never been to Nantucket either so it was nice to have another newbie to explore with.

A month or so before our trip we booked a sunset cruise and were able to get our entire group on the sailboat. We packed wine, cheese, and crackers, and although the night was a bit overcast, we had a wonderful time on the Endeavor. IMG_3247

After our sail, we went to the Lobster Trap for dinner. I swear, I don’t think I can ever have too much lobster. Our whole group piled into a giant booth and everyone ordered some variation of lobster (how could you not at a place called the Lobster Trap).


The next day, we took Chels around the island and did some more sightseeing. We stopped at The Downyflake for breakfast, drove around the island, and we were finally able to get some good pictures thanks to Chelsea our “photographer”

Fortunately, the sun cooperated with us and we were able to make it to the beach for some sunset pictures (are you noticing a trend here?), and then we went to dinner at Millie’s.


Chelsea left the next day and we spent the rest of our trip sampling lobster rolls from different establishments on the island (seriously, I think I had about 8 during this week), and enjoying lots of beach time! That night, Nantucket did their fireworks show (on the 3rd)- we watched the fireworks from a friend’s home accompanied by sushi, rosé, and s’mores (I was in heaven).

Since the fireworks celebration happened on the 3rd, the 4th was kind of a low-key day for us. My boyfriend and I had a solo date night dinner at Straight Wharf (with a pit stop at the Gazebo for a frozen mudslide prior to dinner). My boyfriend had initially planned a romantic night at Oran Mor for the 3rd, but then we had to switch things up once we realized that the fireworks were on the 3rd- so we decided to give Straight Wharf a try.

Our last full day was special in that my boyfriend’s brother and sister-in-law arrived on the island. They got in later in the day so we spent the day at the beach and shopping for souvenirs. We did a family dinner at Black Eyed Susan’s and then called it a night.

On our day of departure, we drove out to ‘Sconset because I wanted to do the bluff walk and I’m so glad we did! The bluff walk is a pretty spectacular sight, both in terms of the homes that you walk past, and the views of Nantucket.


At the end of the walk was the Sankaty lighthouse, where we got my favorite picture of the trip. Thanks to a kind stranger!! IMG_3785

I was sad to leave Nantucket but was already mentally planning my next trip back. This island had a cozy sense of familiarity to it and it truly felt like home. I know it will be somewhere that I visit frequently.

Have you been to Nantucket? What are your favorite spots on the island?

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