Nantucket Anniversary

When planning our first anniversary trip in 2019, I wanted to choose a place that fit both of our tastes. James is more of the city guy and I’m more of the serene, quaint city kind of girl. So we found the best of both worlds by first visiting New York City and ending off the trip at Nantucket! I’m so excited to share about this second half of our anniversary trip. The instant we landed in Nantucket we felt relaxed. There’s something about a small-town community that somehow gives you more air to breathe. For any of you small-town lovers, I’m sure you’ll fall in love with Nantucket just as I did!

DAY 1 —

The start of this trip began with a whirlwind of events. Long story short, we almost missed our flight to Nantucket because we were trying to get some last minute bagels from Russ & Daughters (so delicious, by the way). I was certain we would have to book another flight so it was a miracle that we actually made it! Thank goodness our gate was near the security checkpoint because we made it just as the last few people were boarding. It was an anniversary miracle.

Nantucket was just an hour and a half flight away from New York. The minute we landed James remarked, “It’s like a Red Lobster airport!” (haha!) But in all seriousness, the Nantucket airport was simply adorable. It’s so small and the entire airport was covered in the familiar dark gray wood siding you’d typically find on any Red Lobster restaurant. Which, we would soon find out was a very typical design for most of all the houses on Nantucket island. Definitely had a very characteristic, coastal vibe. 

We decided to rent a car for our 5-day stay since we wanted to be free to explore the entire island. It was our first time renting from Turo and we loved it! Turo is a platform for car owners to rent out their vehicles when they’re not in use. We were able to rent our cute little Fiat for such a good rate! Our Turo car was left for us at the airport which made it super convenient. We loaded our luggage and headed to our AirBNB!

Our AirBNB was literally a 3-minute drive from the airport. We rented a room in a family’s house and absolutely loved our stay there. The place was newly remodeled and squeaky clean. Our host was very accommodating and friendly. When we arrived, he called and told us to go ahead and make ourselves at home. Apparently he lost his key and doesn’t lock his doors. He told us he’s close to all his neighbors and there was nothing to worry about! I was surprised, but I suppose that’s the charm of a small town!

We were quite tired after an eventful day so we took time to freshen up before dinner. Before our trip we had researched where we wanted to make reservations for our anniversary dinner and came across Straight Wharf. I’m so glad we chose the restaurant because it was simply lovely. The restaurant is right at the harbor of Nantucket’s Downtown Historic District. The place looked like a converted house, with tables set up in the main room, dimly lit by flickering candlelight. We wanted to fully enjoy the evening so I didn’t bring my camera with me, but you can take my word that it was the perfect romantic setting. 

The food was also so delicious. We were both sold on the Clam Bake so we each decided to order it. The dish was an array of clams, lobsters, and scallops, topped with a sweet corn pureé and their delectable sauce. We also loved their complimentary bluefish pate, served with parmesan toast. It was so good we asked for another plate! We spent the evening reflecting over our first year of marriage, sharing our favorite memories, talking about we’ve learned and how we can grow more. I had my amazing husband in front of me, delicious food, and a waterfront view all around. It was the perfect way to start off our stay in Nantucket.

DAY 2 —

After a restful sleep we set out to explore the island! The Nantucket Downtown Historic District is the main hub of the island (and only a 10 minute drive from our AirBnB). It’s a quaint little center with so many little shops and restaurants. James and I walked around and explored some of the shops. One of my favorite parts of the district was their cobblestone streets. I love that they kept the original streets! I felt like we were exploring a colonial city. (Side note - James highly disliked driving on them. You literally felt like you were riding the Indiana Jones ride at Disneyland while driving over all the bumpy cobblestones haha. But regardless, I loved it!)

We grabbed some lunch at one of the small cafes called Provisions. James ordered a turkey sandwich and I ordered a garden salad. I regretted my order when I had a bite of James’ sandwich. I don’t know how they make their sandwiches, but they were SO GOOD. And here’s the crazy part. I don’t like bacon (okay, maybe that’s the crazy part), but somehow when I ate that sandwich, I fell in love. It was so delicious! I made sure we came back to Provisions once more before leaving. I honestly still dream about that sandwich…

After lunch we headed out to SiaSconset, another quaint part of Nantucket that is right near the beach. We drove around admiring all the cute houses on our way to see the Sankaty Head Lighthouse. I couldn’t help but stop and take pictures in front of them! They were absolutely adorable, like they came straight out of a children’s book.

The Sankaty lighthouse and scenery looked like it came off a postcard. There were only a few people there at the time so we got to take lots of pictures and enjoy the serenity of the place. It didn’t take much for us to realize why so many spent their summers on this charming island.

I had planned to also visit Great Point Lighthouse (another beautiful lighthouse on the other side of the island), but after doing more research that night, I realized that the only way to get to the lighthouse was through tour or through renting a four-wheel drive vehicle. The lighthouse is surrounded by sand dunes so there was absolutely no way to get to it unless you had the right vehicle (I realized then that was why I saw so many jeeps parked around all the houses). I was disappointed, but at least that’s something to look forward to next time!

DAY 3 —

When checking the weather before the trip, I was so sad to see that it was going to rain our entire time in Nantucket. We prayed hard and thankfully the rain didn’t hit until the afternoon of our third day on the island. There’s something about the small-town charm that made us enjoy a more slow-paced, relaxing agenda. We were on the go throughout our entire New York stay, but were able to take things easy while in Nantucket. We slept in that morning and then headed back to the main part of town to try the infamous Nantucket lobster rolls.

Almost every restaurant in Nantucket sells lobster rolls so it wasn’t hard to find the delicious sandwich. We ordered one to go and really enjoyed it! You can tell the lobsters were freshly caught. We walked around the shops near the harbor just as it started to drizzle. Before the rain got too heavy, we made it back to our car and tried to figure out what we could do in the rain. 

We decided to drive around the other side of the island we had yet to explore and made our way to Madaket Beach. This side of the island seemed to have many larger houses and we loved looking at all the lovely neighborhoods as we drove through the rain. By the time we made it to Madaket Beach it was raining a lot harder so weren’t able to see much. I snapped a few pictures in the rain. Even through the fog and rain Nantucket’s beaches are so pretty! James kept mentioning he felt like he was in a Nicholas Sparks movie. The rain plus the white sand beaches seemed like the perfect setting for one of his iconic romantic stories.

Looked like the weather was set to rain the rest of the day so we made it back to the historic district and decided to hang out at one of the coffee shops and read. On our way there we came across a cute little bookstore and stopped by. I absolutely love finding small bookstores in small-towns. There’s something delightful about these little stores. They bring about a feeling of simplicity and getting back to the roots without the complexity of media and tech devices. Where everything we could ever want to know about can we found within the pages of a book.

We strolled down towards the Corner Table coffeeshop and parked ourselves there for a couple hours, enjoying the warmth while cozy-ing up to a book. James and I always bring books whenever we travel and always try to finish one book by the end of the trip. 

The rain began to subside so we went off exploring again! The historic district is small enough where you can practically walk (or bike) everywhere, so we took off walking. I found this little gem of a store, the Peter Beaton Studio, tucked away in one of the nooks of the town. It was a dainty hat shop where you could personal your own hats! I had some fun trying on hats of all shapes and sizes and fell in love. I felt like Audrey Hepburn! Each of the boxes is personalizable with whatever colored ribbons you desire, and come with their iconic black and white striped hat box. They are more on the pricey side, but are so stylish and very good quality.

With no other plans for the day, we (or rather, I, haha) decided to get some ice cream! I had heard a lot about the Juice Bar and their homemade ice cream so we had to try it. We were welcomed in by the amazing smell of fresh waffle cones being made. We tried a couple flavors, all of which were absolutely delicious, and decided to go with a cinnamon roll flavor. As always, there’s no better way to end off the day than with ice cream!

DAY 4 —

We were so excited to wake up to a sunny day! Starting off the day we had a yummy brunch at Island Kitchen, a local favorite on the island. James ordered an eggs benedict, I ordered a breakfast burrito, and we shared a clam chowder. We were not disappointed! With full stomachs, we headed out to Sconset beach to explore another corner of the island. The rain had left a layer of fog on the beach. We found a short walking trail that led to a private part of the beach and sat and enjoyed the view. We even saw a couple sea lions swimming around! 

On our way back to the main part of town, I asked James to stop on the side of the road. The drive back is filled with these pieces of empty land, filled with trees and greenery (totally my kind of scene!). We parked our little fiat and took pictures!

The spent the remaining day browsing more shops, exploring antique stores (so much fun, by the way!), and just relaxing. It was our last full day in Nantucket so we wanted to take it all in!

DAY 5 —

Our flight back home wasn’t until the afternoon so we decided to visit one more lighthouse before we left. A smaller lighthouse near the historic district, Brant Point lighthouse is another iconic lighthouse on the island. The wind was picking up as we took some photos, but it made for some great shots!

One of the things we wanted to do while in Nantucket was ride bikes. Everything is so close; biking was the perfect way to get from one place to another. However, because of the fluctuating weather, we never got to ride bikes (we didn’t want to risk getting stuck in the rain while riding). We were about to rent some that morning but unfortunately the minimum rental periods were simply too long for us since we had to catch a flight in a couple hours and was simply not worth it. But we did get to meet this adorable, friendly dog outside of the bike rental shop!

Here’s where our trip was was supposed to end. But, unfortunately the weather had other plans for us. Our plane got delayed by one hour. And then another hour. We started to get concerned when take off time continued to be pushed back so we decided to head to the airport and figure it out. Long story short, we waited and waited at the airport, delay after delay only to be officially told that our flight got canceled. Apparently the fog had gotten so thick that the planes trying to land on the island to pick us up couldn’t see where they were landing. It was another turn of events for our anniversary trip.

With no place to stay, we searched for any available hotels. One of the airport attendants was kind enough to recommend a hostel for us to stay at. It was definitely a much cheaper option so we headed out to the hostel. Another one of our fellow stranded passengers joined us in this unexpected situation and we got to make friends with him along the way. He was from Slovenia! Though we were all less than happy about not flying back home that night, it was fun to make a new friend along the way.

The next morning we headed back to the airport only to hear that our morning flight had been delayed again after the fog. Our Uber driver told us the Nantucket fog was known to be this heavy. So much so that they named it the Gray Lady. Apparently many people have experienced unfortunate incidents of being stranded on the island due to the fog, or not being able to fly in because of it. Biggest lesson learned -- don’t visit Nantucket in June. You’ll most likely experience rain and fog. July is a much better time to visit where there’s less chance of fog and rain, plus, hydrangea blossoms are in full bloom! I found hydrangea bushes everywhere we went and was sad they had yet to fully blossom.

After a couple more delays, we finally got the green light to board and head back home. What an adventure. We never anticipated this end to our Nantucket trip, but these are the memories will look back on one day. We’ll be able to laugh and say, “Remember that one time we got stranded in Nantucket and stayed in a hostel with a stranger from Slovenia?” 

Despite the unexpected end to our trip, we loved our stay in Nantucket and hope to visit again! Preferably in a warmer, non-fog month haha. It’s the perfect place to vacation with family and friends. We’re hoping to one day rent a house and visit with a bunch of family and friends! Looking forward to visiting this charming coastal island again.