Nantucket Travel Diary

Good morning lovely people! I hope you all had an amazing weekend!

I am so ready to share with you all my full Nantucket Travel Diary! I know I’ve been blowing up social media with all of my photos lately, but let me be honest and say that this trip topped all of the trips in the past. It was a place I had always wanted to visit, but I also visited with Jacob on my birthday weekend, which made it that much more special. Each day was spent exploring the beautiful island, eating unbelievably great food, and spending quality time together.

Friday, August 31.

Jacob and I flew into Boston and took an Uber to Hyannis so that we could take the ferry over, and it all worked out perfectly! We arrived on the island around noon and started exploring right away!

We walked a few blocks from the ferry port to our hotel, The Roberts Collection, to drop off our bags and we were pleasantly surprised. The Roberts Collection is a group of historic homes renovated to be the most adorable hotel. I honestly do not think I will ever stay anywhere else. The staff was so friendly and helpful, the rooms were adorably decorated, and the location was perfect!

After we dropped off our bags, we grabbed a quick lunch at The Tavern, and then walked the docks. One of mine and Jake’s favorite things to do is walk the docks to see all of the creative boat names and to see where they are from.

Since we had been traveling since 3am (our flight out of Detroit left at 6am, which meant we had to be there around 4am…) we both needed a nap! We decided to head back to the hotel to rest for a couple hours before dinner.

For dinner, I thought it would be fun to grab two pizzas from Oath Craft Pizza and have a little picnic on the beach. First off, the pizza was AH-mazing, but the views by Brant Point Lighthouse were unreal. We watched as the skies turned from blues to yellows to pinks, which was the perfect ending to the perfect first day on Nantucket. I’ll be posting a full blog post with more photos from our picnic later this week, so keep an eye out!

Saturday, September 1st.

We woke up fairly early on Saturday to grab breakfast at the hotel, and then headed out for more exploring. Since our hotel was located right in the heart of town, everything we could have ever wanted or needed was only steps away. We decided to visit a few shops and then walked further inland to see the gorgeous homes that inhabited the island. From white picket fences, to perfectly manicured gardens, I was in love!

After stopping by the hotel to change (and grab more bandaids for my poor little feet), we decided to get lunch near the docks. One of the restaurants that I was dying to go to was Cru. It was located right on the water and are famous for their amazing lobster rolls. My lobster roll was buttery and rich and everything I could have ever wanted! Jake and I also tried oysters, and if you were following along on my Instagram stories, you saw his reaction LOL. Needless to say they were not his favorite.

Fast forward an hour or two and we were heading out on the Endeavor sailboat. This might have been the highlight of our trip. It was so peaceful being out on the ocean with Jacob. If you want to see more photos from our sailing trip, click here!

Now, Jake and I planned to have dinner and drinks and watch live music over at Cisco Brewery, however, that didn’t go quite as we planned. We arrived there around 4:30pm to see a line that wrapped all the way down the street. There was no way we were ever going to make it inside, so we changed our plans and had dinner and drinks at Backyard BBQ in town. I feel like I still dream about their delicious homemade mac & cheese. It was THAT good!

You can’t go to Nantucket and not have an ice cream cone from the Juice Bar! Their homemade ice cream and waffle cones are to die for! I had strawberry with rainbow sprinkles (duh) and Jake had a brownie batter flavored ice cream cone. To be honest, I liked his more than mine, but I think that’s because my sister and I used to make boxed brownies just to eat the batter as kids, and that’s exactly what it tasted like!

We ended the night by enjoying our ice cream on a bench by our hotel. It was a busy, but good day!

Sunday, September 2nd.

I woke up on the morning of my birthday to Jacob playing the song “22” by Taylor Swift. He even brought me breakfast in bed, which made my heart literally explode. I was dancing around to that song all morning while I was getting ready for the day!

Before going out for the day, I enjoyed my yummy cupcakes from Petticoat Bakery. I’m not a huge cake person, mainly because I’m picky with frosting, but these cupcakes were delicious! And get this, the frosting was actually my favorite part!

One of my major Nantucket “must-do” things was walking the ‘sconset bluff trail. It’s a path that goes around and in between the most gorgeous homes in Siasconset. These million dollar houses with the most perfect gardens had my heart skipping beats.

I only wish that the hydrangeas would have been in full bloom with color still. It would have made this walk so much better.  Although, walking next to the ocean with the breeze blowing my hair wasn’t too bad either!

At the end of this trail was Sankaty Lighthouse. It was such a beautiful sight, and I wish I could have enjoyed it more. Long story short, our taxi driver who dropped us off in ‘sconset told us the walk wasn’t long at all. While Jacob and I were weaving through the bluff trail for about 30 minutes, we started to wonder why we weren’t there yet. Jake looked up how much further it was on his phone and it said two more miles!! If you hadn’t noticed in one of the above photos, I was wearing block heels… Definitely not the right shoes to be walking 3+ miles in. By the time we reached the lighthouse, my feet were bleeding (which is why I wouldn’t turn and smile for a photo… I was in tears). It was also the hottest day we were there, and we drank all of the water we had. It was so bad that it’s laughable to think back on now.

We ended up taking an Uber back to town where I wrapped my 18 blisters (I wish I was exaggerating this. There really were 18) in bandaids and we went down to The Tavern for a much needed drink!

For my birthday dinner, Jacob and I went to Galley Beach, one of the best places for dinner and a sunset. I was absolutely blown away at the beauty of this restaurant! The open air patio and the lounge area in the sand were so pretty, but the service at this restaurant was unmatched!

One of my favorite parts of the dinner was talking with the adorable couple next to us. They told us that they had been married for 52 years and that they thought we were the cutest couple. They also met when they were really young, like Jake and I, and they gave us the best life advice.

Probably one of the most breathtaking sunsets I have ever witnessed in my 22 years of existence. As the sun sank into the horizon, the east end of the beach had cotton candy colored skies and pink glow. The west end of the beach glowed with an entirely different shade. It was as if God had hand painted this sky just for Jake and I to see on my birthday. I felt so blessed to end our day there.

Monday, September 3rd.

With only a few hours left on the island, Jacob and I woke up early, grabbed breakfast, and had our bags packed and ready to go. We wanted to get as much shopping and exploring in as we could while we were still there. We tried to hit all of the parts of town that we hadn’t seen yet, and it was a great day!

We hit shops like Milly & Grace, Jack Wills, and of course the Lilly Pulitzer and Vineyard Vines stores! There are so many great places to shop on the island! One thing Jake and I regret was not having more room in our bags for new stuff! Next time we plan to pack an extra bag just so that we can bring back more.

After a few hours of shopping, we needed a little break. We sat up on our hotel’s porch and watched as the people walked by. It was so peaceful with the light breeze. I sat there and dreamed about how badly I want to have a home on Nantucket someday so I can do exactly that; sit on my porch and people watch.

As the day neared the end, Jake and I made our way to the ferry where we would be taken back to the mainland. We were so sad to leave. This little getaway meant so much to the both of us. It is now officially my favorite place in the world and I can’t say enough great things about it. We can’t wait to go back in the Springtime and the Fall next year! I am already counting down the days! xo

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