Memorial Day Weekend on Nantucket is always such a special time, and this year was even more memorable as we came together to celebrate Carolyn! As the maid of honor, I had so much fun planning this trip—it turned out to be the perfect balance of relaxation and celebration. So many of you have asked for the full itinerary, so I’m sharing all the details in today’s post along with a few of my favorite go-to spots on the island. Nantucket truly is such a special place, and I’m so grateful we had such an unforgettable weekend honoring the bride-to-be!

If you want to shop any of the looks we are wearing in this post visit my Memorial Day Weekend shop here. 

Friday

Our weekend kicked off on Friday afternoon as everyone arrived, settled in, and unpacked. My friend was kind enough to host us for the weekend, but scroll to the end of this post to find my recommendations of where to stay! Our journey there was a bit chaotic with canceled ferries, late busses, etc. so we were all so excited when we finally arrived on Nantucket.

Nantucket Magic was at the house setting up when we arrived and our friends welcomed us with cocktails to kick-off the weekend! It was so nice to catch up with everyone and get settled in. I had gifts for all of the girls (see what I included here) and I was so excited to give them to everyone!

We originally planned on an outdoor movie night but due to the weather we decided to move everything inside. The Nantucket Magic team was so flexible and set up the cutest movie night complete with a candy bar, fresh popcorn, and local pizza. If you are hosting any events on island, the Nantucket Magic team truly does incredible works and makes such memorable events!

A cozy movie night was the perfect way to start the trip after a long travel day! We ended up watching the Parent Trap which was so nostalgic for all of us. It was great to have a restful night before a busy weekend ahead.

Saturday

Most of us in the group are early risers so we woke up early and did a quick coffee run into town! We loved renting a Jeep for the weekend that made is easy for us to squeeze everything in. Everyone got a coffee from Handlebar, walked around town a bit, and headed back home for breakfast.

This day was all about balance so we loved starting off with a private yoga class at the house – a peaceful and grounding way to connect before the day picked up pace. Reach out to Emmy if you’d like to plan something similar!

One of our favorite parts of the weekend was Live Music + Drinks at Cisco Brewers, which is always a favorite to visit. The line was so long to get in, but we had the best time once we were in. We danced, listened to live music, and sipped on delicious drinks. A lot of us bought souvenirs to bring home for our boyfriends too.

Dinner at Nautilus was another highlight of our trip- it’s an island favorite known for its vibrant energy, shareable plates, and delicious fresh ingredients. A few favorites are the calamari, blue crab fried rice, oyster tacos, and roasted duck- but truly you can’t go wrong with anything on their menu. We ended our night with a night Out at Gaslight—Nantucket’s iconic nightlife spot where we danced well into the night.

Sunday

We eased into Sunday with breakfast at the house before heading out for a lighthouse excursion and explored town. We drove out to Sconset and saw so many of the charming houses and ocean views, it was such a peaceful way to start the day. We popped by the Sankaty lighthouse which is always fun to see especially if it’s your first time visiting. We freshened up quick and then headed into town for some shopping. A few favorites we stopped into were For Now, Hill House, Beau + Ro, Murray’s Toggery Shop, Four Winds Gifts, Nantucket Crisps, and Alice Walk. We all were able to find something we loved to take home from such a memorable trip! I got the cutestttt sweatshirt from For Now and have been wearing it on repeat since getting home.

In the afternoon, we set sail on a Group Sail on the Endeavor, their crew is always so kind and makes the trip so memorable. I always love getting out on the water and seeing the island from new perspective. Even though it was a bit chilly, we sipped on champagne and loved our excursion. We docked just in time for a stop at Juice Bar—a Nantucket must—for delicious ice cream. My go-to is a waffle cone with a scoop of cake batter and strawberry with rainbow sprinkles.

Back at the house, we gathered for a cozy dinner at home- Maris set a beautiful table and Carolyn made a charcuterie which tasted even better than it looked. On the menu was grilled chicken tacos with rice and fresh chips and guac. Mikayla was also mixing up some delicious cocktails!

Most of the group was leaving early on Monday morning so everyone started to pack up after dinner- we couldn’t believe the weekend was coming to a close!

Monday

Monday morning we brought the girls leaving to their ferry and decided to explore a bit more before heading out. We popped by Lemon Press for coffees and then went for a walk at Steps Beach. We collected shells while we sipped on coffee and enjoyed the beautiful weather. After our walk we grabbed our luggage from the house and popped over to 167 Raw for some lunch before heading out, the lobster roll and ferry were so fresh and delicious.

Overall it was the perfect weekend celebrating my bestie of 20 years! I can’t believe the big day is around the corner and I feel so blessed that we all were able to share such a fun weekend together. I hope if you are planning a trip to Nantucket you are able to find something fun from our itinerary, I’m also sharing my other island favorites below.

Where To Stay:

Sharing a few hotels as well  as a few options on rental sites so definitely browse to find something you love!

• Greydon House
• Life House Nantucket
• White Elephant Resort
• The Nantucket Hotel 
• The Wauwinet 
• 21 Broad 
• Apartment Close To The Beach 
• Rose Covered Guest House
• Cozy Condo 
• ‘Sconset Cottage

Where To Eat:

The island has a so many incredible food options whether you are looking for an elevated dinner or a casual lunch spot, here are my top picks.

• Black Eyed- Susans (breakfast)
• Handlebar Café (breakfast / coffee)
• Lemon Press (breakfast /lunch)
• Claudette’s (breakfast / lunch)
• Bartlett’s Farm (lunch / groceries)
• 167 Raw (lunch / casual dinner)
• Millie’s (lunch / casual dinner)
• Provisions (lunch)
• Fresh Nantucket (lunch)
• Or, The Whale (dinner)
• Straight Wharf (dinner)
• Something Natural (lunch)
• Cru (lunch / dinner)
• The Nautilus (dinner)
• Sister Ship (dinner)
• Lola 41 (dinner)
• Bar Yoshi (dinner)
• Stubby’s (late night)
• Juice Bar (ice cream)

Thanks so much for reading! Enjoy your next trip to Nantucket!