Little Nantucket — or shall I say little but mighty! The island has been on my bucket list for years, and I’m so glad we were able to add it onto our big East Coast trip this year. You can read the first part of our trip here. Knowing Nantucket is insanely expensive, we chose to stay for three full days and three nights, which in my opinion was perfect for a couple. We were able to see most of the beaches, go to the restaurants we wanted to check out and also have time to relax. We did pack it in when it came to activities, so more time definitely wouldn’t be a bad thing. I’d love to come back with a big group of friends and rent a house close to town. I really felt like Nantucket was more of a family or friend place, perfect for large groups. We had a blast during our time there, but it felt like the island was extra special to those with past connections to it, like yearly friend trips or history of going to the island with family growing up. We didn’t see many couples, but we really enjoyed our time together.
I heard that getting to the island is half the battle, but it was so easy for us! I know a lot of people have issues with The Grey Lady rolling in (similar to Carl The Fog in San Francisco) which affects the airlines, but we must have come on a perfect day, it was all seamless! We flew from Charleston Airport on American Airlines and had a short layover in DC. Heading out we took the Seastreak ferry, which is the “speed ferry” that goes straight to New Bedford, MA, where we picked up our rental car that we were driving to Vermont. If we had been going home to SF, we definitely would have flown to Boston from the island. I didn’t want to risk traffic using the Cape Cod ferry, so I didn’t look into the Hyannis port.
Where We Stayed
We stayed at 21 Broad, a boutique hotel owned by Lark Hotel group. We stayed at a Lark property before in Mendocino, so it was an easy choice between here and a few other boutique places in our price range. Nantucket doesn’t have many large hotels, most are bed & breakfast, boutique style places located near the main downtown area. We considered renting a house, and I’m so glad we didn’t! If you’re traveling with a group and could split Ubers/taxis to dinners and activities that would be different, but as a couple I don’t think we would have been very happy being miles away from town where all the action was. I couldn’t believe that we only took one Uber the entire time which was from the airport to our hotel! 21 Broad was a beautiful old home turned into an inn with gorgeous classic New England decor. The hotel seemed new and fresh, which we always love. The cookies in the evening and the small plate style breakfast each morning were special treats that I loved to enjoy on the front porch — the ideal people watching perch, so relaxing! They also have a sister property, 76 Main which I’d recommend checking out if 21 Broad is booked. you’d be surprised how tough it is to get a reservation in the peak season.
We rented bikes at Nantucket Bike Shop for our entire stay. It was kind of a bummer our hotel didn’t provide these for us, but was easy enough to rent. The bike shops are all within a block of each other, so just pop in and see who will give the best deal. I will say the service at the shop we went with was notably welcoming. We took the bikes ALL over! I joked on my Instagram that we went 10 miles one day, with only one severe adult tantrum. Ha!
On our first day, we landed around 11am and hit the ground running — we explored the town and shopped at Skinny Dip (one of our favorite stores we popped into.) We eat a beautiful lunch on the water and grabbed ice cream right near our hotel. We headed to Jetties Beach in the late afternoon, about one mile from our hotel in town, which we walked to since we wanted to get our steps in.
The first full day we biked from the hotel to Madaket Beach, stopping at Millie’s on the way for a marg and fish tacos (much deserved!) after hanging at the beach, we biked to Cisco Brewers, a super fun spot with multiple beer and wine tents, local delicacies and delicious food trucks. We tasted Nantucket Vineyards Rosé and came home with three bottles! Who knew Nantucket could make a good Rosé?! 🙂
On our last full day on the island, we took a LONG bike ride to the other side of the island — about five miles each way in the summer heat! It was so challenging, but beautiful. We ended at the ‘Sconset Bluff Walk, which is a gorgeous path that goes through the backyards of multimillion dollar homes. It might seem strange to walk through the yards, but its open to the public and they’re used to it! The views of the water and stunning flowers were major highlights. On our way back, we made sure to stop at lighthouse. After catching our breath (quite literally) and freshening up, we had sammies in town followed by a much needed afternoon ice cream cone. We finished up the day sailing at 4pm on the Endeavor, a gorgeous sail boat built by the captain himself! This was a must-do activity in opinion. It was fantastic seeing Nantucket from the water while enjoying happy hour in the summer breeze. Ahhh!
Where We Ate & Drank
Cru — The best $35 (yes, $35) lobsta roll you’ll ever have. Rosé and the outside dining made this the perfect first meal on the island
Provisions — The Thanksgiving inspired turkey sammie…life. changing.
Millie’s — Tacos & margs at the beach.
Lola 41 — OMG! This was definitely the best dinner on Nantucket. Go at 4pm to make a same-day reservation, or grab a spot a the bar like we did. Their sushi is fresh and innovative, and their burger is a must try.
Galley Beach — 100% worth the hype and prices. We had the most stunning romantic night dinning on the beach. Make reservations well in advance.
Queequeg’s — We ended up walking by this place and really liked the menu. It has mixed reviews online, but I’m so glad we tried it. The fish special and wine list were memorable.
Afterhouse — The perfect post-dinner wine bar in a cozy atmosphere.
Brant Point Grill at The White Elephant — This is the perfect place for a pre-dinner drink while watching the sunset. We were originally going to eat here but it didn’t look worth the price to us, more like a hotel restaurant (which it is) but perfect for outdoor cocktails.
Sand Bar at Jettie’s Beach — The staff at this beach bar were super nice. A simple beach bar on the way to dinner at Galley Beach, great for afternoon sips or evening sunset brews.
Juice Bar — I don’t even need to add this to the list, you can’t miss the line! Its definitely the most delicious ice cream on the island, but it wasn’t *life changing* as some explained it. I will say it was quite refreshing on the 90 degree days we were there for, and the waffle cones were a highlight.