Nantucket Travel Guide

Recently, the Director of Barrington’s Social Media and her husband went on an anniversary trip to Nantucket. The beautiful scenery was, quite frankly, the perfect backdrop for our monogrammed tote bags!! But more importantly, we thought you might enjoy a Nantucket Travel Guide based on their experiences.

How did you travel to Nantucket?

We flew on American Airlines to Boston, then took Cape Air over to the island. In the Boston airport, you have to leave security, walk over to a different terminal, re-enter security, and check in at Cape Air. You must check in at least an hour before take off. They seem pretty serious about that, so unless you have a generous layover, I suggest carry on bags, such as our Belmont Cabin bag or the Nantucket tote. Also, in the interest of full disclosure, the Cape Air plane is very small — it seats 6-7 people other than the pilot. They even weigh your bags and ask for your body weight! But our flight was smooth and easy.

Pictured:St. Anne Zippered Tote

What did you pack for the trip?

Nantucket is actually a very casual place. You don’t need dressy clothes. White jeans and a cute top will be great at any restaurant. You do, however, need options and layers. It might be a little chilly in the morning, then hot in the afternoon. I also suggest a rain jacket and umbrella. And, most important, take flat and casual shoes. The streets in town are cobblestone and many of the sidewalks are (slightly uneven) brick. Heels would be ill advised! Of course, take a swimsuit and cover up and exercise clothes for biking around the island.

Pictured (Left): Belmont Cabin Bag (Top), St. Anne Zippered Tote (Bottom)

Pictured (Right): St. Charles Yacht Tote

Where did you stay in Nantucket?

We rented a little one bedroom cottage through Airbnb. It was very nice, and a short walk to town. We loved it! There are many inns and resorts on Nantucket, but we loved having a kitchen and a little more space.

Pictured: Westport Wine Tote (Top), St. Anne Zippered Tote (Bottom)

Where Did You Get Breakfast in Nantucket?

First of all, my husband and I enjoy different types of breakfast spots. He wants a diner type situation, and gets scrambled eggs, bacon and sausage EVERY time. Plus, on vacation, he wakes up approximately 2 hours before I do. (What? WHY?) Therefore, he walked to breakfast each morning while I slept. He loved the Fog Island Cafe. Then, he would swing by the Petticoat Row Bakery and pickup either a morning bun or sailor’s knot for me. Delicious with my morning coffee from Handlebar Cafe!

Recommended Nantucket Lunch Spots?

Our favorite lunches in town were at Cru (the lobster roll with fries is a must do!), and Club Car (loved the avocado toast with crispy fried egg). We also drove (you could bike there too) out to Madaket one day and had lunch at Millie’s, which we enjoyed very much. We sat outside, had delicious tacos (the Tuckernuck for me) and quesadillas (the Brant point) for him. Their Dark and Stormy cocktail was yummy as well. (Only had one! We were driving!)

Best Places to Eat Dinner in Nantucket?

We honestly loved every dinner we had on Nantucket. Straight Wharf had scrumptious seafood in a romantic candlelit (exclusively candlelit actually) atmosphere with great service. Need I say more?

Nantucket Prime had outdoor seating on the front lawn with twinkle lights strung around, which was so incredibly pleasant and inviting. Both the hostess who seated us and our waiter were delightful! I had a bibb lettuce salad that I still think about! My husband had steak, which he gave two thumbs up!

At Proprietor’s, located in an historic house with very steep staircase to the second floor, be sure to try the super tasty fried broccoli! And, I enjoyed their Cocktail No.7, which is a little like a spicy margarita.

Our favorite dinner location was the Brant Point Grill. It’s on the water with a beautiful view of the harbor. It’s open-air, but covered. The service was incredible. Listen to this...they made a tiny mistake on my order, that I didn’t even notice. To make it up to me, they brought me an extra cocktail, unannounced, and said, “please accept our apology for the mistake”. I gladly accepted (Because we were walking, ha!).

There are so many great restaurants on Nantucket! These are just the ones we got to experience.

Where to have a cocktail?

Hands down, I’d say Galley Beach! It’s a restaurant in an actual building, but the beach lounge and bar spill out onto the beach. During the day, the dress code is beach casual. And after five, you’ll need to be dressed in clothes, no beach attire. There were several families with young kids there who were sipping a drink while the kids ran around playing lacrosse on the beach. It was fun to watch, but we enjoyed being there kid-less! I’ve been told that Galley Beach is the best place to watch the sunset, but due to the overwhelmingly cloudy weather we had, we saw no sunset.

What’s There To Do in Nantucket?

So many fun things to do on Nantucket!

Rent bikes at Young’s and ride on the bike trail to Sconset where you’ll see the Sankaty Head Light (lighthouse).
Rent a car (also at Young’s) and drive all over the island. It’s a small island!
Stop at Surfside Beach for a few hours. You can rent beach chairs for $8 each!
Shop! Don’t miss the darling Peter Beaton Hat Studio!!! Or, Murray’s Toggery Shop, home of the original Nantucket red pants and shorts!
Go see a play at White Heron Theater.
Go on a sailing excursion.
Walk all over town and gawk at the gorgeous houses and flowers!