As many of you know, I’ve been going to Nantucket for over 25 years, so I think I can offer some advice on how to plan a great trip and how to hit up some of the hottest spots on the island. However, every time I go I feel like I wasn’t able to squeeze in everything that I wanted to do. I certainly have not seen and done it all, but I think that’s what makes it so special. It’s pretty amazing that such a small place (it’s less than 48 square miles!) has so many options and places to explore. It’s without a doubt my favorite place in the world to travel to, and I try to visit as often as possible. Below I’m sharing some of my favorite places to stay, explore, dine and shop on Nantucket incase you’re planning a trip any time soon. Let’s just say… I call myself a tried-and-true Grey Lady devotee.

 

WHERE TO STAY: 

The White Elephant Hotel

An island landmark, the iconic White Elephant hotel is one of the most beautiful hotels on Nantucket. It’s right on Nantucket Harbor and this waterfront resort features chic, light-filled rooms, suites, garden cottages, and in-town lofts. This resort combines luxury with the natural beauty of Nantucket’s timeless surroundings.

The restaurant at the resort, Brant Point Grill,  is simply irresistible. Enjoy early morning views of Nantucket Harbor from the dining room or dine al fresco on the covered deck while you savor everything from omelets and waffles, to an incredible array of homemade pastries. My favorite? The Lobster Bloody Mary. It’s out of this world, and it takes great photos (another plus!)

WHERE TO DINE:

Charlie Noble

This restaurant opened this summer, and I’m glad I stopped by. They had some of the best muscles I’ve ever had in my life! Yes, life. They were really good. Another delicious dish was the Lobster Roll served with Tots! It had very light mayo (which I like) and the tots were covered in pickled red onions… yum!

 

Club Car

The Club Car is an island institution re-imagined for the first time in 40 years. The restaurant’s classic railway car and antique elements are blended with eclectic, modern materials creating a fresh feel that balances old with new. I thought the menu was fantastic. I tried over 9 dishes, and all of them were great. The menu is inspired by California Cuisine with shared plates centered on farm fresh vegetables and local seafood. I had one of the best meals I’ve had in a long time here and I would highly recommend this restaurant to anyone visiting the island. However… I have to say I do miss the old Nantucket charm the restaurant used to have. They went for a California contemporary feel instead of sticking with classic New England.

Oath Pizza

 

Nestled between the yachts and the cobblestone streets. In a tiny little shack with a million dollar view. Well, in Nantucket it’s a ten million dollar view. The one thing I’ve had a difficult time finding on the island in the past few years is a good thin crust pizza. Well, I finally found it. This place has awesome pies, and it’s a great place to stop after a long day out on the water or if you’re headed back to the main land and need a snack for the ferry. I recommend getting ‘The David’, it was delicious.

WHERE TO SHOP:

Perch Nantucket

A women’s contemporary store that has many of today’s coveted and trendy brands. Located on Straight Wharf at 2 Harbor Square in the former Vineyard Vines space, they have some of my favorite brands: Veronica Beard, See by Chloe, Derek Lam 10 Crosby, Rag & Bone and M Missoni. Whether you are going from beach to dinner, attending a fabulous Nantucket wedding or just wanting to stock up on the latest fashions, Perch Nantucket will bring you a beautifully edited selection of pieces you can enjoy or years. Ask for Ally Roach – she helped me pick out some amazing pieces.

Cold Noses

Looking for exceptional pet accessories or pet person gift? They have exclusive Nantucket design collars and leashes, hand-painted breed ornaments, supplies, people gifts and a wide selection of pet bakery and gourmet treats. They also carry Chloe and Max LLC, and we all know how much I love that brand! I bought Chloe a life jacket. She just loves it.

Milly and Grace

Milly & Grace, located in the ivy covered building (it’s gorgeous) just off of Main Street and across from the Compass Rose, is a perfectly feminine and vintage inspired clothing and home decor boutique. Named after her grandmothers, owner Emily Ott Hollister curates her boutiques collection with items that reflect the personalities of her sassy grandmother Milly and her sweet grandmother Grace. With an infusion of her personal feminine style, Emily maintains a balance between contemporary fashions and classic pieces.

Skinny Dip Nantucket

The Skinny Dip is a collective concept store housing a well-­curated mix of men’s, women’s and lifestyle brands, with a focus on introducing fresh and new designers from around the country. It’s where I purchased that navy blue sweater that said “Nantucket” and got me voted “Most Fashionable at Figawi” by Nantucket blACK Book.

Nantucket Whaler

This place is perfect if you’re looking to get the feel for authentic Nantucket. Nantucket Whaler clothing embodies the grit, strength and enduring nature of the sea, and those who journey through it. Purposeful clothing designed on Nantucket. They support New England manufacturers and say “wear the right whale”.

Shift

A prepster’s dream! From classic and polished to contemporary chic apparel and accessories, featuring over 75 women’s brands, including Sail to Sable, Jude Connally, Mahi Gold, Milly, Shoshanna and Kate Spade, Shift has it all! I loved all of the bright colors in the shop, perfect for summer.

 

WHERE TO EXPLORE:

Sconset Bluff Walk

Beyond the gorgeous ocean views, part of the appeal of the walk is that it’s not one kind of experience. You’re cutting through a small neighborhood of houses; then advancing through a manicured backyard; now you’re under tree cover. There are flowers and birds, pathways to the water, and a lineup of places to stop to literally breathe in the scenery. It can be a quick jaunt or part of a long afternoon. Either way, you won’t be disappointed.

Great Point Light House

Great Point Light, officially, Nantucket Light is a lighthouse located on the northernmost point of Nantucket Island. First built in 1784, the original wooden tower was destroyed by fire in 1816. The following year a stone tower was erected which stood until toppled in a storm in March 1984. Rebuilt again in 1986, the stone tower was built to replicate the old one, and still remains in operation today. Take a car and pack a picnic for the day – it’s a sight to see!

Madaket

Madaket, on the far west coast, is one of the island’s most beautiful beaches. The neighborhood offers a relaxed, family-friendly vibe and was once home to Mr. Rodgers. It’s especially beautiful in the evenings, especially to watch the sunsets. Consider riding a bike out there and check out the beaches.

I always tell people, you never want to just come over to Nantucket for a day trip… you’ll be disappointed you didn’t stay at least the weekend.  Soak in the feeling of island time and savor that fresh island air.