The Luxurious Journey

There is a magical island off the coast of Massachusetts that calls to me every summer. It is old and small and the streets are uneven and yet its siren song is irresistible.

It isn’t easy explaining why Nantucket is so special. I could say that it is my absolute favorite place to be in the summer, but that’s not really telling you anything. I could say it has miles of gorgeous, soft, sandy beaches, top restaurants, and fabulous shopping, but that doesn’t really do it either. What makes Nantucket special is how it makes you feel.  

Something happens to you when you arrive on the island. As the Brandt Point Lighthouse greets you, so does the scent that is quintessentially Nantucket, a mixture of lilacs and sea salt that is uniquely its own.

As you look around, everyone else seems to feel it too. Maybe that’s it- everyone seems so happy here?

The harbor area or “Town” is cobblestone streets lined with privately owned shops. No chain stores here (other than Ralph Lauren and Vineyard Vines, which somehow got a pass). There isn’t a Starbucks in sight. But there are tiny, beautiful jewelry shops, quaint cafes, galleries, and chic clothing stores (can you even go to ACK without stopping by Eye of The Needle or Pollack’s?).

Nantucket is small. Much smaller than its other island counterpart, Martha’s Vineyard. An avid biker could ride from one end of the island to the other in less than two hours. It costs a small fortune to bring a car onto the island, a subtle way of discouraging too much traffic, and car ferry reservations are hard to come by. While this may annoy some, it really does help keep this tiny island a little less congested. But fair warning, Ubers and cabs are not inexpensive. Luckily, the Nantucket bus system (The Wave) is very convenient, clean, and easy to navigate.

Also, unlike Martha’s Vineyard (sorry MV) Nantucket’s beaches are plentiful and easily accessible. Our favorite is Surfside, which has chair and umbrella rentals and the Surfside Beach Shack for really good burgers. There are too many beaches to name, but Cisco and Nobadeer are very popular. Madaket offers more privacy and the infamous Millie’s nearby (amazing tacos!), which is always a big draw.

What’s there to do on Nantucket besides eat and relax? Plenty. There are harbor cruises, sailing and deep-sea fishing charters, museums, garden tours, walking tours, an aquarium, live theatre and golf to name a few. Did I mention the shopping? A perfect rainy day option.

The homes range from the adorable to the magnificent and by strict code, almost all have pitched roofs and unpainted shingles to preserve the quintessential Nantucket style.

By most standards, I’m a relative newcomer to Nantucket. Back in 2005, when I was pregnant with my daughter, I was deep in my travel research obsession and I happened upon a small hotel that seemed relatively unknown. I was lucky to book a quick weekend there, only to be put on a 3 month bedrest by my doctor two days later. The following year I was determined to go and so we did, toddler in tow. And we keep coming back. We haven’t missed a summer since.  

Staying on Nantucket means having your choice of 5 star Hotels, Inns, B&Bs and amazing homes. You just need to book early. And by early, I mean book next summer’s home rentals now.

For those of you wondering why I’m writing about Nantucket in August when the season is almost over, I would offer that September is probably the best time of year to go there. The weather is usually great, the water is warm and it’s not impossible to get into the best restaurants. Speaking of restaurants, here are my top 5 in Nantucket. 

Galley Beach

Hands down the best place on the island to watch the sunset. We go every night for a cocktail before dinner because it’s just spectacular. The scene is vibrant and gorgeous, everyone dressed in perfect Nantucket casual chic. As if on cue, just as the bright orange sun begins its descent, the guests rush to the shore to grab that perfect sunset photo which will sit on their mantle to remind them of this magical place. This is fine dining (with a price point to match). There is nothing better than eating at the Galley on a warm summer night at one of the tables in the sand by the shore. A sumptuous lunch here is also a great idea. (*This year The Galley has been closed on Tuesdays and requires reservations for all dining and even for cocktails*)

Le Languedoc Bistro 

Le Languedoc is a small French bistro in the center of town. It has been around forever and is one of the mainstays of Nantucket. We go every year for their lobster which is absolutely legendary. A sizable lobster stuffed with creamy polenta and generous chunks of lobster meat and claw mixed in. If you can snag a table downstairs in the Bistro, you know you’ve made it- especially if Jimmy is making your drinks.

Lola41

One of the most difficult reservations to secure on the island, Lola is a high energy, fun restaurant that serves some of the best food on ACK. Lola takes same day reservations starting at 4pm. Pre-covid you could go early and stand in line to ensure getting a spot, but now the only way is to call. I always feel like a teen in the 80s calling my local radio station for concert tickets trying to get a reservation here. But it’s worth it. The Lola Burger is my favorite burger on Earth. The red onion compote and the rich foie gras sauce on the side just make it unbelievably good. Extra sauce to dip my truffle fries? Yes, please. If you can’t get into Lola41, there is a Lola Burger outpost mid-island (one in Boston too!) for a more casual experience. And if you find yourself in Palm Beach, I highly recommend dining at Lola 41 at the new White Elephant hotel there. The hotel is absolutely gorgeous and the food is just as fabulous as it is in Nantucket.

The Nautilus

At the top of the impossible to get into list is The Nautilus, one of the tiniest restaurants in Nantucket. Reservations open 6 days in advance at 10 am and even if you are online at 9:59 and find a spot at 10, it’s taken by the time you hit reserve. Incredibly frustrating. We somehow got a reservation last year and we still dream about the blue crab fried rice… If you can’t get into the ACK location, Nautilus also has a Boston outpost.

The Pearl

New York meets Nantucket at the Pearl restaurant. The Pearl has won countless accolades and awards for its food and wine and they are all well-deserved. I think of it as refined Asian-fusion with the best martinis in town. It’s sexy and vibrant and the food is really special. Whenever I go, I have to order their Tuna Martini and the Korean style BBQ short rib, which is nothing like it sounds. It is thin slices of the most tender steak on sticky rice with a tangy “green chili love sauce” which is honestly the best name for a sauce I’ve ever heard. That being said, don’t miss the Classic Salt and Pepper Wok Fried Lobster, for which they are famous.

Other notable restaurants are Oran Mor and American Seasons which both offer wonderful, inventive food using the freshest local ingredients. Cru is a great spot for lunch with a view or a fun seafood dinner with a bustling bar scene. And if you’re in the mood for formal elegant dining, Toppers at the Wauwinet Hotel is for you.

And you simply cannot forget The Juice Bar, Nantucket’s famous ice cream shop in the center of town. The lines at night in midsummer span for blocks, but the cones are worth the wait. Go in the afternoon for a midday snack and shorter lines. We try to have at least one cone a day from the Juice Bar. I mean, it is vacation, right?

The hardest thing about going to Nantucket is knowing you have to leave. But as they say, until next summer… I better start planning now!