The best kind of friend is a friend who has a house in Nantucket. That isn’t actually great friendship wisdom, but it does happen to ring true on both accounts for me. I have had the privilege of visiting my friend Lauren and her family for years now on the island. Each time that I arrive surrounded by beautiful hydrangeas in that special salty air, I fall in love all over again.

Many of you have asked me to give my favorite Nantucket recommendations, but I have always hesitated since Lauren is the true islander expert. Today, I have had her share her favorites with us all. Thank you, Lauren for this beautiful guide!

by Lauren Holden:

I’ve been going to Nantucket for as long as I could remember. Each time going, no matter the season, the island still enchants me as if it’s my first trip.

If you ever get the chance to go to Nantucket, run don’t walk. It’s unlike any other place, no matter how many shingle sided homes you may see. Nantucket is truly unique with something to offer for everyone.


Nantucket is no easy place to get to: plane, car, boat—I have done just about it all. Thankfully, in recent years, major airlines have added a few flights from the New York, Boston and DC area during the summer. However in the winter, you are pretty much just left to Cape Air—a staple to Nantucketeers. Christina made it on one of these 8-seater planes, and said that was enough for her. So for many years we took the ferry from Hyannis. There are two options: the Steamship Authority or Hy-Line. Both are just the same, it just depends on your schedule. A fast ferry is a 60 minute trip, or the slow 2 hour ferry brings the cars over. Reservations are needed for the fast ferry or to bring your car on the slow ferry.


While I have been fortunate enough to have family on the island and keep the house full with seasonal guests, I have always tried to keep abreast of accommodations on the island. If I were looking for a romantic getaway, I would suggest the Wauwinet. It’s a beautiful, quaint, Relais & Chateau property on the bay. However, you are removed from town and restaurants (about a 20 minute drive). Even if it’s for a lunch visit, the Wauwinet is a fun destination. I insist on starting each visit there with a Painkiller, a cocktail you will not regret.

For families, the White Elephant (a sister hotel of the Wauwinet) boasts many property options and everything is walkable to town. Aside from these hotels, there are always new B&Bs popping up. Some have been in town forever like Union Street Inn and the Brass Lantern, and some are fresh on the island like the Faraway and Life House.

If I were going with a group of friends, I would without a doubt rent a house. Most real estate companies specialize in home rentals. And each part of the island offers something completely different. Town is a great area to walk to especially for dinner, Madaket has the best sunsets on this side of the Mississippi, Sconset is the most charming little sailors village on the east side of the island, and there are many many more options in between.


Once settled, the first move is to the beach. Unlike the Hamptons, pools are not as common in Nantucket because the beaches are too good to be true. Ask five different people what their favorite beach is, and you’ll get five different answers.

Steps beach—just off of Lincoln Circle, is a short drive from town and offers very calm water and beautiful views of the homes on Cliff Rd. Cisco is one of the best beaches to catch surfers.  Jetties is great for children and just steps from town. Pocomo has very shallow bay waters and Nobadeer is perfect for a social beach day. Theres many more beaches, and some allow vehicle permits in certain areas. Just a few have snack shops, lifeguards and bathroom facilities. Seals frequently pop their heads up along shore so keep an eye out for a friendly face looking back.


If you come to Nantucket on a diet, you’ve come to the wrong place. The restaurants are too wonderful. The island does suffer from temporary waitstaff that changes over year after year so some meals are better than others, but the food is always a star. It is no kept secret that Cru has one of the most amazing lobster rolls. It is always packed, sometimes a bit overpacked, but the lobster rolls and buttered brioche are worth a push and shove. Black Eyed Susans is one of my favorite breakfast spots. This small restaurant doesn’t take reservations and was cash only pre-COVID (tbd if that’s still the case). While the Galley doesn’t shy away from the $20 cocktail, it’s well worth it for the sunsets. Everyone flocks to this see-and-be-seen hangout right before sunset. Company of the Cauldron, a long time staple on Nantucket, has a nightly changing menu and spins the most simple of dishes into the divine. Another favorite, that takes some persistence in the reservation department, is Nautilus; what started here as a delicious fusion restaurant now expanded to Boston. COVID did bring a welcome addition of expanded outdoor dining to most of the restaurants in town. One of the most special nights are the nights spent in, picking up lobster dinners from Nantucket’s many fish shops (I tend to fancy Nantucket Seafood but they are all great).

For lunches, there isn’t a year that goes by without stopping at Provisions sandwiches by the gazebo; they’re famed for their ‘Turkey Terrific’ in case you cannot wait until Thanksgiving to have your stuffing and cranberry fix. I also love Lola Burger near the rotary; Their burgers and truffle fries scream summer to me. Finally, 167 Raw near Bartlett Farms is my favorite food truck and seafood market. Their fish tacos are my regular order, and is the perfect stop to eat on a picnic table and carry-on towards the beach. The list can truly go on and on. A crowd is usually a sign of a good restaurant in Nantucket, especially when it comes to ice cream—in which case, the Juice Bar is the only acceptable answer.

this is Christina here…167 Raw the fish tacos are AMAZING (like best ever) and the best tuna tartare you will ever have…At The Juice Bar you must get the green monster flavor (mint chocolate chip cookie dough)


With the charm of Nantucket always comes the unexpected (albeit anticipated) rainy or foggy day. Most people flock to shop in town on these days. I would always recommend exploring so many of Nantucket’s amazing walking trails. Thousands of acres are protected by the Nantucket Land Bank and the preservation efforts allow the beauty of the island to be shared by everyone. I am also very partial to a historical walking tour at the Nantucket Whaling Museum. There are daily tours throughout town and in adjacent historical sites. As beautiful as the island is, it is incomparable to the history of the island. Christina has fallen victim to my many fun facts as we drive around, but there is a fascinating story behind this little sandbar. A trip to Sconset is not complete without the ‘worst kept secret’ of the Nantucket Bluff Walk—a short walk along the bluffs of Sconset behind some of the most amazing oceanfront homes. A bike is one of the best ways to get around; there are great biking trails from end to end of the island and if you need a little more vroom, most bike shops will rent mopeds.

when to go:

While I definitely am drawn to the magnetic pull of summer on Nantucket, the island is really perfect at so many other times of year. The water and air stay fairly warm until mid-September, and then in October, Nantucket typically prepares for it’s annual Cranberry Festival—a fun, family friendly ode to the cranberry. Thanksgiving brings regulars for the annual ‘Turkey Plunge’ where the brave (or foolish) jump into the harbor for a Thanksgiving morning dip. And the first weekend in December brings a shocking large number to the island for ‘Christmas Stroll;’ stores and restaurants are open for one of the last tourist weekends of the year. In the spring, the season kicks off in April with Daffodil Festival and shortly thereafter on Memorial Day is Figawi, an annual boat race. COVID unfortunately took a toll on most of these events through this year, but hopefully 2022 will bring them back.

Whatever reason brings you to Nantucket, I have no doubt you will fall in love with the island. The hardest part is getting there once, and then just waiting until you get to go back.

-Lauren Holden

Types of Homes you will see on the Sconset Bluff Walk

If you go to Madaket, Millie’s is a must! Millie was friends with Mr. Rogers…

Window boxes and perfect ivy

Mudslides at the Gazebo. Lively, fun, and decadent!

View on take off of Nantucket. The beach with the cars is my least favorite…

Sunset at Galley with a Lilet on ice with a twist of orange. Lauren taught me that drink order and wishes I would keep it a secret 🙂

the flowers are incredible on Nantucket in the summer

Pre Covid, the Fourth of July was always a blast. Everyone gathers downtown and the firetrucks soak everyone! The little kids do too with squirt guns. Lauren is such a good friend, she didn’t tell me this happened…I got drenched and she has never laughed so hard. A fabulous event for families. Until I have kids, I will be at Cru sipping on Rosè. 

Company of the Cauldron is a fixed menu each night. This was some of the best fried chicken I have ever had!

Oh the hydrangeas…Nantucket is so beautiful!