Nantucket, Massachusetts

Nantucket is a special island, rich in history. Over the last twenty years, we have spent much of our time on Nantucket exploring the island. There is so much to share of this special gem of a whaling town that we will have more than one blog post about Nantucket but let’s start here…

The Last Mango at Brant Point in Nantucket, MA
The Last Mango at Brant Point in Nantucket, MA

Nantucket is known for its cobblestone streets, amazing dining, beautiful bed and breakfasts and its picturesque beaches filled with stunning wildlife. It is said that Nantucket takes its name from a Wampanoag word and although the meaning of the term is uncertain, it may have meant “far away island”. If you have been to Nantucket, you will feel as if you are on a far away island of a whaling town that makes you feel right at home. If you have not been to Nantucket, now is your polite nudge to plan to experience this island…you will not regret it!

Let’s dive right in…

What better way to start the Nantucket conversation with none other than our favorite food stops. Nantucket has an awesome food scene full of superb seafood! If you are not a seafood person, there are plenty of other alternatives. The island has some of the best pizza, sandwiches, salads, burgers, chicken and steak we have ever had.

During our most recent stay in Nantucket, we enjoyed a delicious meal with who other than Hank Holliday (check out our Charleston blog for more about Hank)! Hank generously treated us to a wonderful meal at Sayle’s Seafood, which was new to us but it will definitely not be the last time we attend. Sayle’s Seafood is your one stop for a complete Nantucket fish market. Sayle’s offers a variety of fresh seafood to take home for your cooking and/or you can dine in with their ready-to-eat seafood. This seafood market provides much of their seafood to local Nantucket restaurants. When you walk in to Sayle’s, you are greeted with beautiful smiles and a warm welcome from their friendly staff. Our lunch crew opted for Sayle’s Nantucket Clam Chowder, Fried Fish (Cod) with lemon & cocktail sauce and Honey Fried Chicken. We would describe the food as delicious and the company was even better. If you would like to try Sayle’s Seafood from the comfort of your own home, they offer the option to ship their Nantucket Bay Scallops, Live Nantucket Lobsters and Sayle’s Housemade Nantucket Clam Chowder, overnight, to you. It will not be our last trip to Sayle’s and next time, we will treat Hank!

Sayle's Seafood
Sayle's Seafood
Sayle's Seafood Housemade Nantucket Clam Chowder and Honey Fried Chicken
Sayle's Seafood Housemade Nantucket Clam Chowder and Honey Fried Chicken

Another one of our favorite food stops, which is near and dear to our hearts, is The Brotherhood of Thieves. Managed by our dear friend and Mr. B’s dear friend, Jonas Baker, The Brotherhood is a family-friendly restaurant featuring hearty eats, craft beers, an outdoor patio and a cozy fireplace in the dungeon. The Brotherhood of Thieves received its name from the title of a pamphlet written in 1843 on Nantucket by Stephen S. Foster. Foster strongly attacked those who supported slavery. In 2021, The Brotherhood and the entire property was given new life and was recreated to be the best it ever was (thank you, Jonas!). If you have any picky eaters in your group, this is your spot on the island. The Brotherhood has a full sushi menu as well as delectable salads, burgers and sandwiches. Anything you choose at The Brotherhood will be a winner.

The Brotherhood of Thieves
The Brotherhood of Thieves

Downtown Nantucket’s storefronts are unique with most businesses displaying quarterboards. A quarterboard is a long, narrow, ornate sign that was originally placed on the stern and bow of ships, and is now often displayed on houses and businesses. Some of our favorite Nantucket finds are located at Four Winds Gifts Inc. This gift shop is the oldest gift shop on the island. This cute shop has all kinds of unique Nantucket souvenirs and gifts from housewares to clothes. It is your one stop shop on the island and if you cannot make it in the store, you can shop online.

Four Winds Gifts
Four Winds Gifts

Whether you are a kid or you’re growing older but not up, you must stop at TownPool! TownPool has all of your fun shopping needs customized to the island of Nantucket. From custom Nantucket pajamas, to neon art to creative socks; you will have an absolute blast shopping here. If you are twelve (12) and younger, you will be asked if you would like to join in on the scavenger hunt when you enter the store with a postcard and a crayon. As for the end of the scavenger hunt, we do not want to give the surprise away but trust us, you do not want to miss it! If you are unable to make it into the store, you can shop online and their items make the perfect gifts for your friends, family, co-workers and yourself!

Some of our favorite things to search for in Nantucket is where we will stay. There are so many options of bed and breakfasts and inns with many of them having so much history within their walls.

One of our top favorites bed and breakfasts is 29 India House also known as the Albert Wood house. In 1795, Benjamin Swift built 29 India House. This house boasts the timeless Nantucket style in which the whaling captain Albert Wood resided in. On March 4th, 1849, Capt. Albert Wood escaped the jaws of a sperm whale in the Pacific (does Moby Dick ring a bell?!). Four generations have paved the way and now Capt. Albert Wood’s home is open to visitors for this charming bed and breakfast. If you book a room at 29 India Street, let Forrest and Giuseppe know that Capt. Vinnie LaSorsa recommended you stay there!

Another bed and breakfast that we thoroughly enjoyed our time in is the Brass Lantern Inn. The Brass Lantern Inn is a classic setting while delivering traditional Nantucket hospitality. It is located in the Old Historic District on cobblestone North Water Street. In 1846, the Great Fire destroyed the Main Inn at the Brass Lantern Inn. In 1847, a wealthy owner rebuilt the Brass Lantern Inn and it has been a bed and breakfast since. The Brass Lantern in provides seventeen (17) renovated rooms with very comforting and welcoming décor. The inn offers a continental breakfast that is absolutely tasty with homemade granola and yogurt, freshly baked pastries and delectable fruit platters. We would highly recommend attending one of their afternoon teas with their freshly baked out of the oven cookies…ok, ok…we do not recommend attending, we demand you attend it!

We will have much more to come on the more of the best places to dine, play and stay in Nantucket! Until then, if you take a trip to the island; we hope you have a whale of a time!

-Written by Sarah LaSorsa