Sailing Mystic Hearts

Several years ago, when we first decided that cruising would become a part of our lives, we excitedly talked about all of the places that we would go, the things we would experience, and our “must-see” locations up and down the coast. I can’t recall when Nantucket made it onto the list (to be honest, it should have always been on our list), but I do remember planning to visit in 2021 during our first summer in New England. The island left quite an impression on us, and it became our favorite cruising destination up north. Will it be surpassed on our next trip up north as we explore new towns and islands? That is to be seen; I guess we will have to wait and see!

Our summer cruising perfectly aligned for us to spend over a week in Nantucket, including the 4th of July holiday weekend. We used to live in the Yorktown, VA area, not far from the site where American independence was won, so the holiday was always a special time for us as we celebrated at home with friends, family, a BBQ, and watched our neighbors shoot fireworks off over the Chesapeake Bay. While the scenery was different, Fourth of July in Nantucket was equally as incredible. We spent the afternoon on a new-to-us beach, enjoyed hamburgers and strawberry shortcake, and capped the night off on the bow watching fireworks shot from a barge off Jettie’s Beach. While we have no idea how our cruising plans will shape up for this upcoming summer, we’re hopeful we’ll find ourselves back on Nantucket to recreate these memories.

Nantucket has a fascinating history in whaling, a vibrant downtown, and some of the most beautiful beaches we’ve ever seen. We’re happy to share our favorite parts about Nantucket below and hope you’ll find yourself exploring this magical place as well!

FAVORITE ACTIVITIES

SCONSET – Take the bus from the downtown stop on Washington Street across the island to the town of Siasconset (or “Sconset” as it’s known to the locals). Sconset is a charming seaside village on the eastern coast of the island. Make sure you visit during the summer months when the hydrangeas are in bloom. They’re everywhere, and they’re beautiful. As you wind your way northeast through town, you’ll find the entrance to the bluff walk at the end of Front Street. The bluff walk has breathtaking views of the ocean and meanders through the backyards of some of the most expensive homes on the island. When you get to the end of the bluff walk, cut through to Baxter Road and keep heading north toward the Sankaty Head Lighthouse. The lighthouse, built in 1850, is iconic to the island and is worth a photo or two. Before leaving town, visit the Sconset Market (across from the bus stop) and buy some locally made products like jam. We had lunch at Claudette’s Sandwich Shop. It wasn’t anything fancy, but the price was right and it hit the spot.

BEACH DAY – We’ve visited 3 local beaches on Nantucket. The first was Madaket Beach (on the western side of the island in 2021, which is accessible by bus); Jetties Beach (we walked here from downtown; it was a bit of a walk and is definitely a tourist beach); and a beach past the Second Point (just north of the anchorage; dinghy/boat access only).

Madaket Beach wasn’t busy at all when we previously visited. It was beautiful and in a quaint, quiet side of town. Jetties Beach was the busiest beach we’ve ever been to. It wasn’t that big and everyone was crowded like sardines. We wouldn’t go back to this specific spot unless we wanted to also get lunch there at their beachside burger shack called Sandbar. The beach near the Second Point was perfect. We pulled our dinghy up on the beach and set up our chairs with no one in sight. We walked across the thin strip of land to the Nantucket Sound side and found large conch shells in the sand.

WHALING MUSEUM – We haven’t visited this museum since 2021, but it’s definitely one of our favorites. Housed in a historic candle factory from 1846, this museum gives a history of the old whaling days on Nantucket and the men who spent many years at sea in pursuit of sperm whales. If you’re history lovers like we are, you’ll find it extremely fascinating and can easily spend a whole afternoon here. If you’ve read the story “In the Heart of the Sea: The Tragedy of the Whaleship Essex” you’ll have more background heading into the museum. When you’re done exploring the museum, don’t forget to check out the views of downtown from the roof deck.

WALKING TOUR OF DOWNTOWN NANTUCKET – Here are a few recommendations we have if you’re planning to do your own walking tour through downtown: check out Main Street, complete with original cobblestones and large old whaling captain houses; the Old Mill, circa 1746 and the Old Gaol (Jail), circa 1805 are on the outskirts of downtown; the Jared Coffin House, an 1845 mansion (now hotel) that once belonged to one of the most successful ship owners from the old whaling days; the Brant Point Lighthouse, iconic in its own right and marks the entrance into the harbor; and the old wharves, now filled with shops and restaurants.

ACTIVITIES ON THE LIST FOR THE NEXT VISIT

THE LOINES OBSERVATORY – Registration in advance is required to tour the observatory and use their telescopes to see the stars, planets, and galaxies. We wish we had planned to do this on our last visit because we love science and the night sky. If you have a chance to do this, let us know how it goes!

NANTUCKET SHIPWRECK AND LIFE SAVING MUSEUM – The island bus drives right past this museum on one of its routes toward Sconset. We look forward to visiting and learning more about the shipwrecks and rescues that have taken place in the island’s waters.

SURFSIDE BEACH – So many beaches, so little time! This is another popular beach that I wish we had been able to visit. It’s located on the southern side of the island. We’ve now stepped foot on beaches on the western side of the island (Madaket), northern side (Jetties Beach and past the Second Point); and the beach in Sconset.

RESTAURANTS

THE NANTUCKET LOBSTER TRAP – This restaurant is really cozy. Solid wood on the inside and a covered patio outside, we opted to sit outside in the warm air for our feast. Paul previously had a baked stuffed lobster, and this time he enjoyed a surf ‘n turf to have the best of both. A creature of habit, I had a boiled lobster (that you have to crack yourself!) with steamed corn on the cob and potatoes. So, so good.

STUBBY’S – Another favorite stop of ours. Stubby’s makes one of the best bacon/egg/cheese biscuits we’ve had and sells a wide array of foods at affordable prices. It’s definitely one of the best deals on an otherwise expensive island.

EASY STREET CANTINA – This place pleasantly surprised us! It was brand new when we first visited and hadn’t yet been marked on Google Maps (I love rating restaurants and won’t stop at anything averaging less than 4 stars!), so we weren’t sure what to expect. We both got an affordable burrito that came with a small side salad. 

THE JUICE BAR – Our favorite ice cream spot in Nantucket, and definitely in the top 5 of our travels. Located across from the Whaling Museum by Steamboat Wharf, it’s the perfect pre or post-dinner snack with lots of fun flavors to try.

HANDLEBAR CAFE – We love their iced lattes here, and it’s extra convenient being a close walk from the dinghy dock. Random fact: We first heard of this cafe from an episode of House Hunters (or one of the other HGTV shows where people are buying a home) and the couple was looking for a home on Nantucket and planned to open this cafe. Sounds like a dream to move to Nantucket and own a coffee shop!

SHOPPING

LILLY PULITZER – A Palm Beach favorite. I love their bright colors and resort-inspired apparel. Located on S. Water Street in the main part of downtown.

VINEYARD VINES – Trendy apparel that was originally inspired by Martha’s Vineyard. They make some of my favorite classic chino shorts and comfortable t-shirts with their signature whale design on the back.

THE BLACK DOG – Created by a sailor who had a black dog, this brand is known for printing their iconic black dog on everything. 

LEMON & LINE – My favorite handcrafted nautical bracelets! I first discovered this brand while in Newport many years ago (pre-cruising life) and love their look and style.

ANNIE & THE TEES, 3 GIRLS & A DOG NANTUCKET – These two shops are connected and I believe owned by the same company, just with different names. We found our Nantucket shirts here and wear them quite often. Soft and comfortable, they are worth spending a little more for a nice, long-lasting shirt.

HELPFUL INFO FOR BOATERS

PUMP OUT – A free pump out boat will assist boaters in the anchorage and mooring field. Be sure to tip the teenagers who are often the ones running the boats!

FUEL – Located at the Nantucket Boat Basin. Hail VHF channel 9 or 11. We pulled our dinghy up alongside the fuel dock and filled up our diesel jerry cans there.

TRASH – There are dumpsters located next to the Harbor Master’s office after you leave the dinghy dock.

RESTROOMS/SHOWER FACILITIES/LAUNDRY – There are public restrooms with showers located at the Harbor Master’s office. There is no laundry room.

MOORINGS – Hail VHF channel 68 to ask about availability. Be prepared to pay close to double what you would in Annapolis. We found the anchorage to be more than adequate; there is a strong current though, so appropriate ground tackle and anchoring technique is essential.

GROCERY – There is a Stop & Shop only a few blocks from the town dinghy dock. We found almost everything here that we needed to re-provision before heading back south.