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Insider’s Guide to a Perfect Nantucket Weekend

The Donelans love the sea. Whether it’s the Pacific Ocean’s cooling influence that’s ideal for growing fine wine or New England’s bracing Atlantic breezes and vibrant maritime culture, you’ll find the family on both coasts throughout the year.

Aside from Sonoma, Nantucket is the Donelans’ hub. At first, it was their oasis during summers and holidays, but after 40 years it’s become their home. They’ve found a special spot in the island’s community, supporting local businesses and philanthropies, protecting the history and environment, and participating in events like the annual Nantucket Wine Fest. The island has always been an iconic place in America and a hot summer vacation spot. If you’re planning a trip soon, here’s a list of what to see and do during a weekend in Nantucket with a mix of stops for first-time visitors and local favorites.

Friday

First Stop in Nantucket

No visit to Nantucket would be complete without a visit to Cru Oyster Bar. For many, it’s the first quick stop off the ferry because it’s the perfect Nantucket hello. Belly up to the bar or grab a daytime table and order a dozen of the best oysters you’ll ever eat (their oyster menu changes daily with an impressive selection of at least 8). And don’t forget the requisite order of CRU French fries and a glass of bubbly or Donelan Nancie Chardonnay. Combine this decadence with your view of the yachts in the harbor and you’ll be pinching yourself. Yep, it’s real. And this is just the first stop.

Explore the Island

Once you’ve settled into your lodging and enjoyed a CRU “hello”, spend the rest of the day learning the island — all 14 miles of it! There are several driving tours you can arrange; public transportation via “The Wave” electric bus, taxis, Ubers, and bike rentals make learning your way around the island a breeze. If you’ve rented a Jeep, you’ll have the best access to more remote locations and even be able to drive on some beaches. This is a great time to stock up on provisions, grab a book at the Nantucket Bookworks, and depending on your schedule, hit the beach.

Watch the Sunset

Sunsets are special on Nantucket, and most people plan their days according to the weather forecast and the likelihood of a magical one. You can enjoy great sunsets from many locations, but not from town. This is when we suggest booking a table at the Galley Beach Restaurant. Located directly on the water, this is the première spot on the island for a romantic evening. Everything about Galley Beach is classy—from its beautifully crafted cocktails to its carefully curated menu, and its killer wine list. This is THE island location for snapping that classic sunset photo with a fancy glass in your hand.

Wrap Up Your Evening

As you make your way home from dinner, you’ll notice the streetlights are dimmed. That’s thanks to Nantucket’s dark sky movement. Stargazing on Nantucket is incredible when the skies accommodate. Make your way home using apps like “Moon Plus” and “SkyView” and be sure to look up. You’ll be rewarded with the constellations that brought the early settlers here.

Saturday

Breakfast and Sconset

Confident you’ve slept like a baby thanks to that ocean breeze, you’ll be up and out early. Grab a coffee from the Handlebar Café or a smoothie from Lemon Press and head out of town toward ‘Sconset. Getting there early in the day will minimize other tourists and the associated challenges.

Once in Sconset, head toward the Sconset Market where you can park nearby to start your town tour. Early settlers with enough money to do so had their homes in ‘Sconset to avoid the smell of the town’s whale oil factories. They traveled by a special gauge train between the two towns, and its last remaining car is now part of the famous Club Car bar in town. Today, those historic cottages remain, and they are among the most photographed of all Nantucket. If you’re fortunate enough to visit Nantucket at the height of Rose Season, you’ll find yourself wandering street after street wanting more.

While there, make your way to the ‘Sconset Bluff Walk – a public walk through the yards of private properties where you can enjoy scenic views of the ocean and the beauty of private gardens. The walk is about a mile out, not guided, so you can just stroll and enjoy. No trip to ‘Sconset is complete without the classic photo in front of the Sankaty Lighthouse. Just a quick drive from town, you can park there and enjoy the 7-acre property steeped in history.

Lunch and the Beach

By now you’re getting hungry, so either make your way back to ‘Sconset and grab a “sammie” somewhere, or head back towards town and stop at Millie’s newest location at the mid-island rotary. Millie’s is an iconic Nantucket destination at the western end of the island and in 2024 opened “Millie’s Mid-Island at the Rotary” at 1 Sparks Ave. Same great food but accommodates those on tighter schedules.

And now, let’s head to the beach! Grab Nantucket’s Elin Hildebrandt’s latest novel and some sunscreen. Nantucket has 82 miles of coastline and beaches to meet everyone’s greatest desires. South shore beaches are for those who love the surf and north shore beaches tend to be calmer because they are toward the harbor/sound side of the island. Some favorites are Miacomet and Fisherman’s for the south, and Steps and Jetties for the north. Not all beaches have lifeguards or facilities. Choose your beach based on your personal needs.

If you’re not a beachgoer, or if Cisco Beach was your chosen destination, pop into the Cisco Brewers for a post-sun cool down. Located 5 minutes from the beach, the brewery is a happy and family-friendly spot to enjoy live music, food truck snacks, freshly shucked oysters and of course, a taste of the local brew. Check their website to see what’s playing.

If you’re still craving a beautiful sunset, consider a sunset sail on the Endeavor – a 1.5-hour sail that takes you into the harbor or Nantucket sound to get yet another perfect view of the sunset. Captain Jim has done this sail for so many years that he’s a wealth of knowledge of both land and sea. It’s a great group activity and you’re welcome to bring your own refreshments. 

Dinner in Nantucket

For Saturday dinner, we have two great recommendations depending on your mood. Both send you back to town, because visiting Nantucket’s town is just too much fun.

For a quieter and more romantic evening, opt for Greydon House’s cozy restaurant Via Mare. The bar seating is great and the outdoor porch is lovely this time of year. The small plate-style menu is creative and incredibly fresh and the mood is happy, classy casual. For many, it’s their favorite destination.

For a more contemporary get-with-the-beat vibe, look to Lola 41. Popular enough to have opened more locations in Palm Beach and Naples, FL as well as the Boston Seaport, this is the original and one visit will show you why Lola is Nantucket proud. Lola stands for Longitude Latitude and 41 represents the specific parallel on which Nantucket’s Lola resides. The bar is lively and busy, where both cocktails and sushi rolls are made in view. The menu has something for everyone, from their famous Lola burger to fine entrées, and the wine list is fabulous.

If you’re not ready to call it a night…stroll around town. You might find street musicians or just enjoy the window box-lined streets. A stop at SisterShip’s patio is a perfect nightcap or for one last cocktail, decadent desserts, or coffee.

Sunday

Breakfast and Shopping

Sunday is for shopping and strolling the idyllic cobblestone streets. But before you hit the stores, consider either a guided or self-guided morning walking tour. Several organizations in Nantucket offer walking tours that start at different times. These tours are amazing and not to be missed. Some are for gardens, others for architecture, and others for island history. You go places you’d normally never go, and whatever tour you choose will result in one of your favorite memories of the weekend.

For a grab-n-go breakfast, visit Born and Bread with all its fresh baked goods and sandwiches. For a more leisurely sit-down breakfast, both Black-Eyed Susans or Lemon Press are favorites, and both often mean waiting in line.

 

There are so many shopping options. Browse the windows and see what entices you. Current Vintage has an eclectic mix of goods from vintage to new, including clothing, gifts, accessories, wine, and cheese! Once your shopping bags are full, and if you can squeeze in another bite of food, hit Walter’s for their “best value on the island” lobster roll (as rated by the Nantucket Lobster Roll Index) or find a seat at the bar at Brotherhood of Thieves for a “cuppa chowda” at this iconic destination. 

As your weekend hours dwindle and you make your way down the docks to the boat that’ll take you back to ‘Merica, remember… there’s always the next ferry.

Wine in Nantucket

You can’t go wrong with any of Nantucket’s restaurants and their wine lists will not disappoint. If you’re looking for a glass of award-winning wine with Nantucket family roots, look for Donelan on the menu. We love our community and are proud to be served at the following restaurants across Nantucket: 

• Lola 41
• Le Languedoc
• The Pearl
• Galley Beach Restaurant
• Sea Grille
• CRU
• Nautilus
• Straight Wharf
• Ventuno
• Via Mare