A Local's Guide to Hosting Your Own Five-Star Weekend in Nantucket

Ever wished you could gather your closest friends for one unforgettable weekend? That's exactly the idea behind Elin Hilderbrand's best-seller, The Five-Star Weekend. The novel follows Hollis Shaw as she invites one best friend from each chapter of her life to Nantucket for a weekend of beautiful meals, long conversations, unexpected revelations, and unforgettable island moments.

Whether you've read the book or simply love the idea, Nantucket is the perfect place to create your own Five-Star Weekend. With charming vacation homes, incredible restaurants, beautiful beaches, and plenty of opportunities to slow down, the island was practically made for meaningful weekends with the people you love.

The good news is that Nantucket has an endless supply of unforgettable things to do, but the bad news is that you can’t fit it all into one weekend. If your mission is to unwind and experience the island’s more relaxed side, our team has the perfect itinerary for you.

Friday: Arrive and Settle In

• Check into your William Raveis vacation rental
• Take a walk through Town and take in the sites
• Have a sunset cocktail at Galley Beach
• Host a welcome dinner at any one of Nantucket’s iconic restaurants like Cru, Straight Wharf, Company of the Cauldron or Brotherhood of Thieves.

Saturday Morning: Slow Island Mornings

There’s nothing quite like a slow Nantucket morning. The sea breeze makes the island air feel different and it’s an even better experience when you have no place in particular to be. Take the morning at your own pace, but we suggest some island ideas like:

• Visiting Lemon Press for some avocado toast or a smoked salmon bagel
• Walking Brant Point
• Shopping on Main Street
• Biking the Milestone Road path that takes you from Town to Sconset

Saturday Afternoon: Make It Feel Like Summer

As the day starts to warm up, you can choose your adventure:

• Bike to Cisco and spend the afternoon at the beach and brewery
• Sail Nantucket Harbor
• Spa afternoon
• Picnic at Surfside

Saturday Evening: Your Five-Star Dinner

While Nantucket is home to a plethora of five-star restaurants, the true meaning of a five-star dinner is the company. While you may want a night out of the house with friends, you can just as easily order in and recreate one of Hollis’ signature evenings. Just remember to set the phones aside, share a bottle of rosé, and spend the evening catching up with friends you've known for decades.

Sunday Morning

• Grab coffee and or brunch at Island Kitchen or Born and Bread
• Take a long beach walk
• Ferry home

1. A Beautiful Home Base

Choose a vacation rental where everyone can gather for morning coffee, evening cocktails, and conversations that stretch late into the night.

2. Great Food

Fresh seafood, lobster rolls, local ice cream, and dinners that linger long after dessert.

3. Time Outdoors

Whether you're biking, relaxing on the beach, sailing the harbor, or watching the sunset, some of the best moments happen outside.

4. Meaningful Conversations

Leave room in the schedule to simply sit together. The best weekends aren't rushed.

5. The Right People

Whether it's lifelong friends or family members, a Five-Star Weekend is really about reconnecting with the people who matter most.

Elin Hilderbrand's novels have inspired countless readers to fall in love with Nantucket. While the characters may be fictional, the places, scenery, and unmistakable island atmosphere are all very real. Whether you're planning a girls' getaway, celebrating a milestone birthday, or simply carving out time with lifelong friends, there's no better place to create your own Five-Star Weekend than Nantucket. Hilderbrand's books are famous for weaving real Nantucket businesses and landmarks into their stories, making it easy for readers to experience many of the same places for themselves.

The best weekends start with the right home. Browse William Raveis Nantucket vacation rentals to find everything from waterfront estates perfect for large gatherings to charming cottages just steps from Town.