While you could spend weeks here and still feel there’s more to see and do, we will outline a five-day plan (or check out our 3-day itinerary if you are tight on time!) of activities and attractions for you to consider. Since your vacation time is precious, this itinerary can help to ensure that you will experience the best of what Nantucket has to offer. Keep in mind, Nantucket is a relatively small Island, about 15 miles by 4 miles, with an extensive bike path system, and our town is perfect for walking, so you don’t need to bring your car.
A Five-Day Nantucket Itinerary
Day One
Once you arrive on Island and get settled in, you’ll no doubt want to wander back out and begin to explore the historic village of Nantucket. If this is your first visit, a tour of the entire Island is highly recommended, and we will be happy to make those arrangements for you upon arrival.
A tour guide will pick you up at the inn, and the tour will last about an hour and a half for $35 per person. We will also suggest and recommend some of our favorite places to dine. There are many wonderful restaurants just a short walk from the inn. It’s a good idea to make dinner reservations for weekend nights in high season before you arrive on the Island. The town is best appreciated by simply walking around and getting a sense for the beauty and charm of the village, which includes many historic homes, shops, cobblestone streets and harbor views. The Visitor Service center on Federal Street is a good first stop. They offer a wide variety of maps, brochures and other information about Nantucket.
Day Two
After a delicious breakfast and good conversation with new friends, rent bicycles at Cook’s or Youngs bike shop, which is just around the corner and plan a day trip to the beautiful east-end village of Siasconset. The best way to go is via the new Polpis road bike path, which offers scenic views of the central moorlands and cranberry bogs. Stop by the Nantucket Shipwreck & Lifesaving Museum and take a photo of the adjacent marshlands, harbor and wildlife. Take a detour into the moorlands and visit Altar Rock, the highest point on the Island. Continue on to the village of Sconset, have lunch and take a walk around this lovely town. Relax on the beach. Look at the “real” oldest house on the Island: Auld Lang Syne. Detour up to the Sankaty lighthouse and take in a breathtaking view of the Atlantic Ocean from the bluff. Return to Nantucket town via milestone road. After the bike ride or after dinner, enjoy a drink on our lovely garden patio or from our deck with views of Nantucket harbor.
Day Three
Beach Day! Take those bikes, towels, lotion, and a good book and head out to Surfside beach on the Surfside bike path or walk to Jetties beach. These beaches also have regular beach shuttle service in season. Consider either packing up a lunch or eating at the snack bar there. Surfside and Jetties have facilities, as do other Island beaches. Other activities to consider for the day include, whale watching or seal cruise, charter fishing, a charter sail or take a walk through the Sanford Farm Wildlife preserve down to the ocean.
Another adventure is to rent a four-wheel drive vehicle and head out towards the Great Point lighthouse through the Coskata Wildlife Refuge at the northern tip of the Island. Bring along lunch and a surfcasting rod and try catching some bluefish or striped bass! Even if you don’t catch any fish, visit Nantucket’s own microbrewery, Cisco Brewers and Nantucket Vineyard for some tastings and afternoon entertainment.
Day Four
Take a walking tour of Nantucket with the Nantucket Historical Association and learn about Nantucket at a slower pace. Go to a whaling lecture and tour through the Whaling museum. Pick up lunch at Something Natural or Provisions and then walk up Main Street towards the Windmill. Visit the other properties of the Historic Association including the Old Gaol and the Jethro Coffin house.
Day Five
Peruse the shops and make those purchases you’ve been contemplating since day one. Be sure to check out the Nantucket Lightship baskets, scrimshaw, and artwork, which are produced by local artisans and are unique to Nantucket. Consider buying some Nantucket “reds” (pants) or an “ACK” hat to remind you of your Nantucket stay. If you’re taking the ferry back to Hyannis, it’s a tradition to toss a penny over the rail as you round Brant Point to ensure your return to our enchanted Isle.
