Make the Most of Your Time on Nantucket
You could spend weeks on Nantucket and still find something new to love. But if you have only five days, this itinerary will help you experience the very best of the island at an easy, enjoyable pace. If your trip is shorter, be sure to check out our 3-Day Nantucket Itinerary as well.
Nantucket is wonderfully compact. It’s about 15 miles long and 4 miles wide, with miles of bike paths and a walkable historic town. Most guests find they don’t need a car, making it easy to relax and explore.
Day One: Arrival & Historic Nantucket Town
Once you arrive and settle in, ease into island life with a stroll through historic downtown Nantucket. Cobblestone streets, preserved whaling-era homes, waterfront views, and charming shops make this the perfect introduction to the island.
For first-time visitors, a guided island tour is a wonderful way to get oriented. Tours typically include stops at key landmarks and scenic viewpoints, and we’re always happy to help arrange one.
In the evening, enjoy dinner at one of the many excellent restaurants within walking distance of our Inn. During peak season, we recommend making reservations in advance, and we’re glad to share our personal favorites.
Day Two: Biking to ’Sconset & East-End Adventures
After breakfast, rent bicycles from a nearby local shop and head out along the Polpis Road bike path toward the charming village of Siasconset (‘Sconset). The ride offers beautiful views of moorlands, cranberry bogs, and open sky.
Along the way, consider stopping at the Nantucket Shipwreck & Life-Saving Museum, then continue on to ’Sconset for lunch, beach time, and a walk through this postcard-perfect village. Don’t miss the Sankaty Head Lighthouse, where sweeping ocean views make for unforgettable photos.
Return to town via Milestone Road, and unwind in the evening back at the inn, perhaps with a drink on the garden patio or harbor-view deck.
Day Three: Beach Day & Island Adventures
Today is all about the beach. Walk to Jetties Beach for a relaxed, close-to-town experience, or bike out to Surfside Beach for rolling waves and wide open sand. Both offer facilities and seasonal snack options.
If you’re feeling adventurous, other popular options include whale-watching or seal cruises, and charter sailing or fishing. If you love nature, you’d enjoy a walk through Sanford Farm Wildlife Preserve to the ocean.
Later in the day, many guests enjoy a visit to Cisco Brewers, Nantucket Vineyard, and the distillery — a lively spot with tastings, music, and food trucks.
Day Four: History, Culture & Museums
Slow things down with a deeper dive into Nantucket’s history. A walking tour with the Nantucket Historical Association brings the island’s whaling past and preservation story to life.
Spend time at the Whaling Museum, then explore additional historic sites such as the Old Gaol, Jethro Coffin House (seasonal hours), and nearby windmills. Grab lunch from a local favorite and enjoy it picnic-style as you explore.
Day Five: Shopping & Farewell Traditions
Use your final day to browse Nantucket’s unique shops and galleries. Look for handwoven Nantucket Lightship baskets, scrimshaw, artwork, and locally made goods — perfect souvenirs or gifts.
Before departing, many visitors take part in a beloved tradition: if you’re leaving by ferry, toss a penny into the harbor as you pass Brant Point Lighthouse — a wish to ensure your return to this special island.
