![Nantucket Island Nantucket Island](https://media.timeout.com/images/105800891/750/562/image.jpg)
1. Nantucket Island
Nantucket is the place to be in the summer.
Eat at: or, The Whale (38 Main St, 508-825-5897) located right on the cobblestoned main street in downtown Nantucket, if the weather is still nice you can enjoy eating on or The Whale’s back patio.
Stay at: Hotel Pippa (5 Chestnut St, 508-228-5300) at the contemporary boutique hotel, guests can enjoy complimentary breakfast before setting out for the day. The team at Hotel Pippa is happy to assist guest booking a variety of island activities from fishing expeditions to cooking classes. When the day is done, guests can unwind on Hotel Pippa’s cozy patio.
Must do: Visit in early October and travelers can enjoy a brand-new fall festival, The Harvest Fair (220 Milestone Rd) which will take place October 1-2. Historically the Island Fair and the Cranberry Festival happened on separate weekends but 2022 will be the first year the events merge for one large festival.