Evenings in Nantucket are beautiful, with the restaurants and bar being very lovely. This is the time to dress very well and use your best clothes in the closet, such as nice dresses, wedges, boat shoes, pretty purse, and jewelry. Men should be chinos, button-downs, loafers, and belts. If possible, try and wear the classic “Nantucket Reds”.
Biking – Since Nantucket is very small, most people coming for a vacation will not bring a car and will bike everywhere. You can either be a serious biker exploring the islands or have it be your mode of transportation. For this a sundress with exercise shorts or bathing suits under neither is perfect or shorts, polo shirts, comfortable shoes, and backpack are essential.
Beach – The beaches in Nantucket are breathtaking so be sure to go to one of the many when planning your trip. Swimsuits, cover-ups, flipflops, sunglasses, and sun hats are pretty self-explanatory but definitely bring a beach bag too. Fill the beach bag with a beach blanket, sunscreen, towels, snacks, drinks, and anything to make the beach day more enjoyable and relaxing.
Shopping – The main town will have you feeling like you stepped back in time with the cobblestone streets and old buildings. It boasts lovely shops, exquisite art galleries, and quirky gift shops. Stylish but casual clothing is best, allowing you to dress down a bit with shorts, t-shirts and sandals or flipflops. This is the time to buy some souvenirs or Nantucket inspired clothes to remember your vacation.