Nantucket is not the place to go if your taste in nightlife is extravagant, loud and likely to run through until well past dawn. However, having said that, Nantucket does have nightlife with a number of bars and clubs open until quite late, offering a range of choices for eating, drinking, dancing, listening to music, being entertained and generally socialising. Generally nightlife in Nantucket draws to a close at 1am, but during the summer seasons there is usually a wide choice of music venues with live acts, particularly at the Chicken Box which is well known for hosting a large number of excellent bands. There are several theatres which provide a range of films during the afternoons and evenings too.

The peak season for Nantucket is the summer, which is when its population increases by at least twenty percent. It is through the summer months that a wide range of concerts and performances are available, with special festivals, events and exhibitions available. Music plays a significant part on the island, with the Chicken Box hosting music acts since the forties. Children will enjoy the performances that take place on the bandstand by the Children’s Beach, and this can become quite an event, with people bringing blankets and picnics and settling down for quite a stay. The Boston Pops Esplanade Orchestra also put in an appearance during the summer at an annual event held at Jettie’s Beach.

As well as live music, there are a range of lectures, talks and exhibitions on a wide range of subjects, from the history of Nantucket to a variety of arts and science subjects – almost certainly providing interesting opportunities for everyone.

But the entertainment at Nantucket is not limited to the town, or the shores, but even out at sea there is entertainment to be had, in the form of regattas. With so many boats, yachts and vessels of all shapes and sizes, there are regular extravagant regattas with flags fluttering and races to watch. These races become huge spectator events, and are well worth watching. Some of these events are simply for fun, but many are very great tests of sailing expertise, and can involve experienced sailors and novices, testing skills to the limit. There are some races which take an entire weekend, sailing to Nantucket from Hyannis, whilst others are shorter, faster events.