Day 1: Rest & Relaxation

Now that you're settled in, your first day, weather permitting, needs to be your wind-down from traveling. What better way to do that than the beach? Our favorite beach is Surfside, where you can grab a bite to eat right before you stroll on down to the water. Plus, there's plenty of parking, shuttle-service every 1/2 hour on the Nantucket Regional Transit Authority Shuttles (NRTA), and a bike path if you're two-wheeling it.

When you're done baking in the sun, go home, shower up, and head downtown for a fantastic meal at The Even Keel Cafe. After dinner why don’t you catch a sunset cruise on The Endeavor. When you get back onto dry land, grab the famous Juice Bar ice cream. Tell Manager Matt that the folks from Plum say hi, and make sure you try their waffle cones.

Day 2: Shop Till You Drop

Day number two is all about heading downtown for some shopping. Nantucket’s shops are unique to the island, and the many of the goods you get here you won’t be able to find anywhere else. From the leatherware at Craftmasters of Nantucket to the t-shirts at Island Pursuit, you’re bound to find something you love and perhaps want to share with friends and family back at home. Ready for lunch? Pop on into Provisions down on Straight Wharf for their world-famous Turkey Terrific, a bag of Cape Cod Potato Chips and a Nantucket Nectars. Then head on down for a stroll around the docks where all of the enormous boats pull in.

Now that you’ve done a lot of walking, have a seat for dinner and a movie at The Starlight Cafe & Theater. Movie tickets at the island's only movie theater can be reserved with dinner reservations, so book that one early in the day. It’s a pretty small theater with only one screen, so it sometimes sells out fast depending on what's playing.

Day 3: Beach & Brew

Your third day on Nantucket should be another beach day. For a more surfer-esque beach, try Cisco Beach so that after a long hot day at the beach you can head to the brewery. Nantucket’s only local brewery, Cisco Brewery and Triple 8 Distillery, are a must-do when you’re in the mood for some local spirits to taste test. After that, it’s time to hit up The Chicken Box for some musical talent. The Chicken Box brings the noise to the island all year long with some of coolest independent bands and artists, including the popular bands Cowboy Mouth and U2 cover band Joshua Tree.