A fisherman reels in his catch at Great Point.
Bookmark on the Beach was situated on none other than Jetties Beach.
The NRTA Shuttle offers services all over the island.
The front side of The Jetties opens up to the expansive and beautiful Jetties Beach.
I love ice cream.
Sammy and Mary catch up on some summer reading at the beach.
Visitors | Getting Here | Weekend | 7 Days | Kids | Facts | Shopping | Restaurants | Hotels & Inns | Services
Although Nantucket Island looks small on a map, seven days are filled rather quickly when you're visiting The Grey Lady. You know where you're sleeping and you've picked out a few favorite restaurants, but how will you fill up your days? From the fascinating history of the island to the nightlife around downtown, we have some favorites you might want to know about.
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.
Day 4: Strolling Around
The morning of your fourth day should be spent at The Downyflake, with the feel of an “average-joe” diner and the most delicious donuts to dunk in your coffee. After that you can head back downtown to Nantucket Bookworks and pick up a good beach read. This time, it’s just a short walk or shuttle ride to Jetties Beach, where you can relax and watch the boats tack around the harbor. Then grab some lunch at The Jetties restaurant, a brand new restaurant in a prime location. After lunch, take a trip back to town to check out the many galleries around town, from Main Street to Straight Wharf. We recommend The Brigham Galleries, where owner Sarah Boyce showcases some amazing works of art. Now that you’ve got the fine art experience, how about some fine dining at The Pearl. With it’s romantic yet posh and modern atmosphere, The Pearl is a sure bet when you want the best of the best in downtown fine dining.
Day 5: Enjoying Downtown Nantucket
Black Eyed Susan’s is famous on the island for their amazing breakfasts, where you can have some unique flavors thrown into your morning mix. Black Eyed Susan’s also happens to be right down the street from The Hospital Thrift Shop. The best thing about this shop is that they donate their funds to Nantucket’s Cottage Hospital, so you know you’re shopping for a good cause. Catch a bite to eat at Nantucket Gourmet while you’re downtown, and maybe pick up some Nantucket-inspired kitchen essentials while you’re at it. Your visit to Nantucket won’t be complete unless you head to The Nantucket Whaling Museum, where you’ll experience the amazing history of the island in our brand-spanking new facility. Guided tours go every day all summer long, taking you on a journey through time in the once-whaling capital of the world. Still got the ocean-itch after you leave the whaling museum? The Ropewalk will cure your craving for delights from the sea with their raw bar and full dinner menu.
Day 6: Touring the Island
With only two days left, you must go on a tour of the island with Ara’s Tours. Providing plenty of photographic opportunities, Ara’s takes you on a grand show of much of Nantucket, all the way out to Siasconset, or, as the locals call it, ‘Sconset. While you’re out there say hi to Mark Donato at The ‘Sconset Market, and tell him that Plum sent you. Grab some lunch there while you’re at it, and if you decided to stay (maybe Ara will let you catch the NRTA back,) enjoy a stroll around one of the quaintest parts of the entire island. Dinner at The Summer House is, of course, in order, especially if you enjoy a view of the Atlantic Ocean while you’re eating. (Plus the piano playing in the background doesn’t hurt either.)
Day 7: Completing Your Trip
Your last day of your stay on Nantucket should be spent taking it all in for one last time. Enjoy the scenery and market out at the weekly Farmers & Artisans Market that occurs all summer long. Pick up a few local crafts and goodies while you’re there. Lunch at Tacos Tacos is always quick, easy and delish, so go on downtown and grab a genuine Nantucket burrito that you can enjoy on their outdoor patio. A final farewell for the week should be spent at Madaket Beach, where the sunsets are unbeatable and the drive is gorgeous. Located on the western-most part of the island, Madaket is best-known for the picturesque dusk for visitors. After the sun has set, it’s time to enjoy your last evening on Nantucket, and we recommend kicking it off at Cinco, a tapas bar with a most eclectic and unique dining environment, plus a menu to match. Michael Sturgis, owner of Cinco, teams up with Chef Jean Luc on a nightly basis to bring their guests exquisite cuisine and drinks.
If you don’t have to catch the early ferry the next morning, it’s time to enjoy the nightlife one last time. For this, we recommend The Gazebo, where you can sip on a fabulous Banana Daquiri in the company of many others. Take a walk down the docks again at Straight Wharf, all of the boats lit up at night are quite a sight.
We hope you enjoy your week on Nantucket, be sure to check out our “How to get around” guide when you need to make travel and transportation arrangements getting to and around Nantucket. Bon voyage and we hope to see you soon!
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