Three Perfect Days in Nantucket

Miles of sandy beaches, rolling dunes, historic lighthouses, and uniquely New England seaside charm sound like a good break from the hustle and bustle of every day life?  If so, Nantucket is the perfect getaway for you! A special and beautiful place to relax just off the coast of Cape Cod, this island paradise is an easy and quick escape from the Boston area.

A large conservation and preservation effort in Nantucket allows visitors to experience the unique mix of this islands’s modern nautical elegance alongside its feeling of stepping off into the charming village streets of a 19th Century whaling hub frozen in time.

There are festivals to be enjoyed on the island all year long including the Christmas Stroll, Daffodil Festival, Cranberry Festival, Nantucket Wine festival and more. There is something special about Nantucket in every season here. Weathered gray shingled buildings, cobblestone streets, historic sea captain’s homes, inns, and salt air are hallmarks of the Nantucket Town experience but there is so much here to explore new and old – even if you have visited this island many times before there is always something new to fall in love with here.



The Veranda House Inn 
Staying in a quaint bed and breakfast inn in Nantucket Town is an absolute must to live out the idyllic island experience while you are here. Sitting on an elevated vantage point in the heart of Nantucket Town, the Veranda House Inn not only offers harbor views and a convenient town location but is a perfect blend of the modern and historic just like the island of Nantucket itself. The history of this inn dates back nearly two centuries but the décor is fresh and contemporary. There are 18 guest rooms with some offering personal verandas along with those perfect harbor views. There are lots of modern amenities and conveniences but still the charm of an old bed and breakfast. The daily three-course gourmet continental breakfast (which is served out in their lovely patio in nicer weather) is included in your stay as well as a complimentary cookies and wine offering in the afternoon. There are beach chairs and umbrellas available for guests to take to the beach with them as well. A perfect location to start off your adventures – just walk right out and wander to the harbor side beaches or through the many shops, restaurants, and inns of old Nantucket Town.

3 Steps Lane
Nantucket, MA 02554

Photo Credit: The Veranda House

White Elephant Hotel
If you have done the bed and breakfast weekend and are looking for a bit of a larger, luxury hotel experience here is the place to stay. The White Elephant hotel (photo in feature image) offers an amazing waterfront experience located right along Nantucket Harbor. There are lots of lodging options here for parties of all sizes with 67 guest rooms, cottages, and in town lofts available. Complimentary early morning pastries and coffee are available as well as afternoon port and cheese in their library.  The White Elephant also has a full service on-site restaurant The Brant Point Grill which offers amazing water views and delicious local cuisine. The Sunday brunch here is definitely worth a trip! The overall atmosphere at this resort is classic Nantucket nautical elegance and the amenities are luxe. The waterfront near town location make this a great choice for a special stay in Nantucket.

50 Easton Street
Nantucket, MA 02554


Walk, Bike, Tour, Drive
There are so many ways to experience this island – wander through the many shops, galleries, restaurants and cafés by foot, rent a bicycle and explore miles of paths along 12 designated biking routes, or sign up for one of the many tours offered of the island. A fun splurge is to rent a jeep for the day or weekend here so you can explore the island at your own pace and whim. Nantucket is a smaller island, only about 50 square miles, so it is a fun and accessible place to explore for a weekend.

We love just ambling down the cobblestone streets of Nantucket Town peeking in and out of some of the galleries and shops. You won’t find any chain stores here and you will find some very uniquely local items. Starting off the morning by finding some time to pop into The Hub for a coffee and catching up on the local news is a favorite thing to do here. The Hub is located at 31 Main Street in the heart of town and is a longtime favorite spot for catching up with a newspaper, coffee, and browsing their various selection of books and other local sundries.

We also love poking around the long standing general store Sunken Ship for some fun local Nantucket Sundries and beach necessities (they also offer scuba diving lessons, charters, and equipment here).  A beautiful local lifestyle shop with a more upscale boutique vibe to definitely check out while here is the charming Milly & Grace which offers clothing, gifts, and home goods with a fun vintage beachy chic feel. Also be sure to pop into Nantucket Looms a beautiful homestore where they keep the local weaving tradition from which they were born alive and well with hand woven rugs, throws, and other furnishings. This store also offers a variety of many other home goods that are all hand crafted from local artisans. There are so many amazing local shops to explore here (we could go on and on) and you could stroll and explore all day for some amazing uniquely Nantucket island finds.

While in town, take a break from shopping if you can to spend some time exploring the exhibits and galleries of the Whaling Museum. Here you can learn how Nantucket’s past as a 19th century whaling hub still has influence in its seaside village charm today. At some point during your day in town, it will be necessary to find time to reward yourself with a sweet treat and the homemade ice cream and waffle cones at The Juice Bar at 12 Broad Street are the way to do it. The lines can get quite long but it is so worth a wait for the cones here!

There is no better way to get a feel for what Nantucket is all about, along with some amazing breath taking views, than sailing on a boat around the island. There are so many charters, tours and opportunities to choose from in order to experience Nantucket by sea. Our favorite is an excursion on the beautiful sloop sail boat The Endeavor (the longest operating sailing charter on Nantucket). The Endeavor is docked on iconic Straight Wharf and offers sailing excursions from May through October.  We recommend booking a sunset excursion for an extra special experience and some memorable views.  Adding to the overall experience, Captain Jim Genthner built The Endeavor and has tremendous knowledge to share on boat building and the historic waters of Nantucket if you are interested.

Photo Credit: Endeavor Sailing Excursions


Nantucket’s beautiful seashore boasts about 80 miles of sandy beaches. A day at the beach here is time well spent with so many ways to enjoy a day by the ocean. If your perfect day on the beach would not be complete without a beautiful sunset to cap it off then Madaket Beach is a must. Located on the far west end of Nantucket, Madaket is a remote feeling and unique part of the island. It is especially beautiful in the evenings and has the most spectacular sunsets on the island. A bonus here is the iconic Millie’s which is a must visit for baja inspired Mexican eats. In addition to the seated restaurant, Millie’s also has a take out window so you can grab some of their must have tacos to enjoy for an al fresco beach dinner before taking in the sunset views.

Another must visit beach here is at Great Point, located on the northern tip of Nantucket. The beach is part of the larger Coskata-Coatue wildlife refuge and is an amazingly pristine stretch of sandy beach trails and rolling dunes along the sea. Visitors have the opportunity to take a vehicle out onto this beach and after driving out to the outermost northwest tip of the island here it is a short hike out to the Great Point lighthouse (one of three historic lighthouses on Nantucket). This is an amazing stretch of beach to explore and we highly recommend renting a jeep for the day, grabbing a picnic lunch at Bartlett farms, (be sure to spend some time here exploring this beautiful local farm with a gourmet grocery shop) and driving out to Great Point for the afternoon. The feeling out here is gorgeous, remote island beach haven.

If a day at the beach is not complete for you without a cocktail in hand at some point, then Jetties Beach is a must visit for you. A short walk from town, Jetties Beach has has the Sand bar restaurant and café beachside offering a full food and cocktail menu for the beachgoers here.



There are so many amazing restaurants, bars, and dining experiences on the island. It is really hard to pick just a few for the weekend but the good news is there is always an opportunity to visit again and discover more favorites!

If you are out in Madaket, on the west end of the island, dinner at Millie’s is a must. From any part of the island, it is worth planning on a trip out here for this long time favorite. The food is California baja inspired cuisine and their tacos and quesadilla are some of the best anywhere (try the Steps Beach – lobster meat, roasted tomato, grilled zucchini, with jack and chihahua cheese). Millie’s offers a local beer and wine list as well as specialty cocktails served up in classic maison jars. They also have a takeout window so you can grab some of their delicious lighter fare to go.

Back in town, Cru is another definite must visit for Nantucket dining at its best. Sitting at the end of Straight wharf on Nantucket Harbor this island hot spot offers an elevated Nautical vibe and one of the best lobster rolls around. Also try their famously refreshing signature drink, the Crucumber, while sipping cocktails on the dock lounge.

Another great spot in town for dinner is Ventuno, which serves up delicious Italian food infused with local ingredients. It is a great spot for a romantic dinner date. We are still reminiscing about their local burrata antipasti dish and the bombolocini dessert (bittersweet chocolate doughnut dessert served with gelato coffee).

For a more laid back island experience, a stop or a whole afternoon at Cisco Brewery is highly recommended. Home to a local distillery, brewery and winery this is the place on Nantucket for local tastings, tours, live music, and classic Nantucket island fun. You will really feel like you are on island time day drinking the afternoon away here. There are also food trucks at Cisco making for a great lunch spot (including one from Millie’s granting another opportunity to grab a taste of their delicious tacos!)


Also Try:
• Brotherhood of Thieves (
• The Pearl (
• Black-eyed Susan’s (
• Oran Mor (
• The Proprietors Bar & Table (

Know Before You Go

Getting There
Cape Cod Air (
Hy-line Cruises (

Rentals (jeep/bicycles/etc)
Young’s bicycle shop (www.youngbicycleshop.come)
Nantucket Affordable Rentals (

More information for your trip
Nantucket Island Chambers of Commerce (
Coskata-Coatue Wildlife Refuge (

FEATURE IMAGE CREDIT: White Elephant Hotel

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