Nantucket Travel Guide

Nantucket! Take out your map and look at it. See what a real corner of the world it occupies; how it stands there, away off shore…

Herman Melville wrote in Moby Dick.  What was once – in Melville’s time – the whaling capital of the world, is now a popular summer retreat about 30 miles off the coast of Massachusetts.  Yet “away off shore” it remains, only accessible by boat, ferry or light aircraft flying into Nantucket Memorial Airport, “ACK”.  But for most, the remote nature of the island contributes to its appeal, giving it a distinct feel separate from anywhere else on earth.  


When you’re on Nantucket, you may be disconnected from the rest of the world but you are connected to the island, its history, and its community. There is, quite thankfully, nothing to distract you from enjoying everything the island has to offer. The National Parks Service calls Nantucket the “finest surviving architectural and environmental example of a late 18th- and early 19th-century New England seaport town.”

house-7238591This distinction can be observed firsthand while walking down the cobblestone streets and brick sidewalks, in the homes of former whalers and merchants, built in the Federalist style and maintained to their original 1800s appearance. Also seen in abundance are the cedar shingled early New England colonials, Quaker influenced cottages, and Greek Revival, with stately ornamentation, symmetrical chimneys, and white siding. If you look closely, you can spot several houses built with a widow’s walk, a feature adorning the homes of sea captains.

The tourism industry of Nantucket is nothing new, as boarding houses sprouted up prior to the turn of the 20th century, and America’s most well-off families have sought refuge here ever since. With less than 50 square miles of land area, Nantucket is known for sporting some of the highest property values anywhere in the United States. You might assume this comes with a certain air of exclusivity, sitting like a fog over the Island, but instead, tourists from around the world are welcomed every summer to the wonderful restaurants, beaches, and hotels Nantucket has to offer.

I’ve personally had the fortune of summering on Nantucket for a number of years and working as a sailing instructor at Nantucket Yacht Club. Here are my top suggestions for where to eat, drink, and enjoy your time on the island.


Getting there

Being an island, part of the whole appeal of Nantucket is the effort required to even reach it from the mainland. One additional step removed from the already idyllic landscape of Cape Cod, Nantucket has long been a destination of those looking to escape ordinary life for a few days (or more, for those lucky enough to have their summer homes here).

  • By Ferry

    Most of the visitors to Nantucket, along with the majority of the food and goods sold on the island, arrive by ferry from Hyannis. Operated by Hy-Line cruises, the fast-ferry trip takes approximately 1 hour, while the “slow” ferry, operated by the Steamship Authority takes a leisurely 2 hours and 15 minutes, on average. Book your trip early as the ferries notoriously fill up during peak season. While the Steamship Authority boats can take cars, it’s highly unlikely you’ll need (or want) one during your stay. Grab a bike instead, or walk from town to the numerous beaches and destinations mentioned below. A round trip passenger ticket will run you $77 on the high-speed, or around $40 for the traditional ferry.

  • By Plane 

    IMG_2004Nantucket Air, a subsidiary of Cape Air, shuttles passengers between Nantucket Memorial Airport (ICAO: KACK, hence, the origin of the nickname) and several nearby airports including Barnstable, Boston, New York, Martha’s Vineyard, and New Bedford. Don’t expect any 747s here, as Cape Air maintains a fleet of 9-passenger piston engine Cessna aircraft for the majority of their flights. That being said, there are more than a few residents who arrive by their own private aircraft every summer form all around the world.

    Some ACK Facts:

  • Number of landings of private jets by type, per year:
    Learjet 358
    Beechcraft 1,000
    Dassault 786
    Cessna Citation 3,032
    Gulfstream 888
  • Longest Runway: 6,303 feet
  • Runway elevation: 23 feet
  • After Boston’s Logan International, Nantucket Memorial Airport is the busiest airport in New England


  • By Boat

    Should you be friends with a sailor or two, the absolute best way to reach Nantucket, is by the traditional method of sailing there. A day-long journey from Newport, you will pass by the Elizabeth Islands of the Cape and the shoals of Buzzards Bay. The annual Figawi race from Hyannis to Nantucket every Memorial Day weekend draws thousands of sailors to the island, so if you know how to sail, ask to crew, and enjoy the voyage! Sleeping out on a boat moored in the harbor is also a truly unique experience, and some owners even offer their vessels up for (very) basic overnight accommodations Air BnB style.



  • Ladies – Ladies Beach is best described as elusive, but not exclusive.  This beach is housed somewhere between beaches Cisco and Miacomet and offers the surf of the island’s south side without the crowds – if you can find it.


  • Steps – Named after the series of wooden steps leading down to the water from its secluded entrance, Steps Beach is one of the more “local” beaches on the island.  It offers negligible crowds and excellent sunsets while still maintaining proximity to Town on the north side of the island.

Activities / Landmarks

  • IMG_2551Cisco Brewery – “Nice Beer, If You Can Get It” – the official slogan of Cisco Brewery’s small line of beers.  As the only brewery on the island, Cisco is a popular attraction among visitors.  Go for the day and enjoy a flight of assorted ales and lagers while soaking up the sun in their inland courtyard. Must haves include Whale’s Tale Pale Ale, a regional favorite, with a crisp, hoppy profile and aromas best enjoyed beach side. Cisco Grey Lady is their summer Belgian -style whitbeer offering, delivering a deliciously fruity bouquet and a hazy, cloudy pour, reminiscent of a fogged-in day on Nantucket. Interestingly, their offerings extend beyond beer into single malt whiskey. Cisco’s Notch whiskey won the International Spirits Challenge award in 2015 for the best single malt whiskey in the world, outside of Scotland.
  • NCS on Jetties – If you’re just trying to get out on the water, Nantucket Community Sailing has a shack down on Jetties Beach that offers all sorts of rentals, from kayaks and paddle boards to sailboats and windsurfers.  They also offer lessons for beginners that will help get you on your feet in no time.
  • Nantucket Boat Basin – Take a walk down the piers here to check out some truly stunning  sail and motor yachts, which flock to Nantucket every summer from all corners of the globe. Many clocking in at over 30 meters (~100 feet), these $5+ million dollar playthings are often remarkable in their design and size alone. If you are lucky, you just might spot Isabel, Sen. John Kerry’s Friendship 75. My recommendation: walk along the piers at night when the boats have their underwater lighting powered up, and see schools of fish swimming around the sterns.


  • Bartlett’s Farm – Bartlett’s Farm is a local, family-owned farm that provides food to a lot of the island’s restaurants.  It also doubles as a high-end grocery store and to-go food shop.  Grab a salad or sandwich and a jasmine lemonade and hit Cisco Beach


  • Bike to Sconset – Siasconset (read: Sconset) is the other town on Nantucket.  Home to just over 200 local residents, the small village features a cafe, galleries, and a beautiful beach.  Get your bike to Milestone Road and you can’t miss it
  • Jeep to Great Point – If you brought a four wheel drive vehicle, driving out to Great Point Lighthouse is a must.  The only way to get there is to trek along beach, so you’ve got to let some air out of your tires at the waystation.  Bring a picnic and enjoy the remote beach for the afternoon. Hope you’ve got your Oversand Permit!
  • Nantucket Whaling Museum – If…When the weather turns crummy during your visit, the Nantucket Whaling Museum is loaded with enough history to fill your afternoon.  Nantucket was once the whaling capital of the world and holds some incredible stories in its past, including the real-life inspiration for Herman Melville’s Moby Dick.  Among the artifacts housed in the historic building is a full-size whale skeleton suspended from the ceiling.


  • Nantucket Race Week – An annual event to benefit Nantucket Community Sailing, NRW is 9 days of sailboat racing with boats of nearly every class. From Opti and 420s to 50′ racing yachts and international one-design entries, NRW is a sought after event for sailors all over the east coast. The week culminates with the Opera House Cup challenge, which brings some of the most famous vintage wooden yachts in the world to compete off Nantucket Harbor as one of the regattas of the Panerai Classic Yachts Challenge. The Rainbow Fleet Parade is also not to be missed, which draws crowds along harbor beaches as nearly 100 beetle class wooden boats take sail across the basin.




  • hm-block2Murray’s Toggery Shop  – Home of the original “Nantucket Reds” (not pink), Murray’s Toggery Shop is a family-owned clothing store located at the top of Main.  If you’re trying to blend into the Nantucket crowd, Murray’s is your one-stop destination. Local residents pride themselves on their faded reds, which take on their distinguished washed out pink hue after countless hours in the sun and saltwater. Towards the back of the store, there’s an entire room dedicated to their line of Nantucket Reds, which in this authors opinion, is one of the must visit trad meccas of the world, along with other such high temples as the Andover Shop and J.Press of Cambridge. Murray’s also carries unique Smathers & Branson and Castaway items, in addition to other iconic brands such as Duck Head and Barbour.
  • Nobby Clothes Shop – Plenty of ACK emblazoned ties, belts, and other gear to be found here.
  • In the Pink – Nantucket’s own Lilly Pulitzer franchise is a must-visit destination for signature patterns and prints.
  • Mitchell’s Book Corner – Also located at the top of Main, Mitchell’s is the island’s most prominent book store.  In addition to the classics and the new best sellers, the store carries a comprehensive collection of Nantucket books — anything written about Nantucket or by Nantucketers can be found in the back room.  You’ll leave knowing a whole lot more about the island you’re exploring.
  • The Toy Boat – This shop on the end of Straight Wharf carries small, hand carved toy replicas of Nantucket’s famous “Rainbow Fleet”.  Originally a beginner’s boat for the island’s kids to learn to sail, the Beetlecat fleet has since become an icon.  Each boat is equipped with one of 42 colorful sails that form a colorful rainbow when racing in Nantucket Harbor.
  • Hospital Thrift Shop – With proceeds going to the Nantucket Cottage Hospital, this thrift shop (open seasonally) will delight those looking for authentic Nantucket art, decor, furniture, and perhaps best of all, men’s and women’s clothing. Not to be missed for anyone seeking some truly unique takeaways from the island.


Food and Restaurants 

For Breakfast:

  • P1000657Downy Flake – If you’re the morning type, be sure to visit the Downy Flake for the island’s best fresh-baked doughnuts.  There may be a bit of a line, but if you show up early enough they’ll still be hot by the time you get home.
  • Island Coffee – Island Coffee doesn’t serve much, but what they do serve they serve right.  For a genuinely good cup of coffee or some pastries, stop by the compact coffee joint right by the slow-ferry terminal.
  • Black-Eyed Susan’s – A popular breakfast spot on India Street for pancakes and omelettes, Black-Eyed Susan’s also is open later in the day for BYOB dinners.


For Lunch:

  • Something Natural – Something Natural is close to town and is home to hearty sandwiches and locally-bottled drinks.  Great food to eat at the picnic tables out front or to take with you to the beach.IMG_2072
  • Provisions – Similar to Something Natural, Provisions offers generous sandwiches in a fast-casual setting down on Straight Wharf.  Cash only!


For Dinner:

  • Straight Wharf – Seafood right on the harbor with outdoor seating, what more can you ask for?
  • The Pearl – Coastal cuisine with a twist. Known for the Nantucket Salt & Pepper Wok Fried Lobster, a local and critic favorite.
  • Oran Mor – Located right next to the Whaling Museum, Oran Mor is known for seasonal dishes and a more cozy, romantic atmosphere than some of the other rooftop party spots.
  • The Galley Beach Bar – Being directly on Steps beach, The Galley is a popular local hangout with drinks and fare to match. Expect a vibrant crowd most nights, and don’t come in a rush!
  • Company of Cauldron – A culinary delight, Company of Cauldron features a set menu, including a once weekly specialty lobster dish. Not inexpensive by any means, but breathtakingly delicious.
  • Lola Burger – For a change of pace, Lola Burger offers a casual setting while still maintaining the gourmet standard of Nantucket.  Possibly the best burger you’ll ever have, accompanied by delicious truffle fries and a Dutch Chocolate shake – it’s upscale, laid-back dining at its finest.
  • Sayles Seafood – Sayles is first and foremost a local seafood vendor housed in a shack by the water, but if you go in there asking for a lobster roll or crab cakes you won’t be disappointed.  You’ll sit outside on the porch watching the harbor wind down and enjoying what is arguably the best lobster roll on island.


  • Murray’s Liquor Store – Located just down the road from Murray’s Toggery shop, you will find the aptly named store providing wines, beer, and spirits. Make sure to stock up on Gosling’s for your Dark n’ Stormies after dark!
  • Fresh – A gourmet grocery store downtown will have everything you need to pack up for a beach picnic.


Late night:

  • Stubby’s – Open ‘till 2am, Stubby’s is the best place to hit up after the bars close. IMG_2217 Operating as Nantucket’s resident “greasy
    spoon”, you’ll find everything your intoxicated heart could desire.  However, my recommendation is the sausage, egg, and cheese sandwich served on a bagel – it’ll help you end your night on a high note.
  • Juice Bar – Located right in town, The Juice Bar is the ice cream place on island. If you can suffer through the line that wraps around the block, you’ll find yourself confronted with dozens of incredible homemade flavors.  A personal favorite is “cake batter” flavor in a waffle cone. Their signature flavor however, is blackberry. Every now and then, if you’re lucky, they’ll also have a version of the blackberry made using only Nantucket grown berries. As with many places on Nantucket, it’s cash only.
  • Steamboat Wharf Pizza – Casual grab-and-go pizzeria right on Steamboat Wharf, serving thin crust pies and slices



  • Lobster Trap – On Tuesdays, The Lobster Trap has its “Buck a Shuck” special with $1 oysters and cheap drinks – a deadly (good) combination.  Stop in early in the night for ring-toss, drinks, dinner, and a fun, welcoming atmosphere.
  • Club Car – The Club Car is a famous Nantucket bar located inside a retrofitted railway car.  With live piano most nights, it’s a great way to finish your bar crawl through town.  Most of the pianists take requests, but if you want him to play “Piano Man” it’ll cost you extra.
  • Chicken Box – The Chicken Box is the self-described “unpretentious roadhouse of Nantucket with regular concerts, plus pool, ping pong & darts.”  The live music and cheap drinks make it popular with the island’s younger crowd, though all ages are welcome and encouraged.
  • The Gazebo – Look no further than here for a slew of drunken sailors, the Gazebo is an outdoor enclosed bar right down the block from the ferry terminal.
  • Burgee Bar, Nantucket Yacht Club – One of the private bars within the club. Make a friend with a member, or crew/volunteer during Nantucket Race week for easy access.



Since I’ve always stayed at a house, I asked fellow Navy Blazer writer Christen about overnight accommodations on the Island, as she visited Nantucket for her honeymoon a couple summers ago.

“We stayed at the Wauwinet and it was simply the best experience I’ve ever had at a hotel. They have oodles of all inclusive resort quality free amenities. The Wauwinet Lady is a boat that runs from late June to Early September between the Wauwinet and downtown and a jitney shuttle year round so getting around is totally doable.


There are complimentary bicycles, Hunter rain boots, fishing, sailing and kayaking, continental breakfast (baked goods) and the coolest daily port and cheese hour in their library. You get access to private beaches both on the bay and ocean side. The best part of the resort though are the Spring and fall activities – they give tours of the point, Sconset (driven in a 1947 Woody!), a tour of the bay on the Wauwinet Lady, surfcasting, lobstering, a cooking class and culinary experience.

The staff is all incredibly friendly and helpful – I asked to borrow a knife so I could take a fresh cut on my wedding bouquet and they took the flowers for me, made a fresh cut, and re-arranged them in a vase so I could enjoy them for a few more days in our room.”
Ian Leonard
Ian Leonard
Origionally from Chicago, Illinois, Ian Leonard is a college student in Boston who spends his weekends skiing or sailing, weather permitting. He has been a certified US Sailing instructor for over 4 years and has visited 28 countries over the course of his travels. 

Navy Blazer Community
This post was contributed by a member of the Navy Blazer community.

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