Photo by Kim Grant

Nantucket Itineraries

Nantucket as a Day Trip

The "Little Grey Lady" has plenty of one-percenters, but commoners enjoy its allures too

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This “far away island” of Nantucket, just off the coast of Cape Cod, is renowned worldwide for its historic downtown — complete with paved cobblestone streets, brick sidewalks, electrified “gas” street lamps — and a nearby village bursting with 18th century rose-covered cottages.

Gray-shingled houses are nestled close together on winding narrow lanes. Elegant white residences are trimmed with English boxwood hedges, white picket fences, and glorious gardens. In short, it’s breathtakingly gorgeous.

The center of Nantucket, a national historic landmark, boasts more than 800 buildings constructed before 1850, the largest concentration of such buildings in the U.S. Most sites in Nantucket are within a mile of downtown, where the ferry lands.

In addition to the best whaling museum in the U.S. and one-of-a-kind boutique shopping, Nantucket prides itself on offering world-class dining. In fact, many visitors, after they secure accommodations, immediately make dinnertime reservations for each night they are here. Upscale visitors are also justifiably drawn to wide-open beaches, cycling, and sailing.

But make no mistake: it’s difficult to find a grain of sand or a seashell that hasn’t been discovered. With a daily summer population that swells to about 50,000, today’s tourist industry is about as well oiled as the whale industry once was.

Around Nantucket

Although there are pockets of settlements around the island, the only real “destination” is ’Sconset, an utterly quaint village with rose-covered cottages. Yes, quaint. You’ll wish you’d never used that word before walking ‘Sconset lanes.

Elsewhere on the island, more than 60 percent of the island’s 10,000 acres are held by conservation trusts. With a (pricey) rental car, scooter or bike, you’ll be able to explore places where most tourists don’t venture. Luckily, the mostly-flat island boasts excellent bicycle paths and public buses. The almost-limitless public beaches are worth the effort.

A brief history

Although there is more history under “Background” in the yellow bar above, no introduction to Nantucket is complete without touching on it briefly since it shapes every single thing you encounter today.

In 1712, an islander, his sloop blown off-course, harpooned a sperm whale. Whaling then dominated the island’s economy for the next 150 years and made islanders rich. After the “Great Fire” of 1846, the downtown was rebuilt using brick, but when kerosene replaced whale oil as a less expensive fuel, the island returned to relative isolation. What remained during that sleepy century-plus? Architectural integrity, rich history and community spirit.

Enter the modern times: islander, developer and S&H Green Stamp heir Walter Beinecke Jr. declared in the early 1960s that it was more preferable for Nantucket to attract one tourist with $100 than 100 tourists with $1 each. Nantucket’s upscale tourism industry began in earnest. Nantucket quickly became a restrained haven for behind-the-scenes power brokers and mammoth trophy houses. Some call it an economically-gated theme park, where billionaires are the new millionaires. It also quickly became too popular for its own good and was placed on the list of Most Endangered Historical Places, as decreed by the National Trust for Historic Preservation.

Chances are you’ll be taking a ferry from Cape Cod or a flight from Boston and … maybe, just maybe, you’ll even add a trip to neighboring island of Martha’s Vineyard.

Explore a Nantucket Itinerary

If you are short on time for a visit, get started with this Nantucket day trip itinerary.

Adapted from the perennially favorite guide to the region, Cape Cod, Martha’s Vineyard & Nantucket, An Explorer’s Guide, and available from Amazon.

When To Go

Nantucket is a year-round destination. Millions thousands upon thousands of daffodils blanket the island in yellow as the earth reawakens each April. The weather in May and June is slightly less predictable than in fall, but if you hit a nice stretch, you’ll probably muse that life just doesn’t get any better. Gardens are brightest in May and June.

Where once there were whaling ships, yachts now fill the harbor in summer. Warm ocean water and beach barbecues beckon, wild roses trail along picket fences, and many special events are staged.

Come September (my favorite month on-island), the crowds recede a bit. You can swim in the still-temperate ocean by day and not have to wait for a table at your favorite restaurant at night. Skies turn crisp blue, and cranberry bogs, heathlands, and the moors blaze red, russet, and maroon.

Many restaurants that close in mid-October (at the end of Columbus Day weekend) reopen for the long Thanksgiving weekend. The first three weeks of November are very quiet indeed.

Before the monochrome days of winter set in, there is one last burst of activity: Nantucket Noel and Christmas Stroll. In January, February, and March you’ll discover why whaling captains called the island the “little grey lady” — she is often shrouded in fog. It’s a time of reflection and renewal for year-rounders and visitors alike.


Getting There

With high-speed ferry service, day-tripping to Nantucket from Hyannis is more feasible than ever. I recommend spending a few days on Nantucket, though.

By bus

Peter Pan/Bonanza (800-343-9999) travels from points south to Hyannis, where you can catch the boats. Plymouth & Brockton (508-746-0378) runs from Boston to Hyannis.

By boat

From Hyannis

The Steamship Authority (508-477-8600 for information and advance auto reservations; 508-771-4000 for day-of-sailing information in Hyannis; 508-228-0262 for day-of-sailing information on Nantucket; steamshipauthority.com), South Street Dock, Hyannis.

The Steamship, established in 1948, carries autos, people, and bikes to Steamship Wharf year-round. Make car reservations in the spring for the summer if you can; no reservations are needed for passengers. There are six high-season sailings daily and three off-season. The voyage takes 2¼ hours. Cars cost a whopping $450+ mid-May to late October, about $320 off-season—but you really don’t need one. Take it from me, a my-car-is-my-home-when-I-travel nut.

The Steamship Authority’s High Speed Passenger Boat Iyanough (508-495-3278 for reservations; 508-477-8600 for information) sails dock-to-dock in 1 hour, early May through December, and makes four to five trips daily. Reservations strongly suggested.

Hy-Line Cruises (800-492-8082), Ocean Street Dock, Hyannis. Passengers and bicycles to Straight Wharf, late May to mid-October. There are three summertime boats daily, one to three daily off-season.

Hy-Line’s Grey Lady High Speed Passenger Boat (800-492-8082), Ocean Street Dock. This high-speed luxury catamaran costs a bit more, but it operates year-round. Reservations are strongly recommended. There are five to six boats daily.

From Harwich

Freedom Cruise Line (508-432-8999), Saquatucket Harbor in Harwich Port, provides daily passenger service to Nantucket, early June to late September and during the Christmas Stroll. During the summer, two of the three trips are scheduled so that you can explore Nantucket for about 6½ hours and return the same day. In spring and fall, there is only one morning boat daily. Reservations are highly recommended; make them 3 to 4 days in advance. The trip takes 80 minutes each way.

From Martha’s Vineyard

Hy-Line Cruises (508-778-2600 in Hyannis; 508-228-3949 on Nantucket; 508-693-0112 in Oak Bluffs, Martha’s Vineyard). One daily, interisland departurefrom mid-June to mid-September. The trip takes 75 minutes. (There is no interisland car ferry.)

By air

Cape Air/Nantucket Airlines (508-771-6944) offer dozens of daily flights direct from Boston, Hyannis, New Bedford, Providence (T. F. Green), and Martha’s Vineyard. Frequent-flier coupon books for 10 one-way trips are available. Island Air (508-228-7575) offers daily, year-round flights from Hyannis.

Getting Around

By shuttle

NRTA Shuttle (508-228-7025). WAVE information aides and other amenities available at the Greenhound Building at 10 Washington Street. Buses daily late May to early October. This is an economical, relatively convenient (if you pay attention to departure times), and reliable way to travel to ’Sconset (two routes) and Madaket.

Pick up a route map on-island. Shuttles have a bike rack, so you can take the bus out to ’Sconset, for instance, and ride back.Exact change required. The Surfside Beach and Jetties Beach buses run on a shorter season, from mid-June to early September. Ask about multiday passes at the NRTA office at 3 East Chestnut Street.

By car or 4WD

There isn’t a single traffic light in Nantucket, and Nantucketers intend to keep it that way. You don’t need a car unless you’re here for at least a week or unless you plan to spend most of your time in conservation areas or on outlying beaches. Even then, a four-wheel-drive vehicle is the most useful, as many of the stunning natural areas are off sandy paths. Nantucket is also ringed by 80 miles of beaches, most of which are accessible via four-wheel drive. Four-wheel drives are rented faster than the speed of light in summer, so make reservations at least a month in advance in summer. And lastly, parking is severely restricted in the historic center.

Rent from my favorite company, Affordable Rentals (508-228-3501), 6 South Beach Street, early April to late December. Expect to pay $125+ for a compact during the summer, $250+ for a 4WD Jeep. Nantucket Windmill Auto Rental (508-228-1227) is based at the airport but also offers free pickup from the ferry; Hertz (800-654-3131) is also based at the airport. Prices drop by almost half off-season.

If you get stuck in the sand, call Harry’s 24-hour Towing (508-228-3390). Once you do call him, though, wait with your vehicle so he doesn’t make the trek out to fetch you, only to find that you’ve been helped by a friendly local.

Contact the Police Department (508-228-1212), South Water Street, for overland permits, which are required for four-wheel, over-sand driving. Expect to pay $100+ off-season and $150+ in season.

The Coatue–Coskata–Great Point nature area requires a separate permit, available from the Nantucket Conservation Foundation (508-228-2884 information; 508-228-0006, Wauwinet gatehouse, where permits are purchased) mid-May through October. Most beaches are open to four-wheel-drive traffic, except when terns are nesting.

By taxi

Taxi fares can add up, but cabs are a useful way to get to the airport or to an outlying restaurant.

Try All Point Taxi (508-228-5779) or look for one when you disembark from the ferry. Taxis usually line up on lower Main Street and at Steamboat Wharf. Flat rates are based on the destination. Rates are for one person; add a coupla bucks for each additional passenger.

By bicycle

Bicycling is the best way to get around.

By moped

Nantucket Bike Shop (508-228-1999; 800-770-3088; nantucketbikeshop.com), Steamboat Wharf, rents scooters April through October, daily.

On foot

Architectural Walking Tours (508-228-1387; nantucketpreservation.org), 55 Main Street, by the Nantucket Preservation Trust. June through September.

The Nantucket Historical Association leads great historical walking tours.

By van or bus tours

Ara’s Tours (508-228-1951; 508-221-6852) offers a 90-minute island tour that makes stops for photography. On a clear day you can see all three lighthouses. For those that have more time and money, ask about the 3-hour barrier beach tours of Great Point.

Trustees of Reservations (508-921-1944) offers excellent 3½-hour natural history tours from mid-May to mid-October. Tours depart from the Nantucket Shipwreck & Lifesaving Museum, where a guided tour of the museum is followed by a tour of the Coskata-Coatue Wildlife Refuge. Reservations strongly recommended.

Barrett’s Tours (508-228-0174), 20 Federal Street, and Nantucket Island Tours (508-228-0334), 34 Straight Wharf, offer 90-minute narrated mini-bus tours May through October.


Thirty miles out to sea, Nantucket was called “that far away island” by Native Americans. Just 14 by 3.5 miles in area, Nantucket is the only place in America that is simultaneously an island, a county, and a town.

In 1659 Thomas Mayhew, who had purchased Nantucket sight unseen (he was more interested in Martha’s Vineyard), sold it to Tristram Coffin and eight of his friends for £30 and “two Beaver Hatts.” These “original purchasers” quickly sold half shares to craftsmen whose skills they would require to build a community.

When Mayhew arrived, there were more than 3,000 Native American residents, who taught the settlers which crops to farm and how to spear whales from shore. By the early 1700s, the number of settlers had grown to more than 300, and the number of Natives had shrunk to less than 800, primarily because of disease. (The last Native descendant died on-island in 1854.)

In 1712, when Captain Hussey’s sloop was blown out to sea, he harpooned the first sperm whale islanders had ever seen. For the next 150 years, whaling dominated the island’s economy. The ensuing prosperity allowed the island’s population to climb to 10,000. In comparison, there are also about 10,100 year-rounders today.

Nantucket sea captains traveled the world to catch whales and to trade, and they brought back great fortunes. By the late 1700s, trade was booming with England, and in 1791 the Beaver, owned by islander William Rotch, rounded Cape Horn and forged an American trade route to the Pacific Ocean. Fortunes were also made in the Indian Ocean — hence, Nantucket’s India Street. Speaking of place names, the nearby village of ‘Sconset takes its name from the native Indian for “near the great whale bone.” It was first settled three centuries ago as a whaling outpost, around a lookout tower for used for spotting whales.

In its heyday, Nantucket Harbor overflowed with smoke and smells from blacksmith shops, cooperages, shipyards, and candle factories. More than 100 whaling ships sailed in and out of Nantucket. But when ships grew larger, to allow for their longer voyages at sea, they couldn’t get across the shallow shoals and into Nantucket Harbor. The industry began moving to Martha’s Vineyard and New Bedford.

At the height of the whaling industry in 1846, the “Great Fire,” which began in a hat shop on Main Street, ignited whale oil at the harbor. The catastrophic blaze wiped out the harbor and one-third of the town. Although most citizens began to rebuild immediately, other adventurous and energetic souls were enticed to go west in search of gold in 1849. When kerosene replaced whale oil in the 1850s as a less expensive fuel, it was the final blow to the island’s maritime economy. By 1861 there were only 2,000 people on-island.



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