A Nantucket Vacation: Making it Affordable and Easy, From Hotels to the Best Beaches

There once was a man from Nantucket…and because he was a local, he knew exactly what to see and do on the island. For the rest of us, Nantucket is trickier. Not only is it one of the priciest destinations in the United States (in high season), but its limited facilities can also make planning a trip feel like a exercise in compromise. Plus, the Massachusetts isle offers such an unusually rich mix of history, nature, and active activities that many visitors get to the end of their vacations and realize they didn’t do a fraction of what they had planned to. Wanna avoid making rookie mistakes? Read on.

Nantucket’s name probably comes from the Wampanoag word for “faraway island.” That's the first clue that it’s not simple to get to it. Nantucket sits some 30 miles off the coast of Cape Cod. Some people make the island the endpoint of a road trip, taking their cars aboard a 2.5-hour ferry from Hyannis. But that’s a pricey approach, considering that taking a vehicle costs $400–$500 round-trip. My advice: Leave the car behind and sail as a foot passenger (cost $37.50/adult round-trip on the regular ferry, $77–$90 on fast ferries from Hyannis, New Bedford, and Harwich Port). Or better yet, fly. Midweek prices direct from New York City on JetBlue have been known to dip as low as $55 each way with advance purchase.

If you’ve taken my advice, you’ll arrive on island sans car. Stay that way. A fleet of public buses, called The Wave, travel to most corners of the island and cost just $2–$3 per ride, depending on the route. These shuttles stop running at 9pm on weeknights and 7pm on weekends, but cabs and Uber are also widely available. That being said, one the most delightful ways to get around is on two wheels. Nantucket is crisscrossed with protected and often lovely bicycle paths (pictured). Bikes can be brought on the ferry for $7 one-way or rented once you arrive (more about that next).

In Nantucket Town, the main village that's within walking distance of the ferry dock, you'll find two bike rental outfits, Nantucket Bike Shop and Young’s Bicycle Shop. Both will also deliver bikes anywhere on the island. While you could hire a standard cycle, your legs—and rear—will thank you if you opt for a Fatboy. These are cycles with unusually wide wheels, perfect for navigating Nantucket Town’s cobblestone streets and the dirt/sand roads that lead to many beaches and beach houses. Mountain bikes work almost as well.

There aren't many hotels on Nantucket, which means they can pretty much charge what they please. In fact, Nantucket is the only place in North America to regularly exceed the high prices of New York City in the summer; we’re talking $450/night and up! Those in the know tend to either rent rooms in private homes or secure entire houses through such sites as HomeAway, Airbnb, and VRBO. That strategy cuts the cost of lodging in half, especially if you can travel in a group and amortize the rental fee of a cottage. In addition, the island has a cute hostel that’s isn't just a lifesaver for travelers—it’s also in a 19th-century lifesaving station.

Many vacationers who come to the island assume that its classic looks were created for their enjoyment, like a New England-style Disney World. The truth is more complex. For over a century, Nantucket was one of the most prosperous places on the planet thanks to its whaling trade. Fortunes were made and grand mansions were built. But when whale oil, which had been widely used for lighting, was supplanted by kerosene and then electricity, Nantucket's economic decline was stark.

Cut to the 1880s. The last whaling ship had departed the island in 1869, but savvy islanders soon discovered another potent source of income: tourism. They realized right away that to keep the charm of Nantucket intact, they’d need to pass strict preservation laws. So while the island’s structures weren’t built with tourists in mind, they were certainly protected for the good of tourism. Even today, all new homes must have pitched roofs (not flat ones) by law and they must be sided with unpainted cedar shingle that turn a gentle gray and give the settlements a soothing consistency.

The primary lure of a Nantucket vacation is beaches, but this rock in the Atlantic is also home to one of America’s finest history museums. As its name suggests, the Whaling Museum (pictured) is dedicated to the region's former way of life, with compelling exhibits and lectures about life at sea, the tools needed to down a whale, and the impact of the industry on Nantucket. It also sponsors exemplary, twice-daily walking tours ($15) around Nantucket Town. The Egan Maritime Nantucket Lifesaving & Shipwreck Museum, chronicling the heroism of the men and women who helped sailors in distress, is another top attraction. These will be the highlights of a visit to Nantucket—I promise.

Do you like it rough? I’m talking the surf, obviously, and on Nantucket, location determines the ferocity of the waves. South Shore beaches (Cisco, Surfside, Tom Nevers, Miacomet, Nobadeer) get hit with the taller ones and so they're popular among surfers. Families tend to head to the gentler waves on the beaches of protected Nantucket Sound, like Dionis and Jetties (pictured), and to such Harborside sands as Children’s Beach.

But there’s more to beach-going on Nantucket than just the water. Great Point (beach permit and four-wheel drive required) and Sankaty Head (pictured) have lovely lighthouses to admire—and to climb, in the case of Great Point. You can’t beat the sunsets at Madaket. And Great Point and Eel Point are also de facto public zoos thanks to the number of seals that loll on their shores in summer. Click here for our rundown of the pluses and minuses of each beach on the island.

The historic Athaneum is not only Nantcket’s main library. It’s a lecture hall on many nights, too, and it’s also the force behind some of the island’s most interesting events (such as the annual dance festival, which brings in stars from the New York City Ballet and other important companies). Top names who have lectured here over the years include cartoonist Roz Chast, diplomat Richard Haass, Chuck Todd, and historian Doris Kearns Goodwin. Even if you don't have time for a lecture, go up to the top floor to see the splendid high-ceilinged room where abolitionist Frederick Douglass gave his first speech, in 1841. (The building is also a great place to mooch free Wi-Fi, if you're like me and have to work on vacation.)

If you're on a New England holiday, you know your vacation won’t be complete without at least one lobster dinner. But they come with a hefty price at most local restaurants. Instead, contact Souza’s (pictured, at 23 Trotter's Lane, 508/228-9140). It not only sells lobsters (and has its own fishing fleet), but it will also cook small batches for customers with a couple of hours notice. The difference in cost is significant: An average cooked lobster from Souza's is $18, compared to about $40 at a restaurant. Your dinner will be kept in a well-insulated box that keeps it warm.

"We could have eaten anywhere on the island… if I’d remembered to make a reservation a month ago." Cue the sad wah-wah trumpet. That statement was overheard at Stop & Shop, a local grocer, and the man who uttered it did so without irony. Nantucket is blessed with the types of high quality restaurants one usually only finds in major foodie destinations like Paris, London, or New York. But there simply aren’t enough of them to accommodate all the summer visitors, so plan well in advance if you want a blow-out meal. Click here for the Nantucket restaurants we think are tops.

Pictured: Oyster shooters at Breezes Restaurant in the Nantucket Hotel.

Yes, the line at The Juice Bar often stretches down the block in August. But getting a cone at this ice cream parlor is an iconic Nantucket activity. The sweets, all made on-site, are truly scrumptious.

Nantucket bans national chain stores, which has protected the character of the shopping. You’ll find darling boutiques side-by-side with scrimshaw-laden antique stores, old-timey soda fountains, and touristy t-shirt shops. Nantucket Town is also home to the first bricks-and-mortar pop-up of the website Goop. Pictured is Murray’s Toggery, where one can purchase famous “Nantucket Red” slacks and shorts. Alas, the prices at these stores are not old fashioned, but hey, window-shopping is free.

It might as well be against the law to visit this seafaring island without spending some time aboard a boat. Nantucket offers superlative whale-watching cruises, fishing charters, kayak rentals, and other ways to get on the water that made it famous. We have advice on companies to work with here.