Walking is not your thing; neither are stairs
Traffic is about the only stress on Nantucket, and walking is the best way to avoid stress, especially if you stay in town. In fact, it’s why I stay in town. While there are taxis (and the arrival of Uber has made that situation better), several dozen excellent restaurants are within a one-mile radius. It’s faster to walk. It’s daylight until 9 p.m. or later, and the streets are safe, though cobblestones and ancient brick sidewalks can be hazardous. Steep 18th-century staircases are found in many homes, B&Bs and restaurants; elevators are rare.
You don’t feel dressed without your 5-inch Louboutins
See above. It may simply be part of the local folklore, but I’ve been told that falls on the cobblestones and brick sidewalks are the primary reason people go to the Cottage Hospital emergency room. Even flat shoes with thin soles present challenges. You can feel every cobblestone through the soles, and they can be slippery when the stones and bricks are wet.
You’re an impatient/aggressive/fast driver
Top speed on the island is 40 mph, but with 80,000 people packed into the 6×14-mile space at the height of summer, reaching top speed is unlikely. Add to that cobblestones, narrow one-way streets, roundabouts. the complete lack of traffic lights, a culture of yielding the right-of-way to others out of courtesy and pedestrians who are very confident that we have the right-of-way in all circumstances…. Well, you get the picture.
You like driving big, expensive cars
See above. Year-round residents drive Jeeps and Fords (the only car dealer on the island), occasionally small Toyota 4-wheel drive SUVs, mini-Coopers and the like. Occasionally, you see relatively small Mercedes and BMWs—often convertibles, often classic. Parking spaces are rare and treacherous. You are likely to need to jump a granite curb to pull up on the sidewalk or get up close to a bramble of wild roses. And getting sideswiped by a truck trying to squeeze down a narrow street is always a hazard.
You don’t like planning every minute in advance; you prefer spontaneity
While few restaurants are open year round, even the abundance of summer-only eateries cannot handle the crowds of August and major summer holidays. Like everything else on the island, most restaurants are small. When it rains and the outdoor patios close and beachgoers and golfers come into town, the shortage is compounded. Even lunch is difficult for walk-in’s, especially when there are more than four in your group. There are not enough taxis either. You need reservations, especially for the airport and ferries. I have a collection of taxi driver business cards, and I’ve been lucky enough to find an immigrant from Costa Rica who likes me and who is willing to carry suitcases up and down the stairs for my guests and me.
You don’t eat seafood
Like much of Europe, Nantucket is committed to fresh local, seasonal food. This is an island in the North Atlantic. Chefs show off their skills with their preparation and presentation of local fish and seafood. Virtually all restaurants have a chicken and a red meat option, but the creativity is with the seafood. However, because these are sophisticated chefs with sophisticated diners, they are well equipped to deal with special dietary requests. Vegetarian dishes are exquisite, and gluten allergies are taken seriously.
You’re not a foodie
Again, see above. The top restaurants are foodie paradise; and in the historic district, they are easier to find than restaurants that offer simpler fare. Good luck finding a steak and baked potato or entrees where the meat or fish isn’t served on top of medley of vegetables, some of which I had never tasted before.
You crave fried chicken or—heaven forbid—chicken fried steak
This is not the South, and southern food is hard to find. I tried to buy brisket for slow-cook barbecue at Stop & Shop, the island grocery store, and was shown ground beef patties. I haven’t seen any gravy here, and raw oysters from local oyster beds are typically served naked—no red sauce. In fact, it’s hard to find fried oysters.
You’re a smoker
Smoking is so rare on the island—almost always on the sidewalks, often on the benches—that people tend to turn their heads to see where the smell is coming from. With the historic district full of pre-1850 wood buildings and the history of the Great Fire of 1846, which destroyed one-third of the town, smoking is frowned upon. I don’t see “no smoking” signs at outdoor restaurants, but nobody smokes.
You hate the color blue
From clothes to home furnishings, blue reigns surpreme, though you see red on the Fourth of July, and men sport Nantucket red (faded to pink) slacks and Bermuda shorts, generally with blue shirts of course.
You hate bad hair days
Every day is a bad hair day. This is an island. I saw a poor Texas lady with her carefully styled and sprayed big hair on Main Street. Her hair had been lifted in clumps by the prevailing humid breeze. And when I got a haircut, the receptionist took a call from a woman wanting to schedule a “comb out.” I don’t think the receptionist knew what it was. Take comfort in the fact that everyone’s hair looks bad. It’s one of those things you don’t stress about here.
You need a daily newspaper with your first cup of coffee
This is an island. The local paper is a weekly. The Boston Globe, New York Times and Wall Street Journal arrive on the first ferry. Men congregate on benches outside the pharmacy, drinking coffee while they wait for papers to be delivered. But actually, Nantucketers consider America that faraway place across the ocean. What happens there doesn’t seem very important here. It doesn’t have much to do with Nantucket. And vice versa.
You love shopping at national chain stores, eating at national franchises, staying at national brand hotels
By law, they don’t exist on Nantucket. Well, there is a Ralph Lauren shop on Main Street, but islanders were so upset when it opened that they passed an ordinance not allowing any businesses that have more than 14 locations nationwide. Lilly and Vineyard Vines have slipped in with local businesses; but usually the “chains” here are part of Boston, Greenwich, Cape Cod or Palm Beach businesses. Take the ferry to Hyannis if you need a big box store or a KFC fix.
You love bargains
For the summer visitor, there are very few. The hospital thrift shop on India Street is about your best option, though you may find a bargain antique at the weekly auctions and all the summer merchandise is beginning to go on sale now. Almost everything comes in by ferry from the mainland, and the season is very short. Nantucketers need to make their annual profits in the two or three months of the tourist season. That said, prices for food and merchandise are surprisingly fair. The best restaurants, while never cheap, are all significantly less than pretentious, trendy, top restaurants in America’s big cities. Rosé wine from Provence is the beverage of choice, at prices about $11-$15 a glass.
You prefer new, modern and efficient to old, quaint, charming, quirky and historical
Modern hardly exists, though you can find some modern interiors. Historic buildings can’t be torn down on Nantucket, though they can be moved, renovated and repurposed. Even for new structures away from the historic district, there are significant regulations and controls. Virtually all new structures are gray shingle. Where you might see monotony, I see charm and harmony and a wonderful lack of pretentiousness.
You enjoy wearing glitz and bling
Nope. Diamond stud earrings and large diamond engagement rings are generally the extent of the bling. Freshwater pearls must be sold by the bushel basket here, and there’s discreet gold jewelry as well. Insiders recognize jewelry made by local jewelers who incorporate lightship baskets, shells, whales, shore birds and scrimshaw into their designs. Dress tends to range from super casual—including beachware and yoga pants—on the streets in the daytime to smart casual at dinner. Ties for men are an endangered species (Vineyard Vines styles excepted), and generally you only see sweaters and blue blazers when it’s cool. White jeans are ubiquitous.
You need absolute darkness to sleep
Even now, in August, sunrise is before 6 a.m. and sunset, almost 8 p.m. On June 21 sunrise was about 5 a.m. and sunset, about 8:15 p.m. It wasn’t fully dark until after 10 p.m. I have yet to find blackout draperies here, so I have resorted to a sleep mask and count myself lucky when I can sleep until 7.
You’re inflexible about your travel plans
There are only two ways to get to Nantucket—by air and by ferry from the mainland. Fog closes down the airport; high winds, the ferries. Only JetBlue flies big jets to Nantucket; others are commuter flights. And only tiny Cape Air flies year round—from Boston Logan. Flights tend to be full, so if your flight is cancelled, good luck getting on the next one. Of five sets of company that came by commercial air, two got home two days late and one was one day late. In a worst case scenario, one couple took the ferry to Hyannis, a bus to Boston Logan and eventually got back to Texas. It’s easier (and probably cheaper) from me to get from Corpus Christi to London or Paris than to Nantucket.
On the Other Hand…
If, like me, you love flowers, gardens, water, boats, art, architecture, history, cultural activities, cool weather, magnificent sunsets, good food and good shopping on an island that is safe, peaceful, unpretentious, friendly and welcoming, then you will fall in love with Nantucket. The remoteness is part of the charm. Nobody is here by accident. Those who are here want to be here, and it shows.
Five summers ago I came to this island with some trepidation. A recent widow, I had never been anywhere by myself that was so remote, where I knew no one. I moved far from my comfort zone. And I fell in love with this place and these people. I found peace and joy here. I have gone from summer tourist to summer resident. Indeed, this is my happy place. As the end of my stay approaches (I will be back in Texas when this is published), I have sought to imprint favorite sights and experiences in my memory, for joy comes both in memory and anticipation.