Nantucket, MA - Jim Flynn's BestWeekends

Nantucket, MA

Nantucket, MA Overview

About 30 miles off the coast of Massachusetts sits the magical island of Nantucket, unmatched in its beauty and ability to relax even the most ardent Type A personality. Once the whaling capital of the world, Nantucket is 14 miles long and 3.5 miles wide and has a charm like few other places; cobblestone streets and gas lamps, quaint lanes of cedar shingled cottages and homes surrounded by white fences and adorned with window boxes of colorful flowers. Roses and hydrangeas are everywhere and there are miles of pristine beaches to enjoy. Lighthouses and cliffs, ponds and moors, cranberry bogs and fields of wildflowers make the island the perfect romantic hideaway. Visitors and islanders alike are passionate about their island. As a sign says, “God made Martha’s Vineyard, but he lives on Nantucket.”

Nantucket’s year round population of 10,000 swells to 50,000-60,000 at the height of the season and both air and water temperatures average in the mid-70’s in summer. The locals are obsessed with preserving the historical integrity of the island and building and renovation codes are strictly enforced. 40% of the island can never be built upon. There are no fast food outlets, no national chains (except 2 food stores), no neon signs, no garish architecture and no traffic lights.

When To Go

May/June and September/October are the perfect months in Nantucket, the weather is balmy, there is less congestion and little trouble getting a restaurant reservation. Leave July and August to the tourists. April hosts the charming Daffodil Festival, May the Wine Festival and December has the Christmas Stroll.

Getting There

You can fly from Boston or Hyannis to Nantucket anytime, and during the season from other airports like Newark. Most take the ferry from Hyannis, MA. Both the Steamship Authority and Hy-Line Cruises have a regular and a fast ferry. The regular ferry takes about two hours, the fast, one hour. Steamship can also take your car over, but you need reservations well in advance, particularly in-season.

I prefer to take the regular ferry, it helps to unwind for the trip. There is a snack bar and bar aboard, ample seating both inside and outside and the top deck is ideal for soaking in the sun and curling up with your first book of the vacation. Get to Hyannis a little early and enjoy lunch at Baxter’s Fish and Chips, right on the water, next to the Steamship Authority dock.

Nantucket is also accessible by private boat with some of the finest marina and mooring facilities on the East Coast, for boats of any size.

Getting Around

You do not need a car on Nantucket as much of the activity is centered around the town and everything is within walking distance. Shuttle service is available and very reliable for going to other parts of the island or you could rent a bike or moped from Young’s for a day or week. Cars and jeeps are also available for rental. We found Nantucket Windmill (800-228-1227) to have the best prices for jeeps. 4-wheel drive vehicles are allowed on some beaches, so, even if for a day, a jeep rental can be fun.

I like to take my car when staying more than a few days, it allows me to explore the island, drive to my favorite beach and after about three days is less expensive (ferry is @$400 round trip) than renting on the island ($125+ per day)

Things To Do

If you have come to relax and read a book, 82 miles of beaches will do the trick, some secluded, some more populated, all beautiful. Want to be more active? There is plenty to do. For golfers Nantucket boasts two wonderful links type courses; for tennis players, courts at many hotels/inns and for bikers, miles of bike paths crisscrossing the island. You can rent powerboats and sail boats and charter a fishing boat or simply enjoy a ride while someone else does the work. There are museums and tours extolling the rich history of the island and when all else fails there is shopping in the dozens of quaint and unique shops in town. For collectors or just browsers, there are wonderful art galleries and antique stores.


Nantucket enjoys nearly 80 miles of beach with 10 individual beach areas. Some have lifeguards, restroom facilities, playgrounds and snack bars, some are just a secluded beach tucked away in a corner of the island. Roughness of the surf varies by the location on the island. For a beach with all the facilities, I like Surfside Beach, but Miacomet (also known as the “Fat Ladies Beach”) is my real favorite and the one the locals favor. Unspoiled, private, stretching for miles. Sometimes you never see another person. Stop at Bartlett Farms on the way and pick up lunch. On the way back drop in to Cisco Brewers on Bartlett Farms Road for a little “taste”.

In August/September, a nighttime dip at Steps Beach, swimming in the phosphorescence, is pretty incredible. Steps is also right next to Galley Beach one of our favorite restaurants and a great spot for lunch.


Miacomet Golf Club and Sconset Golf Club are links-type courses open to the public.. Sankaty Head, my favorite course, is private, but open to the public in the off season.


Most of the tennis facilities are part of hotels or resorts; however there are public courts at Jetties Beach.


There are miles of bike paths crisscrossing the Island that offer a wonderful opportunity to enjoy the Island’s beauty. Young’s. Broad Street at the Wharf is my choice for bike rentals. Been renting here since we carted our kids around in bicycle rickshaws. Hate to think how long ago that was.

Boat Rental

Island Boat Rentals rents small Boston Whalers for fishing or cruising. Slip 1, Straight Wharf. From $550.

Boat Rides

Try Endeavor Sailing Adventures for a bit of maritime history along the shores of the island. Best trip is the one at sunset ($35 for 1 1⁄2 hours). Shearwater Excursions offers whale watching, seal cruises and eco tours on a clean 49 passenger boat. Editor’s Pick from Yankee Magazine.


Sea Nantucket, Francis Street Beach. Half and full day rentals. Great way to explore the beaches and coves. Pack a lunch and your camera.


Capt Tom’s is the choice for charter fishing, he’s been featured on Field & Stream legends, This Old House and has won the John Havelicek Celebrity Fishing Tournament 11 of the last 14 years. Another good choice is Captain Pete Sheppard of Rusty Fly, particularly for shallow water and fly fishing. There is an abundance of fish off-shore and I have literally seen so many fish that the fishermen couldn’t pull them in fast enough


Gail’s Tours. (508-257-6557). Personal scenic tours of the Island. Voted Best of Nantucket. 10, 1, 3 pm departures. 1 1⁄2 hour tour. Nantucket Ghost Tour Mon/Wed/Fri/Sat/Sun 7pm. Opposite Jared Coffin House. No reservations necessary.

Pick up a copy of Nantucket Historic Walking Tour, a self guided exploration of Nantucket’s history and architectural heritage, presented by the Chamber of Commerce.

There are about a dozen museums on the island, but the one not to miss is the re-opened Whaling Museum, on Broad, downtown.


Some favorites; Antiques; Sylvia, Antique Depot, Rafael Osona Saturday antique auction at the American Legion, Nantucket Country Antiques, Lynda Willauer Antiques.

Galleries: Pierce Galleries, Dane Gallery, Quidley & Co.


Nantucket is filled with wonderful shops and boutiques, many very unique to the Island. Click here for a listing.


AprilDaffodil Festival
MayNantucket Wine Festival; Figawi Boat Race
JuneNantucket Film Festival
July – 4th Celebration;  Annual Green Thumb Flower Show
August – Annual Antique Show
September – Island Fair at Tom Nevers Park
October – Nantucket Arts Festival; Annual Chowder Contest
DecemberChristmas Stroll

Dont Miss

  • Early morning at Surfside Beach
  • A Turkey Terrific sandwich from Provisions
  • View from the First Congregational Church
  • A day at Miacomet Beach
  • Lunch by the harbor at Brant Point Inn
  • An afternoon of music, great beer and cocktails at Cisco
  • A jeep ride among the dunes at Great Point
  • Dinner at Topper’s
  • Show tunes at the Club Car

The Best Of...

Want to get the inside scoop on the island before you get there? here’s the local newspapers: Inquirer and Mirror, and Yesterday’s Island. You can also access the Nantucket Chamber of Commerce and Nantucket’s On-Line Guide.



Virtually all lodging offers breakfast, but should you decide to venture out, here’s our favorites.Top choice is Island Kitchen. Eat inside or out. Cocktails. Turkey hash is amazing. Sit beside the harbor at Brant Point Grill. Try Marcia’s Vanilla Bean and Challah French Toast. or, The Whale has excellent food and a wonderful outdoor patio with tables and umbrella’s. Fantastic buttermilk biscuits.


There are lots of great choices. On the Harbor Cru at the end of Straight Wharf. Eat outside on the Harbor, inside or a combination in the bar where all the walls open onto the water. Excellent fresh fish sandwiches. Brant Point Grill at the White Elephant Hotel. Dine on the patio overlooking the Harbor. Upscale, more expensive. Excellent food. On the Sound Topper’s at the Wauwinet Hotel is one of my favorites for a leisurely and spectacular lunch. Best wine list around. Wonderful $24 lunch. Amazing burger. On the Sound. Make the trek to the Summer House in the charming village of Sconset for a delightful ocean side lunch. Wonderful setting among the dunes. One of our favorites for lunch or dinner, the Galley Beach restaurant, sits right on the beach east of town. The elegant Chanticleer in Sconet has a beautiful rose garden, perfect for a balmy day. Delicious French bistro food. In town, our choice is the Brotherhood of Thieves. They have added a sit down bar, there are fireplaces to warm you and the food (great pizza and burgers) is wonderful pub food. Now with an outside patio. If you like fresh fish sandwiches, the Straight Wharf Fish store has tuna,  swordfish, fillet and soft shell crab sandwiches and delicious 1/2 lb. lobster rolls.


The best traditional burger in town is at the Brotherhood of Thieves at 23 Broad St. plump, juicy with just a slight charbroil crust. But if you really want a treat, the burger at Topper’s at the Wauwinet Inn, just may be the best I have ever had. Made with Kobe beef, short ribs, caramelized onion and capers, this takes the burger to a whole new level and at $25, it’s a bargain compared to the similar burger in NYC at $100.


Tuna Martini at The Pearl. This appetizer is legendary and even if you are not a sushi eater, it’s not to be missed.

Oyster Bar

Hard to top Cru for its location on Straight Wharf, fresh oysters and a very good wine list, albeit very pricey. Always our first stop off the boat.

Afterhouse Seafood & Wine Bar. Oysters, shrimp, chilled lobster, sardines, cheese platter, sushi and more. Great afternoon stop. Fantastic wine selection with many premium wines by the glass. How about a Chateau Figeac, Grand Cru Classe, Saint-Emilion, FRA 2005 at $115 by the Glass?

Wine Bar

These restaurants have a good “by the glass” selection of wines; Brant Point Grill, Straight Wharf, Oran Mor, La Languedoc and Topper’s.  Topper’s is the recipient of Wine Spectator’s Grand Award.


Sit in Adirondack chairs overlooking the Harbor at the Brant Point Grill, stop at Ventuno’s, where the locals drink, at least the affluent ones, and have Johnny B or Jess make you the best dirty martini in town, make your way to Town a local’s favorite with some creative drink selections at the outside Tree Bar and the Ships’ Inn has some wonderful fruit martini’s. Prime at the Jared Coffin House has a stylish lounge and an outside bar and lounge. After dinner try the Espresso Martini at The Pearl or Johnny B’s famous lemon meringue martini with a gram crust rim at Ventuno’s.

Shopping & Activities


Sail Endeavor is a wonderful old Friendship sloop that offers sunset sails each day for $60 per person. Leaving from the Staight Wharf, the boat sails along the coast for the 1 1/2 hour sail. Pack some cheese and crackers, a bottle of wine and a blanket and head for Madaket Beach. Sunsets don/t get any better than this.even in Key West! See Special Things below. Add a sunset to your dinner plans by eating at the Galley Beach restaurant. Arrive early, get a cocktail and sit outside right on the beach.


Cisco Brewers/Nantucket Wines/Triple 8 Distillery, all located in the same complex on Bartlett Farm Road offer beer, wine and cocktails, live music, food trucks and is dog friendly. Lots of fun to taste things that are not on the market yet. You’ll also meet lots of great people out there. This is a must for any visit to Nantucket.

After Dinner Fun

Stop in at the Club Car bar (it’s an authentic old rail club car) on Main Street where there is a nightly piano player, leading the crowd in show tunes. Great fun. If you want something a little more lively with a younger crowd, the Muse on Surfside Road, The Bamboo Supper Club on Chin’s Way and the Chicken Box on Dave have dancing and live music.

While Away a Rainy Day

The Boarding House. When it’s open. Doors open to the street. Great Bloody Marys. Good food. Brotherhood of Thieves. In town. Great pub food. Dark and comfy bar.  Kitty Murtagh’s, pool tables, darts, Guinness and good pub food….what else is there?

Morning Paper

The Hub. Main Street. Opens at 7:30am. Boston and NYC papers.

Wine & Cheese Shop

Epernay has a good wine and cheese selection. Brix Wine Shop is another good choice.

Picnic Fixins

Provisions at the Straight Wharf. Homemade breads, muffins and cookies, wonderful specialty sandwiches, Cape Cod chips and Nantucket Nectars.I love the Turkey Terrific with turkey, dressing and cranberry sauce.


If you are planning to eat at home or perhaps to BBQ on the beach, Cowboys, Bayberry Court, is the place for great meats and other items. Pretty cool store. For fresh seafood, it’s worth the trek to East Coast Seafood, also known as 167 Seafood, at 167 Hummock Pond Road. It’s clean, the fish is fresh, (there’s even a sign that if you ask, you have to go to the back of the line.) I never miss the harpoon caught swordfish.

Sweet Tooth

Aunt Leah’s Fudge. 34 flavors. Chocolate covered cranberries. Best fudge Cape Cod Life. Main Street.


Nantucket Health Club. Young’s Way. The Island’s only full service health club.


Special Things

Start the Day

On a clear day, around 7:15am, stop in town and pick up a cup of coffee and a donut at the Even Keel and a newspaper at The Hub, then drive out Surfside Road toward Surfside Beach. Take a left at the last road before the beach parking lot and go to the end of the road. The rising sun splashes over the length of a long expanse of beach and dunes and there is no more beautiful way to start the day.

The Best Picnic

Rent a jeep from Nantucket Windmill and stop at Provisions at the Straight Wharf and pick up lunch. Try their famous smoked turkey, Thanksgiving dressing and cranberry sauce on Portuguese bread, Cape Cod chips and a Nantucket Nectar. I wait for this every year. Drive out to Wauwinet at the northeastern part of the island for access to the beach leading to Great Point. You’ll drive through dunes leading to the beach and then will be able to drive for miles, literally a few feet from the surf. Park in a little cove and enjoy a magnificent day. The perfect picnic!

Lunch at the Chanticleer

For years The Chanticleer was the favorite restaurant of people with summer homes. Formal, French, with a great wine list and white jacketed waiters, it was a must for every visit. I have always enjoyed it for a wonderful lunch in the rose garden. A few years back the long-time owner sold it and it sat vacant for a time before the owners of the popular Black Eyed Susan’s bought it and turned it into a delightful French bistro with a more casual feel.

Sunset Clambake

Madaket Beach is the place for wonderful sunsets. Stop at the Nantucket Lobster Trap on Washington Street and they’ll prepare a complete Clambake for two with everything except the wine and a blanket. Find a private spot on the beach and enjoy a glorious sunset and a delicious lobster dinner.

End of Year Nantucket Fix

Long about November when you’re dreaming about your time in Nantucket, think about one last trip. The season officially ends with the magical Christmas Stroll, held the first week in December. 150 Christmas trees adorn the town and coupled with the gas lamps and cobblestone streets the feeling is of an era long gone by. The wafting smell of chimney smoke, the sounds of caroling and the holiday conviviality make for a very special weekend. Book well in advance, this event draws as many visitors as the summer months.

Where To Stay

Cliffside Beach Club

OVERVIEW of the Cliffside Beach Club

Begun as a private beach, The Cliffside Beach Club became a private club in 1949 where the same members returned year after year to get the same locker, the same umbrella and the same spot on the beach. The Currie Family bought the Club in 1959 and in…

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Nantucket Hotel

OVERVIEW of the Nantucket Hotel

A few years back, the Snider family purchased the old Point Breeze Hotel (circa 1891), poured a ton of money into a complete renovation and the result is the wonderful, family friendly Nantucket Hotel + Resort. Properties are run better when the owners are also the operators and The…

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Sherburne Inn


OVERVIEW at The Sherburne inn

The words elegant, gracious and tranquil aptly describe this beautiful year round inn, just a block from the center of town. The first thing you notice as you approach the Sherburne Inn is the meticulously manicured lawn and the beautiful rear gardens surrounding an intimate setting of Adirondack chairs.…

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The Wauwinet

OVERVIEW of The Wauwinet

An acclaimed Relais & Chateau property (the only one on Nantucket), the Wauwinet is located about 9 miles from town at the northeastern part of the island and if you like inn accommodations, this would have to top any list. The rooms…

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Union Street Inn


OVERVIEW of The Union Street Inn

Union Street Inn, the only one of our Featured Properties in Nantucket to actually be in-town, is a beautiful circa 1770 inn with wide plank pine floors and 12 luxuriously appointed, guest rooms. Exquisitely maintained and gorgeously decorated, the rooms here (6 have working fireplaces) are among the…

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White Elephant Hotel

OVERVIEW of White Elephant Hotel

Minutes from the center of town and sitting on the edge of the harbor is the elegant White Elephant Hotel, a sophisticated luxury hotel with 53 guest rooms and suites and 11 garden cottages. Personal service, as evidenced by the high staff to guest ratio, is important here and…

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Where To Eat

Company of the Cauldron

I couldn't write a better description of Company of the Cauldron than Malcom A. Willson of Cape Cod Times. "This little Nantucket restaurant has charm written all over it -- from its dark red, ivy-framed, single-story front, pierced by small-paned windows, to its darkly handsome, romantic-as-a-novel interior. The inside's post-and-beam and rough plaster construction seems…

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Galley Beach

Galley Beach is our final night tradition during our stay on the island. It is the best combination of food, ambiance and service on the island. What makes it particularly fun is that everyone seems to know everyone, or you do by the time dinner is over. One night Stiller and Meara sat at one…

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Le Languedoc Bistro

We never miss Le Languedoc Bistro when we are on the island. Eating at the downstairs bar is like coming home to friends. Give me steak frites and a good bottle of red and my trip is complete. There are a number of dining choices here; outside on the terrace, downstairs in the intimate cafe…

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Lola 41

Lola 41, The "41" in the name represents the 41st parallel on which Nantucket sits as well as other influences in the kitchen; Spain, Italy, Greece, China and Japan. They call themselves a "global bistro", I call them just plain fun. This is a "hot" spot on the island, busy every night. Housed in the…

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Oran Mor Bistro

Two friends, Chef Edwin Claflin and Jon Tancinco, who met in culinary school, took over the reins of this island institution in 2016. Oran Mor  has been an island favorite from the time Peter Wallace opened it and Chris Freeman continued the tradition. The transition has been seemless and the restaurant remains an island favorite.…

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It's easy to miss Queequeg's as you walk around town as it is tucked away on a small street, but not if you talk to the local's. It's one of the favorites, both for great food and reasonable prices. Inside, the small, intimate dining room is cozy and comfortable and decorated with faux finished rust…

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Straight Wharf

Straight Wharf is one of the most romantic restaurants on the island and when coupled with its wonderful food, it's the perfect "special occasion" restaurant. Located right on the wharf overlooking the Harbor, you can dine under the stars in good weather or enjoy the view through large paned windows from inside. The interior has…

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The Boarding House

When I want an excellent meal, but something a little less formal, I head to the Boarding House. You have three choices on where to eat; in the romantic candlelit wine cellar, on the patio or at the lively bar. Weather permitting, I like to eat outside and do a little people watching. This is…

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Topper's is our go-to restaurant for a special occasion dinner or a delicious, luxurious lunch overlooking the Great Lawn and Nantucket Sound. The dining room is the most refined on the island. White raised panel walls adorned with softly lit oil paintings, wall sconces, plaid fabric covered chairs, crisp linens, candles, fresh flowers, fireplaces and…

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Ventuno is housed in a beautiful Greek Revivalist building (the former 21 Federal) in the heart of downtown and is run by the folks who own Straight Wharf, another dining "institution" on the Island. The restaurant has a cozy wood paneled bar that is a lively gathering place for locals and the dining rooms are…

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