21 FEDERAL   LE LANGUEDOC    THE GALLEY RESTAURANT
CHANTICLEER INN   THE SUMMER HOUSE RESTAURANT
HENRY'S SANDWICH SHOP   SOMETHING NATURAL
BLACK-EYED SUSAN'S   ESPRESSO CAFE


DEBBIE DOES DINNER

21 FEDERAL
21 FEDERAL STREET, NANTUCKET
(508) 228-2121
21 Federal is a Nantucket institution. This cozy historic colonial home is always packed on weekends with investment bankers and preppy wasps with trust funds. To fit in men just need to show up in a pair of those classic Nantucket Reds and women: your best strand of pearls and a little black dress should do the trick. The food is pricey but good. Go to see and be seen. The bar is always buzzing so sit in the front room for best views. Reservations are a must.
LE LANGUEDOC
24 BROAD STREET, NANTUCKET
(508) 228-2552
Le Languedoc offers fabulous country French food in a charming old inn. You will have one of the best dinners on the island without a doubt. Order the Lobster entrée. It melts in your mouth. Relaxed elegance without the stuffiness.
THE GALLEY RESTAURANT
54 JEFFERSON AVENUE, NANTUCKET
(508) 228-9641
View from the Galley Restaurant
You know the old saying in real estate, "nothing maters more than location, location, location!" Well the Galley has one of the best locations on the Island. It is right ON the sand next to The Cliffside Beach Club on Cliffside Beach. But don’t let the sand fool ya. This is one swanky spot and a favorite amongst the spiffy local summer crowd. Lunch offers a more "casual" setting with positively fab views of the sea. The Lobster Salad Sandwich wasn’t so great but that didn’t really matter. It’s all about the views here, kids.

Dinner is candles, romance and a very chic crowd. Geoffrey and David Silva are the charming "operators" of this popular spot. If you are in town for the fourth of July, this is the only place to be. The fireworks are set off right in front of the restaurant! Be sure to tell Dave that "Debbie" sent you if you happen to pop in. But darlings, don’t embarrass me! Remember to dress the part: a vintage Lilly Pulitzer number is a must.
CHANTICLEER INN
9 NEW STREET, SIASCONSET
(508) 257-4154
If you are planning on proposing marriage anytime soon, run, don’t walk to the Chanticleer Inn. This is the ultimate romantic restaurant and home to many successful proposals! Be prepared to fork over the dough for the right to dine on such French delicacies as frog’s legs and a 1959 Chateau Margeaux. Siasconset is a good seven miles from the downtown Nantucket so if you plan on finishing that bottle of Margeaux, take a taxi back to your hotel…unless you are staying at the wonderful Summer House around the corner.


DEBBIE DOES LUNCH

THE SUMMER HOUSE RESTAURANT
17 OCEAN AVENUE, SIASCONSET
(508) 257-4577
This beach side/poolside restaurant gets debbie’s vote for top lunch spot on the island. What a set up! Between the funky poolside bar that rocks all day long, the beach chic restaurant crowd and the ocean to dabble your toes in…what more do you need? Close your eyes and you may even think you are in St. Barths! A perfect place to spend the day. The Summer House personifies everything that is truly wonderful about Nantucket. If you have one day on the island, then grab a bike, a taxi or a bus and head on out to Siasconset and The Summer House! Be sure to bring your favorite batik sarong to wrap around your suit and a straw hat for the sun. And if you forgot to pack to pack the wrap…no worries. The Eye of the Needle Boutique has a second shop right next to the pool bar. Eat, drink, shop and swim…God, we just love convenience!
HENRY’S SANDWICH SHOP
STEAMSHIP WHARF, NANTUCKET
(508) 228-0123
A wildly popular and very basic sandwich shop that happens to serve the best Lobster Rolls on the Island. Large chunks of sweet, fresh lobster ooze out of a freshly baked bun. Heaven. All this for about nine bucks! Such a deal!
SOMETHING NATURAL
50 CLIFF ROAD, NANTUCKET
(508) 228-0504
Screw the sandwiches…it’s all about the cookies. Grown men fight for them, groveling to take home piles of moist cookies. What? They don’t sell Chocolate Chip cookies in the City? Not like these, baby.


DEBBIE GETS A BUZZ…MORNING BREAKFAST SCENES

BLACK-EYED SUSAN’S
10 INDIA STREET, NANTUCKET
DAILY 7 is to 1 p.m.
Huevos Rancheros, Corned Beef Hash and Sourdough French Toast are all part of Black-Eye Susan’s breakfast specials. Cheap and easy is the deal here. The hot looking patrons are a bonus. Expect a wait for a table. Word has it that they do a great dinner here too.
ESPRESSO CAFÉ
40 MAIN STREET, NANTUCKET
(508) 228-6933
Check out the hung over preppy crowd lined up waiting to order their café lattes and iced coffees. Take yours to go or grab a table in the garden out back!








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