Brunch was a steal—which gives me an excuse to do some shopping. I pop into the Francophile L’lle de France (8 India St.; 508/228-3686), where I eye the steel Cellar Rat candlesticks and a collection of handpainted fleur-de-lis place settings before moving on. At Gypsy (20 Federal St.; 508/228-4404), the Chloé lace blouses and Dsquared2 wool caps are tempting but not within the budget. (A girl can still look, right?) My luck improves at Eye of the Needle (14 Federal St.; 508/228-1923), where I pick up a jeweled Blue Angel T-shirt ($18) marked down from $75.
Sweets are my weakness, so I rationalize a single (okay, double) scoop of butter pecan ice cream ($3) at the nearby Juice Bar (12 Broad St.; 508/228-5799). My cone is so delicious, I begin to wonder if anyone actually orders juice here. I consider a jar of beach plum jam ($5.95), an island favorite, at Nantucket Gourmet (4 India St.; 508/228-4353) but decide to save my money for dinner.
It’s almost sunset, so a 90-minute sail ($35) around the harbor on the 14-seat Endeavor (508/228-5585), which is docked at Straight Wharf, is just the thing. Since it’s BYO for cocktails and food, I decide to cater my own dinner at sea with a split of Korbel champagne ($9.95) from Nantucket Wine & Spirits (31 Sparks Ave.; 508/228-1136) and a lobster roll ($16.75) from the gourmet deli Straight Wharf Fish Store (4 Harbor Square; 508/228-1095).
Maybe it’s the champagne, or maybe it’s the rocking boat—either way, I’m exhausted when I get back onto dry land. "Meet me for a drink," pleads Alexandra, who is on her way to the Nantucket Lobster Trap (23 Washington St.; 508/228-4200). "I’m buying," she says. Suddenly, I get a second wind, which is fortunate since finding the restaurant takes a little longer than expected. My map is missing (did it go overboard?), so I circle the town, lost.
Two blocks south of Main Street, I spot the red door of the Nantucket Lobster Trap. Relieved, I step inside to find Alexandra waiting. We order Elbow Benders, the house drink, made with fruit juices, rum, Cherry Heering, and a secret ingredient that gives it a delicious kick. When I add up my tally for the day, I discover that I have enough (well, almost enough) to buy us an order of Nantucket oysters ($14 for six)—served from the raw bar with nothing more than lemon as punctuation. Now I can call it a night.