Boston Smart Splurges

Fronted by one of the most recognizable hotel facades in the city, the Boston Harbor Hotel's arched entranceway is entirely elegant, with the awaiting reception pleasantly devoid of stuffiness. Whether opting for a room with city views or of sailboats gliding by on the harbor, guests may very well be tempted to just sit tight and enjoy the luxury of this 230-room waterfront property. Onsite hotspots to encourage lingering include the contemporary American Meritage restaurant, where sophisticated presentation and incredible taste are married on every plate, as well as The Spa at Rowes Wharf, with its heated lap pool and eight types of massages on the menu. Amenities include twice-daily maid service, choice of daily newspaper, and complimentary chauffeur service within Boston.

The pioneer of Boston’s boutique-hotel boom is the city’s go-to address for luxury-lovers who like their hotels on the smaller, more personal side, but don’t want to sacrifice extravagant extras common to larger properties. Guests here can expect to be treated, with services like complimentary chauffeur-driven Lexus sedans on hand to jet them around downtown. All of the rooms have an at-home feel (if you live in, well, the coolest house in your neighborhood), with fireplaces, flat-screen TVs, and remote-controlled everything (seriously). Anybody who really wants to feel like they own the place should book a night in a suite and invite friends over for a dinner catered by Mooo, the restaurant's steakhouse.

Boston’s long-defunct Charles Street Jail, built in 1851, was reborn in summer 2007 as The Liberty Hotel, a 298-room luxury property with interiors partially designed by Alexandra Champalimaud, the A-list designer behind New York’s Algonquin, Pierre, and Carlyle hotels. Situated at the foot of Beacon Hill, the stone cruciform building – which retains its historic catwalks and 90-foot central rotunda – is joined by a new, 16-story tower housing the majority of guestrooms. Indulge in guilty pleasures in preserved cells at the lobby’s “jail” bar, then relax in rooms with touch-screen VOIP phones, flatscreen TVs, and views of the bustling Charles River. Booked elsewhere? Drop by The Liberty Hotel anyway – the soaring lobby is a Boston destination in its own right.

Gabriel Bremer (owner and chef) and his wife welcome guests into their cozy Cambridge bistro as...more

This elegant, white-tablecloth eatery located on upscale Commonwealth Avenue takes its direction...more

Become a New England fisherman, at least for a day, under the expert care of businessman-turned-captain George B. Whitehead, who teaches fishing in the 50-square miles of the Boston Harbor. Both experts and first timers will appreciate his knowledge of the area’s hotspots. With six hours at sea, you’re sure to catch a few stripers and bluefish.

Co-author of The Elephant Walk Cookbook, Longteine "Nyep" de Monteiro, teaches weekly three-hour cooking classes at The Elephant Walk Restaurant. Students get a crash course in making spring rolls or in Cambodian-style grilling before dining at the restaurant. Sign up early as Nyep’s expertise is in high demand and classes sell out quickly. Classes take place on Saturdays from 10:30am-1:30pm.