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Connected to the mainland via an earthen causeway and crowned by the c.1851 Fort Independence, Castle Island is New England’s oldest continually fortified site (see Pleasure Bay). Aside from exploring the fort’s bunkers and tunnels, visitors can take in fine panoramic views of Boston Harbor.

Jamaica Plain is home to many artists, musicians, and writers as well as a substantial contingent of Boston’s gay and lesbian community. Centre Street is the area’s main artery and hub. There is a distinctly Latin American flavor at the Jackson Square end, where Caribbean music shops and Cuban, Dominican, and Mexican eateries abound. At the 600 block, Centre Street morphs into an urban counter-cultural village, with design boutiques, funky second-hand stores, and small cafés and restaurants.

A popular choice for business travelers on a budget, this 56-room hotel in the South End is a short walk from Back Bay “T”. Rooms are simple and comfy with TVs and phones with voice mail.

Extra touches, such as handmade quilts hanging on the walls, personalize the surprisingly comfortable rooms at this modern hotel on the edge of Harvard Square. There’s an indoor pool, an outstanding jazz club, Reggatabar (see Regattabar), and a leading Boston restaurant, Rialto (see Rialto).

The Charles River Dam controls water levels in the basin below and maintains separation of the river from the harbor. An ingenious series of locks permit boats to pass from one body of water to the other. Call for tour schedule.

Charm abounds on this bluest of blue-blooded street, which is studded with antique dealers (see Antiques at 99 Charles), specialty grocers, and modern houseware boutiques. Come nightfall, wrought-iron gaslamps illuminate the brick sidewalks, residents hurry home with wine and fresh flowers, and sleek bistros buzz with excitement.

Carved marble fireplaces, Victorian furniture, and some of the finest linens in town give the nine rooms in this Beacon Hill hideaway a feeling of sumptuous luxury. High-speed Internet, mini-fridges, and stereos provide the finishing touches.

Set in an 1892 Back Bay townhouse, the 33 rooms of this boutique hotel feature custom-made furniture, light-toned woodwork, and Italian tiles. Breakfast is included in the astonishingly low (for the area) rates.

Splendid harbor and Downtown vistas.