Drop anchor in these revitalized port cities

Under $250 a day

Where
Portland, Maine

Why
While its seal—a phoenix rising out of the ashes—originally symbolized the city's recovery from a devastating fire in 1866, it could also refer to Portland's recent rebirth as a hot spot for young professionals, as well as cultural attractions like the Portland Museum of Art. Adding to the charm, the city's waterfront has retained its industrial character, and nearly all of the shops along the brick and cobblestoned streets are independently owned.

Room
Built in1885 as an armory, the Portland Regency celebrates its age with dark wood paneling and historic maps and photos, but gives a nod to the new with a well-equipped gym and spa. Standard-priced double rooms numbered from 330 to 338 have high ceilings and more light (800-727-3436; theregency.com; doubles, $149).

Lunch & Dinner
At Duck Fat, order Belgian-style frites with a side of truffle ketchup. Paninis are just as tasty, especially the BLT with goat cheese and applewood smoked bacon (43 Middle St.; 207-774-8080; entrées, $6–$9). The seafood shines at Street and Co., a cozy spot with copper-topped tables and an open kitchen (33 Wharf St.; 207-775-0887; entrées, $16–$25).

Tip
Board the Casco Bay Ferry for the 15-minute ride to Peaks Island, where you can bike the four-mile perimeter road or take a half-day kayaking trip past forts, lazing seals, and hidden beaches with the Maine Island Kayak Company (207-766-2373; maineislandkayak.com; trips, $65).

Under $300 a day

Where
Naples, Italy

Why
This often chaotic but always exciting ancient port city offers up striking architecture and good eats. The Museo Archeologico Nazionale is stuffed with some of Pompeii's and Herculaneum's most important finds (19 Piazza Museo; marketplace.it/museo.nazionale). Reserve an afternoon to wander the backstreets of Spaccanapoli, the city's main thoroughfare: As laundry flutters from dilapidated balconies and couples stroll arm in arm, you'll feel like you were transported to a 1950s Italian film set.

Room
A gem of a guesthouse tucked away in the historic palazzo of San Teodoro, in the chic Riviera di Chiaia district, the three-room Riviera 281 mixes modern with classic—polished concrete floors and bright-red walls, velvet settees and chandeliers. Splurge for the suite (39-081-764-1427; riviera281.it; doubles, $193; suite, $238).