The place: Portugal

It's a poor man's: Italy

The financial analysis: Yes, it's on the euro, which is bad news for us poor saps getting paid in dollars. But Portugal is still a cheaper option than almost any place in western Europe, partly because it hasn't seen the economic boom of the likes of Ireland, nor the tourist hordes of Italy or Spain. Once you arrive, spend a few days in Lisbon, then drive north to the coastal city of Porto. Portugal's laid-back second city is filled with old-world charm, fantastic port wine, and cheap fun.

Price of a beer: Who cares? Port is what you'll drink here, and a glass of the same sweet, silken wine that would set you back $12 in Madrid or $16 in London will cost only about $7 in most of Porto's bars and restaurants.

What to do: Music aficionados and architecture fans alike will enjoy the Casa da Música, Porto's concert hall, designed by Dutch architect Rem Koolhaas. Construction was completed three years ago, and the result—a giant, misshapen box—will make you feel like you've had one too many glasses of 20-year-old tawny. Average tickets are around $22, and you can see everything from classical symphonies to jazz musicians like Dhafer Youssef.

Hotel: Ten minutes from central Porto is the Castelo Santa Catarina, a 25-room villa built in the late 1800s. What it lacks in flat-screen TVs and iPod docks it makes up for in antique furnishings, impressive tile mosaics, and an outdoor patio filled with flowers and palms. Doubles start at a super-affordable $75 a night.

Cheap eats: Taverna dos Bêbobos is the oldest (founded in 1876) and smallest (really, really small) restaurant in a town where age and tininess are points of pride. Set on a dock overlooking the Douro River, the Taverna has a view as appealing as its Portuguese specialties: grilled sardines, cod with béchamel, and fresh fish from the waters just outside. Many entrées run less than $10, and the restaurant's name translates as "Tavern of Drunks," so you're covered in the wine department.

How to get there: Try TAP, the Portuguese airline—its fares tend to be cheaper than the American carriers, and even its business class prices can offer splurge-worthy savings.

Casa da Música
Tel: 351 220 120 220

Castelo Santa Catarina
Tel: 351 225 095 599

Taverna dos Bêbobos
21-25 Cais da Ribiera