Portland was first settled in 1632, and in spite of two devastating fires that destroyed early landmarks, it retains the character etched upon it over its centuries of existence as a thriving commercial port. Today, history is well preserved in Portland, but this is also a thoroughly hip city — home to sophisticated hotels, coffee nooks, brewpubs, swank shops, ethnic eateries, a minor league baseball team, and world-class entertainment. Portland remains New England's largest tonnage seaport, and it is also emerging as a cruise ship destination, with more than 40,000 passengers exploring the port city each year.

Freeport, a town synonymous with shopping, is located a short drive north of Portland. Since venerable Maine retailer L. L. Bean set up shop here in 1917, the town has mushroomed into a retail bonanza of designer outlets and specialty stores selling everything from home furnishings and apparel to Maine-made products and mooselania. It was also in Freeport that Maine citizens contemplated a revolution in the early 1800s. Mainers were seeking their independence not from Britain but from governance by Massachusetts. In 1819, Massachusetts gave Maine the go-ahead to petition for statehood, and in 1820, Maine became the last New England state to join the Union.

Southern Maine is home to the state's two oldest towns — Kittery and York — but it isn't history that lures hordes of travelers to the region. This part of Maine, unlike the far northern reaches, is close to the rest of New England, and it's also an area that most Maine visitors must traverse on their way to more remote destinations. Of course, many vacationers never get much farther than the south shore once they discover the allure of outlet stores, cozy harbors, coastal towns, and beaches.

Of course, southern Maine isn't exactly the most tropical place. Ocean temperatures may make you say, “Brr!” even in July and August, so the peak season in this waterside destination is a bit abbreviated. On the flip side, if you plan your vacation for the off-season, you're likely to find lodging deals and to feel as if you have the place largely to yourself. That is, until you make your obligatory stop at the legendary outlets in Kittery, where bargain hunting is always in season.