This small maritime city—the Pine Tree State's largest—has plenty of main attractions: a lively waterfront, hip shops and galleries, and a celebrated culinary scene. (Not to mention the lighthouses, the lobsters, and L.L.Bean.) Before you pack your windbreaker, tell us more about you.

For the best views on Portland's peninsula, go east—as far as you can go—to the Eastern Promenade, a 68-acre park overlooking Casco Bay. Farther south (5 miles from downtown) stands the white-stuccoed Portland Head Light, the state's oldest lighthouse and one of the country's most photographed. Explore the tower's grounds and the adjacent Fort Williams Park as you hunt for the optimal angle from which to snap your own postcard-worthy pic. Want to get even closer to the water? Reserve a spot on Casco Bay Lines' mailboat for a three-hour boat that delivers loads of cargo—and scenic vistas.

Inn by the Sea:

Pair a decadent dinner with ocean views at the on-site restaurant before kicking back in a luxe cottage at this Cape Elizabeth spread.

Portland Harbor Hotel:

Looking for location and comfort? This Old Port gem, just a stone's throw from the historic waterfront oozes elegance in all 101 rooms.

Black Point Inn:

Choose from ocean or bay views at this high-end Prouts Neck hotel, which offers kayak, bike, and fishing equipment rentals.

Cross-country skiing:

Carter's X-C Ski Center in Oxford, an hour north, boasts 25 miles of New England’s best beginner and intermediate trails. 

Snowshoeing: 

Make fresh tracks in untouched snow during a guided trek offered by L.L.Bean Outdoor Discovery Schools. 

Hiking: 

Traipse through diverse ecosystems in southern coastal Maine on 7 miles of trails at Wells Reserve at Laudholm.

Holiday shopping list looming large? Cross off a few items as you wind through the cobbled lanes and handsome brick facades of Old Port, a six-block stretch of locally owned antique shops, art galleries, clothing stores, and restaurants (for mid-spree refueling). A few favorite finds: Kazeem Lawal's impeccable mix of modern duds and vintage home goods at Portland Trading Co.; Angela Adams' nature-inspired collection of area rugs and interior furnishings; and Pinecone+Chickadee's handmade crafts, hand-printed tees, and otherwise quirky curiosities.

Heron Point Gallery:

Bonnie Faulkner uses Maine color palettes in her striking fused-glass mandalas.

Lisa-Marie’s Made in Maine:

Support local craftsmen at this family-run boutique showcasing the works of more than 400 of the state's top artisans.

Edgecomb Potters:

Take home a handmade mug, vase, platter, or pie plate from this Commercial Street staple. 

L.L.Bean:

The outdoor apparel and equipment retailer's first and largest store stays open 24/7/365 for all your flannel needs.

Portland Flea-for-All:

On weekends, peruse this two-story, indoor market in Bayside for vintage vinyl, jewelry, clothing, and more.

EcoHome Studio:

Make your place a little greener (no, not the hue) with eco-friendly furnishings from this Oakdale home store.

Oysters from the Gulf of Maine, sea rocket from forager Evan Strusinski, and pasture-raised lamb from North Star Sheep Farm just 16 miles away. With access to this caliber of ingredients, restaurants like Hugo’s are providing farm-to-table fiends with ample dinner options. The best of the best? Fore Street, where chef-partner Sam Hayward has been recognized for his sustainability efforts (and charcuterie boards); Vinland, where not a single bite originates more than a few dozen miles from your fork; and, of course, Hugo's, where the tasting menu is divided into Foraged & Farmed, From the Sea, and Forest & Field.

Sonny's:

Sit up front for kitchen views at this Latin-inspired lounge, housed in an old savings bank. The empanadas with chili sour cream should pique your interest.

Grace:

Blessed with new life, this Gothic Revival church now serves upscale fare and cleverly named cocktails like the Holier Than Thou.

Salvage BBQ:

Once a railroad post office, this rustic shack has put its stamp on the area's barbecue scene with Southern-style smoked meats.

Five Fifty-Five: 

Here’s what you're ordering: the lobster mac, featuring chunks of butter-poached lobster and black truffle shavings. 

The Lobster Shack at Two Lights: 

Crack some claws at a red picnic table perched above the craggy shores of Cape Elizabeth. 

DiMillo's on the Water: 

This converted car ferry docked in Portland Harbor has been reeling in seafood lovers since 1982.