Published July 12th, 2012

When you fly into Portland on your way to French’s Point, you’ll land in the International Jetport, a big-sounding name for a fairly small and easy-to-navigate airport. The Portland jetport recently expanded and now sports a beautiful, sun-drenched atrium, but it also still retains a lot of its user-friendliness. You’ll be in and out of there in no-time, usually without any hassle at all, and you can grab a rental car at any one of the major companies based at the airport, including Hertz, Budget, and Enterprise.

Once you’ve picked up your rental car at the jetport, head into Portland, dubbed by the famous 19th-century poet Henry Wadsworth Longfellow the “city by the sea”. Portland is one of our favorite cities. It’s small, artsy, friendly, and has a ton of famously diverse and award-winning restaurants. Head all the way into the Old Port and try and park along Commercial Street or on Exchange or Middle streets, right in the heart of the old cobblestone commercial district. Shoppers might want to check out the clothing store Bliss, the made-in-Maine shoe store J.L. Coombs, or any of the other small boutiques along these narrow streets. There are a ton of specialty coffee shops in town that take their brew very seriously and a few of the best are right in the Old Port, including Bard Coffee, Arabica Coffee, and Mornings in Paris. All of them roast their own beans and Mornings has a bunch of French pastries for your sweet tooth.

When it comes time to eat, there are so many fantastic places in town you shouldn’t really waste your time on anything that doesn’t get a ringing endorsement on Yelp. Street & Co., Fore Street, and the chic sushi spot Miyake are a few of the best spots to eat in the Old Port (Street & Co. and Miyake do local fish particularly well), but they aren’t cheap. If you want a more affordable spot, try the taqueria El Rayo on the neighborhood’s outskirts, Flatbread brick-oven pizza (perfect for families and right on the water), Duckfat (whose staff chef has won on Food Network’s show “Chopped”), The Thirsty Pig or the East Ender, a bright, family-friendly tavern on the east end whose chef-owner comes up with surprising takes on BBQ and pub grub. For simple but delicious takes on lobster, check out the Portland Lobster Co. right on the wharf. And, last but not least, the best place to get good chowder is Gilbert’s on Commercial Street. Inside tip: make sure you get the super-seafood upgrade. Chock full doesn’t begin to describe the difference it makes. Yum.