Portland Maine, Maine

Coolness is subjective of course but we love the Right Coast Maine. It has so much less of the Portlandia vibe, and so much more of the old-timey waterfront feel. Since it’s 10x smaller than the other one it has a manageable, homey feel with a cool art District, beautiful cobblestone streets, and more micro-breweries than the other Portland has hipsters.

At just 65,000 residents Portland has a tough time supporting small businesses and as a result, there aren’t many jobs. Tourists give you a bit of a boost if you’re a service biz but come winter things get quiet. Simply put it can be hard to make a living here. If you’re moving to be a remote worker, or you’re an empty-nester or retiree then it is amazing but don’t move here to make a living off the city economy.

Portland is SMALL for a well-known city, so expect inventory for buying a condo or renting an apartment to be sparse and for others to be in on the bids. There is a new development, mostly in condos, but if you can snag one expect an extremely walkable, liberal, young (for Maine), diverse (for Maine), experience. Lots of breweries, good food, and boutique retail, surround an utterly charming, brick and cobblestone city.

If you want to see all that goes on in Portland check out the calendar of events.

We highly recommend visiting Portland and staying in the community in a VRBO rather than a hotel to get a feel for living among the locals. You can also receive discounted travel fares via our partnership with Expedia.

Things are crazy out there right now and if you’d like to step back from the craziness (and cost) of Boston, New York or wherever you’re from but maintain some city energy then Portland’s the spot for you. If you’re young it’s amazing; more breweries per capita than any other city on the planet. If you’re empty nesting or retiring the healthy, active, outdoor senior lifestyle is perfect as well.