3. Portland, Maine
Maine’s largest metro area was in good company when it landed on Jetsetter’s coolest small towns list. The fresh lobster alone is worth allowing your attendees to enjoy a taste of the destination for a meeting, as the Potato Association of America did in 2015. The waterfront city known for landmark lighthouses has a natural beauty few can match. New boutique hotels like 250 Main and the newspaper-themed Press Hotel—part of Marriott’s Autograph Collection—will entice planners looking to splurge. Both debuted in 2016.