The best picks from my June '16 trip to Vacationland.
  1. Central Provisions
    Awesome small plates and craft cocktails, beer + wine. I was drinking the Marguerite.
  2. Pinecone+Chickadee
    Perfect combo of a vintage + handmade at this local boutique. Clothing, homewares, books, cards, accessories, and more.
  3. Eventide
    Fresh Oyster bar, innovative seafood dishes and craft cocktails, beer + wine.
  4. Portland Headlight
    A must-see lighthouse at Fort Williams in Cape Elizabeth (20 mins from downtown). My second trip there... and I'd go back every time. Best on a clear day. Note: currently getting an update/scaffolding around the main lighthouse.
  5. Bite Into Maine
    Lobster roll food truck that can't be beat. Every weekend at Portland Headlight. Choose from an assortment of rolls - Maine, Connecticut, Chipotle, and more.
  6. Flea-For-All
    Weekend market with several permanent stalls - loads of vintage Americana, clothing, furniture, and handmade jewelry.
  7. Fore Street
    Epic farm to table dining and adult beverages. Amazing pate + meat platter.
  8. Sunset Cruise from the Ferry Terminal
    A bit too long (2.5 hours), but a great way to see Portland's many surrounding residential islands.
  9. Maine Beer Company
    Eco-conscious brewery that makes highly regarded and innovative craft beer. Beer flights + they had fresh pretzels/pizza on the weekend. About 15 minutes from downtown in Freeport (near LLBean Village).
  10. L.L.Bean
    World HQ of the outdoors brand. Their retail store is essentially a mecca for the outdoorsy type (setup similar to REI, but several times the size). Open 24 hours a day, classes every weekend (we caught a kayak demo in the pool), and pose with the giant bean boot. Also, several other shops + outlets in the town. About 20 mins from downtown in Freeport.
  11. Westin Bar
    Cocktail lounge on the top floor of the Westin hotel. Overlooks downtown Portland + the water.
  12. Morrill Mansion B&B
    8 Bedroom Mansion — gorgeous rooms, walkable to everywhere downtown + David the owner makes an assortment of breakfast items and snacks including a mean whoopie pie.