Portland has more restaurants per capita than almost any city in America, and you’ll feel it walking through the Old Port. Cobblestone streets, Casco Bay island ferries, Portland Head Light, and a food scene that punches way above its weight.
Portland
Plan a Trip to Portland →Scroll
↓
↓
Region
maine
Best Time
May, Jun, Jul +3 more
Daily Budget
$60–$350 USD
Getting There
Fly into Portland International Jetport (PWM). Amtrak Downeaster from Boston (2.5 hours). Drive from Boston via I-95 (2 hours).
Before You Go: Travel Insurance
Unexpected injuries on mountain trails or winter roads can lead to costly medical bills. We recommend SafetyWing for every trip — it's affordable, covers medical and evacuation, and you can sign up even after you've left home.
"We've thankfully never had to file a claim, but having it is peace of mind every time we board that plane." — Scott
Check SafetyWing Rates →Affiliate link — we earn a commission at no extra cost to you. Full disclosure.