Someone was asking about what to do in Portland Maine on Reddit,and I went WAY overboard; so I figured I would paste it here for more to read
Day 1. Walk around Congress Street and the Old Port, maybe stop at Holy Donut or one of the other fabulous bakeries. There are also various tours you can take. Definitely don’t miss dining at a restaurant by the water. Some favorites are Dimillo’s and Portland Lobster Co. but there are plenty of options. Check out Becky’s if on a budget.
Day 2. Take an early ferry to Peaks Island and spend the day.
Get snacks at the store and visit the umbrella cover museum. Rent a bike or golf cart and explore around the island stopping at the Fifth Maine Museum, Battery Steele and various shops and beaches. There are also tours. Perhaps get dinner at one of the restaurants by the harbor while you wait for the ferry, or at the Old Port when you return.
Day 3. Cape Elizabeth/South Portland.
By Car: Drive up Shore Road to Cape Elizabeth, stop at the Cookie Jar for sugar fix, continue to Fort Williams to see Portland Head light and walk the cliffs to your left to the fort. Look around for food trucks, if not there you can eat at Two Lights or pick something up at the Shack right before Kettle Cove Road, then continue to Kettle Cove if You like beautiful peaceful beaches.
By bike: over the bridge to Ferry Village/ Bug Light
By bus: Take to SMCC, check out Willard Beach, Spring Point Lighthouse and Fort Preble
Of course you can do them all by car and much of it by bike, but if you have a car I would spend more time in Cape Elizabeth. (Just keep in mind some of these places charge for parking, although Kettle Cove used to be free on Sunday’s.)
Day 4: [Boat tour]
(https://www.visitportland.com/visit/things-to-do/activities/cruises-tours/), or perhaps shopping in Freeport or otherwise exploring, Perhaps walk the Prouts Neck or Harpswell cliff walks, or Visit Mackworth Island.
If you want to be more adventurous there are plenty of nice drives within two hours. Old Orchard Beach, Ogunquit, the Yorks and the Kennebunks are great beach towns to your South, I particularly like parking at Ogunquit and walking the Marginal Way to Perkins Cove for lunch or dinner.
Bath, Brunswick, Boothbay/ Camden are among the great little towns up the northern coast. I personally prefer Rockland for shopping and eating, and they have great art museums, the Breakwater lighthouse and harbor trail.
And then North Inland is the Sebago lake area, with great hiking, swimming and kayaking. I am particularly fond of the towns of Bridgetown and Naples.
Day 5: Use what you have learned so far to plan your last day, perhaps take it a bit easier and explore further the nooks and crannies of Portland, check out the Observatory east end and Eastern Prom, or the Arts District, West End and and Western Prom.
