Portland Maine: City & 3 Lighthouses Tour with Real Local

Summary

Portland’s lighthouses, cobblestones, and stories from a born-and-raised local guide

You’ll join a small group exploring Portland’s cobblestone streets, iconic lighthouses like Portland Head Light, and hidden corners only locals know. With stories from your born-and-raised guide and time to wander parks overlooking Casco Bay, you’ll feel more connected to Maine than you expected — maybe even enough to try saying “Casco” right yourself.

What’s the experience like?

We were already rolling down Commercial Street when I realized how much I’d been missing by just wandering on my own. The bricks underfoot looked older than most things back home, and our guide — who grew up right here in Portland, Maine — kept pointing out details I’d never have noticed. He joked about the “real” way to pronounce Casco Bay (I still can’t do it), and you could tell he actually knew half the folks we passed by name. There was this salty tang in the air from the harbor, mixed with something sweet drifting from a bakery somewhere up the block. It felt like the city was waking up around us.

I didn’t expect to care so much about lighthouses, but when we pulled into Fort Williams Park and got out at Portland Head Light, it kind of hit me. The wind off the water stung my cheeks; gulls shrieked overhead; everyone fell quiet for a second looking out at those rocks. Our guide told us how his dad used to bring him here as a kid — apparently he once tried to climb part of the fort (don’t try it). After that we stopped at Spring Point Ledge Lighthouse, where someone’s dog kept trying to chase the waves along the breakwater. You get close enough to see all the chipped paint and rust on these places — not just postcard-perfect stuff.

The drive through Eastern Promenade was one of those stretches where you wish you could press pause. Victorian houses lined up like they were waiting for some old sea captain to come home. At Victoria Mansion, our guide launched into this story about a librarian discovering an old diary in the attic — not sure if he was pulling our leg or not, but it made me want to peek inside every window in town. Somewhere between Longfellow’s statue and Bug Light (yes, that’s really what they call it), I realized I hadn’t checked my phone once.

Step-by-step itinerary

Day 1 — Portland city and lighthouse tour

• Start at historic Commercial Street
• See beautiful granite building
• Drive through Fort Allen Park
• View Victorian homes on Eastern Promenade
• See maritime signal tower
• Learn about oldest cemetery
• Explore Portland's downtown and arts district
• View neo-Gothic cathedral
• Visit Portland's oldest church
• See Henry Wadsworth-Longfellow's childhood home
• Tour downtown Arts District
• View New England art museum
• See Henry Wadsworth Longfellow statue
• View Victoria Mansion
• Enter Fort Williams Park and drive to Portland Head Light
• Explore Portland Head Light and Fort Williams Park
• View Fort Preble
• Photo at Spring Point Ledge Lighthouse
• Enjoy panoramic Portland skyline views
• View Liberty Ship Memorial
• Photo at Portland Breakwater Light ("Bug Light")
• See statue of distinguished movie director
• Explore Old Port waterfront district

Top questions

How long is the Real Portland Tour?

The tour lasts approximately 1 hour and 45 minutes.

Does this Portland Maine tour include lighthouse visits?

Yes, you’ll visit three lighthouses including Portland Head Light.

Is transportation included on this city & lighthouse tour?

Yes, transport is provided in an air-conditioned 13-passenger Ford Transit van.

Where does the tour start?

The tour begins at historic Commercial Street in downtown Portland.

Are hotel pickups available for this tour?

No, all guests must meet at the starting point; there is no hotel or cruise terminal pickup.

Is lunch included on this day trip?

No meals are included; food stops are not part of the itinerary.

Is this a private or group tour?

This is a small-group public tour with up to 13 people per van.

Can wheelchairs or walkers be accommodated?

No, unfortunately wheelchairs and walkers do not fit in the van.

Are pets allowed on this tour?

No pets or animals can be accommodated on board.

What’s included

Your day includes transport by air-conditioned van with a local guide who grew up in Portland and has twenty years’ experience sharing its stories. You’ll stop for photos at three lighthouses including Portland Head Light, stroll through parks overlooking Casco Bay, and hear both history and current happenings along the way before returning downtown together.