Portland: Casco Bay Tall Ship Cruise on Historic Schooner

Summary

Sailing past lighthouses and seabirds on casco bay from portland

You’ll board a historic Maine schooner in Portland for a two-hour Casco Bay cruise—spotting lighthouses, seals, and seabirds along rugged coastline. Bring your own picnic or join in raising the sails with the friendly crew. Whether you relax or get involved, there’s this calm joy that sticks with you long after stepping back onto shore.

What’s the experience like?

The first thing I noticed was the creak of old wood under my feet—Bagheera, our schooner for the morning, felt alive in that way only something built by hand can. We’d barely left Portland’s harbor before the city faded behind us and Casco Bay opened up, all cold blue water and those little islands scattered like someone dropped them by accident. Our captain, Sam (he said his family’s been here for generations), pointed out a lighthouse off to starboard—Portland Head Light, I think—and told a story about foghorns that made everyone laugh. The air smelled like salt and pine needles, which sounds weird but somehow fits.

I brought coffee in a thermos, but someone else had packed wine and cheese—nobody seemed to mind sharing. There was this couple from Boston who tried to help hoist the sails; the crew showed them how to pull in rhythm (“one-two-pull!”) and we all cheered when they got it right. A seal popped up near the bow for maybe three seconds before slipping away again. I tried to take a photo but missed it—still kind of annoyed about that. You can just sit back and watch everything drift by or get hands-on with the ropes if you want; nobody pressures you either way.

What surprised me most was how quiet it got once we were out past Peaks Island. Just wind in the canvas and water against wood, plus gulls yelling at each other overhead. There’s something about seeing Casco Bay from a tall ship that makes you feel both tiny and lucky at the same time. I kept thinking how these old windjammers—Bagheera’s from 1924!—have seen so much weather, so many faces passing through. When we finally turned back toward Portland, I didn’t really want it to end yet.

Step-by-step itinerary

Day 1 — Two-hour tall ship cruise on Casco Bay

• Board Bagheera, Wendameen, or Timberwind
• Sail along Maine coast and see lighthouses
• Observe seals, seabirds, and rugged coastline
• Bring meal and drinks to enjoy onboard
• Optionally help crew hoist sails or steer

Top questions

How long is the Portland tall ship cruise?

The cruise lasts approximately two hours.

Where does the cruise depart from?

The schooner departs from Portland, Maine.

Is food included on the Casco Bay cruise?

No food is included; guests are encouraged to pack their own meal or snacks.

Can children join the tall ship cruise?

Yes, all ages are welcome aboard the schooner.

Are life jackets provided on board?

Yes, life jackets are available for both adults and children.

Which ships operate this tour?

The cruise may be aboard Bagheera, Wendameen, or Timberwind—all historic Maine-built schooners.

Is public transportation available nearby?

Yes, public transportation options are available near the departure point in Portland.

Can guests help sail the ship?

Yes, guests can assist with hoisting sails or even try steering if they wish.

What’s included

Your day includes two hours sailing aboard a historic Maine-built schooner from Portland across Casco Bay; life jackets for adults and kids are provided; you’re welcome to bring your own picnic or drinks; plus you can join in helping raise sails alongside an experienced local crew before returning to shore.