Portland & Casco Bay: Private Boat Cruise with Local Guide

Summary

Private boat tour exploring Casco Bay’s islands and lighthouse views

You’ll board a private boat in Portland with a local guide at the helm, cruise through Casco Bay’s islands spotting seals and seabirds, then pause by historic Portland Head Light as waves crash below. Warm blankets and cold drinks are always within reach. Expect laughter, quiet moments, and that salty Maine air lingering long after you return.

What’s the experience like?

We’d barely untied from the dock in Portland when Captain Mike asked if we wanted to steer for a bit. I laughed — I mean, I’ve never even parallel parked well, but he just grinned and handed over the wheel anyway. The air smelled like salt and pine needles, and there was this low hum from the harbor that faded as we slipped past lobster boats bobbing at their moorings. It felt like everyone on shore was waving, or maybe I just imagined that because I was already a little giddy.

Casco Bay is bigger than it looks on any map. We drifted past Little Diamond Island while Mike pointed out a pair of seals sunning themselves on a rock — honestly, I almost missed them because I was too busy watching the way the light hit the water. There were gulls everywhere, screeching and swooping around us. At one point, someone (I think it was my sister) tried to name all fourteen islands in Casco Bay but gave up after five. The wind picked up just enough that we grabbed the blankets from under the seat — they’re surprisingly soft — and settled back with cold water from the cooler.

I didn’t expect to feel so small when we pulled up near Portland Head Light. It’s old — 1791, Mike said — but somehow it looks even older in person, perched above those jagged rocks with waves crashing below. He told us about shipwrecks and how the lighthouse still guides tankers into Portland Harbor today. There was this quiet moment where nobody said anything; just the sound of water slapping against the hull and that far-off clang from a bell buoy somewhere behind us. I still think about that view sometimes.

On our way back through Casco Bay, we passed a couple of kayakers who waved like they knew us (maybe they did). The sun started dipping lower and everything turned gold for a few minutes — you know that kind of light where even your phone photos look good? We didn’t want to head in yet but eventually Mike steered us home. So yeah, if you’re thinking about a private boat tour in Portland with someone who actually knows these waters, this is probably it.

Step-by-step itinerary

Day 1 — Private 2-hour Casco Bay boat tour

• Tours of Casco Bay islands
• Pass Portland Head Light
• Explore Casco Bay coastline

Top questions

How long does the private Casco Bay boat tour last?

The private boat tour lasts approximately 2 hours.

Is pickup included for this Portland & Casco Bay cruise?

The tour departs from Portland; hotel pickup is not mentioned as included.

What can you see during the Casco Bay boat tour?

You’ll see several Casco Bay islands and visit Portland Head Light.

Are drinks or snacks provided on board?

Water is provided along with plates, ice, cups, towels, and blankets.

Is this private boat tour suitable for children?

Yes; infants and small children can ride in a pram or stroller.

Are service animals allowed on this cruise?

Yes; service animals are allowed on board.

Is public transportation available near the departure point?

Yes; public transportation options are available nearby in Portland.

Can travelers with limited mobility join this tour?

The tour is suitable for all physical fitness levels but not recommended for those with spinal injuries or poor cardiovascular health.

What’s included

Your day includes towels and warm blankets for chilly breezes out on Casco Bay, bottled water to keep you refreshed, plus plates, ice, and cups if you bring snacks along. A knowledgeable local guide steers you through island channels before returning to Portland’s harbor as evening falls.