PORTLAND BOAT TOUR FIELD GUIDE
Half-day on Sasa: Sail Past Portland Head Light and the Rocky Islands of Casco Bay
A private, fully customizable 4-hour sailing charter from downtown Portland that lets small groups relax, swim, take the helm, and view Portland Head Light from the water.
Half-day on Sasa: Sail Past Portland Head Light and the Rocky Islands of Casco Bay.
Aboard Sasa, a thoughtfully restored family-run yacht, a half-day charter peels you away from downtown Portland and out into the scattered, wind-sculpted islands of Casco Bay. The experience is simple and deliberately uncrowded: a private sail tailored to your group’s idea of a perfect few hours—sights of lighthouses, rocky island passages, and the option to drop anchor for a swim or quiet soak in the sea.
Highlights
Outing Highlights
Portland Head Light from the Water
One of the trip’s signature moments is a close-up passage by Portland Head Light—an iconic coastal beacon you’ll approach from the sea as part of a frequently requested route through Casco Bay.
Weave Through Rocky Islands
The charter threads through the classic rocky islands that define this stretch of Maine coast, offering the textured coastlines and island scenery that make Casco Bay unique.
Small-Group, Fully Custom Days
Each half-day is private and customizable for your party—Sailing Sasa limits charters to no more than six guests so the day feels personal, relaxed, and built around your group’s vision.
What the day feels like
What the Half-day Feels Like
Over four hours the rhythm is unhurried: depart downtown Portland, slip into Casco Bay, pass the lighthouse and island shoals, and anchor when the mood or weather invites a swim or a stretch of quiet. The boat is run by a small family operation and the charter is designed to feel warm, comfortable, and genuinely personal.
Suitability
Who it's for
Who this charter suits — and who should consider alternatives.
Practical planner
Details to review before reserving
This is a half-day private charter with a typical duration of four hours.
The itinerary commonly includes an opportunity to drop anchor for a swim; plan accordingly if you intend to swim and for a comfortable, seaside few hours.
Trips begin in downtown Portland and depart from the city harbor before heading into Casco Bay.
Charters are private and fully customizable for your group; the operator limits bookings to no more than six guests.
Review cancellation policies before reserving.
Frequently asked questions
Planning Your Outing
How long is the half-day charter?
The typical duration is four hours.
Is this a private trip?
Yes — charters are private and designed for small groups, with a maximum of six guests onboard.
Will we see Portland Head Light?
A frequently requested route passes Portland Head Light for a close-up view from the water.
Can we swim during the trip?
Yes — the crew commonly drops anchor when timing and conditions permit so guests can swim, relax, or soak in the surroundings.
Where does the trip depart from?
Trips begin in downtown Portland and head out into Casco Bay from the harbor.
Is the trip customizable?
Yes — every sailing day trip is fully customizable and built around your group’s vision of a perfect day on the water.