PORTLAND BOAT TOUR FIELD GUIDE
A Private Yacht Across Granite and Light — Sailing Sasa’s Casco Bay Charters
A private, customizable half- (4 hours) or full-day (7.5 hours) charter from downtown Portland that pairs lighthouse views, island stops, swimming and relaxed sailing for groups of any age.
A Private Yacht Across Granite and Light — Sailing Sasa’s Casco Bay Charters.
Sail Maine’s rocky coast from a thoughtfully restored, family-run yacht that’s reserved entirely for your group. Sailing Sasa runs private, customizable charters out of downtown Portland into Casco Bay, where days are built around your vision — whether that means close-up lighthouse passages, weaving among the bay’s classic rocky islands, anchoring for a swim, or going ashore on a quiet island or coastal town.
Highlights
Outing Highlights
Portland Head Light up close
One of the most requested legs of the route is a water-side passage past Portland Head Light, offering a close perspective on this iconic beacon as you continue into the maze of Casco Bay islands.
Island stops and shoreline exploration
On a full-day charter the itinerary commonly includes stepping ashore at one of the bay’s islands or coastal towns — options like Peaks, Great Diamond or Jewell — for a waterfront lunch, a short hike, or relaxed exploring.
A fully private, 56-foot sailing yacht
The trip is entirely private: a 56-foot yacht restored and outfitted to feel welcoming and comfortable, with the day’s pace and stops customized to your group’s preferences.
What the day feels like
What the day on the water feels like
You board in downtown Portland and ease out into Casco Bay for a sail that can be tailored to your group and the wind that day. The rhythm is simple: sail past lighthouses and through the bay’s rocky islands, pause the engine to anchor for a swim or sun on deck, and on full-day trips step ashore at an island or coastal town for a stroll or lunch before a relaxed return to the harbor.
Suitability
Who it's for
Who this private sailing charter suits — and when to choose a half- or full-day.
Practical planner
Details to review before reserving
Charters are offered as a half-day (4 hours) or a full-day (7.5 hours); full-day trips commonly include time to go ashore at an island or coastal town.
Expect opportunities to swim and to spend several hours on deck—bring swimwear and sun protection; pack what you need for a half- or full-day away from shore.
Trips typically begin in downtown Portland; boarding and exact departure details are arranged with the operator at booking.
Review cancellation policies before reserving.
Frequently asked questions
Planning Your Outing
How long are the charters?
Charters are offered as a half-day (4 hours) or a full-day (7.5 hours).
Where do we board?
Trips commonly begin in downtown Portland; exact boarding details are provided by the operator when you book.
Is the boat private?
Yes — these are private charters, meaning the 56-foot yacht is reserved entirely for your group and the day is customized to your preferences.
Can we go ashore on islands?
On full-day charters there is time to go ashore at one of Casco Bay’s islands or a coastal town for a walk, lunch or exploration; half-day trips typically focus on sailing and shorter on-water stops.
Are the trips suitable for children and older guests?
The operator describes the experience as appropriate for all ages; itineraries and activities are tailored to the group’s needs.
What will we see?
Expect passages past Portland Head Light, sailing through the classic rocky islands of Casco Bay, with options to anchor for swimming and to visit islands or coastal towns on full-day trips.