ROCKLAND BOAT TOUR FIELD GUIDE
Private Penobscot Bay Sailing: A 56‑Foot Yacht to Yourself for Half- or Full‑Day Exploration
A private, customizable charter from Rockland (or Deer Isle) that lets small groups design a half- (4 hr) or full‑day (7.5 hr) sail through Penobscot Bay.
Private Penobscot Bay Sailing: A 56‑Foot Yacht to Yourself for Half- or Full‑Day Exploration.
On a private charter with Sailing Sasa you step aboard a thoughtfully restored, 56‑foot yacht and sail Maine’s Penobscot Bay at your own pace—passing lighthouses, threading island‑strewn channels, anchoring in secluded coves, and going ashore at coastal towns when you choose.
Highlights
Outing Highlights
Rockland Breakwater Lighthouse Up Close
A frequently requested favorite is a close approach to the iconic Rockland Breakwater Lighthouse, seen from the water as the yacht leaves downtown Rockland and enters Penobscot Bay.
A Private, Customizable 56‑Foot Charter
Sailing Sasa is a family‑run operation; the 56‑foot yacht is reserved for your group and every charter is tailored to your vision of the perfect day—relaxed cruising, swimming from secluded coves, or exploring a waterfront town.
Islands, Hikes and Waterfront Stops (Full‑Day Option)
On full‑day charters the itinerary often includes going ashore at a nearby island or coastal town—options guests request include Camden, Turner Farm on North Haven, or a secluded hike and swim on Vinalhaven.
What the day feels like
How the Day Feels
Whether you pick the easy half‑day or the full‑day itinerary, the trip is built around your group: depart from Rockland or Deer Isle, sail past the breakwater lighthouse, weave among rocky islands and quiet coves, stop to swim or relax on deck, and—on a full day—tie up ashore for a waterfront lunch or a short walk before returning to the harbor.
Suitability
Who it's for
Who this private charter suits—and who should check details before booking.
Practical planner
Details to review before reserving
Charters are offered as a 4‑hour half‑day or a 7.5‑hour full‑day option.
Rockland departures use the Landings Marina dock; Deer Isle departures use the Stonington Harbor Public Landing.
Each trip is tailored to your group and the day’s wind conditions; common elements include leaving downtown Rockland, passing the Rockland Breakwater Lighthouse, and exploring islands and coves.
Bring weather‑appropriate layers, sun protection, a swimsuit if you plan to swim, and any personal items you need for a half‑ or full‑day on the water.
Review cancellation policies before reserving.
Frequently asked questions
Planning Your Outing
How long are the charters?
Charters are available as a 4‑hour half‑day or a 7.5‑hour full‑day sail.
Where do departures leave from?
Rockland departures: Landings Marina Dock. Deer Isle departures: Stonington Harbor Public Landing.
Is the boat private for our group?
Yes. Charters with Sailing Sasa are private and fully customizable for your small group aboard the 56‑foot yacht.
Can we go ashore during the trip?
On full‑day charters there is time to go ashore at an island or coastal town for a walk, a waterfront lunch, or a short hike.
Will we see lighthouses and islands?
A typical route includes sailing past the Rockland Breakwater Lighthouse and weaving through rocky islands and quiet coves in Penobscot Bay.
What should we bring for a swim?
Bring a swimsuit and towel; charters make time for anchoring and swimming in sheltered coves when conditions allow.