Private Half Day Sailing Charter in Penobscot Bay

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4 hours (approximately)
Offered in: English

There are a lot of ways to get out on the water in Maine, but at Sailing Sasa, we make every charter feel personal, relaxed, and genuinely memorable. We’re a small, family-run sailing charter, and Sasa is a thoughtfully restored and beautifully outfitted yacht designed to feel warm, welcoming, and comfortable from the moment you step aboard.

Every sailing day trip in Maine we offer is fully customizable and built around your group’s vision of a perfect day on the water. Whether we’re exploring the islands, sailing past lighthouses, or anchoring at a secluded cove for a swim, the goal is simple: give you a day that feels easy, personal, and genuinely fun.

What's Included

Beautifully outfitted sailing yacht, coast guard certified captain + crew
Option to take the helm or brush up on your sailing trimming skills
Light refreshments including locally inspired, chef-curated charcuterie
A post-swim digestif, including a crisp, refreshing glass of wine or local beer, and non-alcoholic options such as sparkling waters and sodas
A flexible route based on conditions and your vibe
Snorkelling masks and fins and wetsuits available
Time to swim or relax at anchor
Onshore stops for exploring (like Vinylhaven). For onshore stops, book our Full Day Charter

Meeting and pickup

Meeting point

Guests should park at Landings Marina. The captain will meet you on the Marina Dock and transfer you to the boat aboard our private tender.

End point
This activity ends back at the meeting point.

What to expect

A half-day sail is the easiest way to get out on the water and see the Maine coast from a completely different perspective. This private Maine sailing charter is perfect if you want a relaxed few hours to cruise, take in the views, and maybe sneak in a swim on a warm day.

Each trip is tailored to your group and the wind conditions that day, but a frequently requested guest favorite begins in downtown Rockland before setting sail into the stunning waters of Penobscot Bay. From there, we’ll pass the iconic Rockland Breakwater Lighthouse for a close-up view from the water before weaving through the rocky islands, quiet coves, and calm sailing waters that make this stretch of the Maine coast so special.

Along the way, we’ll pass not one, but two additional lighthouses, with plenty of opportunities to take in the scenery from the deck or even take the helm yourself. When the timing feels right, we’ll drop anchor so you can swim, relax, and soak it all in with refreshments in hand before a peaceful sail back toward the harbor.

Additional info

  • Infants and small children can ride in a pram or stroller
  • Service animals allowed
  • Public transportation options are available nearby
  • Specialized infant seats are available
  • Suitable for all physical fitness levels
Supplied by Sailing Sasa

Tags

Sailing
On the Water
Seasonal

Cancellation Policy

For a full refund, cancel at least 24 hours before the scheduled departure time.

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