Casco Bay Sailing Escape Half day Custom Boat Charter

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4 hours (approximately)
Offered in: English

Each trip is tailored to your group and the wind conditions that day, but a frequently requested, guest favorite sailing route begins in downtown Portland before heading out into Casco Bay. From there, we'll pass Portland Head Light for a close-up view from the water and weave through the classic rocky islands that make this stretch of coast so unique. When the timing feels right, we’ll drop anchor so you can swim, relax, or just soak it all in, refreshments in hand, before a peaceful sail back toward the harbor.

What's Included

The option to take the helm, trim the sails, and brush up on your sailing skills
Light refreshments including locally inspired, chef-curated charcuterie
A post-swim digestif, including 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
Beautifully outfitted sailing yacht, coast guard certified captain + crew
Time to swim or relax at anchor
Onshore stop for lunch, shopping, or exploring. For this bonus adventure, book our full-day charter.

Meeting and pickup

Meeting point

Guests should park in the Cutter Street Parking Lot at East End Beach. The captain will meet you at the designated pickup point and transfer you to the boat aboard our private tender.

End point
This activity ends back at the meeting point.

What to expect

There are a lot of ways to get out on the water in Maine, but 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.

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.

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
  • Our charters are family-friendly. We’ve spent countless hours sailing with our own children, starting as young as 7 weeks old, so little ones (even infants) are always welcome.
Supplied by Sailing Sasa

Tags

Sailing
Nature and Wildlife Tours
Honeymoon Packages
On the Water
Swimming
Wildlife Watching
Seasonal
Small Group

Cancellation Policy

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

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