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Casco Bay Sailing Escape: Half Day Custom Boat Charter

Portland Head Light

  • 4 hours
  • Free cancellation up to 24h before
  • Guided in English
  • Instant confirmation

Highlights

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. 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 small group Maine sailing charter is perfect if you want a relaxed few hours to cruise, take in the views, brush up and your sail trim, or just relax and maybe sneak in a swim on a warm day.

Inclusions

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

What's not

  • Onshore stop for lunch, shopping, or exploring. For this bonus adventure, book our full-day charter.

Cancellation

Free cancellation up to 24 hours before the experience starts, for a full refund.

Know before you go

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.
Pickup
Everyone meets at the starting point; there is no pickup.
Ticket type
Mobile or paper ticket accepted
Group size
Up to 6 travellers
Operated by
Sailing Sasa
  • 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.

How it compares in Portland

  • Its from-price is 132% above the median of the 92 experiences we list in Portland.
  • It is longer than most of them.
  • The operator lists free cancellation on it.

About Portland

Portland is Maine's largest city, a working harbour on Casco Bay with a cobbled old port, a lighthouse and a celebrated food scene.

Portland sits on a hilly peninsula in Casco Bay, a working harbour with fishing boats, ferries and a historic district, the Old Port, of brick warehouses and cobbled streets. The Portland Observatory, a shingled signal tower of 1807, is the last of its kind in the country, and the Victoria Mansion is a richly decorated Italianate house of the 1860s. The poet Henry Wadsworth Longfellow was born here in 1807.

Top-ranked sights in Portland: Portland Head Light, Victoria Mansion (Morse-Libby House), Fort Gorges.

See all 92 experiences in Portland

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