Casco Bay Sailing Escape: Half Day Custom Boat Charter

4 hours Free cancellation

Casco Bay Sailing Escape: Half Day Custom Boat Charter, photo 2 — Photos: the activity supplier, via Viator

About this activity

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.

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

At a glance

Duration: 4 hours
Confirmation: Instant confirmation
Ticket: Mobile or paper ticket accepted
Group: Up to 6 people
People per booking: 1–6
Guide: English
Operated by: Sailing Sasa

Ages: Infants (0–2 years) · Children (3–12 years) · Adults (13–100 years)

What is included

Included

Included: The option to take the helm, trim the sails, and brush up on your sailing skills
Included: Snacks: Light refreshments including locally inspired, chef-curated charcuterie
Included: Alcoholic beverages: A post-swim digestif, including crisp, refreshing glass of wine or local beer, and non-alcoholic options such as sparkling waters and sodas
Included: A flexible route based on conditions and your vibe
Included: Beautifully outfitted sailing yacht, coast guard certified captain + crew
Included: Time to swim or relax at anchor

Not included

Not included: Onshore stop for lunch, shopping, or exploring. For this bonus adventure, book our full-day charter.

Itinerary

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. Example Itinerary: 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.

Stop 1
Casco Bay
Portland Head Light
Portland
Peaks Island

Meeting point and pickup

Everyone meets at the meeting point.

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

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.

Cancellation

Free cancellation

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

If you cancel	You get back
At least one day before	100%
Less than a day before	0%

The operator may cancel if the weather does not allow it; you then get another date or your money back.
The operator may cancel if too few people book; you then get another date or your money back.

Good to know

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.