Portland Half Day Sailing Escape on a Cozy Yacht
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Experience the Maine coast like never before with the Casco Bay Sailing Escape: Half Day Custom Boat Charter. As a small, family-run sailing charter, we focus on making every trip feel personal, relaxed, and truly memorable. Step aboard Sasa, a beautifully restored yacht designed to feel warm, welcoming, and comfortable from the moment you arrive.
This half-day sail offers a perfect way to enjoy the water, whether you're looking to unwind, brush up on your sailing skills, or simply take in stunning coastal views. With a small group of up to six people, you'll have plenty of space to relax, explore, or even take the helm if you wish. On a warm day, you might even enjoy a refreshing swim at anchor.
Join us for a flexible route tailored to the weather and your vibe. Enjoy light refreshments, including locally inspired charcuterie, and unwind with a post-swim drink—whether it's a crisp glass of wine, local beer, or a non-alcoholic option. This experience is perfect for anyone seeking a laid-back, memorable day on the water in Maine.
Frequently asked questions
How long is the sailing trip?
The sailing experience lasts approximately 4 hours.
What languages are spoken during the trip?
The tour is conducted in English.
What is the group size?
Up to 6 guests can join each trip.
Is the activity suitable for children?
Yes. Infants (0-2), children (3-12), and adults (13-100) are all welcome. Infants and small children can ride in a pram or stroller, and the experience is suitable for all physical fitness levels.
What’s included in the experience?
Guests can take the helm, trim the sails, and brush up on sailing skills. Light refreshments, including locally inspired charcuterie, and a post-swim drink—wine, beer, or non-alcoholic options—are provided. The route is flexible based on conditions and your vibe. The beautifully outfitted yacht is coast guard certified, with a captain and crew onboard. You also get time to swim or relax at anchor.
Are there any exclusions?
This half-day sailing does not include onshore stops for lunch, shopping, or exploring. For those activities, consider booking our full-day charter.
Free cancellation
For a full refund, cancel at least 24 hours before the scheduled departure time.
Reserve now
Check a date here, then finish booking with our partner. Payment options are confirmed at checkout.
Duration 4 hours
Check availability to see start times.
Live tour guide
English
Key facts
What's included
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 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
- Beautifully outfitted sailing yacht, coast guard certified captain + crew
- Time to swim or relax at anchor
Not included
- Onshore stop for lunch, shopping, or exploring. For this bonus adventure, book our full-day charter.
Itinerary
Enjoy a relaxed 4-hour sailing trip along the Maine coast with a flexible route tailored to your preferences and weather conditions.
Meeting point & pickup
Meet at the designated start 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.
Open in Google MapsCancellation & confirmation
Free cancellation
For a full refund, cancel at least 24 hours before the scheduled departure time.
- 100% refund if cancelled at least 1 day before
- 0% refund if cancelled within 0–1 day
- May be cancelled for bad weather
- May be cancelled if there are not enough travelers
Instant confirmation
Your booking is confirmed immediately after checkout.
From $199.00 per person
- Free cancellation
- Secure checkout with our booking partner
