Portland Half Day Sailing Escape on a Beautiful Yacht
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Experience the Maine coast from a whole new perspective with the Casco Bay Sailing Escape: Half Day Custom Boat Charter. This small, family-run sailing adventure offers a relaxed, personalized atmosphere aboard a beautifully restored yacht, designed to feel warm and welcoming from the moment you step onboard.
Whether you're looking to brush up on your sailing skills, enjoy a peaceful cruise, or simply unwind with stunning views, this half-day sail provides the perfect escape. You can take the helm, trim the sails, or just sit back and soak in the scenery. On warm days, there's also time for a refreshing swim at anchor, making this a memorable way to enjoy Maine’s coastline.
With a flexible route tailored to weather conditions and your vibe, this experience is ideal for small groups up to six people. It’s accessible for all ages and fitness levels, making it a great outing for families, friends, or solo travelers seeking a laid-back adventure on the water.
Frequently asked questions
How long is the sailing trip?
The trip lasts approximately 4 hours, giving you plenty of time to relax, sail, and enjoy the scenery.
What’s included in the experience?
You’ll have the chance to take the helm, trim the sails, and improve your sailing skills. Light refreshments, including locally inspired charcuterie, are provided. After a swim, enjoy a refreshing glass of wine or local beer, or opt for non-alcoholic drinks like sparkling waters. The route is flexible based on weather and your preferences.
Is this activity suitable for children?
Yes. The experience is suitable for all ages, from infants in strollers to adults up to 100 years old. Infants and small children can ride comfortably in a pram or stroller.
Where do we meet?
Meet at the Cutter Street Parking Lot at East End Beach. The captain will greet you there and transfer you to the yacht aboard a private tender.
Can I cancel if my plans change?
Yes. You can cancel for a full refund if you do so at least 24 hours before the scheduled departure. Cancellations made within 24 hours are non-refundable and the trip may be canceled due to bad weather or insufficient travelers.
Free cancellation
Cancel at least 24 hours before your scheduled departure for a full refund.
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
- Opportunity to take the helm, trim the sails, and improve your sailing skills
- Light refreshments, including locally inspired, chef-curated charcuterie
- Post-swim digestif with a glass of wine or local beer, plus non-alcoholic options like sparkling waters and sodas
- A flexible route based on weather and your preferences
- 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, book the full-day charter.
Itinerary
A relaxing half-day sailing experience tailored to your group's vibe and the weather, with opportunities to sail, swim, and enjoy scenic views.
Meeting point & pickup
Meet at the starting point
Guests should park in the Cutter Street Parking Lot at East End Beach. The captain will meet you there and transfer you to the yacht aboard a private tender.
Open in Google MapsCancellation & confirmation
Free cancellation
Cancel at least 24 hours before your scheduled departure for a full refund.
- 100% refund if canceled at least 1 day in advance
- No refund if canceled within 24 hours
- Trip may be canceled due to bad weather or low enrollment
Instant confirmation
Your booking is confirmed immediately after checkout.
From $199.00 per person
- Free cancellation
- Secure checkout with our booking partner
