Private Half Day Sailing Charter in Portland, Maine
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Experience the Maine coast like never before with a private half-day sailing charter in Portland. Departing from downtown Portland, you'll set sail aboard Sasa, a charming family-run sailboat with a coast-guard certified captain. This personalized adventure takes you through the scenic Casco Bay, offering stunning views of landmarks such as Portland Head Light.
Whether you want to relax, take a swim in secluded spots, or try your hand at sailing, every aspect of this private experience can be tailored to your group's preferences. Enjoy light refreshments, including locally inspired, chef-curated charcuterie, as you soak in the beautiful surroundings. You might even get a chance to take the helm or trim the sails—making this a truly memorable day on the water.
Perfect for small groups up to six, this 4-hour sailing adventure combines comfort, fun, and a touch of adventure—all set against the stunning backdrop of Maine's coastline.
Frequently asked questions
How long is the sailing experience?
The private half-day sailing charter lasts approximately 4 hours.
Can I participate in sailing activities?
Yes, you have the option to take the helm or brush up on your sailing skills during the trip.
Are there any onshore stops included?
This tour focuses on sailing and relaxing on the water. For onshore stops like Peaks Island, consider our full-day options.
What refreshments are provided?
Light refreshments include locally inspired, chef-curated charcuterie, plus a post-swim digestif such as wine, local beer, or non-alcoholic drinks like sparkling waters and sodas.
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
- Option to take the helm or brush up on your sailing skills
- Beautifully outfitted sailing yacht, coast guard certified captain + crew
- Light refreshments including locally inspired, chef-curated charcuterie
- Snorkelling masks, fins, wetsuits available
- A post-swim digestif, including a glass of wine or local beer, and non-alcoholic options
- Flexible route based on conditions and your vibe
- Time to swim or relax at anchor
Not included
- Onshore stops for exploring (like Peaks Island). For onshore stops, check out full-day options.
Itinerary
Enjoy a flexible, private sailing adventure around Casco Bay, with options to swim, relax, or take the helm. The route adapts to weather and your preferences, ensuring a personalized experience.
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 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
Instant confirmation
Your booking is confirmed immediately after checkout.
From $475.00 per person
- Free cancellation
- Secure checkout with our booking partner
