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. Whether you're seeking relaxation or adventure, this personalized trip offers stunning views of Casco Bay and iconic landmarks such as Portland Head Light.
During your 4-hour journey, you can choose to swim in secluded spots, take the helm, or simply unwind while enjoying light refreshments. The yacht is fully equipped, and the captain and crew are there to ensure your day on the water is memorable and tailored to your preferences.
This private sailing experience is perfect for groups of up to six people, making it an intimate way to explore the coast, learn new sailing skills, or just enjoy quality time on the water with friends or family.
Frequently asked questions
How long is the sailing trip?
The private half-day sailing charter lasts approximately 4 hours.
What is included in the experience?
You’ll enjoy a beautifully outfitted sailing yacht, a coast guard-certified captain and crew, light refreshments including chef-curated charcuterie, snorkeling masks and wetsuits, and the option to take the helm or improve your sailing skills. There’s also time to swim or relax at anchor, with a post-swim drink of wine, beer, or non-alcoholic options.
Can children participate?
Yes. Infants and small children can ride in a pram or stroller, and the trip is suitable for all fitness levels.
Are there any onshore stops?
This experience is focused on sailing and relaxing on the water. For onshore stops like Peaks Island, consider our full-day options.
What should I bring?
Bring swimwear, sunscreen, and any personal items you might need for a relaxing day on the water. All snorkeling gear and wetsuits are provided if you wish to snorkel.
Is there a cancellation policy?
Yes. You can cancel for a full refund at least 24 hours before the scheduled departure. Cancellations made within 24 hours are non-refundable and trips may be canceled due to bad weather.
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, and wetsuits available
- A post-swim digestif, including a glass of wine or local beer, and non-alcoholic options like sparkling waters and sodas
- A 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
A flexible 4-hour sailing adventure tailored to your group's preferences, including time to swim, relax, and enjoy the scenery.
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
- Trips may be canceled due to bad weather
Instant confirmation
Your booking is confirmed immediately after checkout.
From $475.00 per person
- Free cancellation
- Secure checkout with our booking partner
