Private Half Day Sailing Charter in Portland Maine

5.0 (one review) 4 hours Free cancellation Private tour

out of 5

one review

5.0

Private Half Day Sailing Charter in Portland Maine — Photos: the activity supplier, via Viator

Private Half Day Sailing Charter in Portland Maine, photo 2 — Photos: the activity supplier, via Viator

About this activity

A half-day sailing charter offers a unique and personalized way to explore the stunning Maine coast. Departing from downtown Portland, this private experience aboard Sasa, a family-run small business charter sailboat, with a coast-guard certified captain, allows you to cruise through Casco Bay, enjoying views of iconic landmarks like Portland Head Light. With options to swim in secluded spots or simply relax, every charter is tailored to your group's preferences. Enjoy light refreshments and the chance to take the helm or trim the sails, making for an unforgettable day on the water.

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At a glance

Duration: 4 hours
Confirmation: Instant confirmation
Ticket: Mobile or paper ticket accepted
Group: Your group only
People per booking: 1–8
Guide: English
Operated by: Sailing Sasa

Ages: Infants (0–2 years) · Children (3–13 years) · Adults (14–110 years)

What is included

Included

Included: Option to take the helm or brush up on your sailing skills
Included: Private transportation: Beautifully outfitted sailing yacht, coast guard certified captain + crew
Included: Snacks: Light refreshments including locally inspired, chef-curated charcuterie
Included: Use of snorkeling equipment: Snorkelling masks and fins and wetsuits available
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: Time to swim or relax at anchor

Not included

Not included: Onshore stops for exploring (like Peaks Island). For onshore stops, check out full-day options.

Itinerary

A half-day sail is one of the easiest (and best) ways to get out on the water and experience the Maine coast from a completely different perspective. This private sailing charter is designed for a relaxed few hours—cruising through Casco Bay, taking in the views, stopping for a refreshing swim, and enjoying the best view of Maine from the deck with refreshments in hand. 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 before a peaceful sail back toward the harbor.

Stop 1
Portland Head Light

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.