A Luxury Sailing Experience

Peningo is a Family Owned & Operated Charter Boat based out of Boston. The most beautiful sailboat in Boston Harbor, sponsored by COMPASS. A perfect setting for executive entertainment, celebrating a special day with friends or just unwinding for an afternoon or sunset cruise on Boston Harbor and the Harbor Islands! Accepting bookings starting June 2025 through October. Get ready to have a blast and explore Boston from a unique new perspective on our amazing 49’ sailboat. Click below to schedule your charter today and
welcome aboard Peningo!

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About the Boat

Peningo is a Custom Dubois ‘49 world class racer/cruiser designed by super yacht designer Dubois and built by super yacht builder Pendennis in the UK.

Location - Charlestown Marina (1 pier 8, 13th St, Charlestown, MA 02129)

Designer - Custom Dubois ’49 world class racer/cruiser

Manufacturer - Pendennis Yachts - https://pendennis.com

Sponsored By - www.compass.com

Skipper - Genevieve Dougherty

The Story Behind Peningo

Video By: Thomas Noah from OTB x Air Boston

Captains Log

“Thank you for such a fantastic trip! We loved the harbor views, the chatter, and the amazing time on board. We can’t wait to do it again! You guys are awesome!”

— Hilam

“Best day in Boston BY FAR! This Texas couple had the best day ever, THANK YOU ALL!”

— Stephen & Sally

“Thank you for a beautiful September day spent sailing the waters of Boston. We all really enjoyed the sail on Peningo with some fantastic company! A perfect way to close out Summer!”

— Lyle & Alyssa

“Quality adventure, extremely qualified skipper, and amazing views. This landlubber had an amazing time!”

— Dana

“Hands down the best company outing we have ever done. What memories we have made as a team today. This was the perfect way to end the summer. Thank you again so much - we had a blast!”

— Sheila

“WOW! Thank you all so much for making our sailing adventure magical! Our guests had such a blast! Perfect day too! Thank you for everything!”

— Todd & Kat

“Best day of my life! Leaving Peningo engaged to the love of my life!”

— Christa