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Premier Boat Charter Experiences in Chatham
Son of a Sailor was founded from a deep passion for boating and a desire to share the beauty of Cape Cod's waters with others. Our team combines decades of maritime experience with a commitment to personalized service, offering guests the opportunity to explore Stage Harbor and Nantucket Sound aboard a J/97 sailboat or a 22' Angler powerboat. Captain Drew Meincke, a USCG Licensed professional with over 20 years of boating expertise, brings extensive racing and commercial fishing experience to every charter.

We prioritize safety, flexibility, and unforgettable experiences, accommodating up to six passengers per trip while offering opportunities to engage with sailing under expert supervision. Our operations reflect a deep understanding of local waters, seasonal conditions, and the unique needs of our guests.
Services
Half Day Sail Full Day Sail Sunset Sail Harbor Cruise Sunset Cruise Additional Charter Hours
Highlights and features
  • Over 20 years of boating experience with USCG Licensed Captain
  • Flexible availability including nights and weekends
  • Family-friendly vessels accommodating up to six passengers
  • Unique racing heritage and local water expertise
  • Opportunity for hands-on sailing experience under supervision
What people say
Unique perspective Knowledgeable crew Memorable experiences Highly recommended
Services
Full Day Sail
Experience an 8-hour sailing adventure aboard our J/97 sailboat Adrenaline. Ideal for groups seeking extended exploration of Nantucket Sound and Stage Harbor. Includes expert navigation, safety instruction, and opportunities for hands-on sailing participation under professional supervision.
Half Day Sail
Enjoy a 4-hour sailing experience perfect for morning or afternoon outings. Our J/97 sailboat provides comfortable exploration of coastal waters with expert guidance. Combines scenic views with optional sailing participation for an immersive maritime experience.
Sunset Sail
Witness Cape Cod's stunning sunsets during a 2.5-hour evening sail. This specialized charter offers prime photography opportunities and romantic settings while maintaining our standard safety protocols and expert navigation.
Harbor Cruise
Explore Chatham's coastline aboard our 22' Angler powerboat. This 2-hour daytime tour provides accessible coastal views and educational commentary about local marine ecosystems and maritime history from experienced crew members.
Sunset Cruise
Experience Chatham's evening beauty on our powerboat sunset cruise. This 2-hour evening charter combines scenic coastal views with relaxed atmosphere, offering optimal conditions for photography and casual maritime appreciation.
People
Drew Meincke
USCG Licensed Captain
With over 20 years of boating experience, Drew is a licensed captain who has raced in prestigious events and fished commercially for 18 summers. He brings extensive maritime expertise to every charter.
Questions
What types of charter services do you offer?
We offer half-day, full-day, and sunset sails aboard our J/97 sailboat, plus daytime and sunset harbor cruises on our powerboat with additional hours available.
How do I book a charter?
Contact us via phone at (774) 994-0637 to schedule your charter. Reservations require 24-hour cancellation notice and payment at the start of your trip.
What payment methods do you accept?
We accept cash, checks, and Venmo payments for all charter services. Full payment is required at the beginning of your scheduled trip.
How does weather affect sailing schedules?
Charters depend on tide and weather conditions. The captain monitors patterns closely and may reschedule if conditions aren't suitable for safe sailing.
Can passengers participate in sailing activities?
Yes, passengers may try steering under the captain's supervision. Our family-friendly boats accommodate up to six guests with safety as our top priority.