Charter Captain Services
Your Charter, Your Way
Captain Ruddy is available for hire on your own vessel or on a vessel you've chartered. Whatever your perfect sailing experience looks like, Captain Ruddy is ready to bring it to life. From quiet day sails and sunset cruises to multi-day passages and overseas voyages, every itinerary is entirely custom-fit to you. Ruddy has run these trips many times before and knows how to make them work for just about any group, mood, or occasion.
How Involved Do You Want to Be?
One of the things that sets Ruddy apart is how adaptable the experience can be. You decide how the day runs:
Full captain mode — Captain Ruddy handles everything. Navigating, docking, sailing, You just sit back, enjoy the winds and the sea, and focus on having a good time.
Learn while you sail — Wish to better your skills along the way? Ruddy seamlessly weaves in instruction throughout the trip, so you're gaining real experience without it ever feeling like a class.
Guided independence — You and your crew take the helm, make the calls, and run the charter yourselves, with Ruddy there as a calm, experienced safety presence, stepping in with guidance when needed, and staying out of the way when it doesn't.
Whatever your choice, expect your voyage to be easy, personable, and a lot of fun. Ruddy's done this enough times to know that the best charters aren't just about seamanship, but about the people on board having an experience they'll talk about long after they're back at the dock.
Do you have a few friends or sailing buddies who each want to charter their own boat and explore together? That works too. Ruddy is experienced in leading flotillas, coordinating routes, briefing each skipper, keeping an eye on the fleet, and making sure everyone arrives happy. It's a fantastic option for having a stress-free sailing vacation, with a safety network around you in your early chartering journey.
Our Pricing
Charter captain services are $100 per hour, or $500 to $800 per day for longer adventures (depending on distance, trip complexity, and availability).
Because every trip is unique, these rates can vary slightly based on your location, specific requirements, or any special conditions for the voyage. Travel expenses and basic needs are covered by the client, and we’ll always chat through these and agree on everything upfront so there are never any surprises.
Planning a flotilla trip with multiple boats sharing the cost? We can easily customize the pricing to fit your group setup—just reach out and Ruddy will work out a fair arrangement for everyone. The same goes for trips abroad or extended multi-day passages, where a flat daily rate usually makes the most sense.
We believe in keeping things completely transparent and flexible. Drop us a line via email or the contact form with your ideas and any questions you have. We are here to tailor the experience to your exact trip and make sure everything is clearly settled before you throw off the lines!
Looking forward to hearing about your plans!