Thinking about planning a bareboat charter? This episode gives you sharp, practical tips to make your charter more efficient, fun, and far less stressful. Two pro instructors share their insights: when to DIY and when to call the base, what to actually pack (hint: leave the tools at home), and why a recommended skipper can be “the cheapest insurance policy you’ll ever get.” Learn how to present a convincing sailing resume, which certifications matter, and when coastal complexity or local licensing should change your plan.

Get concrete advice on: quick troubleshooting vs. hands-off repairs, team-building day-one routines, provisioning surprises and creative onboard cooking, and dialing in your expectations so you sail more and motor less. You'll hear: “If they’re suggesting a skipper, they’re suggesting it for a reason,” and “Experience is the best teacher, but not always best practice.” From family charters to first-time catamaran trips and picking ideal regions, this is a chartering toolbox for sailors who want smarter, safer, and more relaxing charters.

If you already know how to sail and you charter, this episode is your shortcut to smoother, smarter, and more relaxing trips. Four veteran instructors lay out practical, no-nonsense guidance for competent sailors who want to stop wasting time, avoid stress, and squeeze more enjoyment from every charter. Expect clear takes on what to bring (and what to leave at home), when to try a quick fix yourself, and when to put the tools down and call the base.

Highlights include:

• What to pack and what not to: “I don’t want them to come back and say, ‘you tried this and now you owe us money,’” one pro warns. Keep it simple: basic spares, personal items, and smart provisioning.
• When to be hands-off vs. self-sufficient: In many popular charter regions, a hands-off approach is fine. In more complex waters, expect bases to want proof of experience or recommend a skipper. “If they’re suggesting a skipper, they’re suggesting it for a reason — it’s the cheapest insurance policy you’ll ever get.”
• How to present your resume: Be honest and specific. Crossing as crew is valuable, but docking, close-quarters handling, and local seamanship matter more for independence in challenging regions.
• Certification and training that actually help: Formal courses like ASA/IYT build safety-first practices and seamanship that insurers and charter bases respect. “Experience is the best teacher, but it’s not necessarily best practice.”
• Team building and crew dynamics: Use day one to set expectations and roles. A skipper or instructor on board transforms family trips and mixed-skill groups by reducing stress and letting everyone relax.
• Provisioning and onboard cooking: Discover local ingredients, catch-and-cook opportunities, and small provisioning hacks. Cooking aboard creates memorable meals and saves money.
• Choosing destinations and tempering expectations: Shorter hops often mean more sailing; exotic or crowded areas may demand different skills. Recommendations include BVI for simplicity, Grenada for character, and the Pacific Northwest for variety—plus tips on when Europe’s tight marinas might be nerve-wracking even for experienced skippers.

Listen for quick, punchy quotes and actionable checklists that will help you decide when to DIY, when to bring a skipper, and how to get the most from the charter experience. Whether you’re planning a family catamaran, a skills-boosting trip, or scouting boats before buying one, this episode is a practical toolkit to charter smarter, sail more, and worry less.

Guests:
Tracy Sarich of Voyager Makers
Diona Young of American Sailing & LTD Sailing

Music:
Carrion by Stands For Nothing

John Neal on Boat Choices, Outfitting, Insurance, and Experience

This is a topic that every sailor eventually faces, and that's choosing the right boat, navigating insurance, understanding the market and important outfitting considerations. Our guest today is John Neal. John is widely respected in the sailing community for his decades of passage making experience and for his consulting work, helping sailors select seaworthy boats for offshore voyaging. We first connected with John years ago when we made the transition from sailing separately on two small boats, to joining forces on one larger boat and eventually a shared last name. John's guidance played a huge role in the boat buying process, helping us kind of weigh our values and our experiences against what the different models could offer.

Preconceived ideas of what you might think would be the ideal blue water boat will change. Naval architecture develops and continues to improve. Boats that were recommended 45 years ago can often be "doggy boats" with minimal interior volume, tankage, tender, and not necessarily a comfortable ocean passage making boat. Designs do change and fortunately, in some instances, improve.

John Neal: Mahina Offshore Services

Music: Stands For Nothing

This episode is all about cruising the Med. We also get into cruising with kids, because both our guests are cruising with kids. Learn about the weather, the mooring techniques, the cost of cruising the Med, resources and guides, the latest intel on Orcas, and get great insight into why both our guests loved it so much—that Will and Sarah are heading back again after crossing the Caribbean just last year.

Will & Sarah Curry aboard SV Kaia II of Vancouver
https://www.instagram.com/sailing.kaia/
https://hydrovane.com/

Jillian Greenwalt aboard SV Mug up
https://www.instagram.com/jillian.greenawalt/
https://www.predictwind.com/tracking/SV_MugUp?visibleTrackDuration=0

Music: Stands For Nothing (Ben's band)