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)

Our guests this episode are Scott Woodruff, a seasoned boat broker and consultant, and Ian Stewart, an experienced marine surveyor. It's a great episode, worth careful listening for the nuggets are plentiful and the conversation moves quickly through a bunch of great topics. This episode dives into how to buy and sell used cruising sailboats wisely, focusing on when you absolutely should hire a marine surveyor, what “big‑ticket” items really matter, and how keel type, rig age, and moisture issues can make or break a deal. We discuss and compare the casual, trust‑based sales with thorough, survey‑driven purchases. We dive into how insurance companies and smart buyers now expect rigging within a certain age, documented keel and grounding history, and solid structural condition. Scott and Ian, our guests highlight how meticulous maintenance records and independence between brokers and surveyors build buyer confidence, protect both parties, and meaningfully increase a boat’s resale value. Finally, they offer practical tips on choosing a good surveyor—like reviewing sample reports and looking for NAMS or SAMS accreditation—especially when you lack personal recommendations or are buying in a new region.

We get into the issues of trust and clear communication with a surveyor, and why buyers should attend the survey day to see and feel issues firsthand rather than relying only on paperwork. Scott & Ian also discuss managing emotions and expectations on survey day, the role of insurers in approving a deal, and how a good surveyor presents facts and costs without telling you whether to buy—framing the boat as a “problem” you may or may not want to own. They emphasize that there is no perfect boat, that online design dogma (like insisting on a full keel) can mislead buyers, and that both bolted and encapsulated keels have failure modes that a survey should uncover. Finally, they highlight practical takeaways: build a long‑term relationship with a qualified surveyor, review the full written report before deciding, keep realistic expectations about age‑related wear, and, if you’re selling, invest a weekend in cleaning and organizing the boat—especially the bilge—to show care and give buyers confidence in its condition.​

Find out more about our guests:

Scott Woodruff:
https://www.thebrokerage.yachts/
https://collectionyachts.com/scott-woodruff/

Ian Stewart:
https://www.shearwatermarinesurveying.com/

Music:
Tim Eriksen (Ben's Brother)
https://timeriksenmusic.com/

This is a fascinating episode with lots of great insights and experience shared!

Sailing across the Atlantic Ocean is a demanding undertaking! In this episode we discuss the preps and plans for a West to East crossing with two sailors, who recently made the passage. We discuss what they were thinking about before departure, the projects they did, the weather planning and routing decisions, the watch systems, maintaining morale plus managing the boat and a family of 5!

Chris Lobel
is a RYA Yachtmaster Instructor and the skipper/owner of Saga47swan sailing. Chris and his partner Nathalie take up to 4 crew on offshore adventure sailing trips on their classic Swan 47.
https://youtube.com/@Saga47swanSailing
www.Saga47swan.com
https://www.instagram.com/saga47swan
https://www.facebook.com/saga47swan?

Jillian Greenawalt
left upstate New York with her husband and 3 kids aboard a 1972 Bowman 46 in 2021. Together, they've cruised the east coast, the Eastern Caribbean and are now in the Mediterranean. Their boat is called Mug Up!

Music: Stands For Nothing, Ben's band with his brother Tim Eriksen

The trend in bluewater cruising, liveaboard, oceans sailing yachts has been moving towards bigger boats, comfortable living spaces with multiple cabins, galley, and larger bathrooms. But these sailboats are expensive to buy, maintain, and insure, requires more crew, are more difficult to handle, both offshore and in marinas or tight areas.

We talk with Kim Stephens & John Harries about what makes a boat too big to handle safely, and why bigger might not be better sometimes. We analyze some of the pitfalls of this trend, and some of the value added.

Kim Stephens is sailing aboard a Stevens 47, S/V Meraviglia, with her husband, Bob. They are long time health care professionals and in 2022 decided to take a break and experience life on the water while we had the physical ability to do so. They did a total refit of their vessel, working, on her full time from June of 2023 to February 2024. They are currently in Aruba after beginning our journey in Brunswick, Georgia in February and working their way down the thorny path. They plan to transit the Panama Canal in December and explore the South Pacific in 2025.

Website: https://sailingmeraviglia.com/
Instagram: @SailingMeraviglia

John Harries was born and brought up in Bermuda and started sailing as a child, racing locally and offshore before turning to cruising. He has sailed over 150,000 miles, most of it on his McCurdy & Rhodes 56, Morgan’s Cloud, including eight ocean races to Bermuda, culminating in winning his class twice in the Newport Bermuda Race. He has skippered a series of voyages in the North Atlantic, the majority of which have been to the high latitudes. John has been helping others go voyaging by sharing his experience for nearly 30 years, first in yachting magazines and, for the last 22 years, as co-editor/publisher of AAC.

Website: https://www.morganscloud.com Attainable Adventure Cruising

Music: Stands For Nothing, Ben's band with his brother Tim Eriksen

World schooling is the educational approach where learning takes place primarily through travel and experiencing different cultures and environments around the world.

Sometimes, World Schooling can involve short-term trips, like the 3-months Teresa and I are currently spending in Italy while our son, Haven, attends a school here. We’re doing this with a program called Boundless Life. Sometimes, world schooling involves long-term travel or even a full-time nomadic lifestyle, like the many sailing families we’ve had on this show in the past.

By the way, If you've got remote work and want to try living in another country, let us know! Boundless Life is amazing, and I'm happy to pay it forward with a discount. Just mention "Carey Family." 👩‍💻🌐

So, while we’re here in Italy, Teresa sat down with two world schooling parents. Her first guest is Steve Crider, a self-employed consultant with a lot of work flexibility. He and his family just started some extended travel across the US and Europe. We met them here in Italy through the Boundless Life program, and their children attend school with our son.

Our other guest is Maggie Hirt, an author and mother who “boatschooled” her four children on a global voyage with her family. The trip lasted several years and she is planning to get back to it.

Steve, Maggie, and Teresa talked about worldschooling and what works best for their families.

Music: Stands For Nothing, Ben's band with his brother Tim Eriksen

This Episode:
Today we’ll eavesdrop on a conversation Ben had with two sailors who are cruising in the Bahamas. Our guests are Nica Waters, who you may know from the Boat Galley Podcast or her blog Fit2Sail, and Dave Martin, a former MoA Student and Marine industry professional turned (mostly) full-time cruiser. Ben talked with them about their recent crossings to the Bahamas, which they did earlier this season. So, if you’re looking to spend the winter in the Bahamas but nervous about the crossing, which, for a lot of people crossing to the Bahamas is often their first overnight passage, so, if that's you, then you’ll love this episode because they compared notes, they talk about weather windows, destinations, and anchorages and discussed the ins and outs of getting your boat to the Bahamas for a relaxing and exciting winter.

The Music:
Stands For Nothing