Ask a Captain: Cruising on a Budget, Storm Tactics & Is 80 Too Old to Sail?

Thu, 09 Jul 2026 19:30:03 +0000

In this video, I’m tackling a list of questions collected by my moderator from our recent live streams! From the best pocket cruisers for a Pacific crossing to the raw reality of catamarans vs. monohulls in bad weather, we cover it all. I’m also diving into storm tactics (heaving to vs. running with a drogue), whether sailboats are truly money pits, advice for sailing with kids, and why I’m currently taking a temporary break from the live-aboard life.

Join me every Saturday at 3 PM Eastern Time for our live streams where I give away signed copies of my book!

⚓ RECOMMENDED GEAR & STORES

Defender Marine has been outfitting boaters since 1938, with trusted brands, expert advice, and everything you need for maintenance, upgrades, and refits.
👉Shop Defender Marine: https://defender.com/en_us/

Get 10% off your next Defender Marine order when you purchase a copy of Be The Captain through the link below.
👉Get the book and claim your discount: https://bethecaptain.com/

CHAPTERS
00:00 - Introduction & Saturday Live Streams
00:24 - Is a Submarine a Good Cruising Boat?
00:55 - The Biggest Mistake Offshore Sailors Make
01:51 - Smallest Boats for a Pacific Crossing
02:42 - Monohull vs. Catamaran for Heavy Weather
03:52 - What’s My Next Boat & Why I’m Taking a Break
06:03 - Is the Scanmar 40 Good for Circumnavigation?
08:29 - The History & Legacy of the Cal 40
10:26 - Storm Tactics: For Reaching, Downwind, or Heaving To?
12:25 - Running with a Drogue: Can You Still Steer?
13:10 - How to Adjust a Drogue (and Jordan Series Drogues)
16:18 - Should You Remove Solar Panels Before a Storm?
17:44 - Junk Sails and Unstayed Masts for Cruising
19:52 - Thoughts on Arrow Rigs & Complex Sailing Systems
21:02 - Can You Wrap a Fiberglass Mast in Carbon Fiber?
22:11 - Are All Sailboats Money Pits? (Buying Under $100k)
23:57 - Best Mid-Size Budget Monohulls for Island Hopping
25:06 - Setting a Realistic Maintenance Budget
26:43 - The Reality of Insuring Older Boats (1980s Hulls)
27:57 - Is 80 Years Old Too Old to Start Offshore Sailing?
29:52 - The Pros and Cons of Solo Sailing
31:29 - Managing Watch Schedules for Couples vs. Extra Crew
33:07 - How to Get Into Sailing (Local Clubs & Dock Walking)
34:25 - Crucial Advice for Sailing with Kids
35:48 - Lightning Round: Lazy Jacks, Autopilots, & Pullman Berths
37:21 - Unexpected Sights & Smells at Sea
38:26 - The Truth About Carrying Weapons on a Boat
40:21 - Why Aren't You Sailing Right Now?