The History of Sailing Doodles
- How I got my start, how I found my first sailing opportunity, the first boats I sailed and owned, finding crew, starting up the Youtube Channel, what happened after my boat's engine fire, and what's next for Sailing Doodles
Sailing Destinations
- Insights on costs, weather, safety, activities on worldwide destinations
Cost of Cruising
- Marina and mooring costs depending on location (and being aware of extra fees)
- Provisioning: helpful tips, what's tricky to find while cruising
- Customs and immigration
- Maintenance Costs: average cost per month, getting parts, learning to DIY
- Onshore costs: expenses in different destinations, where's cheap and where's not
- BOTTOM LINE: what are the bare minimums you'll need per month to cruise?
Choosing Your Boat
- Power vs Sail
- Monohull vs Catamaran
- Pros and cons, considerations and costs, lifestyles and atmosphere
Cruising with Pets
- Security and comfort, health and care (seasickness, vet checks and which countries need paperwork), exercise and walks, potty training, clearing in and air travel
Social Life While Cruising
- Choosing a sailing partner or crew, meeting people, social media, kids on board
Handy Apps and Resources I Can't Live Without
- Essential for cruising - plus a demonstration
Safety at Sea and Anchor
- Piracy, firearms policies for different locations
Final Thoughts
- My personal tips on how to make that leap
Q&A
- How is a sailboat better in weather vs a motor yacht?
- My worst weather experience
- How do I find crew? What are the criterion I use for selecting crew?
- Insights on 24/7 passage sailing
- Chartering tips
- Dinghys
- How emergency beacons work
- ...and more!

PLUS... a BONUS top-secret sneak peak of Bobby's upcoming new boat, currently being made!