How To Go On An Epic Sailing Adventure And Live The Dream

Let’s Face it, we have all at some point in our lives dreamed about selling everything and setting sail into the orange glow of the setting sun. Dropping anchor off a deserted tropical island and catching fish for dinner. We then come to the realization that we can’t, for one reason or another. We have a family, career, or don’t know how to sail, or not enough money etc… Those rationals are enough to keep you land locked until… you want it bad enough. When you want it bad enough there is always a way. Here are the steps and things to think about when setting up for your sailing adventure.

1. Read, Read, Read!

Study Material

Read books on sailing, boat types, and stories of hardcore cruisers. Pay close attention to boat design, size, and characteristics. Learn from others’ mistakes and take their advice. Here are a few books that I highly recommend.

Twenty Affordable Sailboats To Take You Anywhere

Twenty Small Sailboats To Take You Anywhere

This Old Boat

The Voyagers Handbook

The Self Sufficient Sailor

The Capable Cruiser

Cruising Under Sail

2. Sail Everything And Anything

I learned how to sail from kiteboarding. I had a very good “feel” for how the sail worked, how far I could point into the wind, and when to sheet in and out.

Kiteboarding To Sailing

The hardest part for me was to translate that “feel” into taking what I SAW on a bigger boat and realizing what was going on with the sails, wind, and boat. They say the hardest boats to sail are dinghies because everything happens much quicker and more technical than on a bigger boat. Sail anything you can get your hands on from small sunfish to ocean going yachts. Volunteer as crew in local races or as a deckhand in a delivery. The more you sail and the more variety of boats you sail the better sailor you will become. You will understand sailing more, read weather better, and know what to do in a variety of situations. Sailing a sunfish can also be some of the most fun you will ever have as you can see in this video Sunfish Sailing – Pure Joy.

Sailing With Chris, Deb, and Fin!

3. Keep Your Eyes Peeled For Your Boat

There are many places to look and many things to look out for when searching for a cruising boat. If you are anything like me you want a fixer-upper for a great price – like next to nothing.  Craigslist and Ebay are great places to keep a watchful eye but the real deals are in the corners of boatyards or in the backyard of someones house.

Tula Abandoned In A Boat Yard

Walk around the boat yard and look for any signs of abandonment or ask the yard manager if they have any boats they are trying to get rid of. Whatch out for the following: rotting wood boats, delimitation, non-running engines, leaky portholes, rotting decks, blistering hulls, and always know that however much you think you will have to spend to get the boat back into sailing shape will probably be double.

4. Find The Right Hull

Tula Is A Classic Double-Ender With A Full Keel

The classics catch my eyes. Offshore cruisers with beautiful lines. Tula is a double-ender pocket cruiser. A boat small enough to be easy to maintain and single-hand but solid and strong enough to take anywhere around the world. You can see and read more about Tula here. When you are searching for your small ship keep a few of these things in mind. shape, size, resell value, hull condition, reputation, build quality, what it comes with, engine.

5. Start Stripping

I Stripped Everything Off Tula’s Decks And Took Pictures Along The Way

Depending on how good a deal you got and how much work needs to be done determines how far you are going to have to strip down your boat. Tula needed everything stripped off her deck, lifeline stanchions, cleats, winches, handrails, even the broken bowsprit. The only thing I left on deck was the mast and standing rigging. Remember to set up a really good shelter over your boat before you strip everything down so that water doesn’t leak into the open holes and cause more rot than what she might already have.

6. Start Working

Early Morning Grinding

It’s probably going to take a lot longer and a lot more work than you thought to get your ship into ship shape. I woke up at 5am on summer mornings to get a coat on the woodwork or a layer of glass on deck before I had to go to work. Then I would stay till 10 or 11 at night under flood lights rigged to the boom to get as much as I could done before the next morning. This Old Boat describes how to do a lot of the work that needs to be done. On Tula it was rebuilding the stern deck, bulwarks, bowsprit, and re-glassing a lot of delamination. You can get a glimpse of the extent of her restoration here.

7. Stay Motivated

Visions Like These Kept Me Going

The way I stayed motivated through all the fiberglass dust and rotting wood was with pictures of crystal blue water lapping against the hull in my head. Sometimes I would even take a nap in Tula in the boat yard and dream of being anchored off a tropical island. Keep reading and sailing during work breaks to keep the feeling of that dream alive. Think about how good it is going to feel to be sailing YOUR SHIP WHEREVER YOU WANT when all the hard work is done! Also, keep working your ass off. This helps keep the momentum up and keeps you excited about seeing the progress (when you finally start seeing it).

Who Cares If It’s Hand Written? I Was Quitting.

Oh, and start setting your life up around your departure. I submitted my resignation letter so that I would have absolutely no excuse to finish he work and nothing holding me back from casting off the lines. Start selling your stuff, simplifying, and getting ready for your journey. Don’t look back, the only way is forward.

8. Reap The Benefits

Sailing With Friends

When You finish that last coat of paint, rip the tape off, and start mounting the hardware you will start to get really really excited. The feeling when the lift dropped Tula in the water for the first time was amazing. Now it’s your time to sail the hell out of your boat and feel the freedom. Stay local first. Sail around the bays, take your friends and family out, and sail in all conditions. Test out your ship, learn what to do in all situations, and make the modifications needed. Really put her through the paces here at home because you would rather break something close here than 1,000 miles away from all your familiar resources.

Sailing With Famiy

9. Shake Down

My Shakedown Trip Was Up To Beautiful Nantucket In The Fall

Go on your shakedown trip. Take a week or two and sail away from home. Pretend like you are on the beginning of your journey and prepare that way. When you come back you will know the things that you will NEED to modify and the things that you might have thought you needed but you really don’t. Get rid of the latter.

10. Go, Go, GO!

Out The Inlet

You will never finish everything on that list. When I left out the Fire Island inlet aboard Tula only about 80% of the woodwork was oiled, her sail bag was still ripped, and there were a few small electrical issues to take care of but I knew from our shakedown trip that I had enough done to be able to GO! Don’t worry about getting everything done, it will never happen, take care of the important things and do the rest along the way! Plan, but not too much, plans change along the way and you don’t want to be stressed trying to stick to a detailed plan. Don’t be a salmon, go with the flow.

These Views Await

Once you set sail your adventures will have just begun. You will learn a lot along the way, meet new people, and have good and bad times. Here are a few posts about my experiences sailing south, what I have learned, and tips and advice. 6 Lessons I Learned Sailing Solo, 2 Simple Steps For Extraordinary Experiences, Short Video Of My Sailing Adventure South, Why You Should Never Take Anything For Granted, 10 Reasons Why Living On A Small Boat Is Amazing.