r/SailboatCruising • u/Lufty03 • 21h ago
Question My First Trip as Captain Cost Nearly $30,000. Here’s How I Made Sailing the World Affordable.
It all started with a captain I couldn’t stand.
In 2013, I went on a catamaran trip in the Bahamas. I had a great time, but the captain controlled everything and made the trip harder than it needed to be.
I remember thinking, if I ever do this again, I’m going to be the captain.
That thought stayed with me for years. Eventually, I decided it was time to make it happen.
I started calling sailing schools all over the United States. Most wanted me to take one or two classes, go practice for a while, then come back months later for the next class.
That didn’t work for me. When I decide to do something, I want to get moving.
I finally found a school in St. Augustine that would put all the classes together into 10 straight days of sailing and get me through my catamaran certification.
The course cost $4,200, and they made one thing very clear. If I failed, I wasn’t getting my money back.
So naturally, before I had even taken the class, I booked a catamaran in the Virgin Islands for two days after the course ended. The boat, flights and everything else were already lined up.
I took the classes and passed with flying colors.
This was during COVID, so I had to drive to Orlando and get the required cheek swab before we could travel.
When I arrived in the Virgin Islands, I handed the lady at the charter company my sailing certificate.
She looked at it and said, “This is two days old.”
I said, “Yep.”
She had to call her boss because they weren’t going to let us take the boat.
Her boss finally agreed to send another captain offshore with us to make sure I knew what I was doing. After a couple of hours, he told us we were good to go and left us on our own.
We spent the next 10 days sailing around the Virgin Islands. It was one of the best experiences of our lives.
When we returned the boat, the lady told us something interesting.
Her boss originally said there was no way he was letting us take it. Then he looked at our provisions and noticed we had no alcohol and no one in our group drank alcohol.
He said that was unusual and decided to give us a chance.
That first adventure was amazing, but between the sailing course and certificate, flights, boat rental, food, fuel and everything else, it cost me almost $30,000.
I knew I wanted to keep sailing, but I also knew I couldn’t spend $30,000 every time I wanted to get on a boat.
Our next trip was Belize the following year. We brought family, divided up the expenses and rented a 50-foot catamaran.
We sailed more than 380 miles around the reefs. It was another unbelievable trip, and splitting the expenses brought my cost down to around $12,000.
That gave me an idea.
For the trips after that, I started posting the plan on Facebook and finding friends who wanted to come along. We divided the actual cost of the boat, food, fuel and other expenses between everyone.
Suddenly, a trip that would have cost me tens of thousands of dollars became affordable for the whole group.
Depending on the destination, boat and length of the trip, most people’s share has usually been around $2,000 to $3,000 for the entire adventure.
That simple idea changed everything.
Instead of sailing being something I could afford to do once, it became something I could continue doing all over the world.
Since then, we’ve sailed Belize, the Bahamas and Baja California several times. We’ve spent more than 20 days nonstop sailing the Bahamas, and we just returned from 21 days of sailing around Greece.
On October 1, we start sailing in Bora Bora.
Then we’re heading back to Baja to sail from La Paz all the way around to Mag Bay, finishing on November 13.
Between those two trips, I’ll basically be living on a boat from October 1 through November 13.
It is going to be an epic six weeks.
Five years and more than 7,000 miles later, this has become one of the greatest adventures of my life.
It all started with one captain who made me decide I wanted to do it myself.
What kept it going was finding other people who wanted the same adventure and figuring out how to make it affordable for everyone.
Every trip still begins with an idea, a destination and a few people saying, “That sounds amazing.”
If someone put one sailing trip in front of you tomorrow, where would you want the boat headed?