Term Charters

One couple's story of how they got started in the term charter industry in the US Virgin Islands (Part 1)

Post by
Samantha Hardcastle

September 22, 2021

One couple's story of how they got started in the term charter industry in the US Virgin Islands (Part 1)

Tippee and Wade knew they wanted a different sort of early retirement than most. After working in corporate America for decades, they were looking to produce income but wanted to have fun and live in a beautiful place. After a few trips out to the Caribbean, they knew a life on the water operating a term charter was something they could get on board with (literally). 

They sold their house, their cars, purchased a boat, and started Raisin’ Sail Island Charters. But of course, there’s so much more to this story than that. In just a year (starting summer of 2020 in the height of COVID) Tippee and Wade have created a successful term charter business in the U.S. Virgin Islands. We asked them to share all their wisdom with us so we could share it with you. 

As Tippee said during our meetup, “you don’t know what you don’t know” and learning from other people is the most important thing you can do when getting into the term charter business. In this 2-part article, we share the most important things to keep top of mind as you go through your own term charter operation journey! 

Start with the Sailing Basics & Give Yourself Ample Time to Learn

When operating a new business, it can be easy to get swept up in the fun and exciting details. But if you’ve never sailed before, start with the basics. Can you pull the boat off the dock and redock it? Can you get it to your final destination safely? 

Only once you’ve covered the foundations of operating a large catamaran are you truly ready to spend time on things like marketing, menu development, and attaining bookings. As Tippee shared, “we didn’t need three months, we needed six!” to get acclimated to this new way of life.  

Spoiler alert: you can’t learn to sail a catamaran in a week. It takes lots of practice. “We would practice drills for hours in the Charleston harbor, going around a marker 25 times one way and another way as the tide changes.” (And a small side tip to those on the East Coast looking to practice: If you can sail in the Charleston harbor, you can sail anywhere - due to the sheer number of boats!) 

Seemingly little things, like having your sail up at the wrong time, could even ruin your boat, as this duo nearly learned. If you’ve never sailed a boat at this large of a size (compared to say, a hobie cat) the techniques are very different. All the ropes and lines can be very overwhelming. Before you start sailing, find someone who understands the ins & outs to teach you, so you don’t lose steerability.

Over time you will begin to understand how the wind impacts the sails and how to read the weather. Basing your actions on the clouds may not be something that comes naturally, but the more you spend time out on the water, the easier it becomes. 

The good news: for operating a term charter in the Caribbean, you don’t be a master sailor. You’re either going East or West, and you’d have to make a special effort to go a direction that allows you to sail. Most time sails aren’t up unless a group says they want to go out and sail. “We try to throw them up – and ask the guests how much they want to sail,” shared Wade. Usually, one person in the group that wants to sail but most people just want to be out on the water. 

Roll with the Waves

You can spend a lot of time planning, but the nature of this operation can often present obstacles. Tippee and Wade were planning to sail in June to the Caribbean once they bought their boat. They soon learned this was not going to work because this is prime hurricane time in the Caribbean. So (a) Insurance wasn’t going to like that and (b) all the haul out slots book out a year in advance. 

This put a wrench in their plan, and they had to take a step back and re-evaluate. As Tippee shared, “three things would go in our favor, and then we would get knocked back.” Such as a lightning strike to their boat only one hour after closing, which resulted in costly repairs and major headaches for this adventurous duo. 

Once they got their boat fixed, they had to find a new home for their 75-foot mast catamaran. Turns out with a mast this high, you can’t sail down intercostal water ways. Not to mention, the bridges in Charleston are max 65 feet. So, changing their schedule meant finding a place to keep their boat for 3 months, and there were only 2 marina options. Thankfully one of them was a good fit and they were able to pivot successfully. 

Timing, the weather, and other obstacles (big and small) are a semi-regular occurrence when you’re getting your term charter business up and running. For example, repairs are not a matter of “if” but when. When a new part was needed for the boat right around Christmas, Tippee and Wade had to drop their holiday celebrations to work with their supplier on a tight turnaround schedule for their next charter. 

Even on a smaller scale, you can have two things go wrong in one day, go a week without any issues, and then something else comes up. Little things like the icemaker breaking, lights going out, and clogged toilets, which may seem like minor challenges on land, are a bit more difficult to sort out on the water.  

A Boat is Nothing Like a House or Car

Which takes us to our next point: you can be the handiest person in the world, but boats are another animal. All the electrical systems are unique on a boat and every make & model is completely different. There’s very little overlap which makes it difficult to learn from others. There are always going to be surprises and things to learn, and it takes time to keep those systems up and running. 

Take plenty of time to go through the manual and learn where everything is and how often things need to be changed. If you find someone who knows your boat, ask them for help! That’s what Tippee and Wade did, when they became acquainted with someone who knew all the systems on their boat. 

But even then, it can be hard to absorb all the information from a simple walk through. Someone can give you enough information to be dangerous, but it’s up to you to get hands-on and learn things for yourself. 

Raisin' Sail is customer of Junglebee for term charter booking system.

Click here to continue reading their sage advice in Part 2! 

Get started!
No monthly fee, no setup fee