Term Charters

One couple's story of how they got started in the term charter industry in the US Virgin Islands (Part 2)

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 2)

After a series of obstacles (covered in part 1), the resilient duo of Whiskey Business was ready to get out sailing and operating their term charter. The sail from Charleston to St. Thomas took one month, so this was time Tippee and Wade felt like they had to spend more time thinking about the charter business side of things. During this sail they had a fellow captain on board to show them the ropes too, so they could continue their learning efforts. Which brings us to our first point: 

Lean on Others For their Expertise

In the world of chartering and boat operations, you can always learn from others about doing something better and more efficient. Talk to people who have been through it and find out the lessons they learned so you don’t have to repeat them. Ask for help. Oftentimes you don’t even know the right questions to ask, 

“The more people they talked to, the more confident they became. If they can do it, why can’t we?” Tippee shared that the most important thing is to be open minded, and don’t close yourself off from people’s advice. You don’t know what you don’t know about sailing, buying a boat, chartering, and living in the Caribbean. 

One of the people that helped them most was Hank of Paradise Yacht Management, whom they met at the Annapolis boat show early on in their journey. He gave them an idea of what the charter business looks like. His story was so similar to theirs and inspired them to believe they could do it. 

Getting Certified 

While a captain’s license is the obvious need for anyone operating a boat, an often overlooked necessity to be in international waters with paying customers is your STCW safety license. This is a strenuous course in putting out fires (literally), inflating life rafts, and other things you need to know to keep your guests safe. 

This wasn’t on Tippee and Wade’s radar, and they found out just weeks before departing for Saint Thomas. Thankfully they were able to squeeze in their STCW training right before they left. But this is just another example of “you don’t know what you don’t know” and an important aspect of getting your term charter operation set up. 

Sharpen Your Skills (All of Them) 

Being on the water requires serious sailing and safety skills, but that’s not all. You also have to have your hospitality hat on as a term charter operator. This means you’re “on” 24/7 and should do what you can to become an accommodating host. 

Tippee stressed the importance of becoming well-rounded. “What looks good when someone goes to your website? Know what sort of credentials you need to start and then explore what you can tack on as you venture out.” Broadening skills can align with your interest. For example, if you love cooking, what classes can you take to sharpen your skills?  

Build In Recuperation Time 

“We knew it was going to be hard work, but we didn’t know how hard” Wade shared. In between charters everything must be cleaned, and sometimes you only have a few days to take care of laundry, maintenance, provisions, and food prep. After a week of working 12+ hour days, there’s a lot of work that goes on in between to prepare for your guests. Back-to-back charters can be tough and don’t give you free time, so consider how much time you want to build in to recuperate and take care of yourself. 

Experiment with Day Charters

After some setbacks at the beginning, the team has seen some amazing profits from their efforts in just a year. They are already seeing repeat charters and word-of-mouth, especially from some of the day charters they took on. While some in the industry may dissuade you from taking day charters on, Tippee and Wade found this to be a great source of referrals. “Our day charters were a gateway for us.” 

That being said, this season they will scale back on day charters as their term charter business has grown. The lesson they learned: treat every day-charter as gold! This can be a great strategy for new charter operators looking to make a splash. 

They did so well in their first year that they are already almost completely booked up for their upcoming season, and even have a few bookings for the season after that. Tippee shared that social media is one of their biggest booking drivers, and they see upwards of 2k engagements a week between their website and social media marketing. And Junglebee helps make sure all their bookings and credit card processing goes smoothly!

The Guests Make the Hard Work Worth it 

And of course, after all the hard work there’s some serious reward: the people you meet. “The friendships you build make it all worth it,” both Tippee and Wade agreed. They still communicate with the people they host and have a blast with their guests despite the need to keep things operating smoothly. 

Be prepared for interesting requests and try to find out before the trip what your guests would like to do. Tippee and Wade have had some interesting requests, from cliff jumping to spear fishing and catching lobsters. “This is our boat, people are here to have fun, but there’s a spectrum where safety is important and you have to be careful,” shared Wade. 

Some final words of wisdom from Tippee and Wade? “You have to push through it.” Eventually you’ll learn what you need to know, and it will become easier. Like all good things that are worth it, you must put your time in in the beginning to get comfortable. We wish Tippee and Wade many years of fun & success in the Caribbean sun!

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