Going South? Here’s How to Afford a Winter in the Sunshine State

Going south affordably is all about the answer to one question: how much sweat equity are you willing to put in? If you’re willing to work your tail off, you can go to Ocala for the winter for virtually nothing. But, if you’re looking for a high-end, bougie, show-every-weekend, type of experience – that’ll be a bit more expensive.

Photo courtesy of Phyllis Dawson and Team Windchase.

Pick Up a Working Student Gig

There are many benefits to being a working student for the winter. Not only do you get to spend the colder months in the always sunny horse capital of the world, but you also get to learn a lot. As a former working student, I can attest to the fact that every day is the equivalent of an 8-hour riding lesson — not only do you get lots of time in the saddle, but you get to learn about farm management, how to care for horses while traveling, and the nitty-gritty of shows.

Being a working student is also great for equestrians who are in between horses. You’ll get lots of saddle time without having to pay for lessons. You may even get to catch-ride at shows, depending on the arrangement you have with the barn you’re working for.

However, being a working student isn’t all rosy. You probably won’t get many days off and you will have to work from sunup to sundown taking care of the horses. Being a working student can be so rewarding, but you have to be truly passionate about the sport. If you’re looking for a working student gig, you might have some luck on this Facebook group.

Globetrotting freelance event groom Bettina Cardi. Photo by Tilly Berendt.

Groom on the Weekends

Are you organized and efficient, and do you have an eye for details? Being a groom could be the perfect gig for you — and in Ocala, there’s always someone looking for a groom. Contrary to popular belief, you don’t have to pick up grooming as a full-time gig. Instead, you can freelance groom on the weekends for whoever needs it.

If you’re an experienced horse person, picking up occasional grooming gigs can help offset your costs. You’ll still get to go to horse shows and be enveloped in the excitement of a showing atmosphere. Grooming can be even more fun if you groom for someone you know or are close to, like your trainer or friend.

While you groom on the weekends, you can spend your time during the week doing whatever you’d like to do. Trail riding through Florida’s state parks, taking lessons with some of the biggest names in the business, going out to Ocala’s restaurants — you’ll be able to experience everything Ocala has to offer, despite grooming on the weekends. The only catch is that this could impact your own ability to show, as you could be too busy grooming to compete yourself.

Start your grooming career by checking out jobs available for freelance grooms here.

William Fox-Pitt teaches at Liz Halliday-Sharp’s winter base, Horsepower Equestrian in Ocala. Photo by Lisa Madren.

Tag Along with Your Trainer

Nothing’s better than going to Ocala with your barn family! If your trainer is already heading down to Florida, you may be able to work out a deal where you can work off some of your expenses. For example, it’s often mutually beneficial for both you and your trainer if you offer to take care of the horses and barn several days a week in exchange for discounted board or lessons.

This method of going to Ocala is really the best of both worlds– you’ll get to learn about barn management and get your dream experience in Ocala without having to groom on the weekends or work 24/7 as a working student. You’ll also get to be with your barn family. Is there anything better than getting to explore Florida with some of your favorite people from the back of your favorite horse? (The only right answer here is no, there’s not.)

Leslie Law and Countess Cooley. Photo by Shelby Allen.

Go for a Short Getaway

Unfortunately, being an adult means you have to work for a living. Often, the most expensive part of going down to Florida is taking the time off work. I don’t know about your boss, but most employers don’t appreciate it when their employees take off for three months every winter. If you’re lucky enough to work remotely and you can work from Florida over the winter, more power to you! But, if your boss isn’t really happy about you taking a sabbatical every year, you can go for a short trip, no longer than your average vacation.

Going to Ocala for a week or a long weekend is a particularly great option if your trainer is already wintering in the Sunshine State. You may be able to stay with your trainer, and you’ll have someone to take lessons with and who can show you the ropes while you’re down there. Plus, if your trainer has a spare horse you can ride, you won’t have to worry about the costs of bringing your own horse south.

Photo by Alison Green for Shannon Brinkman Photo, shared via Ocala Jockey Club International Three-Day Event on Facebook.

Rent a Stall, Not a Barn

Going solo or just with a few friends? Instead of footing the bill to rent an entire barn that you don’t really need, rent a stall at a nice facility. Many places in Ocala are set up to accommodate the large influx of seasonal equestrians, and that includes having short-term rental stalls available. However, there are a few things you need to consider before going this route.

Many of these places are self-care only, so you have to be comfortable caring for your horse yourself. It also means that you’ll need to be cognizant of when you need to be back at the barn to finish the day’s chores and feed. You’ll need to be comfortable, too, with taking on the risk of the spread of disease that can happen when there are lots of horses from different areas going in and out of the barn.

At the end of the day, there are lots of different ways you can creatively approach going to Ocala for the winter with your horse. If you’re willing to invest some of your own sweat equity, then heading south for the winter can become surprisingly affordable. Plus, going to Ocala isn’t an all or nothing situation. You can balance how much work you want to put in with how much relaxing you want to do on your trip to create the perfect situation for you.

If you decide to rent a stall, or a few, check out this Facebook group for resources.

Have more tips we didn’t mention? Be sure to comment on this post on social media to share your advice for us to share!

This article was sponsored by Ocala Horse Properties, your go-to resource for finding your dream farm in the horse capital of the world. Explore all the farms Ocala has to offer right from your laptop. Shop their selection of homes and horse farms on their website.

1 2 votes
Article Rating
Notify of
Inline Feedbacks
View all comments