How I Afford to Travel: The Long-Term Strategy

There are lots of short-term tips out there for how you can afford to travel: take on extra part-time jobs, live beneath your means, shop at thrift stores, or look beyond traditional hotels. They are all great, and they all work. But, the method that has provided my family and me with an ongoing travel budget is purchasing our Hilton Head Island beach house and renting it weekly to beach vacationers.

Eighteen years ago we went on vacation with some friends to Hilton Head Island, South Carolina. Our three families loaded up our respective mini-vans and headed to the beach, where we rented a condo. It was a fun family week of beach time, pool time, family dinners in, and restaurant dinners out. The men golfed, the women parasailed, and the kids went on a crabbing excursion. Memories were made, and we knew this was a family tradition we wanted to continue.

One day I went for a run in the almost 100-degree heat. When I got tired the only air-conditioned place to escape was a real estate office. I walked in and started reading the bulletin board filled with listings. By the time I left I had an appointment to bring my husband back to look at villas. We made a purchase, and our side hustle of being vacation rental owners began. We’ve never looked back. I suppose my story falls into the category of turning your passion into a business.

The men golfed, the women parasailed, and the kids went on a crabbing excursion. Memories were made, and we knew this was a family tradition we wanted to continue.

Eighteen years later we own a vacation home that is worth more than our first home, the mortgage is paid, and the property makes more income than I could spend traveling in a year. You see, when you love to travel, it is easy to “sell” travel to other people. I value the family beach experience and I want every family to have that experience. Here are some tips to get started and realize your dream to be able to afford to travel:

Yes, you do need a down-payment and an emergency fund to get started. Use the same short-term travel saving tips you use to save for a trip to save for a vacation home. It may take a bit longer, but the long-term rewards are worth it.

If you need to, start small. There are many one and two-bedroom vacation condos and villas available, and the income will pay the expenses. As you learn the business you can take more risks and buy a larger place that accommodates more people, or buy several smaller units. More renters are looking for clean, safe and functional holiday homes than fancy and expensive ones.

Manage your own rentals through an online rental site. A management company will take 25-30% or more of your rent. Take matters into your own hands with a good local cleaning and maintenance company. Ask your realtor for recommendations of good, local service providers. I take payments, program door codes, schedule cleaning and maintenance and many other tasks from my laptop, wherever I am in the world.

When you love to travel, it is easy to “sell” travel to other people.

Choose a place with a long season. Our place is available to rent all year. If you choose a place with a short season, be sure the rents still cover an entire year of expenses.

Go to your property 2-3 times per year for maintenance trips. It is not completely a vacation, but I would rather be cleaning and painting at the beach than at home! If you have the time, do the work. If you don’t have the time or skills, pay someone. Life is always a time and money trade-off.

Maximize the use of your property by joining a house-swapping organization. You can trade a week in your vacation home with house swappers from all over the world. This is usually a cashless barter, except for the cleaning fee.  Owning a vacation rental home can give you free accommodation anywhere when you trade. This is not a quick fix strategy to fund your next trip, but a long term commitment to guaranteeing a lifetime of travel in more ways than you can ever imagine.

Finally, get started! The sooner you begin this side hustle, the sooner the mortgage will be paid, and you will have created an evergreen stream of travel funds.