Invest Like You Vacation: Turn Your Favorite Cities Into Your Next Real Estate Empire

Ever notice how people spend more time planning a vacation than they do planning their financial future? Seriously, you’ll see folks researching the best pizza in Miami, the best rooftop in Boston, or the best beach in Tampa months in advance. But when it comes to investing? Crickets.

What if I told you that your favorite vacation spots could become your personal gold mines? That all those miles you rack up flying from city to city could also be racking up cash flow, equity, and long-term wealth? That’s what I mean when I say…

“Invest Like You Vacation.”

It’s not just a catchy phrase—it’s a real strategy. One that’s worked for me and for thousands of investors I’ve coached.

Let me break it down.

How It All Started: A Real Call With a Real Investor

On a recent call, an investor said to me:

“Hey, I’m looking for some wholesale deals… maybe something I can fix up and rent out.”

So, I asked where he was based. His answer?

“I bounce between Atlanta, Charlotte, and Tampa. I’m in Atlanta for the summer, Charlotte in the fall, and Tampa during the winter.”

Boom.

Right there, I saw opportunity. I told him, “Man, that’s a nice triangle!”

But in my head, I was thinking: This guy is sitting on the real estate investor’s dream setup and doesn’t even know it.

Why This Triangle Works

When you spend time in a city, you know the rhythms. You know where people hang out, where the new restaurants are popping up, what areas feel safer today than they did five years ago. You become a local without even trying.

That means:

• You understand demand. If you love spending time in an area, chances are renters will too.

• You’ve got boots on the ground. Even if those boots are flip-flops.

• You know the red flags. You’ll notice a shift in the vibe faster than some spreadsheet can tell you.

• You can inspect properties while enjoying brunch. Multi-tasking like a boss.

Let’s Talk Comfort Zones

People think they need to invest in the city they live in full-time. Not true. The better move is to invest in the cities you already feel comfortable in. That might be your winter getaway or the place you fly to for family.

In this investor’s case, Atlanta, Charlotte, and Tampa aren’t just vacation spots—they’re data sources. He knows what rent goes for in Brickell. He knows which Atlanta suburbs are appreciating. He knows Tampa’s housing shortage in winter.

That’s called local knowledge, and it’s powerful.

What I Do With This Info as an Investor and Broker

After investing in 30 rentals and doing over 3,500 deals, I look for every possible edge. If a client tells me they’re already spending time in a city, that becomes part of the investing strategy.

For this investor, I suggested he start by evaluating which of his three cities had the best combination of:

1. Low acquisition cost

2. High rent-to-value ratio

3. Strong property management team (aka us)

In many cases, the answer is Tampa. But sometimes, depending on what you want—cash flow vs equity—the answer can shift.

Our System: Built For This Kind of Investor

At Graystone, we’ve created a system that supports out-of-state investors and vacation-based strategies. We offer a VIP program that:

• Costs $4,000/year

• Gets refunded if we can’t help you

• Pays you $2,000 back per closed deal (so 2 deals = breakeven)

But the biggest value isn’t the program. It’s the connections.

You get access to:

• Our full contractor crew (30-40 active handymen)

• My dad, who oversees projects with 50+ years of experience

• Enrique, my AC guy who gave me cologne for Christmas (true story)

• Property managers, realtors, lenders—all dialed into your deal

Rehab Philosophy: Tonka Thinking

We don’t believe in lipstick on a pig. We believe in forced equity done right.

As long as the 4-point inspection checks out (roof, electric, plumbing, AC), the rest can be renovated. We focus on durability. That’s what I call Tonka Thinking:

“Like the toy trucks—not sexy, but built to last.”

You don’t need granite counters to make money. You need:

• Waterproof vinyl flooring

• Durable kitchen cabinets

• Neutral paint that renters love

• Energy-efficient systems that cut your long-term expenses

Communication Like You’re on Vacation

Forget endless email chains. We use WhatsApp to manage everything.

• Group chats with me, my VP, acquisition team, and property manager

• Real-time video walkthroughs

• 50+ photos during rehab

• Instant Q&A if you’re unsure about something

It’s like a family group chat… but for wealth-building.

Making It Personal

We don’t do cookie-cutter investing here. If you want to invest in Tampa because you spend your winters there—amazing. We’ll help you.

If you want to build a portfolio in Miami because your family lives nearby—let’s go.

If Atlanta is your summer spot and you think you can rent to college students and professionals all year—we’ll guide you on what areas and strategies make sense.

We’ve worked with:

• Doctors who bought 3 homes in their vacation town

• Military families who stationed in Florida and started investing there

• Tech workers who live in New York but visit Tampa for Bucs games and started building passive income here

Some Real Questions to Ask Yourself

Here’s how to use the “Invest Like You Vacation” method:

1. Where do you already go 2-3 times per year?

2. Which city do you feel comfortable navigating without GPS?

3. Where could you reasonably fly in for inspections, meetings, or closings?

4. Which area do you love so much, you’d be excited to visit your investment property?

That’s your triangle.

And the Bonus Tip: Tax Deductions

When you own property in a city you also visit for leisure, guess what? A portion of your trip might be tax-deductible. Hotel? Write-off. Meals? Write-off (within reason).

Talk to your CPA, but the general idea is this: if the trip has a business purpose and you document it, it can often count as a business expense.

Suddenly, that Miami trip isn’t just for beach time—it’s an annual property check-in. With tax perks.

Closing the Loop

That investor who called me? He’s exploring opportunities now and getting a feel for how investing could work in his favorite cities.

It’s always exciting to help someone connect the dots between where they love to spend time and where they could build long-term wealth.

You Can Do This Too

If you’re thinking: “Well, I only travel to one city regularly” — that’s still enough.

Start there. Start small. Buy a house, fix it smart, rent it, repeat.

Then maybe one day, you’re investing in three cities you love. You build your own triangle. You create a system where your vacation spots pay for themselves.

And if you need help? You already know who to call.

Save my number: 813-679-6177. Text me on WhatsApp. Let’s talk deals, cologne-worthy contractors, and how to turn your travel into true wealth.

This article was inspired by a real call between an investor and our CEO, Jorge Vazquez—sharing real strategies, real stories, and real results.

Written by Jorge Vazquez, CEO of Graystone Investment Group & its subsidiary companies and Coach at Property Profit Academy

Property Profit Academy:
✔ Learn to buy properties with little to no money down.
✔ Build a $10M portfolio step by step.
✔ Master strategies like BRRRR and house hacking.

Meet our Team of Experts!

My team and I bring over 20 years of real estate experience, with deep roots in Florida’s investment scene. As a licensed MLO, I’ve helped close millions in loans and investor acquisitions. We’ve built strong relationships with wholesalers, probate attorneys, and sellers to source real deals—not just listings. My goal is simple: align your investments with your vision and deliver results that exceed expectations. Connect with Cody at https://graystoneig.com/cody

Hi, I’m Lisa-Kaye Price, Real Estate Lending Specialist at Graystone Investment Group. With 20 years of experience as both a licensed Realtor® and Mortgage Loan Originator, I specialize in helping investors secure smart financing for powerful real estate moves. Let’s connect and talk strategy! Connect with Lisa at https://graystoneig.com/lisa-kaye-price

Jay Michalec is the COO of Graystone Investment Group and a proud U.S. Army veteran. With 25 years in hospitality, Jay brings leadership, service, and operational excellence to real estate. He’s known for keeping things running smoothly and supporting both the team and clients every step of the way. 📅 Connect with Jay: https://graystoneig.com/jay