If you want to own overseas in 2026—safely, intelligently, profitably—you need more than a hot tip.
You need a roadmap.
Right now, I’m in the middle of delivering exactly that to members of my Real Estate Trend Alert (RETA) group in a live, five-week online masterclass.
And today, I want to give you a look inside…
In a moment, I’ll share a clip of me and my Senior Researcher Margaret Summerfield profiling one of the most compelling real estate destinations on the planet—a place we’ve been scouting for decades and that I’ve ranked among the 25 best places in the world to own property in 2026.
It’s a perfect-weather city in South America with “Eternal Spring” temperatures, mountain backdrops, and leafy neighborhoods filled with cafés and co-working spaces.
Digital nomads, remote entrepreneurs, and in-the-know expats have been gravitating here quietly for years. And yet you can still secure high-quality condos here in the mid-$200,000s…and generate double-digit gross rental yields. You’ll find the clip below. First, a little background on the masterclass…
This South American city has become a major hotspot for snowbirds, digital nomads, and work-from-anywhere professionals thanks to its outstanding climate and high quality of living. Margaret and I discuss it in Session 2 of the masterclass.
Back in 2008, I founded my RETA group to bring together like-minded folks who understand the incredible opportunities in international real estate.
Using the group-buying power of all RETA members, I negotiate exclusive, off-market deals with developers. That means members get in first on best-in-class communities…at prices ordinary investors never see.
Access to exclusive deals like these is the biggest benefit of membership. But RETA members also get access to a vast library of resources and events, including private online masterclasses…
As I write this, I’m in the middle of hosting a five-week online masterclass called Your RETA Roadmap to Wealth, Freedom & a Boundless Life in 2026.
Held live on Zoom, it’s a complete blueprint to owning overseas today.
We started this masterclass by “profiling ourselves”—identifying our goals whether that’s lifestyle, income, capital appreciation, legacy, or some combination of all of them. Then in Session 2, we began matching those profiles to our perfect destinations.
In upcoming sessions, we’ll move on to other topics like how to get financing…strategies for maximizing rental income…or how to manage property simply and effectively.
Today and tomorrow here in Overseas Dream Home, I want to give you a sneak peak inside this masterclass…
In Session 2 of the masterclass, we dove into six of the best places to buy overseas in 2026—from historic towns in Old-World Europe to vibrant cities in Latin America to emerging luxury enclaves in the Caribbean.
Below is a short clip where Margaret and I discuss one of these standout destinations—a perfect-weather South American city beloved by expats and investors.
In this clip, Margaret and I discuss a vibrant, international urban market known for its “eternal spring” climate. Click to view…
Members’ Questions…Answered Live
One of the most valuable aspects of this masterclass is that it’s live and interactive. We end every session with open Q&A, so members can put their real concerns directly to us.
Here are a few recent questions—and my and Margaret’s answers (edited for clarity):
Q: What percentage cashflow are you experiencing from rentals, and which locations are best for ROI?
A: There are excellent destinations right across our beat for earning rental income. Take where I’m staying today—Los Cabos.
In Cabo, if you rent long term—whether that’s in Copala where I’ve owned for 10 years or in in the community of Monte Rocella where I’m about to take possession of two new condos (as I shared in my article yesterday)—you can achieve gross yields in the region of 11% to 12%. And to my mind, when you’re pairing that level of income with the kind of capital appreciation we’ve seen there, that’s extremely compelling.
You can potentially do better on short-term rentals. But at this point, personally I’m prioritizing simplicity. I like the low-maintenance nature of long-term tenants. It’s steady, it’s predictable, and it allows me to capture strong income without adding operational complexity. If your goal is maximizing ROI, renting short term in a destination like Cabo would likely work better for you.
Q: What’s your take on Spain removing 200,000 Airbnb rentals? Do you think the new Airbnb regulations in Spain will impact rental yields significantly?
A: Spain has tightened short-term rental rules in certain select cities, and has moved to remove certain properties that aren’t conforming to the rules. Properties in places like Malaga and the Costa del Sol that are following the rules aren’t impacted.
What tends to happen in situations like this is weaker, non-compliant inventory falls away, while well-located, fully licensed, high-quality properties become even more valuable.
In markets like Barcelona, where restrictions are stricter, you have to be extremely careful about what you buy and ensure it’s legally rentable. But in the right locations—where short-term rental licenses are secure and supply is constrained—regulation can actually strengthen pricing power.
The key, as always, is buying the right property, in the right location, with the right legal footing.
Q: Do we have an upcoming RETA members-only deal in Cabo, Estepona or Greece?
We’re working on opportunities in Cabo and in some of the lesser-known Greek islands. What I’m looking for is a place that’s Santorini levels of beautiful, but without Santorini price tag, and we’re also looking on the north coast, along the coast from Thessaloniki. We’re talking to some developers who own land there and who are looking to create the type of project that would meet the RETA criteria. As for Estepona, we also have our feelers out…
I’ll be back tomorrow with another sneak peek inside the Masterclass.
Session 3 goes live today at 1 p.m. ET for RETA members. Watch your alerts if you’re a member—I’ll send you the link to access today’s session before we go live.
If you’re not yet a member, stay tuned. This weekend, I’m unveiling a special offer to get a trial RETA membership for just $7. This will give you full access to our off-market deals…the vast library of RETA resources…and our live masterclasses, including the complete recordings of this Masterclass. Stay tuned…
Wishing you good real estate investing,
P.S. If you have a question like those above about buying real estate overseas, or have suggestions for destinations my team and I should put on our scouting list, remember you can always drop me a line here.
