How to Choose a Country for Wintering: A Comparison of Popular Destinations

As remote work and location-independent lifestyles grow in popularity, so does the trend of wintering abroad — escaping cold, gray winters in favor of warmer, sunnier climates. From retirees to digital nomads, more people are asking the same question each year: where’s the best place to spend the winter?

Choosing the right country for wintering isn’t just about the weather. It involves weighing factors like cost of living, visa policies, infrastructure, safety, healthcare, and the ease of blending into the local culture. Among the many options available, Turkey is increasingly standing out as one of the most practical and affordable choices — especially since buying property there can offer a fast track to legal residency.

Let’s take a look at some of the most popular wintering destinations and see how they compare.

1. Thailand

Thailand remains a favorite among long-term travelers, offering stunning beaches, delicious food, and a welcoming culture. Chiang Mai and Phuket are especially popular with winterers.

Pros: Affordable, excellent food, warm climate, established expat communities.
Cons: Visa runs are often required, language barrier, seasonal tourist crowds.

2. Spain

Southern Spain — particularly Andalusia and the Costa del Sol — attracts many Europeans looking for mild winters in a Mediterranean setting.

Pros: EU standards of living, great healthcare, friendly visa options for EU citizens.
Cons: Higher cost of living than Southeast Asia or Turkey, complex visa options for non-EU citizens.

3. Turkey

Turkey is gaining popularity as a wintering destination for those seeking a balance between affordability, comfort, and culture. Cities like Antalya, Alanya, and Fethiye offer mild winters, low living costs, and beautiful coastal landscapes.

Pros: Inexpensive housing, good infrastructure, easy residency through property purchase, diverse expat communities.
Cons: Turkish language may be a challenge, currency fluctuations can affect budgeting.

4. Portugal

The Algarve region in southern Portugal offers one of the best climates in Europe during winter and is known for being friendly to foreigners.

Pros: High quality of life, good healthcare, Golden Visa options.
Cons: Rising property prices, visa complexity for non-EU citizens.

5. Mexico

Cities like Playa del Carmen and Puerto Vallarta are popular with North American snowbirds thanks to warm weather and proximity to the U.S. and Canada.

Pros: Accessible, vibrant culture, low living costs.
Cons: Safety concerns in some areas, bureaucracy can be challenging.


Key Considerations When Choosing

  • Visa and Residency Options: Can you stay longer than 90 days? Do you need to leave the country and come back?

  • Healthcare: Is private or public healthcare available and affordable?

  • Internet and Infrastructure: Especially important for remote workers or families.

  • Cost of Living: Daily expenses, rent, and lifestyle flexibility.

  • Cultural Fit: Will you feel comfortable in the local environment?


While all of these destinations have something unique to offer, Turkey strikes an impressive balance — offering warm coastal cities, excellent value for money, and a relatively straightforward legal path to staying longer than just a few months. For those considering a wintering spot that could turn into something more permanent, it’s certainly worth serious consideration.