Escape & Stay Awhile: Top Long-Stay Holiday Destinations for Canadian Travellers

Okay Canada, we've made it through another travel crisis, and flights are taking off again! Summer's coming to a close, fall will be upon us in no time, which means winter's bitter bite is just around the corner. For those of us who don't live for that Après life, a week in the sun isn't enough, and if this is resonating with you, you're not alone. Whether it’s snowbirds escaping long winters, remote workers wanting to log in from sunnier time zones, or families wanting to embrace slower travel, long-stay vacations are having a moment. But choosing the right destination goes beyond good weather—it’s about affordability, accessibility, internet reliability, safety, and proximity to things that matter: cafes, clinics, nature, and community.

From the cobbled streets of Portugal to the beaches of Southeast Asia, I've compiled some of the best long-stay holiday destinations for Canadians in 2025 and beyond, each offering a unique balance of comfort, culture, and connectivity.

1. Portugal: The Charm of the Algarve

For Canadians looking for Europe without the sticker shock, Portugal’s Algarve region is one of the best bets. With its Mediterranean climate, affordable cost of living, and its becoming a long-stay favourite—especially among retirees, families, and remote workers.

The region offers over 300 days of sunshine per year, fresh seafood, and well-developed infrastructure. Towns like Lagos, Albufeira, and Tavira offer a peaceful, scenic environment with walkable centres, beach access, and modern amenities. The public healthcare system is highly rated, and private insurance is affordable for foreigners.

Like the rest of Europe, Portugal has excellent connectivity, beautiful co-working spaces, and a burgeoning community of expats (and digital nomads.) If after a long stay, Portugal gets its hooks in you (trust me, it will) there's a D7 visa for non-EU visitors, which makes extended stays accessible to Canadians looking to slow down without going off the grid.

Best time to stay: October to April (mild winters, fewer tourists)

2. Mexico: Sun, Simplicity, and Seamless Connectivity

Mexico remains a top long-stay choice for Canadians—not just because of its proximity and affordability, but also due to its diversity of regions. From the beach towns of the Riviera Maya to the colonial cities like Mérida or San Miguel de Allende, Mexico offers something for every lifestyle.

Canadians can stay in Mexico for up to 180 days without a visa, making it easy for extended escapes. Riviera Maya destinations like Playa del Carmen and Tulum attract remote workers and snowbirds alike, thanks to their beachfront resorts and apart-hotels, co-working cafes, and walkable neighborhoods. You’ll also find large grocery chains, international clinics, and cultural programming year-round.

Those craving cooler temperatures and old-world charm often gravitate to highland towns like San Miguel or Lakeside Chapala, both with strong expat communities and a thriving arts scene. Access to Canadian consular services, daily direct flights from most Canadian cities, and bilingual professionals make Mexico feel comfortably close to home.

Best time to stay: November to March (dry season)

3. Thailand: Culture Meets Comfort

For the more adventurous Canadian long-stayer, Thailand offers incredible value, lush landscapes, and welcoming locals. Cities like Chiang Mai and beach towns like Hua Hin or Phuket have become havens for digital nomads and retirees seeking affordability without sacrificing amenities.

Thailand’s low cost of living means your dollar stretches far—think $2 street food, monthly rentals under CAD 1,000, and easy access to wellness services like massages, yoga studios, and healthcare.

Chiang Mai in particular is a long-stay favourite, with modern condos, farmer’s markets, and a serene pace of life. Meanwhile, Hua Hin, a royal beach resort town, offers walkable beachfronts, golf courses, international restaurants, and medical clinics that cater to expats.

Best time to stay: November to February (cool, dry season)

4. Spain: Coastal Comfort in Costa del Sol

Spain has long been a European favourite, but Costa del Sol is especially suited to Canadians seeking sunshine, healthcare access, and easy rail connections. Towns like Marbella, Nerja, and Fuengirola are some of my client's favourite long-stay spots because they offer a blend of relaxed coastal living with the conveniences of modern Europe.

Many Canadians choose Spain for its infrastructure and quality of life. The high-speed trains make weekend city breaks to Seville, Madrid, or Barcelona simple and affordable. In the Costa del Sol region, many locals and service providers speak English, and the international expat scene means new friendships are never far away.

Canadians are currently permitted to stay in Spain for 90 days (per 180 days), but long-stay visas require more planning. New digital nomad and non-lucrative visa options are making it easier to stay legally and comfortably. The public transportation system is efficient, health care is excellent, and there’s no shortage of beaches, tapas bars, and festivals.

Best time to stay: September to May (milder temperatures, fewer crowds)

5. Costa Rica: Pura Vida Meets Practical Living

It should come as no surprise that chasing the 'pura vida' makes this an idyllic destination for long stay holidays for Canadian travellers. With its lush rainforests, welcoming people, and commitment to sustainability, Costa Rica has been a longtime vacation rental spot for Canadians, but it's now a rising star among long-stay travellers. While it may not be as inexpensive as Southeast Asia, the trade-off comes in the form of safety, eco-living, and a strong healthcare system.

The Guanacaste region is a hub for beach lovers, surfers, and retirees, while San José and the Central Valley offer cooler temperatures and access to world-class hospitals and city comforts. Many communities are bilingual, and Costa Rica continues to invest in digital infrastructure, making it viable for remote work.

Nature is never far—volcanoes, waterfalls, cloud forests, and beaches are all within reach. If you're seeking creature comforts, rest assured, grocery stores carry many familiar brands, and organic markets are widespread. Costa Rica's relaxed pace, environmental leadership, and strong community spirit make it an ideal place to recharge.

Best time to stay: December to April (dry season)

6. Bali, Indonesia – A Serene Haven for Balance and Beauty

Oh Bali! I'm a little biased, but if I could take off tomorrow with my son for a long stay, Bali would be my top choice! For Canadian travellers seeking a soulful, wellness-focused, and culturally immersive long-stay destination, Bali continues to shine as a top choice. Known as the Island of the Gods, Bali blends natural beauty with a vibrant spiritual energy that appeals to digital nomads, creatives, families, and retirees alike

Bali's charm lies in its balance: lush rice terraces, cascading waterfalls, and peaceful beaches coexist with lively towns, yoga hubs, co-working cafés, and local warungs. Long-stay guests often find comfort in areas like Ubud for its wellness scene and artistic atmosphere, or Canggu for its modern villas, surf culture, and walkable lifestyle.

Connectivity has improved dramatically in recent years, with high-speed fibre available in most tourist zones and abundant co-working spaces like Outpost and Tropical Nomad. Bali is also budget-friendly: monthly villa rentals with pools can be surprisingly affordable, and day-to-day expenses—meals, transportation, massages—are gentle on the wallet. Many properties offer discounts for stays of 28 days or longer.

The island’s cultural rhythms are another reason guests linger. Local ceremonies, daily offerings, and open-air temples enrich everyday life with meaning and beauty. Canadians who are looking to slow down, live more intentionally, or take a break from the rat race; Speaking from personal experience, I found Bali to be both grounding and inspiring.

The best time to stay in Bali long-term is during the dry season, which runs from May to October, offering sunshine, breezes, and ideal conditions for exploration. Avoid the rainy season (November to March) if you’re not a fan of high humidity or potential flooding in rural areas.

As of 2025, Canadians can enter visa-free for up to 30 days, but for longer stays, it’s recommended to apply for a Visa on Arrival (VoA), which can be extended to 60 days, or a B211A Social/Cultural Visa for longer visits. For remote workers or business travellers, Indonesia is rolling out more flexible visa options, including a digital nomad visa, so be sure to check the latest consulate updates.

Croatia: Coastal Charm with a Cultural Twist

For Canadian long-stayers seeking a mix of seaside beauty and old-world charm, Croatia delivers in spades. From the medieval walls of Dubrovnik to the vibrant harbour front of Split and the laid-back island life of Hvar, there’s no shortage of postcard-worthy backdrops to call home for a while.

While not as budget-friendly as Southeast Asia, Croatia still offers excellent value compared to Western Europe. You’ll find comfortable apartments in coastal towns starting under $1,500 CAD per month, fresh seafood straight from the market, and an

abundance of ferry routes to explore neighbouring islands. Daily life is relaxed yet rich in culture, with festivals, art galleries, and historic architecture at your doorstep.

Dubrovnik and Split are the top picks for urban convenience and history, while islands like Korčula (the birthplace of Marco Polo) and Brač promise quieter stays with stunning beaches and a strong sense of community. Add in the country’s reliable public transport, Mediterranean climate, and friendly locals, and you have all the ingredients for an unforgettable long-term escape. And let's not forget set-jetting: Croatia has been the backdrop for products like Game of Thrones, Star Wars, The Witcher, and The Day of the Jackal, among many more.

Best time to stay: April to June or September to October (pleasant weather, fewer crowds) Ready to Test out Long-Stay Life?

Whether it’s the sun-soaked shores of Portugal, the cultural crossroads of Thailand, the timeless coastlines of Croatia, or another dream destination, 2025 is the year Canadians are embracing longer, more meaningful stays abroad. Beyond just a vacation, these extended getaways offer a chance to slow down, live like a local, and stretch your travel budget further while enjoying the comforts of home. No matter where you choose to unpack your suitcase, long stays open the door to deeper connections, richer experiences, and the freedom to design a lifestyle rooted in discovery.