Weekend Getaways from Mexico City, Lisbon, and Chiang Mai
You live abroad now. Your weekends just got a lot more interesting.
This post contains affiliate links. If you book through our links, we may earn a small commission at no extra cost to you. We only recommend services we’d use ourselves. Full disclosure here.
Day trips are great. But some places deserve more than a rushed round trip. A weekend away — two nights, three days — gives you enough time to actually settle into a place, eat a few meals, and come back feeling like you discovered something instead of just checking a box.
Here are the best overnight escapes from each of our three cities, with realistic costs and how to get there.
From Mexico City
Oaxaca
Getting there: 1-hour flight (VivaAerobus or Volaris, $40-100 CAD one-way) or 6.5-hour ADO bus ($35-50 CAD one-way). The flight is worth it.
Why go: Oaxaca is widely considered Mexico’s cultural and culinary capital. The food alone justifies the trip — mole negro, tlayudas, mezcal tasting, chapulines (grasshoppers, if you’re feeling brave). The city is colonial, colourful, walkable, and surrounded by archaeological sites and indigenous villages.
Don’t miss: Monte Albán ruins (30 minutes from the city centre). The Benito Juárez market for fresh food and local crafts. A mezcal tasting in the Valles Centrales.
Weekend budget: $150-300 CAD per person (flight + 2 nights accommodation + food + activities). Find accommodation in Oaxaca.
Guanajuato
Getting there: 4.5-hour bus from CDMX (ETN or Primera Plus, $30-45 CAD one-way) or 1-hour flight to León/Bajío airport
Why go: A hillside university town built in a ravine, painted in every colour imaginable. Underground streets that were once rivers. The Callejón del Beso (Alley of the Kiss) where balconies are close enough to lean across. The Mummy Museum if you like the macabre. At night, estudiantinas (student troubadour groups) lead singing processions through the alleys.
Don’t miss: The Pípila viewpoint at sunset. San Miguel de Allende is 1.5 hours away if you want to extend the trip — it’s beautiful but significantly more expensive and tourist-oriented.
Weekend budget: $120-250 CAD per person. Find accommodation in Guanajuato.
Hierve el Agua (via Oaxaca or as a Standalone)
Getting there: Best combined with an Oaxaca weekend. From Oaxaca city, it’s a 2-hour drive through the mountains.
Why go: Petrified waterfalls — mineral-rich water has been flowing over a cliff for thousands of years, creating rock formations that look like frozen cascades. Natural infinity pools at the top with views over the valley. It’s surreal.
Weekend budget: Add $30-50 CAD to an Oaxaca trip for transport and entrance. Browse Hierve el Agua tours from Oaxaca.
Veracruz
Getting there: 4.5-hour ADO bus ($25-40 CAD one-way) or 1-hour flight
Why go: Mexico’s most important port city. Caribbean vibes, live music in the main plaza every night, fresh seafood, and the fortress of San Juan de Ulúa. It’s hot, humid, and completely different from the altitude and cool air of Mexico City. The malecón (boardwalk) at sunset is special.
Don’t miss: Coffee in Coatepec (30 minutes inland) — one of the best coffee-growing regions in Mexico. La Parroquia de Veracruz for the famous café lechero.
Weekend budget: $120-220 CAD per person. Find accommodation in Veracruz.
Tepoztlán
Getting there: 1.5-hour drive or bus from CDMX (OCC bus, $10-15 CAD)
Why go: A small pueblo mágico tucked beneath dramatic cliffs. The hike to the Tepozteco pyramid (a hilltop Aztec temple with valley views) is the main attraction — about 45 minutes up, moderate difficulty. The weekend market is excellent for crafts and street food. The town has a spiritual, slightly hippie energy that’s a total contrast to CDMX.
Weekend budget: $80-180 CAD per person — one of the cheapest weekend escapes from CDMX. Find accommodation in Tepoztlán.
Read more: Day trips from Mexico City | Mexico City Cost of Living
From Lisbon
Porto
Getting there: 3-hour train (CP Alfa Pendular, $30-50 CAD one-way) or 1-hour flight (TAP, $30-60 CAD with Ryanair)
Why go: Portugal’s second city deserves more than a day trip. The Ribeira waterfront, the port wine cellars in Vila Nova de Gaia, the Livraria Lello bookshop, the Clérigos Tower, and the food — francesinha, bacalhau, and pastéis de nata from the source. Porto has a grittier, more authentic energy than Lisbon.
Don’t miss: Walk across the Dom Luís bridge at sunset. Visit a port wine cellar (tastings run $10-20 CAD). The São Bento train station’s azulejo tiles are worth the entrance even if you’re not catching a train.
Weekend budget: $150-350 CAD per person. Find accommodation in Porto.
The Algarve
Getting there: 3-hour train or bus to Faro, Lagos, or Albufeira ($25-45 CAD one-way)
Why go: Portugal’s southern coast. Dramatic sea caves, golden limestone cliffs, and some of the best beaches in Europe. Lagos and its Ponta da Piedade rock formations are stunning. Faro’s old town is underrated.
Don’t miss: A boat tour of the Benagil sea caves ($25-40 CAD). They’re accessible only by water, and the light inside the main cave is extraordinary. Book ahead in summer.
Weekend budget: $150-350 CAD per person (varies hugely by season — summer is double winter prices). Find accommodation in the Algarve.
Douro Valley
Getting there: 2-hour train from Porto to Pinhão or Régua (the scenic train along the river is the whole point)
Why go: Portugal’s wine country. Terraced vineyards lining the Douro River, port wine quintas (estates) offering tastings and tours, and some of the most beautiful river scenery in Europe. Best combined with a Porto weekend.
Don’t miss: The train ride itself — it follows the river through tunnels and along cliff edges. Book a seat on the right side (heading east) for the river views.
Weekend budget: $150-300 CAD per person (add to a Porto trip). Browse Douro Valley tours.
Évora
Getting there: 1.5-hour bus from Lisbon (Rede Expressos, $15-25 CAD one-way)
Why go: The capital of the Alentejo region. Roman temple, gothic cathedral, the famous Capela dos Ossos (Chapel of Bones), and some of the best regional Portuguese food you’ll find anywhere. The Alentejo is warmer, drier, and more rural than the Lisbon coast.
Don’t miss: The bone chapel is exactly what it sounds like — walls and columns made of human bones. It’s eerie, beautiful, and unlike anything you’ve seen.
Weekend budget: $120-250 CAD per person. Find accommodation in Évora.
Read more: Day trips from Lisbon | Lisbon Cost of Living
From Chiang Mai
Pai
Getting there: 3-hour minivan from Chiang Mai (about $10 CAD one-way, 762 mountain curves — take motion sickness pills if you’re prone). Or a 25-minute flight on Kan Air (seasonal, pricier).
Why go: A small mountain town that’s part backpacker haven, part hippie commune, part natural paradise. Pai Canyon at sunset, Tham Lod cave (bamboo raft through a river cave), hot springs, and a walking street night market that punches well above its weight.
Don’t miss: Rent a motorbike (about $7 CAD/day) and explore the countryside — rice paddies, waterfalls, and viewpoints you’ll have to yourself on weekdays.
Weekend budget: $60-150 CAD per person. Find accommodation in Pai.
Koh Lanta
Getting there: Fly Chiang Mai to Krabi (1.5 hours, $40-80 CAD on AirAsia) then ferry or minivan to Koh Lanta (2 hours)
Why go: A quieter Thai island — less party, more hammock. Long beaches, excellent seafood, and a laid-back vibe that attracts long-term travellers and remote workers. The old town on the east coast is a charming stilted fishing village.
Best as: A 3-4 night trip. The travel time from Chiang Mai makes a 2-night weekend feel rushed.
Weekend budget: $150-300 CAD per person (including flights). Find accommodation on Koh Lanta.
Chiang Rai (Overnight Version)
Getting there: 3-hour bus (Green Bus, $7 CAD one-way)
Why go: The White Temple, Blue Temple, and Black House are better with overnight pacing. But the real reason to stay is the Chiang Rai night bazaar, the clock tower light show, and the slower pace of Thailand’s northernmost major city.
Extend to: The Golden Triangle (where Thailand, Laos, and Myanmar meet) is 1.5 hours north of Chiang Rai. You can take a boat across the Mekong to Laos for a day.
Weekend budget: $60-150 CAD per person. Find accommodation in Chiang Rai.
Sukhothai
Getting there: 5-hour bus from Chiang Mai ($15-20 CAD one-way) or rent a car
Why go: The ruins of Thailand’s first capital. A UNESCO World Heritage Site that’s less visited than Ayutthaya but equally impressive. Rent a bicycle ($3 CAD/day) and ride through the historical park — Buddha statues, lotus ponds, and crumbling temples spread across manicured lawns. It feels like having a ruined city to yourself.
Don’t miss: The central zone at sunset. The Si Satchanalai Historical Park (50 km north) if you have a third day — even fewer visitors and wilder ruins.
Weekend budget: $80-180 CAD per person. Find accommodation in Sukhothai.
Read more: Day trips from Chiang Mai | Chiang Mai Cost of Living
Weekend Trip Tips for Expats
Book accommodation 2-3 weeks ahead. You’ll get better prices and more options than last-minute. For popular destinations (Oaxaca, Sintra, Pai) during high season, book a month ahead. Search accommodation across all destinations.
Take the overnight bus. Mexico, Portugal, and Thailand all have excellent long-distance bus services. An overnight bus saves you a night of accommodation and maximizes your weekend time. ADO in Mexico and NCA in Thailand offer semi-cama (reclining) seats that are genuinely comfortable.
Fly budget airlines for longer distances. Make sure your travel insurance covers the countries you’re visiting. VivaAerobus and Volaris in Mexico, Ryanair and TAP in Portugal, AirAsia and Nok Air in Thailand — all offer domestic flights cheaper than a nice dinner. Book directly through their apps for the lowest prices. Travel light to avoid baggage fees.
Travel with your laptop. If you work remotely, a weekend getaway can double as a “workcation.” Check your accommodation’s Wi-Fi speed before booking. Many Airbnbs in popular expat destinations now list their internet speed in the description.
Don’t overplan. Two activities per day is plenty for a weekend trip. Leave room for wandering, accidental discoveries, and the restaurant you walk past that smells incredible. The best travel memories rarely come from itineraries.
New to living abroad? Start with our scouting trip guide or explore the basics for Mexico, Portugal, or Thailand.
Transport schedules, pricing, and availability change regularly. Costs shown are approximate and in CAD based on early 2026 rates. Always verify current information before booking. Some destinations may have seasonal closures or limited access during certain months.
Congratulation!