5 Trips to Take This February when Winter Feels Endless
February in Calgary is that point in winter when the novelty has worn off and the forecast still looks cold and grey. The holidays are long past, daylight is still limited, and winter routines start to wear thin. Travelling this month isn’t about escaping reality or chasing “perfect weather.” It’s about finding places that are genuinely easier to be in places where the weather, pace, and local culture make your days feel a bit smoother. This guide walks through five destinations that make sense for February travel with details that help you plan: flight times from Calgary, recommended hotels, and some of the best local dishes to try. This list focuses on destinations that make sense in February. Three offer reliable warm weather outside of Canada. Two stay closer to home while still offering a noticeably different winter experience than Calgary.
For many of these locations there aren’t direct flights from Calgary, so flight times include typical connection routes and overall travel expectations.
Some of the links below are affiliate links, including Booking.com, which means I may earn a small commission if you book through them, at no extra cost to you. I only share places I genuinely love or would book myself! If you’re enrolled in their Genius program you can also find flights that are cheaper then you may find anywhere else.
Oaxaca, Mexico
Oaxaca is a city that rewards time and attention. It is compact, walkable, and structured around neighbourhoods that each feel distinct without being difficult to navigate. February is one of the most comfortable months to visit, with warm daytime temperatures and cooler evenings that make long days outside manageable. Unlike resort destinations, Oaxaca does not require constant planning or transportation. Many of the best experiences happen on foot, often unexpectedly, through markets, plazas, and side streets.
Food is the central organizing feature of daily life in Oaxaca. Meals are not rushed, and the city’s reputation as one of Mexico’s most important culinary regions is reflected everywhere from street stalls to formal restaurants. February is a good time to explore local markets such as Mercado Benito Juárez and Mercado 20 de Noviembre without extreme heat or heavy crowds. Cultural sites, including churches, museums, and artisan workshops, are easy to layer into a day without feeling like a checklist.
A flight from Calgary International Airport (YYC) to Oaxaca International Airport (OAX) usually requires a connection, often in Houston or Dallas. Total travel time is typically around 10 to 11 hours including layovers.
Oaxaca has comfortable warm days in February. The weather is stable, not humid, making it easier to explore on foot, visit markets, and take city tours without extreme heat.
Where to Stay in Oaxaca
Hotel Escondido Oaxaca
Average $500-750/night
Hotel Escondido Oaxaca is located right in Oaxaca’s historic center, just steps from Santo Domingo Temple and within easy walking distance of the city’s best cafés, galleries, and markets. Despite its central location, the hotel feels like a quiet retreat, tucked behind a minimalist concrete façade. One of its most distinctive features is the rooftop terrace, which includes a pool and panoramic views over the city—an ideal place to cool off after a day of exploring. Designed with a modern, understated aesthetic, the hotel blends traditional Oaxacan materials with contemporary architecture, creating a calm, design-forward space that feels both elevated and deeply connected to its surroundings.
Hotel con Corazon Oaxaca:
Average $350/night
Hotel con Corazón is located just outside Oaxaca’s downtown core—close enough to reach major landmarks like Santo Domingo and the Oaxaca Cathedral, but far enough to feel calm and residential. What makes this hotel truly special is its mission: it’s a socially responsible hotel that reinvests its profits into local education projects. The property itself is simple, bright, and peaceful, with open terraces and a central garden that invite you to slow down. Staying here feels meaningful—you’re not just visiting Oaxaca, you’re directly supporting the community while you do.
NaNa Vida Hotel Oaxaca
Average $200/night
NaNa Vida Hotel Oaxaca is tucked into a quiet corner just a short walk from the heart of Oaxaca City—less than 10 minutes from both the iconic Oaxaca Cathedral and Santo Domingo Temple. The location makes it easy to explore the city’s historic streets while still having a peaceful place to return to at the end of the day. What makes NaNa Vida feel especially welcoming are its thoughtful touches, from its leafy garden terrace to its on-site restaurant serving traditional Mexican cuisine with vegetarian and gluten-free options. The hotel also offers wellness services and curated tours, making it a great home base for travelers who want both comfort and connection to the local culture.
What to Eat in Oaxaca
Oaxaca is considered one of Mexico’s most significant food cities, anchored by a rich regional cuisine. Some dishes to prioritize:
Tlayuda – Often called a “Oaxacan pizza,” this large, crisp tortilla is topped with beans, cheese, meat, and vegetables.
Mole – Oaxaca is famous for its “seven moles,” rich sauces served over chicken, pork, or other meats with deep, layered flavours.
Tamales Oaxaqueños – Corn dough filled and steamed in banana leaves.
Quesillo/Oaxacan Cheese – A stringy, mild cheese used in many dishes.
Oaxaca combines manageable weather with deep culture and food. It’s possible to explore markets and colonial streets without feeling rushed. The city is compact enough that you can cover a lot of ground without long transit times.
Costa Rica – Nicoya Peninsula / Santa Teresa
The Nicoya Peninsula offers a version of Costa Rica that is calm, sun focused, and uncomplicated. February sits firmly in the dry season, which means reliable weather and days shaped by daylight rather than rain patterns. Travel here tends to revolve around beaches, light activity, and rest, rather than sightseeing or packed itineraries.
Santa Teresa and surrounding areas are well suited to travellers who want flexibility. Days can be structured or left open without consequence. The infrastructure supports this pace with walkable beach access, casual dining options, and accommodations that prioritize outdoor living. February conditions allow for swimming, walking, and movement without needing to plan around weather shifts.
There aren’t direct flights to Santa Teresa itself; the closest major airport is Liberia (LIR) or San José (SJO), both requiring at least one connection from Calgary. Flights to San José often take 9 to 10 hours including layovers in U.S. hubs (e.g., Dallas or Houston). Once in Costa Rica, you can arrange transfers to the Nicoya Peninsula.
February sits in Costa Rica’s dry season, especially on the Pacific coast around the Nicoya Peninsula and Santa Teresa. This means more sun and less rain, making it one of the most reliable times to visit.
Where to Stay (Santa Teresa)
Playa Cielo Beachfront Hotel
Average $750-1,000/night
Playa Cielo Beachfront Hotel is located directly on the beach in Santa Teresa, offering immediate access to the sand and ocean just steps from your room. The beachfront setting gives it a relaxed, tucked-away feel while still being close to the town’s restaurants and surf spots. One of its most unique features is the open-roof showers in each room, which bring the outdoors in and add to the tropical experience. Rooms also include kitchenettes and private terraces, making it especially comfortable for longer stays. With its beachfront pool, on-site restaurant, and help arranging local activities, Playa Cielo is ideal for travellers looking to fully settle into Santa Teresa’s slow, coastal rhythm.
Believe Surf & Yoga Lodge Santa Teresa
Average $85-100/night
Believe Surf & Yoga Lodge is located in Santa Teresa surrounded by lush greenery, offering a peaceful retreat just minutes from the beach and main town. The property is designed with wellness in mind, featuring daily yoga classes, a fitness space, and a tranquil pool area. Many rooms include kitchenettes and balconies overlooking the garden, which makes it ideal for longer, slower stays. The on-site restaurant focuses on fresh, nourishing meals with plenty of vegetarian and wellness-focused options, making it a natural fit for travelers coming to Santa Teresa for surf, yoga, and a more intentional pace.
Hotel Santa Teresa:
Average $175-200/night
Hotel Santa Teresa is perfectly located just 50 yards from Playa Carmen, right in the center of Santa Teresa’s main strip. You’re within walking distance of surf spots, restaurants, cafés, and shops, which makes it an incredibly convenient base. The hotel blends boutique comfort with eco-conscious design and recently underwent a full renovation. One of its standout features is the ESSENTTIAL Spa, along with included Costa Rican breakfasts featuring fresh fruit, gallo pinto, and made-to-order eggs. Its central courtyard pool, spacious balconies, and proximity to everyday essentials like grocery stores and boutiques make it especially easy to settle in for longer stays.
Blue Mist Hotel
Average $275-350/night
Blue Mist Hotel sits directly on Playa Hermosa in Santa Teresa, offering true beachfront access just steps from the sand. The adults-only setting gives it a peaceful, elevated feel—ideal for couples or anyone looking for a quieter stay. One of its standout features is the combination of ocean-view balconies, a beachfront infinity pool, and an on-site spa and fitness center, which makes it easy to fully settle into vacation mode without leaving the property. The hotel’s modern restaurant and private beach area make it just as appealing for relaxing days in as it is for exploring Santa Teresa.
What to Eat in Costa Rica
Costa Rican cuisine in beach towns focuses on fresh, local ingredients:
Casado – A typical plate with rice, beans, plantains, salad, and protein (fish, chicken, or beef).
Gallo Pinto – Rice and beans stir-fried with spices, common for breakfast.
Ceviche – Fresh raw fish or seafood marinated in citrus with herbs.
Patacones – Fried green plantains, often as a side or snack.
Local restaurants often serve seafood and tropical fruit juices that make straightforward meals feel fresh and satisfying.
Thailand – Chiang Mai
Thailand is a practical choice for February travel if you are looking for a full break from winter and have enough time to justify the long flight. February falls within the country’s cooler dry season, which makes it one of the most comfortable months for travel across multiple regions. This flexibility allows travellers to combine cultural destinations with beach time without dealing with extreme heat or monsoon conditions.
The country’s strength lies in its infrastructure. Domestic flights, trains, and accommodations are widely available, which makes it possible to move between regions without excessive stress. February is also a period when popular destinations feel active but manageable, provided you plan pacing carefully.
There are no direct flights from Calgary to Thailand. A typical trip via major hubs (e.g., Vancouver or U.S. airports) to Bangkok or another major Asian city means total flight times to Bangkok or Chiang Mai are often 17 to 20+ hours including at least one stop, with additional domestic flights if connecting to Chiang Mai.
Because flight durations are long, this option is best for travellers who can take at least two weeks or more.
February falls in Thailand’s “cool” season, which is often dry and warm without the high humidity or monsoon conditions of other parts of the year. It’s a comfortable time for both cultural visits and beach-side days.
Where to Stay in Chiang Mai
Thai Akara - Lanna Boutique Hotel
Average $175-200/night
Thai Akara – Lanna Boutique Hotel is located in the heart of Chiang Mai’s Old Town, just a short walk from landmarks like the Three Kings Monument and many of the area’s most beautiful temples, cafés, and markets. The hotel blends traditional Lanna design with modern comfort, creating a space that feels both culturally rooted and relaxing. One of its standout features is the peaceful courtyard pool, surrounded by greenery, which feels like a quiet escape from the busy streets outside. With an on-site Thai restaurant, fitness center, and thoughtful service, Thai Akara makes an ideal base for exploring Old Town while still having a calm, retreat-like atmosphere.
Ping Nakara Boutique Hotel & Spa
Average $425/night
Ping Nakara Boutique Hotel and Spa is located just outside Chiang Mai’s Old Town near the Ping River, within easy walking distance of the Night Bazaar and riverside restaurants. The hotel itself is set in a beautiful colonial-style building, which gives it a romantic, old-world charm that feels distinct from many other properties in the area. Its spa is one of its most memorable features, offering massages and wellness treatments that make it easy to slow down after a day of exploring. The outdoor pool, quiet library, and handcrafted furnishings throughout the hotel create an atmosphere that feels intimate, elegant, and deeply relaxing.
Arak 9 Villa in the Old Town
Average $350/night for the entire villa (fits 10 people)
Arak 9 Villa is located directly in Chiang Mai’s Old Town, just an easy walk from Wat Phra Singh, local markets, and many of the city’s most important temples. Unlike a traditional hotel, this private four-bedroom villa offers a much more spacious and residential experience, making it ideal for families or groups traveling together. The villa includes its own garden, sun terrace, full kitchen, and multiple living spaces, allowing you to fully settle in and experience Chiang Mai at a slower pace. Its central location combined with the privacy of a standalone home makes it a unique option for travellers who want both convenience and a more personal, home-like stay.
Looking for some options under $100/night but not a hostel?
Check these out for some great options in Old Town: Rich Lanna House (we stayed here!), Wannamas Chiangmai Boutique House, Sathu Hotel, Cozy Inn Chiang Mai, Eleven Pillar Site Chiangmai
What to Eat in Thailand
Thai food varies by region but here are essentials:
Khao Soi – A creamy coconut curry noodle soup popular in northern Thailand.
Pad Thai – Stir-fried noodles with egg, tofu, and peanuts.
Som Tam – Green papaya salad with lime and chili.
Massaman Curry – A milder, aromatic curry.
Mango Sticky Rice – Sweet dessert with mango and coconut rice.
Thailand’s food scene is broad, so exploring night markets and local eateries often offers the best value and variety.
Want more about Thailand? Check out my other posts:
Vancouver Island, Canada
Vancouver Island offers an alternative approach to February travel that does not rely on escaping winter entirely. The island’s coastal climate brings milder temperatures, rain instead of deep cold, and landscapes that remain green throughout the season. This shift alone can make February feel more manageable, even without sunshine.
Victoria and Tofino serve different travel needs. Victoria offers structure, walkability, and consistent access to dining and cultural activities. Tofino is quieter and more dependent on weather, which makes it better suited to travellers who want unstructured days shaped by landscape rather than plans. February is a good time to visit both because expectations naturally align with the season.
Flights from Calgary to Victoria (YYJ) are usually just over 1 hour and 45 minutes, depending on connection routes. And can be as cheap as $350 RT from Calgary. Many flights connect via Vancouver and total travel time with layovers might reach 2.5 to 3 hours. Local airports also connect to Nanaimo and other island gateways with similar durations.
It’s still winter, but Vancouver Island is significantly milder than Calgary. The coastal climate brings rain rather than deep freeze, and the landscape feels more dynamic with ocean views and green forests.
Where to Stay
Victoria (City + Harbour)
Hotel Grand Pacific
Average $250-300/night
Hotel Grand Pacific is located directly on Victoria’s Inner Harbour, just steps from the Parliament Buildings and ferry terminals, making it one of the most convenient bases for exploring the city on foot. Its waterfront setting means you’re within minutes of Beacon Hill Park, the harbor walkway, and downtown restaurants and shops. Many rooms include private balconies, allowing you to take in the coastal atmosphere right from your room. The hotel also features an indoor pool, hot tub, fitness center, and an on-site restaurant and terrace, making it easy to relax and settle in between days spent exploring Victoria.
The Fairmont Empress
Average $350-500/night
Fairmont Empress is located directly on Victoria’s Inner Harbour, placing you within easy walking distance of the Royal BC Museum, waterfront paths, and the city’s historic downtown. As one of Victoria’s most iconic landmark hotels, it blends historic grandeur with modern comfort. One of its most distinctive experiences is its traditional afternoon tea, served in an elegant lobby overlooking the harbor—a longstanding tradition that feels deeply connected to the city’s heritage. The hotel also features the Willow Stream Spa, indoor pool, and beautifully preserved Victorian architecture, making it feel as much like a destination as it is a place to stay.
Tofino (West Coast, Pacific)
Pacific Sands Beach Resort
Average $750/night
Pacific Sands Beach Resort is located directly on Cox Bay, offering one of the most scenic and immersive beachfront stays in Tofino. Surrounded by rainforest and ocean, the resort feels deeply connected to nature while still offering modern comfort. Each suite features full kitchens, fireplaces, and floor-to-ceiling windows, allowing you to fully take in the coastal views. The resort is especially known for its surf culture, with on-site surf lessons, rentals, and easy beach access. Unique touches like Nordic-style beachfront saunas, storm-watching amenities, and guided nature walks make it an ideal place to experience Tofino’s rugged, restorative west coast atmosphere.
Long Beach Lodge Resort
Average $700/night
Long Beach Lodge Resort is located directly on Cox Bay along the Pacific Rim Highway, one of Tofino’s most iconic surf beaches and just minutes from Pacific Rim National Park. The beachfront setting gives the resort an immersive, west coast feel, with uninterrupted ocean views and easy access to the sand. One of its most unique features is its on-site surf club, offering private surf lessons year-round, along with opportunities to book whale watching and boat charters nearby. The Great Room restaurant, with its floor-to-ceiling windows overlooking the ocean, creates a cozy place to watch storms roll in or sunsets over the Pacific.
The Shoreline Tofino
Average $200/night
The Shoreline Tofino is perched along the water’s edge just outside Tofino’s town center, offering peaceful oceanfront views while still being close to restaurants, beaches, and the harbor. The property feels quiet and tucked into nature, surrounded by coastal greenery. One of its standout features is its private cabins and suites with ocean-facing balconies, kitchenettes, and outdoor seating areas, allowing you to fully slow down and take in the landscape. The addition of a sauna and outdoor hot tubs makes it especially ideal after long beach walks or surf days.
These offer choices from central urban stays to locations where weather and landscape are fronts of their own kind of experience.
What to Eat on Vancouver Island
Island food reflects Pacific Northwest ingredients:
Salmon – Wild-caught when in season, prepared grilled or smoked.
Oysters – Fresh from local waters, often served raw or grilled.
Japadog-style street sausages – Vancouver-inspired fusion snacks.
Local craft beer and cider – Many island breweries offer seasonal selections.
Eastern Canada – Montreal or Quebec City
Montreal and Quebec City offer winter travel experiences that feel intentional rather than endured. Both cities are built to function well in cold weather, with strong transit systems, dense neighbourhoods, and a culture that supports indoor gathering during winter months. February is not treated as an off season, but as a continuation of cultural and culinary life.
Montreal offers scale and variety, with distinct neighbourhoods, extensive dining options, and museums that support full winter itineraries. Quebec City is smaller and more compact, with a historic layout that feels especially cohesive during winter. Both cities provide a sense of place that makes cold weather feel secondary rather than dominant.
Flights from Calgary to Montreal (YUL) typically take around 4.5 to 5 hours non-stop. Flights to Quebec City (YQB) usually have one stop, and total travel time can be around 6+ hours including connection.
Both cities are designed to handle winter weather and have strong indoor cultural options.
Eastern Canadian cities embrace winter. Instead of pretending it doesn’t exist, they offer ways to experience it with structure — indoor museums, cafés, and a built environment that feels lively even when temperatures are lower.
Where to Stay in Montreal
Auberge du Vieux Port
Average $300/night
Auberge du Vieux-Port is located directly along the St. Lawrence River in Old Montreal, placing you within easy walking distance of the Old Port, Notre-Dame Basilica, and the city’s cobblestone streets filled with cafés and galleries. Set inside a historic warehouse, the hotel blends original architectural details with modern comfort, giving it a warm, boutique feel. Many rooms offer river views, and its French-inspired restaurant and rooftop terrace make it easy to fully experience the charm of Old Montreal without ever leaving the property. The combination of waterfront location and historic character makes it one of the most atmospheric places to stay in the city.
Sonolux
Average
SonoLux is located in the heart of Old Montreal, just steps from Notre-Dame Basilica and a short walk to the Old Port waterfront. Its central location makes it easy to explore the city’s historic core, restaurants, and riverfront paths entirely on foot. The hotel offers a more modern, minimalist experience, with soundproofed rooms and clean, contemporary design that create a calm escape from the busy streets outside. Its on-site restaurant and bar, along with concierge services, make it a convenient and comfortable base for exploring Montreal while still having a quiet space to return to.
Quebec City
Fairmont Le Château Frontenac
Average $315-350/night
Fairmont Le Château Frontenac is located in the heart of Old Quebec overlooking the St. Lawrence River, and is widely considered the most iconic hotel in the city. Its castle-like architecture defines the skyline and places you within walking distance of historic streets, landmarks, and scenic viewpoints. Beyond its historic setting, the hotel offers a full-service spa, indoor pool, and multiple dining options, allowing guests to fully settle in and experience the property itself. Staying here feels like stepping into Quebec City’s history while still having the comfort and amenities of a modern luxury hotel.
Hotel 71
Average $275/night
Hotel 71 is located in the heart of Old Quebec’s historic district, just steps from Place Royale, the St. Lawrence River, and some of the city’s most charming streets. Housed in a beautifully preserved 19th-century building, the hotel blends historic architecture with modern interiors and large windows that overlook the city. Its location makes it especially easy to explore Old Quebec on foot, with cafés, boutiques, and cultural landmarks right outside the door. The hotel’s intimate scale and refined design give it a boutique feel that fits seamlessly with the surrounding historic neighborhood.
What to Eat in Eastern Canada
Quebec and Montreal offer distinct culinary traditions:
Poutine – Fries topped with cheese curds and gravy.
Smoked meat sandwich – Montreal classic deli staple.
Maple desserts – Taffy on snow or maple pie.
Tourtière – Traditional meat pie.
Bagels (Montreal style) – Denser and sweeter than typical bagels.
Looking for other Canada Adventures? Check out my other posts below:
February travel does not need to be ambitious to be effective. The goal is not to escape life, but to step into a setting that makes daily routines feel lighter. Warm weather destinations such as Oaxaca, Costa Rica, and Thailand offer physical relief from winter conditions. Vancouver Island and Eastern Canada provide contrast without requiring a full seasonal shift. If February feels long, choosing the right trip can make the month feel manageable rather than something to endure.
Love,
M