Sun-Soaked Winter Escapes for Travelers Craving More than the Resort Experience
This winter, why not skip the buffet line at the all-inclusive and choose your own adventure in one of these sunny destinations instead?
As the last leaves fall and nights grow colder in Canada, I'm already dreaming of my favourite warm-weather escapes. As beautiful as autumn is, there's something irresistible about swapping chilly days for sandy beaches, ocean breezes, and golden sunsets.
While all-inclusives can be an excellent way to shut off for a week, they don’t show you the real heart of a place. Sometimes, those “deals” leave you tired and overfed (and often even cost more than going it on your own).
So, if you’re ready to break free from winter’s chill and dive into something different this year, here are my top destinations for sun-drenched relaxation and discovery. From vibrant cities to secluded islands, these picks offer an authentic taste of each destination—no wristbands or buffet lines required.
Disclosure: Midlife Nomads often refers and links to websites, apps, and products/services we actually use. Sometimes, we receive compensation if readers sign up or make a purchase. A girl’s gotta eat – and travel!
Caribbean: Crystal Waters and Island Charm in the Bahamas, Turks & Caicos, and Aruba
If you’re looking to swap the winter blues for some serious island vibes, the Caribbean has it all. I’ve been lucky enough to explore the Bahamas, Turks & Caicos, and Aruba, and each destination offers its own slice of paradise.
I’ve found that getting around on these islands can be a bit tricky without a car, especially in the Bahamas and Turks & Caicos, so renting your own wheels is well worth it to fully experience these islands. Here’s a closer look at each of these incredible destinations.
The Bahamas
The Bahamas’ 700+ islands offer a bit of everything, from buzzing resort areas to tranquil escapes. In Nassau, we found that beaches like Sandyport and Cable Beach were perfect for a more relaxed vibe—definitely preferred over the busy Atlantis area. Don’t miss Clifton Heritage National Park, where you can snorkel to see the stunning Ocean Atlas underwater sculpture.
Nassau & Paradise Island are perfect if you’re after vibrant nightlife, luxury resorts, and historic sites like the Queen’s Staircase, which give you a taste of Bahamian history and culture. For something more laid-back, the Exumas are ideal, with turquoise waters and famous swimming pigs! It’s a natural, serene side of the Bahamas that feels worlds away from the busier hubs.
Whether you’re into snorkeling, diving in blue holes, sailing, or eco-tours, the Bahamas is packed with outdoor activities to keep you as active or relaxed as you like.
Turks & Caicos
Turks & Caicos, and especially Grace Bay Beach in Providenciales, is heaven on Earth if you’re a beach lover. The soft, powdery sand and impossibly clear water make it one of the world’s best beaches, hands down. I’d recommend a car here as well—doing a road trip through North and Middle Caicos was one of my favorite ways to experience the island’s secluded, wild beaches without the crowds.
Underwater explorers head to Turks & Caicos for stunning coral reefs with diving and snorkelling experiences that reveal an array of marine life.
If you’re looking for a sophisticated and peaceful escape, the resorts here range from luxurious hotels to private villas that feel like your own slice of paradise. I’ve had good luck with Airbnb here, too, and enjoyed a stay in a local woman’s granny suite off the main house.
For a taste of local flavour, fresh conch is a must. Join in on a weekly fish fry, where you can experience the island’s lively culture firsthand.
Aruba
Aruba offers a different kind of Caribbean vibe, with an unusual mix of desert landscapes and pristine beaches. You’ll see cacti-lined trails and rugged coastlines alongside classic white-sand beaches, and you should be prepared for strong winds year-round.
Eagle Beach is one of Aruba’s most beautiful spots, and if you’re up for some light adventure, Arikok National Park is a must-visit, with its wild terrain and ancient cave paintings. You can also snorkel in the calm waters of Baby Beach, where you’re likely to spot colorful tropical fish in the shallow lagoon.
Getting around Aruba can be challenging—while taxis are available, they’re on the pricier side, and buses are a decent option if you’re not in a rush. For those comfortable with a bit of fast-paced driving, a rental car gives you the freedom to explore more remote spots.
With near-constant sunshine, Aruba is an ideal destination for guaranteed warmth any time of year, but fair warning, it’s among the pricier places on this list. If you’re looking for a budget destination, Aruba likely isn’t it.
Travel Tip: Each of these islands offers something unique. If you’re looking for nightlife and a range of experiences, the Bahamas is a great choice. Turks & Caicos can’t be beaten for tranquillity and luxurious beach time. And if you’re after a warm, year-round climate with pristine white sand beaches and a bit of luxury, Aruba is just the ticket. If you plan on renting a car, get your International Drivers Permit, just in case.
Cape Town, South Africa: Where Urban Chic Meets Coastal Bliss
In 2022, I spent a month in Cape Town and fell in love with its incredible mix of natural beauty, rich cultural history, and perfect weather.
Though I didn’t always feel particularly safe within the city itself, and this isn’t a place I’d recommend wandering around on your own, Cape Town stands out for me because of its surrounding regions, which offer some of the best day trips you could ask for.
Natural Beauty
Cape Town’s scenery is absolutely stunning, and the city’s crown jewel is Table Mountain. The iconic flat-topped mountain provides a dramatic backdrop to the city and a playground for outdoor enthusiasts.
Around every corner, you’ll find gorgeous beaches, rugged coastlines, and sweeping views that make Cape Town a photographer’s dream. Whether you’re relaxing on Camps Bay Beach or hiking along the Cape Peninsula, Cape Town’s landscapes are simply unforgettable.
Wine Country
One of my favorite parts of the Cape Town area is its proximity to world-class wine country. Just an hour’s drive from the city, the charming towns of Stellenbosch and Franschhoek offer some of the best wines in South Africa.
These regions are ideal for a day of leisurely wine-tasting in stunning vineyard settings, often paired with gourmet food experiences. Each vineyard has its own unique ambiance and story, making it a must-do for any wine lover. And if you get a chance to take the Wine Train—do it!
Cultural Experiences
Cape Town’s cultural richness is compelling, with layers of history that have shaped this vibrant city. While I didn’t spend much time in the inner city, I made it a point to visit key historical sites like Robben Island, where Nelson Mandela was imprisoned, and the District Six Museum, which offers insight into the city’s complex past.
Cape Town’s markets, like the Old Biscuit Mill and Greenmarket Square, are also great places to experience local crafts and foods, and to see Cape Town’s mix of cultures in action. The Oranjezicht Night Market is definitely worth a night out with friends, and be sure to go hungry. They have all kinds of local and international food and beverages to try.
Outdoor Adventures
If you’re an outdoor enthusiast, Cape Town’s surrounding areas are paradise. A sunrise hike up Lion’s Head gives you incredible views of the city and coastline, while Boulders Beach, home to a colony of African penguins, is a delightful stop for animal lovers.
Another favourite of mine was exploring the Cape of Good Hope, the southernmost tip of the Cape Peninsula, where you can hike, spot wildlife, and enjoy some seriously dramatic seascapes.
Local Flavor
Cape Town’s culinary scene is as vibrant and diverse as the city itself. With influences from Dutch, Malay, Indian, and African cuisines, the food here is a delicious fusion of flavors.
Be sure to try local specialties like bobotie, a spiced meat dish, and Cape Malay curry. The city’s growing farm-to-table scene also highlights its fresh produce and innovative chefs, making it a fantastic destination for food lovers.
Pro tip: The summer months from December to March bring warm weather and are ideal for beach outings, hiking, and winery visits. This is a great time to soak up the sun and explore the outdoor beauty Cape Town and its surroundings have to offer. I traveled here with a group and was glad I did.
Mexico: Warmth and Wonder in Oaxaca, Tulum, or Mexico City
If you’re looking for cultural depth, beachside relaxation, or bustling city life, Mexico has it all. A few years back, I spent six weeks there in the beach areas and another month in Mexico City, and I would go back in a heartbeat.
As with any destination, safety is important. While Mexico is welcoming and vibrant, basic precautions—sticking to known areas and keeping valuables secure—make for a worry-free trip. Here are three fantastic options to soak up Mexico’s warmth and charm.
Oaxaca
Oaxaca is a feast for the senses. It celebrates tradition with deep-rooted Indigenous history, vibrant colonial architecture, and lively markets. The food scene here is world-famous—try Oaxaca’s seven varieties of mole, smoky mezcal, and unique market snacks like tamales and chapulines (crispy grasshoppers!).
Must-dos include exploring Monte Albán's ruins, relaxing at mineral springs, and wandering Oaxaca’s colourful streets, filled with murals and artisan shops. While Oaxaca is generally safe, sticking to the central areas, especially at night, is a wise choice.
Tulum
Tulum is a paradise for beach lovers. Its Caribbean beaches, with turquoise water and white sand framed by palm trees, offer the ultimate escape. Adventure seekers can snorkel in nearby cenotes (natural sinkholes) and explore Mayan ruins perched along the coast.
You can even hop over to Cozumel for world-class snorkelling and diving, with a quick ferry ride from Playa del Carmen up the road. I highly recommend renting a scooter to circle the island while you’re there.
Stay at an eco-luxury resort or boutique hotel in Tulum for a peaceful, sustainable retreat. Its lively tourism scene means you’ll want to keep an eye on your valuables, particularly in busy spots or at the beach.
Mexico City
If you crave city energy, Mexico City is a vibrant metropolis with a world-class art scene, fascinating history, and some of the best food on the planet. Start your culinary journey with street tacos or splurge at one of its Michelin-starred restaurants. Key sites include Frida Kahlo’s Casa Azul, Chapultepec Park, and the grand historic center. I stayed near Chapultepec, and it quickly became my daily route for walks.
For day trips, head to the ancient pyramids of Teotihuacan or drift along Xochimilco’s colourful canals, where mariachi music and bright trajineras (boats) create a festive atmosphere. Even just wandering the streets and enjoying the graffiti made for a fun afternoon out.
In Mexico City, sticking to well-traveled areas, using registered taxis, and staying aware of your surroundings make for a safe, unforgettable experience.
Quick tip: For culture, choose Oaxaca; for beach relaxation, head to Tulum; for urban excitement, dive into Mexico City’s endless sights and flavors. Expedia has a decent selection of hotels and room options for Mexican destinations, and you might want to check Airbnb, as well.
Nicaragua: Unspoiled Beauty, Endless Adventure & the Nicest People You’ll Meet
Nicaragua holds a special place in my heart. I've been visiting since 2017, and my love for this country runs so deep that I even bought a piece of land there with dreams of building one day. Last winter, I spent most of my time in Nicaragua, with occasional trips back to Canada and a jaunt over to Portugal.
From its breathtaking natural landscapes to its warm and welcoming communities, Nicaragua is a hidden gem of Central America, offering endless opportunities for adventure, relaxation, and cultural immersion.
Ometepe
Ometepe is truly one of the most magical places I’ve ever been. This island, set in the middle of Lake Nicaragua, is formed by two towering volcanoes that give it an otherworldly vibe. Ometepe has a rustic, off-the-grid charm that makes it feel like a peaceful retreat.
Outdoor enthusiasts will find endless options here: hike the volcanoes, take a kayak out on the lake, or trek through lush forests to discover hidden waterfalls. There’s something almost mystical about Ometepe, a place where time slows down and nature takes center stage. Give yourself lots of time, or go with a guide, like we did, so you can get the most out of your time there.
Granada
For a dose of colonial charm and convenient city amenities (without all the chaos of Managua), Granada is the place to be. Its colourful streets, grand churches, and lively markets make it one of the most picturesque cities in Central America. On hot days, head to the nearby Laguna Apoyo for a swim in the tranquil volcanic lake or hop on a boat for a leisurely tour of Lake Nicaragua’s small islets.
Granada also offers plenty of opportunities for cultural immersion—take an art class with local artist Nasser Moreno, visit the chocolate shops, wander the city’s art galleries and artisan markets to appreciate the vibrant local crafts, head up to Catarina for stunning views and the local flower shops. The market in nearby Masaya is worth the drive, as well. Granada’s mix of history, culture, and natural beauty makes it ideal for longer stays.
San Juan Del Sur
If you’re a beach lover, you’ll want to spend some time in San Juan Del Sur. This relaxed beach town on the Pacific coast is known for its stunning beaches, laid-back atmosphere, and fantastic surf. Whether you’re a seasoned surfer or just want to try your hand at riding the waves, San Juan has waves for all levels.
And don’t miss the sunsets—they’re absolutely breathtaking. The town is also a lively social hub, making it a great place to meet other travelers, kick back at beachside bars, and enjoy the friendly vibe that San Juan is famous for. The surrounding beaches are stunning (though you can’t swim at the beach in the town itself) and you might find opportunities for sunbathing, beach sports, or even watching sea turtles nest at night.
Matagalpa and Estelí
For a different side of Nicaragua, head to the highlands of Matagalpa and Estelí. These cooler, mountainous regions are ideal for nature lovers and anyone looking to escape the heat. The highlands are lush and green, with coffee plantations and eco-lodges that offer a tranquil escape.
Waterfall Adventures & Other Good, Clean Fun in Northern Nicaragua
You can go hiking, explore hidden waterfalls, and even learn about Nicaragua’s coffee and cigar-making industries. Matagalpa and Estelí showcase Nicaragua’s incredible diversity, offering an experience that’s both relaxing and educational.
Insider’s tip: To experience the full range of Nicaragua’s charm, combine a stay in the highlands with some time on the beach or in Granada. Each region has its own unique appeal, and together they create an unforgettable journey through Nicaragua’s landscapes and cultures. For logistics like transportation and guiding, we highly recommend Victor Ubau at Nicaragua Trips.
Thai Islands: Chilled Out Tropical Bliss in Koh Lipe and Koh Lanta
Thailand’s islands are paradise personified, each with its own unique blend of natural beauty, cultural experiences, and endless warmth. If you’re looking to escape the winter chill, Koh Lipe and Koh Lanta offer two distinct island vibes that capture the essence of a tropical getaway.
Koh Lipe
For those seeking a quieter escape, Koh Lipe is a true slice of paradise. Known for its small size and laid-back ambiance, this island is home to some of the most pristine beaches and clearest waters in Thailand. Koh Lipe’s pace is slower, ideal for unwinding and leaving the busyness of everyday life behind.
Underwater enthusiasts will find themselves in heaven here—snorkeling and diving spots around Koh Lipe are world-class, with colorful coral reefs and abundant marine life just off the coast.
And when evening falls, the island’s charming beach bars are the perfect spot to unwind with a cocktail and take in the stunning sunsets. There’s something about Koh Lipe’s calm, secluded setting that makes it feel like your own private oasis.
Koh Lanta
Koh Lanta offers a bit more variety and a family-friendly atmosphere, making it a great choice for travelers seeking both relaxation and adventure. Known for its calm, welcoming vibe, Koh Lanta has accommodations and activities that suit all ages and preferences, from beachside bungalows to eco-luxury resorts.
The island has a strong focus on eco-conscious tourism, with nature reserves, wildlife sanctuaries, and elephant conservation efforts that allow visitors to explore responsibly. Koh Lanta’s local experiences are also a highlight—take a Thai cooking class, visit a traditional sea gypsy village, or trek through the lush jungles.
Recommendation: Choose Koh Lipe if you’re craving quiet seclusion and a more intimate beach experience. For those who want more variety in activities, accommodations, and eco-friendly attractions, Koh Lanta offers a bit of everything. Always protect your trip! I’ve used WorldNomads with good success and also find Generalii’s pricing and coverage is decent, depending on your destination.
Madeira, Portugal: Europe’s Island of Eternal Spring
Madeira, often called “the Island of Eternal Spring,” is a lush, subtropical paradise that offers mild weather year-round, making it a perfect escape from winter’s chill. Located off the northwest coast of Africa, this Portuguese archipelago is a dream destination for nature lovers, adventure seekers, and anyone looking to bask in a warm, vibrant setting.
Madeira’s landscapes are an explosion of greenery, flowers, and mountains that seem to touch the clouds. With its unique microclimate, the island is home to diverse flora and fauna that thrive in its mild temperatures.
Outdoor Adventures
Madeira offers diverse outdoor adventures, with the levadas (irrigation channels) forming an extensive network of scenic hiking trails.
From gentle walks through flower-filled valleys to challenging hikes with cliffside views, the levadas cater to all fitness levels. If you’re seeking more adrenaline, Madeira also offers thrilling activities like mountain biking and paragliding, where you can soar above the island’s rugged coastlines and forested hills.
Scenic Coastline
Madeira’s coastline is dotted with natural pools, carved out of volcanic rock and filled by the ocean’s tides. One of the best spots to experience these unique pools is Porto Moniz, where you can swim in the clear, salty waters surrounded by dramatic rock formations.
Another coastal gem is the fishing village of Câmara de Lobos, a charming spot with colorful boats, cobbled streets, and a slow pace that invites you to linger.
Local Culture
Madeira’s culture is a rich tapestry of Portuguese tradition with local flavors. A visit wouldn’t be complete without sampling Madeira wine, known for its distinctive, fortified sweetness.
Stroll through the Mercado dos Lavradores in Funchal, where vendors sell fresh produce, fish, and flowers that reflect the island’s bounty. In the evenings, treat yourself to a Fado music performance, where soulful Portuguese ballads set the mood for a memorable night.
The city’s waterfront is lined with restaurants offering fresh seafood and traditional Madeiran dishes, all with a view of the shimmering Atlantic. Funchal’s mix of history, nature, and dining make it a lovely base for exploring the island.
Travel tip: Madeira is a great choice for outdoor enthusiasts who want to experience Europe’s natural beauty without the winter chill. The island’s unique blend of Portuguese culture and breathtaking landscapes makes it an unforgettable destination for a winter escape. Book your airport transfers ahead of time with Intui Travel.
South America: Sun and Adventure in Colombia or Peru
South America offers diverse destinations for those seeking both sun and adventure, and Santa Marta, Colombia, and Lima, Peru, are two standout options. Bonus: if you’ve never been and are unsure about heading to South America solo, Hacker Paradise has organized group trips to each place this winter, and they’re perfect for remote workers and digital nomads.
Santa Marta, Colombia
Santa Marta is a nature lover’s paradise, where the beach meets the jungle in a setting that feels untouched and wild. This coastal city is the gateway to Tayrona National Park, known for its secluded, idyllic beaches framed by dense jungle and towering mountains. Tayrona is a haven for those who love hiking, swimming, and experiencing Colombia’s incredible biodiversity up close.
For a deeper dive into local culture, explore the indigenous heritage of the area, including the nearby Sierra Nevada mountains, home to several indigenous communities with unique customs and traditions. Santa Marta’s coastline is also a fantastic spot for scuba diving and snorkeling. Its reefs are teeming with colorful marine life, making it one of Colombia’s best destinations for underwater adventures.
Lima, Peru
For those drawn to urban energy and rich culture, Lima is a dynamic coastal metropolis that has earned a reputation as a culinary capital of South America. Overlooking the Pacific Ocean, Lima combines beautiful ocean views with historic sites and vibrant neighborhoods, each offering a unique glimpse into Peru’s past and present.
Lima’s food scene is world-renowned, so if you’re a foodie, this is the place to be. Sample fresh ceviche at a local market, or treat yourself to a tasting menu at one of Lima’s Michelin-starred restaurants. Beyond the food, cultural highlights abound. Don’t miss the Larco Museum’s impressive collection of pre-Columbian art, the bohemian neighborhood of Barranco with its art galleries and street murals, and the city’s scenic seaside promenades.
Recommendation: If you’re a nature lover looking to explore beaches, jungles, and local indigenous culture, Santa Marta is the perfect choice. For those drawn to food, art, and a vibrant urban atmosphere, Lima has it all. Check LATAM Airlines for flight deals to South America.
Winter Sun Awaits: Where Will You Escape the Cold?
As the winter chill settles in, the world has plenty of warm escapes waiting to be explored. Each destination we’ve shared—from the vibrant culture of Mexico to the tranquil beaches of Turks & Caicos—offers a unique experience, perfect for those looking to trade heavy coats for flip-flops.
So, where will you escape the cold this winter? Let us know in the comments! And be sure to follow along for more tips, updates, and travel stories to inspire your next journey.
Safe travels, and here’s to finding a little extra sunshine this season!
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I love Nasser's work too. Just ate at Pita Pita (Granada), you should be here!