Best Travel Destinations for Fall & Winter 2023

A Digital Nomad's Guide

Picture of Madison

As the seasons change and temperatures drop, the allure of a workcation becomes more and more enticing.


Imagine embracing the crisp autumn air while tapping away on your laptop amidst vibrant foliage, or finding inspiration in the cozy ambiance of a winter wonderland. In our quest to discover the best workcation destinations for fall and winter in 2023, we embark on a global journey to cities that offer a unique blend of remote work opportunities and enchanting experiences.


From the sun-kissed shores of Sydney, Australia, to the captivating landscapes of Sicily, Italy, these destinations promise a fresh perspective for digital nomads seeking a change of scenery. Explore the artistic haven of Asheville, North Carolina, or immerse yourself in the tranquil traditions of Kyoto, Japan. For those craving a deeper connection with nature, the Serengeti in Tanzania offers the chance to work alongside awe-inspiring wildlife.


Heading to the Southern Hemisphere, Auckland, New Zealand, welcomes remote workers with its picturesque landscapes and outdoor adventures. Further east, Chiang Mai, Thailand, beckons with its rich cultural tapestry and affordability. Discover the ancient wonders of Cairo, Egypt, or find serenity on the shores of Bali, Indonesia.


Finally, experience the glitz and glamour of Dubai, U.A.E., where modernity meets luxury. These destinations promise to turn your workcation into an unforgettable journey filled with diverse experiences, cultural immersion, and the perfect blend of productivity and relaxation.

room filled with plants and high ceiling with many windows
Asheville, North Carolina
Asheville, North Carolina

Asheville, North Carolina, is a charming and vibrant destination that holds a special allure for digital nomads, especially in the fall and winter seasons. Nestled in the Blue Ridge Mountains, and in the fall, it transforms into a picturesque wonderland with vibrant foliage. The stunning landscapes provide a serene and inspiring backdrop for remote work. Fall in Asheville boasts mild and comfortable temperatures, making it an ideal time to explore outdoor workspaces and enjoy the region’s natural beauty.


Best Places to Work Remotely:

  • Battery Park Book Exchange and Champagne Bar: This unique spot offers a cozy atmosphere with books, wine, and a charming courtyard.
  • Asheville Coworking: A dedicated co-working space with flexible membership options.
  • Trade and Lore Coffee: A local coffee shop with a welcoming ambiance.
  • Hatch Coworking Asheville: Providing you with day passes with access to free locally sourced coffees, 24/7  available desk space, meeting and conference rooms surrounded by plants and natural lighting.

Best Places to Eat:

  • Curate: A top-notch Spanish tapas restaurant offering a delightful culinary experience with a refined but friendly atmosphere settled in downtown historic space with shareable favorites like goat cheese-stuffed piquillo peppers, jamon Iberico, and Galician-style octopus.
  • OWL Bakery: the place to go for perfect baguettes and sourdough loaves, as well as croissants, tarts sparkling with crystallized herbs, sugared Scandinavian cardamom buns, and other pastry delights.
  • Rhubarb: A farm-to-table restaurant known for its seasonal and locally sourced cuisine.
  • Tupelo Honey: Comfort food with a Southern twist, perfect for a winter meal.

Best Places to Stay:

  • Outsite Asheville: A co-living and co-working space that combines comfort and community.
  • The Omni Grove Park Inn: A historic luxury resort with stunning mountain views.
  • The Foundry Hotel: A boutique hotel with a cozy, rustic feel, ideal for a winter retreat.

Best Landmarks to Visit:

  • Blue Ridge Parkway: Drive along this iconic scenic highway for breathtaking vistas.
  • Biltmore Estate: Explore America’s largest home and its beautiful gardens.
  • Grove Arcade: A historic public market with unique shops and dining options.
  • WNC Nature Center: Explore local wildlife and nature in a serene setting.

Asheville’s cozy and inviting atmosphere, combined with its artistic culture, makes it an ideal destination for winter. You can enjoy the warmth of the local community and explore vibrant arts and crafts scenes. Embracing the holiday spirit with festive decorations, holiday markets, and special events, making it a magical place to spend the winter. Whether you choose to visit Asheville in the colorful fall or during the enchanting winter, this North Carolina gem promises a warm and welcoming environment for digital nomads seeking inspiration and a change of scenery.

Sydney, Australia

Sydney, Australia, offers a fantastic destination for digital nomads during the fall and winter seasons. Sydney experiences mild and pleasant weather during the fall months. With temperatures averaging around 68-77°F (20-25°C), it’s an ideal time for outdoor work and exploration.


Best Places to Work Remotely:

  • Fishburners: A vibrant co-working space in the heart of Sydney’s startup community.
  • Work Club Global: A premium co-working space with multiple locations offering a professional atmosphere
  • Tank Stream Labs: A co-working space in the heart of Sydney’s central business district.

Best Places to Eat:

  • Sydney Fish Market: Savor fresh seafood and dine by the waterfront.
  • Chinatown: Explore the diverse culinary offerings of this vibrant district.
  • The Grounds of Alexandria: A popular urban oasis offering excellent food, coffee, and a rustic atmosphere.
  • Quay: A world-renowned restaurant with panoramic views and contemporary Australian cuisine.

Best Places to Stay:

  • The Collective: A trendy co-living space in the heart of Sydney, fostering a strong sense of community.
  • The Langham Sydney: A luxurious hotel with stunning views of Sydney Harbor.
  • The Old Clare Hotel: A boutique hotel with stylish design and a central location.
  • The Capsule Hotel: A unique budget-friendly accommodation option for a memorable experience.

Best Landmarks to Visit:

  • Sydney Opera House: Iconic and architecturally stunning, it’s a must-visit cultural landmark.
  • Bondi Beach: Enjoy the beautiful coastline and vibrant beach culture.
  • The Rocks: Explore Sydney’s historic district with cobbled streets and colonial architecture.
  • Royal Botanic Garden: Stroll through lush gardens and enjoy panoramic views of the harbor.

Sydney’s mild fall and winter seasons, along with its rich cultural scene and diverse culinary offerings, make it an excellent choice for digital nomads seeking a change of scenery while maintaining productivity.

Kyoto, Japan

Kyoto, Japan, is a captivating destination for digital nomads during the fall and winter seasons. Renowned for its stunning autumn foliage (koyo), and the fall season, usually from late October to early December, the city transforms into a colorful wonderland, offering a serene and inspiring backdrop for remote work. Fall in Kyoto also sees various cultural festivals, including tea ceremonies, traditional performances, and temple illuminations, providing opportunities to immerse in Japanese culture.

Best Places to Work Remotely:

  • Cafe Bibliotic Hello!: A cozy café with a library atmosphere and good Wi-Fi.
  • Regus Kyoto: A professional co-working space in central Kyoto.
  • The Aoyama: A chic café with a serene ambiance and quality coffee.
  • Kyoto International Community House: A hub for international exchange with a co-working space.

Best Places to Eat:

  • Nishiki Market: Explore this bustling food market with a wide array of street food and local delicacies.
  • Kaiseki Ryori: Indulge in a traditional multi-course Japanese meal at a kaiseki restaurant.
  • Yudofu (Tofu Hot Pot): Savor a warm and nourishing bowl of yudofu, a traditional Kyoto dish.
  • Nabe (Japanese Hot Pot): Enjoy a communal meal with friends at a nabe restaurant.

Best Places to Stay:

  • Kyoto Ryokan SAKANOUE: Experience traditional Japanese hospitality at this cozy ryokan.
  • COCON Kyoto: A stylish and modern co-living space in a traditional Kyoto machiya house.
  • Nine Hours Kyoto: A stylish and minimalist capsule hotel for a modern stay.

Best Landmarks to Visit:

  • Kinkaku-ji (Golden Pavilion): Admire the stunning Zen temple covered in gold leaf.
  • Fushimi Inari Taisha: Explore the iconic shrine with thousands of vermilion torii gates.
  • Arashiyama Bamboo Grove: Wander through the enchanting bamboo forest.
  • Higashiyama District: Explore the historic streets and temples of this picturesque area.

Winter, from December to February, is considered the low tourist season in Kyoto. With fewer crowds, you can enjoy the city’s attractions and workspaces more peacefully. Kyoto’s winter is the perfect time to experience traditional Japanese hot spring baths (onsen), which are particularly soothing in the colder months. Kyoto’s fall foliage and tranquil winter ambiance, combined with its rich cultural heritage and culinary delights, make it an ideal destination for digital nomads seeking inspiration and a unique working environment.

people swim in blue waters in front of tan buildings and mountains
Sicily, Italy
Sicily, Italy

Sicily, Italy, is a captivating destination for digital nomads, offering a unique blend of rich history, stunning landscapes, and delectable cuisine. Fall, from September to November, brings mild and pleasant weather to Sicily. With fewer tourists, you can enjoy the island’s beauty without the summer crowds. Fall is the grape harvest season in Sicily, making it a fantastic time to explore vineyards, enjoy wine tastings, and immerse yourself in the island’s winemaking traditions.


Best Places to Work Remotely:

  • Impact Hub Palermo: A co-working space in Palermo, the island’s capital, offering a productive environment.

  • Wine Bars: Sicily has numerous wine bars where you can enjoy a glass of local wine while working on your laptop.

  • Local Libraries: Many towns have public libraries that can provide a quiet space for remote work.

Best Places to Eat:

  • Trattoria da Nino: Savor traditional Sicilian dishes in a friendly atmosphere.
  • Palermo Street Food Markets: Explore local street food markets for authentic culinary experiences.
  • Ristorante La Madia: Experience contemporary Sicilian cuisine in a Michelin-starred restaurant.
  • Local Pasticcerias: Indulge in traditional Sicilian pastries and desserts, such as cannoli and cassata.

Best Places to Stay:

  • Catania Coliving: A co-living space in Catania, ideal for digital nomads.
  • Villa Ducale: A boutique hotel in Taormina with panoramic views of the Ionian Sea.
  • Taormina Apartments: Self-catering apartments in the heart of Taormina, suitable for longer stays.
  • Agriturismo Farm Stays: Consider staying in an agriturismo for a unique rural experience.

Best Landmarks to Visit:

  • Valley of the Temples (Agrigento): Explore ancient Greek temples and archaeological sites.
  • Mount Etna: Hike or take a tour of Europe’s most active volcano.
  • Palermo’s Historic Center: Explore the capital’s historic neighborhoods, markets, and architecture.
  • Villa Romana del Casale: Admire the well-preserved Roman villa with intricate mosaics.

Sicily’s winter, from December to February, offers a mild Mediterranean climate with daytime temperatures ranging from 50-60°F (10-15°C), making it a comfortable season for exploration. Sicily’s winter season features various cultural festivals and events, providing opportunities to engage with the local community and traditions. The fall and winter seasons offer a more tranquil and authentic experience compared to the peak summer months, making it an excellent choice for digital nomads looking to immerse themselves in the island’s culture, history, and culinary delights while maintaining a productive work routine.

Cairo, Egypt

Cairo, Egypt, is a city rich in history and culture, making it an intriguing destination for digital nomads in the fall and winter seasons. Fall, from September to November, offers pleasant temperatures in Cairo, making it an ideal time for outdoor exploration and comfortable remote work. Fall is a season of cultural events and festivals in Cairo, providing opportunities to immerse yourself in Egyptian traditions and art.


Best Places to Work Remotely:

  • Cafés with Nile Views: Many riverside cafés along the Nile offer Wi-Fi and a serene atmosphere for work.
  • Startup Grind Cairo: A co-working space with a focus on entrepreneurship and networking.
  • El Sawy Culturewheel: A cultural center with a riverside café offering a relaxed work environment.

Best Places to Eat:

  • Koshary El Tahrir: Try Egypt’s beloved koshary dish, a comforting mix of lentils, rice, pasta, and more.
  • El Fishawy: Visit this iconic café in Khan el-Khalili for Egyptian coffee and traditional sweets.
  • Felfela: Enjoy authentic Egyptian dishes, particularly falafel and taameya (Egyptian falafel).
  • Zooba: Try modern twists on traditional Egyptian street food.

Best Places to Stay:

  • The Greek Campus: A co-living and co-working space with a creative atmosphere.
  • The Nile Ritz-Carlton: A luxurious hotel with Nile views and top-notch amenities.
  • Cairo Co-living Spaces: Several co-living spaces have emerged in the city, catering to digital nomads.
  • Sofitel Cairo El Gezirah: A luxury hotel offering breathtaking Nile views and a central location.

Best Landmarks to Visit:

  • Pyramids of Giza: Explore the iconic pyramids and the Sphinx.
  • Egyptian Museum: Discover an incredible collection of ancient artifacts and treasures.
  • Khan el-Khalili: Explore the historic market district for souvenirs and local goods.
  • Citadel of Saladin: Visit this medieval fortress for panoramic views of Cairo.

Cairo’s winter, from December to February, offers mild and sunny weather, making it a pleasant season for both outdoor activities and work. The holiday season in Cairo is marked by festive decorations, vibrant markets, and cultural celebrations, adding a unique charm to the city. Cairo’s fall and winter seasons offer an excellent blend of mild weather, cultural experiences, and unique workspaces, making it a fascinating destination for digital nomads seeking an immersive and culturally rich workcation.

Auckland, New Zealand

Auckland, New Zealand, offers a compelling destination for digital nomads during the fall and winter seasons. Fall in Auckland features mild temperatures and less rainfall than the summer months, creating pleasant working conditions and comfortable outdoor exploration. Auckland hosts various cultural festivals and events during the fall, providing opportunities to immerse yourself in the local culture and community. Auckland’s Diwali Festival is a vibrant and colorful celebration of the Indian festival of lights. Typically held in October, this event features traditional Indian dance performances, music, cultural exhibitions, and, of course, delicious Indian cuisine. Visitors can witness the lighting of traditional lamps, enjoy henna art, and explore the rich heritage of Auckland’s Indian community. 

Best Places to Work Remotely:

  • GRID AKL: A prominent co-working space located in the innovation precinct of Wynyard Quarter.
  • Central City Library: Auckland’s public library offers free Wi-Fi and a peaceful work environment.
  • Chuffed: A charming café with a welcoming atmosphere, perfect for remote work.
  • Generator Britomart Place: A co-working space offering modern facilities and networking opportunities.

Best Places to Eat:

  • La Cigale French Market: A vibrant market with a variety of food stalls and fresh produce.
  • Federal Street: Known for its diverse dining options and trendy eateries.
  • Ostro Brasserie & Bar: A waterfront restaurant specializing in seafood and New Zealand cuisine.
  • Depot Eatery & Oyster Bar: A popular spot for oysters and local delicacies.

Best Places to Stay:

  • Sofitel Auckland Viaduct Harbour: A luxurious waterfront hotel with stunning views.
  • The Shakespeare Hotel & Brewery: A historic boutique hotel with character.
  • The Green House: A cozy co-living space designed for comfort and community.

Best Landmarks to Visit:

  • Sky Tower: Auckland’s iconic landmark offers panoramic views of the city and beyond.
  • Auckland Art Gallery Toi o Tāmaki: Explore an impressive collection of New Zealand and international art.
  • Waiheke Island: Take a ferry to this beautiful island known for its vineyards, beaches, and art galleries.
  • Auckland War Memorial Museum: Explore New Zealand’s history and culture in a stunning neoclassical building.

Auckland experiences a relatively mild winter compared to many other destinations, making it an attractive choice for those seeking a comfortable workcation during the colder months. Auckland’s winter brings a cozy ambiance with warm cafes, fireplaces, and cultural activities that make it a delightful time to explore the city. Whether you choose to visit Auckland during its mild and eventful fall or its cozy and comfortable winter, this city provides an excellent balance of work-friendly environments, cultural experiences, and scenic beauty for digital nomads.

Chiang Mai, Thailand
Chiang Mai, Thailand

Chiang Mai, Thailand, is a popular destination for digital nomads, and the fall and winter seasons offer several compelling reasons to visit. Fall brings cooler temperatures to Chiang Mai, making it a more comfortable time to explore the city and work outdoors. The Loy Krathong Festival, usually held in November, is a cultural highlight. Celebrated by releasing decorative lanterns into the night sky and floating krathongs (decorative baskets) on waterways, it’s a visually stunning and memorable experience.


Best Places to Work Remotely:

  • Punspace: A popular co-working space in Chiang Mai known for its vibrant community and facilities.

  • C.A.M.P.: Creative And Meeting Place, a unique co-working space with a relaxed atmosphere.

  • The Barisotel by The Baristro: A cozy café with excellent coffee and a relaxed environment.

Best Places to Eat:

  • Huen Phen: A traditional Thai restaurant serving authentic Northern Thai dishes.
  • Chiang Mai Gate Market: An evening market offering a wide range of street food and local delicacies.
  • Street Food Stalls: Explore the numerous street food vendors for delicious and affordable Thai dishes.
  • Dash Teak House: A unique dining experience in a traditional teak house with Northern Thai cuisine.

Best Places to Stay:

  • Nimman Mai Design Hotel: A stylish boutique hotel located in the trendy Nimmanhaemin district.
  • HUB53 Coworking & Coliving Space: A combined co-working and co-living space with a welcoming community.
  • Anantara Chiang Mai Resort: A luxurious riverside resort offering a serene retreat.

Best Landmarks to Visit:

  • Doi Suthep: Visit the stunning Doi Suthep Temple, perched on a mountain with panoramic views of the city.
  • Chiang Mai Old City: Explore the historic center with its ancient temples, moats, and charming streets.
  • Mae Sa Waterfall: Explore the stunning natural beauty of the Mae Sa Waterfall area.
  • Chiang Mai Night Safari: An immersive wildlife experience with nighttime animal encounters.

Chiang Mai’s winter season (from November to February) offers the most pleasant weather, with cooler temperatures and low humidity, making it perfect for outdoor activities and exploration. Winter is the season for various festivals and markets in Chiang Mai, including the Winter Flower Festival and the Night Bazaar, offering unique shopping and cultural experiences. Chiang Mai’s pleasant weather, cultural richness, and digital nomad-friendly environment make it an appealing destination for remote work and exploration during the fall and winter months.

small pond in front of palm trees and distant building
Dubai, United Arab Emirates
Dubai, UAE

Dubai, UAE, is a compelling destination for digital nomads during the fall and winter seasons. Fall in Dubai, from September to November, brings cooler and more comfortable temperatures than the scorching summer months. It’s an excellent time to explore the city and work outdoors. Dubai hosts the annual Dubai Fitness Challenge during the fall, encouraging a healthier lifestyle with various fitness activities, events, and wellness programs, which can be a great way to balance work and health.


Best Places to Work Remotely:

Best Places to Eat:

  • Al Ustad Special Kabab: A hidden gem serving delicious and affordable Arabic kebabs.
  • Ravi Restaurant: A local favorite known for its flavorful Pakistani and Indian dishes.
  • Pierchic: A fine dining seafood restaurant set on a pier with breathtaking views.
  • Al Fanar Restaurant and Café: Taste traditional Emirati cuisine in a nostalgic setting.

Best Places to Stay:

  • The Ritz-Carlton, Dubai: A luxurious beachfront resort with excellent amenities.

  • COLIV Hotel Dubai: A modern co-living space designed for convenience and collaboration.

  • Jumeirah Al Naseem: A luxurious beachfront hotel with access to private beaches.

  • Best Landmarks to Visit:

    • Burj Khalifa: Experience the world’s tallest skyscraper and its mesmerizing views from the observation deck.
    • Dubai Creek: Explore the historic heart of Dubai along the creek, with its bustling markets and traditional architecture.
    • Dubai Mall: Explore one of the world’s largest shopping malls and visit the Dubai Aquarium and Underwater Zoo.
    • Dubai Marina: Enjoy the waterfront promenade, trendy restaurants, and stunning skyscrapers.

Dubai’s winter, from December to February, brings the most comfortable weather with daytime temperatures ranging from 68-79°F (20-26°C), making it perfect for outdoor activities and workspaces. Winter in Dubai is synonymous with the Dubai Shopping Festival, offering incredible discounts, entertainment, and cultural experiences. It’s a great way to enjoy leisure time outside of work. Dubai’s fall and winter seasons offer an enticing blend of pleasant weather, cultural events, and numerous opportunities for digital nomads to work, explore, and indulge in a variety of experiences.

a blue pool and chairs overlook a mountain view
Serengeti, Tanzania
Serengeti, Tanzania

The Serengeti in Tanzania is primarily known for its incredible wildlife and safaris, rather than being a typical destination for digital nomads. However, if you’re seeking a unique and adventurous workcation, there are plenty of reasons to consider visiting during the fall and winter seasons. The fall and winter months in the Serengeti, from June to October, offer pleasant weather with cooler temperatures. The dry season during these months makes it an ideal time to explore the national park and its wildlife. Providing a one-of-a-kind backdrop for working remotely, this allows you to enjoy the breathtaking landscapes and wildlife between work sessions.


Best Places to Work Remotely:

  • Safari Camps: Some safari camps and lodges in the Serengeti offer Wi-Fi in common areas, allowing you to work surrounded by nature.

  • Bush Offices: Embrace the wild and set up a mobile workstation with a laptop and mobile hotspot in the heart of the Serengeti.


Best Places to Eat:

  • Safari Camp Dining: Enjoy delicious meals prepared by camp chefs, often served with stunning views of the savannah.

Bush Picnics: Experience outdoor dining with packed lunches or picnics in the wild during your game drives.



Best Places to Stay:

  • Safari Camps and Lodges: Many offer comfortable accommodations with stunning views, and some have workspaces in common areas.
      • Singita Sasakwa Lodge
      • Mwiba Lodge
      • Namiri Plains
  • Mobile Camps: Consider staying in a mobile camp, which moves to follow wildlife migrations, for a unique and immersive experience.
        • Sanctuary Kichakani Camp
        • Bushtops Luxury Tented Camp
        • Lamai Camp
  • Best Landmarks to Visit:

    • Great Migration: Witness one of the world’s most incredible wildlife spectacles as millions of animals move across the Serengeti in search of food and water.
    • Serengeti Visitor Center: Learn about the park’s ecosystem and conservation efforts.

While visiting the Serengeti as a digital nomad might not offer the typical amenities and workspaces found in urban areas, it presents a rare opportunity to combine remote work with a remarkable safari adventure. The stunning natural beauty and diverse wildlife make it a once-in-a-lifetime experience for those seeking an unconventional workcation.

child plays in pool pf water at an egyptian park

Enjoy your workcation this fall and winter!

Always blue skies ✈️