Best Workcations for Fall & Winter 2023

A Guide for Digital Nomads

As we navigate the ever-evolving landscape of remote work and global mobility, the concept of the “workcation” has become an enticing reality for digital nomads and expats alike.


The allure of combining work with leisure, while exploring new cultures and landscapes, has never been stronger. As we look ahead to the fall and winter of 2023, the world beckons with a fresh array of destinations that offer the perfect blend of productivity and adventure.


In this blog, we’ll embark on a virtual journey to uncover the most alluring places for workcations during these upcoming seasons. From tranquil coastal escapes and bustling urban hubs to serene mountain retreats and cultural gems, each location on our list promises a unique tapestry of experiences for those seeking to redefine the boundaries of their workspace.


Whether you’re a digital nomad in search of Wi-Fi havens, an expat looking to balance your career and exploration, or simply someone yearning for a change of scenery, our curated selection of destinations will inspire your next workcation adventure. Join us as we explore the best places to work, live, and savor life in the fall and winter of 2023.

Take your company on vacation with The Offsite! Founded in 2018, The Offsite team works to seamlessly blend the culture between colleagues and friendships through well-curated company and executive retreats. From arrival to departure, The Offsite team provides you with a Retreat Producer to manage and guide your trip every step of the way. With assistance in tracking budgets, selecting the perfect destination venue, creating custom team building activities for you and your cohorts, The Offsite is proud to let you relax while they take to take the wheel and boast an 8%-12% savings rate as a white glove vendor management community. Visit their site to get a Free Retreat Proposal and schedule dates for your next work retreat!

Noma Collective offers remote workers extended retreat stays which provide their travelers with built-in community with daily events, stunning accommodation, co-working environments, and wellness practices across the globe! Their mission is specializing in life changing experiences, fostering meaningful connections, and curating adventures around the world.

🇵🇦 Bocas del Toro, Panama (October 8th-29th)

  • Bocas del Toro, Panama, casts its spell on digital nomads, making it an enticing destination for fall and winter workcations. As the wet season subsides, this tropical paradise emerges with lush greenery and inviting waters. With its remote island charm, a burgeoning co-working scene, and opportunities for eco-adventures like snorkeling and rainforest exploration, Bocas del Toro offers the perfect blend of work and leisure. Whether you’re captivated by the vibrant Caribbean culture, inspired by the stunning marine life, or simply seeking a tranquil retreat, this Panama gem beckons digital nomads for a rejuvenating and productive stay. Check out Noma Collective’s site for more info on how to add yourself to the roster!

🇦🇷 Buenos Aires, Argentina (October 29th-November 19th)

  • Buenos Aires, Argentina, holds a magnetic allure for digital nomads in search of culture, creativity, and a vibrant workcation experience during the fall and winter seasons. As the temperatures in the Southern Hemisphere turn milder, the city’s European-inspired architecture, bustling arts scene, and rich cultural heritage come alive. Buenos Aires boasts a thriving co-working culture, an array of cozy cafes for remote work, and a passionate tango rhythm that infuses every corner of the city. Whether you’re drawn to its historic neighborhoods, world-class cuisine, or the opportunity to immerse yourself in Spanish language and culture, Buenos Aires offers a dynamic and inspiring workcation destination for the discerning digital nomad. Noma Collective Buenos Aires edition is just a few short weeks away so grab all your info here for all the details!

🇧🇿 Belize (November 26th-December 17th)

  • Belize, with its breathtaking natural beauty and diverse ecosystems, is an irresistible destination for digital nomads seeking adventure and a productive workcation during the fall and winter seasons. As the weather turns cooler elsewhere, Belize welcomes visitors with its warm, tropical climate and abundant sunshine. This Central American gem offers an array of co-working spaces, beachfront relaxation, and opportunities for exploring lush jungles, pristine beaches, and ancient Mayan ruins. Whether you’re drawn to snorkeling in the crystal-clear waters of the Belize Barrier Reef, exploring dense rainforests, or simply relishing the laid-back Caribbean vibe, Belize promises an extraordinary blend of work and leisure for the adventurous digital nomad. Visit Noma Collective’s Belize pagefor more info on this trip.

Dance with My is a dance focused community centered around release from emotions, elevation of confidence, and exploration of inner self. Whether you have zero-dance experience or dance frequently, you are guaranteed to have a memorable and freeing experience. 


Founder, My Nguyen, hosts The Confidance Retreat (October 22nd-29th) in 🇲🇦 Taghazout, Morocco the year.


Throughout this retreat, expect an immersive experience that helps participants unleash self-confidence through the art of dance. With a diverse range off dance styles, styles, well-being, and personal development activities (yoga, breathwork, reiki, sound bath healing, workshops from nutritionists, confidence and relationship coaches), this retreat is designed for you to tap into your inner self while discovering the joy and freedom of dancing.


This curated program will help you enhance your confidence, discover your unique voice through movements, and most importantly, have a lot of fun. By the end of the retreat, you will gain a renewed sense of self-confidence and a deeper connection to your body and emotions. Visit Dance with My to get more info on her upcoming trip taking place in Taghazout!

Headquartered in Seattle and Bangalore, India, Nurall serves as a lifestyle curation company and tech startup with a mission to promote a lifestyle of adventure, choice, and freedom and cultivate the next generation of digital nomads!

With their offerings of accomodation, coworking opportunities, curated residencies and retreats, we’ve compiled some of their upcoming destinations for you to select a spot to spend your fall or winter season!

🇹🇭 Timea, Thailand (October 22nd-29th)

  • Tranquil and culturally rich, Timea, Thailand, emerges as an inviting destination for digital nomads seeking solace and inspiration during the fall and winter months. As the cool season arrives, Timea’s lush landscapes come alive with pleasant temperatures, making it an idyllic setting for remote work amidst nature’s beauty. With its vibrant local culture, peaceful co-working spaces, and access to nearby natural wonders like waterfalls and hiking trails, Timea offers a harmonious blend of productivity and adventure. Whether you’re drawn to its tranquil temples, local cuisine, or the warmth of its welcoming community, Timea in the fall and winter promises an enriching workcation experience for the discerning digital nomad. Nurall has limited spots left on this upcoming venture but don’t let that deter you! Check out more details on their website to see if Timea is your October escape. 

🇲🇽 Tulum, Quintana Roo (November 2nd-5th)

  • Tulum, Mexico, beckons digital nomads with its irresistible blend of natural beauty and laid-back bohemian charm, making it an ideal destination for a fall or winter workcation. During these seasons, Tulum boasts a more temperate climate, providing the perfect backdrop for productive remote work by day and tranquil beachside relaxation by evening. The town’s eco-conscious accommodations, beachfront co-working spaces, and thriving expat community offer a seamless integration of work and leisure. With the allure of crystal-clear Caribbean waters, ancient Mayan ruins, and a thriving wellness scene, Tulum promises not only a conducive work environment but also a rejuvenating and culturally enriching experience for digital nomads seeking respite from the winter chill. Only five openings are left for this trip so read up on all you’ll need to know before securing your spot!

🇮🇳 Goa, India (Year Round Program)

  • Goa, India warmly invites digital nomads with its enchanting blend of sunny shores, cultural vibrancy, and serene landscapes during the fall and winter seasons. As the monsoon season gives way to milder weather, Goa becomes a haven for remote work and relaxation. With its beachfront co-working spaces, diverse culinary scene, and rich history, Goa provides an ideal workcation setting. Whether you seek inspiration from the vibrant markets, rejuvenation in yoga retreats, or immersion in the state’s unique fusion of Indian and Portuguese cultures, a fall or winter stay in Goa promises a harmonious balance of work and leisure for the intrepid digital nomad. With the option to customize a 7-day itinerary, Goa could be the perfect place for you to spend away from the cold!

Flashpack exists to fulfill an impactful mission: to foster and nurture 1 million friendships from their extended international trip program. They take great pride in the 80% of their group travels who remain in close contact even after their adventure together is over. With almost 50 different destination options to travel solo or take a group trip to share the memory making fun across five continents and almost 40 countries, there are so many incredible possibilities awaiting.

* Dates vary October-December

🏖️ Beach Holidays 

🏙️ City Escapes 

🏝️ Escape the Crowds

Enjoy your trips this fall and winter season!

Always blue skies ✈️