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To T&T Carnival Tuesday Mas on D’ Road!  Book NOW!

Speak to a Travel Concierge 312-912-7502

Endless experiences await you

WORK & PLAY REMOTE TRAVEL PROGRAM

What is Work & Play Remote?

Remote working programs are paid travel experiences that appeal to people who want a work-life balance that allows them to explore the world instead of staying home.

Work & Play Remote is an extended-stay work and travel program that caters to the needs of digital nomads, enabling all location-independent professionals and entrepreneurs to travel and work in unique places.

We enthusiastically support your nomadic lifestyle by providing assistance with housing, transportation and professional resources; ensuring high-speed connectivity; fostering international networking; building friendly connections and facilitating immersive experiences in your chosen destinations based on your desired level of interaction.

HOW WE PLAY

Experience the undiscovered Caribbean with a team of local experts who will:

  • Curate unique experiences both in & surrounding your destination
  • Recommend the best places and activities for a truly authentic experience
  • Facilitate private and group events throughout different regions of your island
  • Ensure your safety and comfort within your new environment

WORK & TRAVEL, WORRY FREE

Now with more travel options than ever, Work & Play manages the logistics for flexible lifestyle seekers to join a community of like minded individuals exploring the idea of living in other countries, together.

Simply repurpose your monthly living expenses for a once-in-a-lifetime remote living program.  Try it for a month or a quarter. Save money or treat yourself! Dig deep and share with our relocation experts, who will guide you through the most flexible part – creating the experience you want!

Live like a local while discovering the best of one amazing destination or journeying across several different islands.  Bring your job, studies, or passion project to work remotely while exploring the hidden gems of the Caribbean.  We’ll take care of all the details so you can make the most of your adventure.

Shared accommodations are typically an apartment, private home or grand guest house with 1 – 5 other participants. We always aim to provide private bathrooms but when it’s not possible, never more than a total of 3 participants share.

Deep dives, day trips. island-hopping! Every week there’s an island tour waiting for you!  Just step outside your front door with an open mind ready to be whisked away on a new adventure with cool people.  We got you!

WHAT TO EXPECT

Meetings with your travel coordinator and hosts through your entire planning and booking process.

Webinar with Q&A detailing your planned experience prior to your departure.

Be met by your local team at the airport and transferred to your accommodations.

Settle in, set up your designated work space and transportation needs.

Endless opportunities for networking, socializing and learning the local scene

Discovering local gems - both popular and hidden on locally guided tours

Total Cost

3 Month Immersion Experience. Choose 1 of 5 Caribbean Islands.

4 Month Journey through the hidden Caribbean. Your choice of islands listed.

Program Cost and Payments

The entire cost of a Work & Play program is divided into a deposit, down payment and program fees. The deposit officially reserves your spot on a Work & Play Program and allows us to begin booking your arrangements. The down payment is due 60 days prior to the start of your program. Program fees are due monthly by the 25th of the month before service. Think of these fees as your “monthly living expenses” covering everything at each location including housing, flights, workspace, excursions, events, 24/7 on-site support, and much more.

Experience the islands with a team of local experts who will

  • Curate unique experiences both in & surrounding your destination(s)
  • Recommend the best vendors for a truly authentic experiences
  • Facilitate community building with group events throughout the destination(s)
  • Ensure your safety and comfort in every new environment on your tour