Curious About Cuba?
We Can Help.

Itineraries + Maps + Expert Advice

Our Travel Tools

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We offer four ways for travelers to save money, plan efficiently, and have more authentic cultural experiences.

Planning Sessions

A 30 minute virtual meeting with a local CAYOS team member! Share thoughts ahead of the call and we’ll offer expert recs, answer questions, and send a follow-up email with notes and links from the conversation.


Meticulously curated and organized by theme, our maps gather the best places to eat, drink, dance, explore culture and get weird. (We even have ones for touristy places!) Pins save offline so you can navigate without internet during your trip.


Insider tips + activity recommendations + maps allow you to peruse options and add favorites as you go. Choose from different themes and locations to customize your guide and save time as you put together your plan.


The perfect way to jumpstart your planning, with built-in options that make it easy to customize and finalize to your liking. Complete our questionnaire and get a personalized, ready-to-use plan with editable blocks, allowing you to update as you see fit.

The Works

We’ll save you time and money by guiding you through the process to help secure flights, visas, lodging, guides, transportation, and anything else you need. The result: an expertly curated itinerary full of insider knowledge ensuring you have an unforgettable experience.

Why Plan Your Own Trip?

Authentic Experiences

Tours end up going to the same places that cater to the needs of tour companies and end up cultivating a cottage industry of “authentic” experiences that are not always the most representative of the place you’re visiting. Creating your own itinerary, with the help of insiders like us, allows you to explore on and off “the beaten path” as much as you want, leading to richer, more authentic exploration.

Planning is Fun

Yes, traveling can be complicated, especially to places where cultural differences are great, but with a few helpful resources, the plan starts to take shape quickly. Package tours do all of the work for you, but we happen to think that part of the fun, and the responsibility, of travel is taking some time to plan and be intentional about where you choose to go and what you choose to do.

Save Money

Tour companies charge huge sums to travelers for accommodations, transportation, tours, and other amenities that aren’t always necessary and can easily be booked directly, without a middle man. To do it, you just need to know where to go to find the right info, and luckily, you found us!

Personalized Plans

Every place we visit has such a rich and interesting variety of things to see and experience—food, history, politics, nature, arts, language…—planning a trip that fits your unique interests is a great way to create an entry point into a deeper understanding and appreciation of the place you are visiting, and makes the work spent getting there that much more worth it!

Guides and Articles


Don’t be a stranger—whether you want more details about our tools or answers to random travel questions, we’d love to hear from you!

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