Welcome to a different kind of Caribbean journey.

Sun & Stilettos Trips offers expert-led cultural tours to the Caribbean. Yes, the Caribbean!part of the world offering so much more than beaches and rum. From cacao farms to drum makers, architectural wonders, indigenous groups, and a spectacular reef-to-peaks scenery, this regional melting pot remains under-explored.

The trips focus on immersive, adventure filled days with a custom-crafted itinerary that brings you the essence of a place while you travel in comfort. Each journey is designed and joined by award-winning travel journalist, Moon Guides author and photographer Lebawit Lily Girma, building on her 11 years of experience and contacts living in and exploring the Caribbean. Since 2008, her popular travel, culture, and photography blog Sunshine & Stilettos has also served as a platform to inspire others to dig deeper into the Caribbean. 

Now, she’s taking you along for the ride. Join small groups of like-minded, active travelers passionate for meaningful, fun, culture-rich experiences. And of course, beach time along the way.

Read more about the Sun & Stilettos trip philosophy, the founder, and sign up for the newsletter to stay informed on upcoming tours.