Sun & Stilettos Trips are for those seeking custom-crafted, culture-rich escapes to the Caribbean region, with unique itineraries designed to show you the country through the eyes of locals, while traveling in comfort. Activities, lodging, meals, and every detail are picked out by an expert in the region and a longtime Caribbean travel journalist. Local guides and experts lead us along the way, giving us as authentic an insight as possible on the destination. 

And for those who are wondering, the name Sun & Stilettos comes from Lily’s long-time, eponymous travel and photography blog which became her brand when she went from lawyer to travel writer in 2009. She ended up ditching the stilettos for the Caribbean! So there are no stilettos required for any of these journeys.

Sample highlights of a Sun & Stilettos Trip:

  • Take a traditional dance lesson from a generation of local musicians
  • Stay in a 16th century colonial convent turned boutique hotel
  • Enjoy a hike through the countryside and glimpse rural life, while meeting locals along the way
  • Plant cacao while touring a plantation
  • Marvel at sunsets or mountaintop views with a meal
  • Get insider info and expert recommendations from the trip leader
  • Dance at traditional carnivals with folkloric characters
  • Go on a scenic drive past farmlands at 4,000 ft. above sea level
  • Sample plenty of local cuisine along the way

1   23

Using her intimate knowledge of the Caribbean, including relationships and contacts she has built over the last 11 years, founder and trip leader Lebawit Lily Girma customizes each itinerary, and shares experiences that will give the traveler a balanced overview of the country.  She also selects local first to ensure your travel is with purpose, and your contributions trickle far.

Sun & Stilettos Trips are women-only for now, but co-ed tours will be considered if there is demand.


Sun & Stilettos' Trip Philosophy

  • It’s about comfort and safety while traveling. It’s also about an immersive, cultural experience, which means adapting to the local spirit of doing things.

It’s not about over-the-top luxury. There will be dining and lodging in nice places, but also in local spots. 

  • It’s about remembering that we are guests in a foreign country.   

It’s a community experience, where like-minded travelers bond and create a positive setting for all.

  • It doesn’t matter if you’ve gone around the world before or you’re a newbie. 

It is not a trip for the nitpicky, fussy traveler–this is the Caribbean. The going can be slow, there are mosquitoes, and yes, occasionally there may be toilet paper missing. But we have fun anyway! 

  • It’s about respecting locals and tipping when happy with their service.

It’s about learning about the country visited and its people, without judgment. It’s all about exchange.

  • We leave place exactly as we found it. Preferably better. Nothing more or less.

Travel is for everyone, and we can all learn from each other.

Sun & Stilettos Trips: A Glimpse