Discovering The Dominican Republic with Sun & Stilettos Trips

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Sun & Stilettos Trips offers custom-crafted, cultural tours to the Caribbean. Yes, the Caribbean! A 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 an expert-built 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 (read our interview with her about her Moon Belize guide). Since 2008, her award-winning 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.

Jamaica! From Sun & Stilettos Trips


Belize. From Sun & Stilettos Trips


Join Lily and a small group of like-minded wanderers passionate for meaningful, fun, and culture-rich experiences. And don't worry, there will always be beach time along the way! The first trip, Discovering The Dominican Republic, is for women-only and will take place in March 4-11, 2017. Registration is now open for 10 spots on a first-come, first-booked basis.

Discovering The Dominican Republic in Lily's words:

Come on a different kind of Caribbean journey, expert-crafted and led by me! 

Discovering The Dominican Republic with Sun & Stilettos Trips

7 Days. March 4-11, 2017.

$1,499 pp. Deposit $500. 

Launched with 10 spots a day ago. Now 8 spots. First-come, first serve! If you want to secure your space, make your deposit by November.

The most geographically diverse destination in the Caribbean, the Dominican Republic is full of surprises, and full of life. Even with five million visitors a year, few have explored this country's cultural pulse–a blend of Taino, African, and Spanish–or its breathtaking range of scenery. 

We go from the capital's Colonial City–a UNESCO World Heritage Site–to the mountains and verdant valleys of the Cibao, close to the tallest peak in the region, onto the fishing villages and cacao farms of the north, and the cayes and coveted beaches of the northwest.

We'll stay in unique lodging, from a restored 16th century colonial building to riverside cabins–surrounded with birds, vegetable fields, and sea breezes–and beachfront stays.

Along the way, we meet farmers, fishermen, musicians. We dance, we hike, we swim in rivers, dine on mountaintops, and maybe even learn a few words of Dominican Spanish (inevitable).

Discovering The Dominican Republic with Sun & Stilettos Trips

Discover the real DR for an incredible value–with a perfect mix of culture, nature, and relaxation!

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

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
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.

Martinique. From  Sun & Stilettos Trips




All information and photos contained herein courtesy and copyright Sun & Stilettos Trips