For your convenience, our most frequent reader questions are answered right here. Not finding what you want? You can reach out directly through the Contact page.

Q: What makes Sun & Stilettos Trips different from what other Caribbean tour/travel company offer?

A: Sun & Stilettos Trips offers curated cultural tours to the Caribbean. We don’t do large, all-inclusive type of travel and steer away from the large resort type of vacation or the mass excursions that are plaguing this region. Instead, we show you the heart of this diverse part of the world so often under-explored–its cultures, landscapes, and people in each of the destinations we visit. We support authentic travel, supporting as many locally-run establishments, cooperatives, and local entrepreneurs as is feasible. This means at least 50% of your trip fees trickle directly to locals.

Our groups are never larger than 10, because we want to travel responsibly and have the most positive impact on a place as possible. Each trip offered will have an itinerary that is crafted by an award-winning, multilingual travel journalist and author who has specialized in Caribbean travel for the past 11 years and has lived in the region long-term. As a Caribbean expert, she has extensive contacts and knows the cultural highlights of a place, how to identify the communities that would most benefit from these visits, while providing you with fun and memorable experiences. She takes you well beyond the beaches and rum this region is known for–all while having a fantastic time.

The trips focus on immersive, adventure and nature-filled days. It shows you a Caribbean that few get to see, want to but don’t know how–and for a great value.  No one else out there is offering the kind of cultural experiences found on Sun & Stilettos Trips–whether it’s spending an afternoon with generations of local musicians, or staying at a river lodge run by an entire community as part of their sustainability efforts.

It takes time, effort, passion, and destination expertise to create a uniquely cultural itinerary to the Caribbean. That’s what we offer and we are confident you will note the difference.

Check out the first trip to the Dominican Republic as an example. And read more on the About page.

Q: Why is it called Sunshine & Stilettos Trips? Do I have to pack stilettos? 

A: Stilettos are not required! The trips are named after founder Lily’s travel and photography blog, Sunshine & Stilettos, which she first created in 2009 when she went from lawyer to travel journalist. She ditched the stilettos and office life for the Caribbean (you can ask her all about that on a trip). So no, you don’t need to bring heels and won’t need them most of the time as we will navigate countrysides, beaches, hills and cobblestoned cities. But it’s entirely up to you if you want to squeeze in a pair–just know they might end up staying in your suitcase.

Q: What kind of traveler joins a Sun & Stilettos Trip?

A: Sun & Stilettos Tours participants are interested in traveling in small groups, on an expert-crafted trip that takes them deep into a destination and its culture. They want to explore with like-minded, fun travelers and have an immersive, meaningful journey without having to design it all themselves–which would be difficult without local expert insight.

The women-only tours are for all age ranges, and for all travel experiences, for friends, or family members who wish to travel together. Why women-only? Because it’s an amazing opportunity to bond with other like-minded individuals who may well inspire and change your life. It’s like a retreat, except with plenty of exploration along the way, from food to sights and cultural events.

It doesn’t matter if you’re a solo traveler, or would like to travel with your mom, or maybe with your best friend. You are all welcome! The trips are also open to anyone in the US, Europe, Canada, or maybe even as far as Australia. You make your own way to the destination, but after that the itinerary is there to create a unique, authentic experience for you.

We just launched, but hope to offer co-ed tours in the near future.

Q: What is your trip philosophy?

A: We’re glad you asked. You can read more about the trip philosophy here, and get a sense of what Lily believes in and what each trip is about.

Q: How do I guarantee my spot on a Sun & Stilettos Trip?

A: To guarantee a saved spot on the tour, you will need to send in the deposit amount for that specific tour. Once we receive it, we will notify you and send a registration form within 24 hours, along with a waiver and release, and will need you to email those back completed and signed. After these are all received (deposit and forms)–your spot will be saved. Please note the refund and cancellation policies for your chosen trip before booking.

Q: Does the pricing include airfare?

A: No, our prices are always land-only. You are responsible for purchasing a separate ticket to and from the destination–as well as the airport. But we can certainly help advise on getting great deals.

Q: What should I wear?

A: Wear whatever is comfortable for you. It is recommended to have a sturdy pair of broken-in hiking shoes, or sneakers. It is preferable to that will wick away perspiration (cotton) and keep you dry and comfortable. For evening dinners in a city, you may want to jazz it up a bit. Think beachwear, hiking clothes, and comfortable shoes.

Q: What should I pack?

A: You will need Caribbean or tropical weather essentials such as sunscreen, mosquito repellant, long sleeve shirts for boat rides (in addition to swimwear), long pants for hiking if applicable (and inland excursions), sunglasses, and your happy self!

When you register for a trip, you will receive a welcome packet which will include a list on what to pack.

Q: Will I receive a refund if I cancel my participation in a trip?

A: The deposit for a trip is non-refundable, unless we cancel the trip on our end. Aside from the deposit, whether or not you receive a partial refund depends on how far in advance of the trip you cancel. Please note the refund and cancellation policy under each specific tour, as well as our Booking Terms and Conditions. This is also covered on our Registration form that you’ll receive within 24 hours of booking/sending your deposit.

If you are owed a refund according to our policy, they will be sent to you via Paypal. If Lily is traveling during the time you make your written request (email is fine), then please allow at least 2 weeks for processing.