1. Home
  2. /
  3. FAQ

Frequently Asked Questions



Do I need a passport if I’m traveling? 

If you are traveling in waters that are not within US territory, then you will need a passport. Traveling within US waters, including Puerto Rico and the Spanish Virgin Islands does not require a passport.  


What if I want to go somewhere that’s not featured on your site?  

Call us! We are in 50 countries and would love to organize a truly unique getaway for you.  

What are the best months to travel?  

With destinations around the world, all months are the best months to travel! The best months to travel the Caribbean will be between October and May. Shopping and restaurants are open and communities are lively. Weather is near perfect and the bug populations are lower than in other times of the year. For the summer months, the Mediterranean is the ideal destination. The weather is always calm and the seaside villages are alive with travelers from throughout Europe. 

What do you recommend for a person traveling alone?  

We tailor all excursions by the needs of our guests, no matter the size of their party. Currently, we are developing soirees for world travelers and digital nomads.  

Do I have to book my own flight?  

Not unless you want to. We can organize the logistics of your travel to and from your getaway.  During our initial call, we request your flight preferences and details to either earn you frequent flier miles or utilize them towards your getaway. You tell us what you want to do. 

What if I miss my flight? 

Our concierge will help you get on the next flight and be in contact with your local host to change your itinerary and handle any necessary accommodations. 

How far in advance do I need to make my reservation?  

Scheduling varies on season and vacation. We recommend at least 8 to 16 weeks in advance for peak seasons (December/January in Caribbean and August/September in Mediterranean). There can be more flexibility during the other seasons. 

What if I need to change my reservation?  

Call us as soon as you are aware of your travel concerns and we will work with you and do our best to adjust your reservation accordingly.  

What is required to travel to the Caribbean? 

The essentials to be allowed entry is: Two forms of identification, including a passport outside the US territories; Proof of accommodation; and Communication 

Personal concerns

Will I have cell service? 

The Caribbean has cell service. Check with your carrier to determine if the service on your destination is compatible with your phone. Data charges may apply, according to your cell plan, so contact your phone service provider to ensure your global plan is in place. 

I only speak English; will that be a problem?  

The Caribbean is an international paradise, but fortunately most people speak English. In most cases, the servers at the stores and restaurants will speak very good English. Our local concierge are fluent English speaker so there shouldn’t be any issues getting your needs met. Your Regatta Getaway Travel Prep Kit will include some tips and tricks for feeling comfortable communicating in other languages. 


How do I do laundry?  

If you are staying in a villa, you will either have a washer/dryer in your villa or your host concierge can accommodate servicing your laundry. 

Can I bring my pet?  

It depends on the experience and your pet’s comfort. Many villas are pet-friendly, so our concierge will be able to assist. 


I have COVID questions. 

The COVID restrictions are constantly changing and different from island to island. Regatta actively stays abreast of the requirements to ensure our customers are prepared and the impact of covid precautions are minimal.  

Can my health regimen and or dietary needs be accommodated? 

Yes. We plan your vacation around your needs and wellbeing. During our initial consultation we will ask about any special diet needs and preferences. 

I have a personal safety concern, where should I address it?  

We’ll discuss safety precautions before your trip and how we can best accommodate you. Some locations are safer than others. Did you know Tortola has almost a zero crime rate? If a concern arises during your trip, you’ll have access to your local host 24/7 for hands-on support. 

How can I make it home if there is a personal emergency?  

If a personal emergency comes up and you need to return home as soon as possible, we will arrange the necessary transportation for you immediately. 

What precautions are taken in the event of a weather or local emergency while I am there? 

We recommend that you consider both traveler’s trip insurance and traveler’s health insurance. For US citizens and nationals, you may consider registering with the US Embassy to ensure you’re taken care of in case of national or weather emergency. We can discuss each of these options and other considerations during the planning process. Most important, no matter what may happen on your journey, our concierge service will be there with you to help connect you with the local services and assistance you need.  

Can I drink the water? 

Most destinations in the Caribbean have clean drinking water. All water in the villas are filtered and safe to drink. We do not recommend drinking water outside the villa or restaurants. When in doubt, carry bottled water with you.  

Do I have to purchase my own food?  

This is based on the vacation you design. Villas include most meals, you can either pre-order your groceries or shop when you get there. Some villas even come with a chef! These are all items we will help you craft to make your vacation perfect.