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Trip Planning 


Do I need a passport if I’m sailing? 


If you are sailing in waters that are not within US territory, then you will need a passport. Sailing 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. 


Do I need to bring my own scuba gear? 


Each boat provides basic scuba gear. Some have tanks as well. If scuba is your preferred activity then we’ll make sure your boat is equipped. For Villa renters, every destination has premium snorkeling gear and scuba rentals (and guides) that your host can arrange 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 alive with travelers from throughout Europe. 


Will I be provided with any information on local customs and experiences?  


Yes. Two weeks before your getaway, you will receive your own unique Regatta Getaway Travel Prep kit with your itinerary, travel and safety tips, including covid protocols, and information on local culture and experiences. 


What do you recommend for a person traveling alone?  


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


Reservations and Bookings 


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. 


Can I use my frequent flier miles? 


Yes. 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. 


Can I rent a villa and a boat?  


Of course! We recommend at least five days on charter and five days on villa that way you don’t miss out on what each experience offers.   


It is worth mentioning, we have some surf and turf options. We can arrange a combination villa stay and boat charter to get the best of both experiences. Island hop by day, then sleep in the luxurious villa at night; or use the villa as a launching point for long bot trips between major islands. We even have access to an exclusive private islands in the Virgin Islands that come with a spacious villas, yachts, and watersport toys and gear.  Call us for details! 


Do I get to pick my villa/boat? 


Yes. We will give you options of different accommodations based on your choice of activities.  


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 




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. 


Food & Drink  


Can I drink the water? 


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


Do I have to purchase my own food?  


This is based on the vacation you design. Most boat trips include most meals, with some reserved to be had on the beach restaurants. In most villas you can either pre-order your groceries or shop when you get there. Some boats and villas come with a chef! These are all items we will help you craft to make your vacation perfect.   


Fun Facts  


Do barracudas bite? 


Are the Barracuda the world’s most ferocious fish? Well, they certainly look like it. They can be the size of you, they have massive teeth, and they swim like lightning. However, an attack by a Barracuda is exceptionally rare. As one captain put it, “I don’t know anyone who knows anyone who got bit by a Barracuda.” That said, our Captain stated, “The first time I saw a live Barracuda, I literally jumped out of the water and into the boat. They’re huge!” These beast have no interest in people and they are way too smart to mistaken shiny objects for fish. Unlike most fish, the Barracuda swim very slow at the top of the water, so they are easy to spot.  


Nonetheless, here are three golden rules when it comes to barracudas: 

Do not wear shiny jewelry or shiny swim attire while snorkeling 

Don’t go snorkeling after handling chum 

Don’t swim with this guy 


How do I do laundry?  


If you are on a sailboat, laundry services are on the main dock only 

If you are on a yacht, laundry services are on board 

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. Possibly yachts, depending on the experience and your pet’s comfort. To ensure the safety and comfort of your pet, we do not recommend pets join you on a sailing adventure. 


What are some items a savvy traveler would bring that which others wouldn’t think?  


Check out our Sun Chair Logbook for tips and tricks on traveling savvy. 




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.  


How do I prevent seasickness? 


Ginger tablets are great for curing seasickness. Olives the night before are great for preventing it. Staying outside of the boat’s cabin, in the fresh air, and looking out to the horizon will stop your inner-ear’s confusion, which is the cause of typical seasickness. We suggest natural remedies over prescribed because the drug solutions tend to make the passengers tired and limit their enjoyment. Check out our Sun Chair Log for more health tips. 


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 asking 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.