Caribbean Yacht Charter Frequently Asked Questions

Why book through a yacht charter brokerage like Sailing Directions?

What can I expect from a crewed yacht charter?

How do I reserve a charter yacht and what are the payment terms?

What's included in the yacht charter fee?

What is the best time of year to sail in the Caribbean?

What are the passport & visa requirements?

Do I need trip insurance?

How can I be reached in an emergency?

Is SCUBA diving equipment and air included in the charter fee?

Should we bring the kids?

What is the standard crew gratuity?

Why choose the Virgin Islands?

Where can I view a sample itinerary?

What are our customers saying about their vacation?

Who do I contact if I can't find the answer to my question here?

caribbean yacht charter

Why book through a Yacht Charter Broker like Sailing Directions?

Choosing the right charter yacht and crew is vital in ensuring that you get the most out of your charter vacation. When you use a charter brokerage that knows the boats and the crews personally you can get accurate and un-biased information on all the options that are available to you.

When you book through Sailing Directions the charter cost is the same as when you deal directly with the yacht owner, but you get a great deal more peace of mind; for example:

  • Our information is current, accurate and unbiased.
  • You have the protection of the standard CYBA charter agreement and your deposit is held in an independent and safe escrow account until just a few days before your charter begins.
  • We will always be here to help and advise you on your best options - and if you are new to chartering we provide a wealth of information and support. We can also provide additional travel products and services that you may need to make the most of your charter experience.
  • We offer you extensive and ongoing after-sales support, assisting in all aspects of your vacation preparation and managing your relationship with your crew.
  • If, for any reason, the yacht has any problem and is unable to take your charter we will be here to assist you. We can move fast to find you the very best resolution to the problem (or refund you in full) - another piece of mind when you book your Caribbean yacht charter through Sailing Directions.

You can see some of our customer's feedback and charter reviews here.


How do I reserve a charter yacht and what are the payment terms?

Once you decide on the perfect yacht for your charter vacation we will place a temporary hold on the yacht for the dates of your choice. This hold guarantees availability while you make your final decision. To confirm the reservation we require a 25% deposit and the signed charter agreement (which we will email to you once the yacht is on hold). A second 25% deposit is due 6 months prior to your charter; with the final payment due 60 days out. 


Passports & Visas

Passports are required for all visitors in the Caribbean.

The United States Government will require a valid passport to regain entry into the US. Please remember to bring passports for each member of your group.

US Citizens: For information on renewing your US passport or obtaining your first passport please click here.

British Virgin Islands:
US Citizens can enter the British Virgin Islands with a valid passport - no visa is required.

Non-US Citizens may require a visa to enter the US and / or British Virgin Islands. For a list of countries that qualify for the US visa waiver program please see: US Visa Requirements

For more information on Visa requirements for the British Virgin Islands please see: BVI Visa Requirements

Many other Caribbean nations offer tourist visas, some of which must be applied for in advance. Please let us know if we can help you with any questions.


What time of year is best to sail in the Caribbean?

Mid-December through to the end of April is the "high season" in the Caribbean as travelers flee cold northern climates to bask in the tropical sunshine. For the peak periods of Thanksgiving, Christmas, New Years and the Spring Break months of March and April, charter yachts should be reserved well in advance.

December through May is considered the dry season while June through November is generally the more humid season. However, in our experience, rain or clear skies can occur at any time during the year. Rainstorms often pass quickly and there is sunshine on most days during the year. Average air temperatures in coastal areas range from 72º to 86º F. The warm coastal water temperatures stay between 68º and 74º F.

The northern summer is considered to be low season in the Caribbean, however the months of May, June, early July and late November are still great times to visit the islands; charter rates and flight prices can be lower and the beaches, roads and restaurants are rarely crowded.

Atlantic Hurricanes can occur any time from August through October; with the most active month being September. The good thing is that every year brings more sophisticated storm warning systems and it is unusual for any one island to be severely affected more than once or twice every 10 years and your actual odds of experiencing a hurricane are very low. You can purchase travel insurance to cover force majeure as soon as you confirm your travel plans. 


Do I need Insurance?

While we hope that your trip is relaxing and worry-free, we'd like to remind you that situations may arise before departure or during your trip that are out of your control. Having travel insurance can be a valuable asset.

When purchasing trip insurance, please make sure that the policy you choose provides coverage for your insurance needs. This may include:

  • Medical coverage
  • Delayed or canceled flights
  • Lost or damaged luggage
  • If you need to cancel the trip for any reason

We are pleased to offer trip insurance coverage from all the major insurance providers. Purchasing trip insurance within 21 days of confirming your reservation gives you the benefit from additional coverage which is available only within this 21-day period.

You can compare all insurance packages and prices here or you can generate individual quotes and purchase directly from these providers:


How can I be reached in an emergency?

All vessels have VHF radios and cell phones. You can of course bring along your own cell phone (please check with your provider that you have roaming capability in the area you are visiting). Many of the yachts also have wireless internet available on-board available for guest's use. 


Is scuba diving equipment and air included in the charter fee?

This can vary from yacht to yacht. Some boats are fully equipped with scuba equipment and a dive master or dive instructor as part of the crew (often the Captain), while others will only allow rendezvous diving (where a local dive shop's dive boat will meet you at a specified dive site). We can provide you details on individual yacht's dive policies. 


Should we bring the kids?

Kids are seldom bored on charter. They really get into the sailing and particularly the snorkeling and playing on the beach.

The yacht's crew is employed to maximize the enjoyment and safety of your vacation however please note that they can not take responsibility for over-seeing the welfare of children at all times. Children under the age of fourteen must be under the direct supervision of a parent, child-minder or other appointed adult. 


Crew Gratuities

Gratuities of 10% - 20% of the charter fee are the norm when the service merits it. Please remember that your crew work hard to ensure your vacation is a great one, that will be remembered for many years to come. They are your chef, bartender, waiter, tour guide..

Your crew is happy to accept gratuities cash, traveler's checks or personal checks.

The best way to handle the gratuity is to place the amount into an envelope addressed to the crew and either hand it to the captain or leave it on the saloon table on your departure from the yacht. 


Who do I contact if I can't find the answer to my question?

If we have not addressed any of your questions, please contact us and we will be happy to help you further!