Why book through us

For over 12 years Sailing Directions has been a leading crewed yacht charter brokerage helping customers choose and reserve quality yachts and crews to create relaxing, fun vacations for families and groups of friends sailing the Caribbean.

Our team attends the Tortola, St Thomas and Antigua yacht shows annually to inspect the entire fleet and to keep in touch with crews and meet new crews to maintain regular, first-hand knowledge that helps us recommend the best quality yachts and friendly, service orientated crews that match up well with your party.

These direct relationships plus the high volume of charters we book along with our pre and post-booking online account enables you to receive the best pricing and an ease of booking. Our service comes at no cost to you.

We are sailors at home and also regularly sail in the beautiful Caribbean waters to keep in touch with the region. When you contact us you will work with one knowledgeable broker throughout the process of your reservation, right through until you return from your vacation.

Unbiased recommendations

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 agent that knows the yachts and their crews personally you can get accurate, un-biased information on all the options that are available to you.

Our website works for you

Our website allows you to search for current yacht availability for your travel dates, lists any special offers available and features our own recent, quality photos of the yachts, giving you the most up-to-date information available.

When you ask us to hold your favorite yacht for your vacation dates you can login and view the full details of your charter including dates, times, locations, additional terms, deposit details and the charter agreement, all in one convenient place.

Ease of booking and payment

To confirm your reservation all we need is a signed charter agreement and deposit. We offer the convenience of deposit payment by Visa/MasterCard/Amex through our secure website and also accept wire transfers and checks. Pay all together or split payments between members of your group.

Once you confirm your charter vacation you will be able to login at any time and see all of the charter details including the preference sheet, crew contact information, transportation tips and preparation information customized to your sailing ports. Making this information accessible to you at any time, and having the option to share the login details with the other members of your group, makes your role as lead passenger easy!

Established excellence

Sailing Direction's President is an active member of CYBA (the Charter Yacht Brokers Association) and our brokerage adheres to the association's operational guidelines.

We are also an A+ member of the highly regarded Better Business Bureau's Online Reliability program and the BVI Charter Yacht Society.

When you book through Sailing Directions you receive a great deal of peace of mind - for example:

  • Our information is up-to-date, accurate and unbiased. You can see in-depth information about the yachts and crews and we're on hand to answer any questions.
  • You have the protection of the CYBA charter agreement. Deposits are held in an independent escrow account until just a few days before your charter begins.
  • We accept payment by Visa, MasterCard and Amex securely and conveniently through our website with no processing fees.
  • We offer you constant after sales support with the same broker assisting you in the lead up to your vacation.
  • Our website offers you customized travel and preparation information for your destination and charter type.
  • If, for any reason, the yacht has a 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), which is another peace of mind when you book your Caribbean yacht charter through Sailing Directions.

What our customers are saying

"Sailing Directions itself did everything I could ever ask. We were matched with a perfect vessel and the support from the booking through the cruise was thorough and professional. Thank you again for everything!"

Take a look at what our customers have been saying about Sailing Directions and our services on the yacht charter review page.

Sample crewed yacht charter videos:

Charter Brokers

John Lane

John Lane

Mei Li McNeil

Mei Li McNeil

Get in touch for more information:


Caribbean Yacht Charter
Interested in becoming a part of our team? We are looking for a customer focused professional yacht charter broker or skilled, service driven charter crew member to expand our friendly sales and service team. Send us your resume for consideration!