Skip to main content.


A boat in the water.
A boat in the water.


Missing a trip is bad enough. Losing the money you paid for it is even worse. The Sail Caribbean Travel Protection Plan may provide protection for your travel investment, your belongings, and most importantly you.

We offer travel insurance through travel protection plans from Trip Mate, which are available to US residents. These plans include trip cancellation coverage, which reimburses non-refundable program expenses if you cancel your program due to a covered reason, such as sickness. Plans also include missed connection, trip interruption and travel delay coverages. COVID-19 is treated the same as any other sickness under the terms of the plans.

For additional protection, families may also choose plan F4340D which includes the Cancel for Any Reason Benefit (CFAR). If your payment for this plan is received within 30 days of the date your initial payment or deposit is made for your trip, this benefit can reimburse up to 75% of your non-refundable program expenses if you cancel your program at least two days before your scheduled program departure date for any reason not otherwise covered by the plan, including fear of contracting COVID-19 during the program. CFAR does not cover: 1) penalties associated with any air or other travel arrangements not provided by Sail Caribbean; or 2) the failure of Sail Caribbean to provide the bargained for travel arrangements due to cessation of operations for any reason. CFAR is not available to residents of New York.  Click here for plan documents regarding plan F4330D. Click here for plan documents regarding plan F4340D. For pricing and further information please contact us at 800-321-0994 or


Benefit TypeMaximum Benefit F4330DMaximum Benefit F4340D
Trip CancellationTrip CostTrip Cost
Trip Interruption125% Trip Cost125% Trip Cost
Missed Connection$500$500
Travel Delay (Up to $200 per day)$2,000$2,000
Cancel Fo Any Reason Benefit*N/A75% of Non-Refundable Trip Cost
Medical Expense/Emergency Evacuation
Accident & Sickness Medical Expense$50,000$50,000
Emergency Medical Evacuation$100,000$100,000
Non-Medical Emergency Evacuation$25,000$25,000
Baggage and Personal Effects$1,000$1,000
Baggage Delay$250$250
* Not available to New York Residents


General Global AssistanceIncludedIncluded

Other benefits of Trip Mate:

  • Injuries during amateur, organized, and intramural sports are not excluded;
  • Scuba diving, as delivered by Sail Caribbean (and in compliance with Sail Caribbean’s rules), is not excluded so this plan can be used to satisfy our dive insurance requirement;
  • Mental, nervous or psychological conditions are not excluded.

Plan F4330D is only available prior to, or at the time of, full payment for your trip. Prior to full payment, Plan F4330D may be purchased at any time.

Plan F4340D, which includes the Cancel For Any Reason Benefit, is only available for purchase within 30 days of the date that Sail Caribbean receives your initial payment or deposit.

The best way to purchase your trip insurance is through your My Sail Caribbean account, using the link in the Documents section.

If you have questions regarding how to purchase the plan, please call our NY Office at 800-321-0994 or 631-754-2202 or email us at

For specific questions regarding the Travel Protection Plan, please call Trip Mate directly at 833-297-2255 and refer to Plan ID# F4330D or F4340D.

This advertisement contains highlights of the plans, which include travel insurance coverages underwritten by United States Fire Insurance Company under form series T210 et. al. and TP-401 et. al. The Crum & Forster group of companies is rated A (Excellent) by AM Best 2022. C&F and Crum & Forster are registered trademarks of United States Fire Insurance Company. The plans also contain non-insurance Travel Assistance Services provided by Generali Global Assistance. Coverages may vary and not all coverage is available in all jurisdictions. Insurance coverages are subject to the terms, limitations and exclusions in the plan, including an exclusion for pre-existing conditions. In most states, your travel retailer is not a licensed insurance producer/agent and is not qualified or authorized to answer technical questions about the terms, benefits, exclusions, and conditions of the insurance offered or to evaluate the adequacy of your existing insurance coverage. Your travel retailer may provide general information about the plans offered, including a description of the coverage and price. The purchase of travel insurance is not required in order to purchase any other product or service from your travel retailer. Your travel retailer maybe compensated for the purchase of a plan. CA DOI toll free number: 800-927-4357. The cost of your plan is for the entire plan, which consists of both insurance and non-insurance components. Individuals looking to obtain additional information regarding the features and pricing of each travel plan component, please contact Trip Mate. Trip Mate Inc. (dba Trip Mate Insurance in CA and UT) P.O. Box 527 Hazelwood, MO 63042, 1-833-297-2255; CA license # 0805270

Be a part of our next adventure