Home > Travel Insurance Reviews > Island Windjammers Travel Insurance – 2021 Review

Island Windjammers Travel Insurance – 2021 Review

Island Windjammers Travel Insurance Review

Island Windjammers Travel Insurance Review
Insurance Partner
Coverage Options


  • Adequate Medical Evacuation limits
  • Cancel For Work Reason included


  • No option for Cancel For Any Reason
  • Low Medical Insurance
  • No Missed Connection benefit
  • Only two insurance choices

Island Windjammers sails 2 yachts carrying between 10 and 26 passengers. Itineraries move at a relaxed pace and offer extended times in port. They spend the winter and spring in the South Pacific, and summer and fall in the Caribbean.

Unfortunately, Island Windjammers cruises offers only two travel insurance options when booking a cruise on their website. Both policies are underwritten by Generali and administered by TripAssure. Generali is a reputable insurance partner.

Overall, Island Windjammer provides comprehensive travel insurance plans for a reasonable price. However, the Asset plan lacks adequate Medical Insurance.

But, compared to the broader travel insurance market, Island Windjammers' customers can find better protection for less money.


Our Sample Cruise: 6 Night British Virgin Island Cruise

Our sample couple, ages 55 and 60, are taking a 6-night Island Windjammers cruise in the British Virgin Islands. The total cost for both travelers is $6,000.

Island Windjammers’ Asset plan costs $301 for both travelers, and the Bridge policy costs $392.


Comparing Island Windjammers Trip Insurance to Other Plans

How do we know if Island Windjammers offers a competitively priced travel insurance program? We compare it to other options on the wider Travel Insurance Marketplace.

We set up a quote on AARDY for the same trip using the same traveler ages and travel dates. AARDY's travel insurance website provided dozens of quotes. It automatically puts the "recommended" plan at the top of the list. It sorts the rest of the options by price, lowest to highest.

The recommended plan is always the least expensive policy with at least $100,000 Medical Insurance, $250,000 Medical Evacuation, and, when possible, a Pre-existing Medical Condition Waiver. The least expensive plan that meets these criteria is the Trawick First Class for $270.27 for both travelers.


The next plan we look at is Seven Corners RoundTrip Choice CFAR 75% because it is the least expensive policy that offers Cancel For Any Reason.


Below, we compare both plans from Island Windjammers with the Trawick First Class and Seven Corners RoundTrip Choice CFAR 75%.


Island Windjammer Asset

Island Windjammer Bridge

Trawick Intl First Class

Seven Corners RoundTrip Choice (CFAR 75%)

Trip Cancellation

100% Trip Cost

100% Trip Cost

100% Trip Cost

100% Trip Cost

Trip Interruption

150% Trip Cost

150% Trip Cost

150% Trip Cost

150% Trip Cost

Medical Insurance





Medical Evacuation





Baggage Loss/Damage





Baggage Delay

$250, 12 hour delay

$400, 12 hour delay

$400, 12 hour delay

$300, 12 hour delay

Travel Delay

$150, 6 hour delay

$750 max

$200, 6 hour delay

$1,000 max

$200, 12 hour delay

$1,000 max

$300, 6 hour delay

$600 max

Missed Connection



$1,000, 3 hour delay

$1,000, 3 hour delay

Cover Pre-existing Condition

Yes, if purchased within 15 days of initial deposit

Yes, if purchased within 15 days of initial deposit

Yes, if purchased within 14 days of initial deposit

Yes, if purchased within 20 days of initial deposit

Cancel For Work Reason





Cancel For Any Reason




Yes, 75% cash refund

Accidental Death & Dismemberment

$25,000 anytime

$25,000 anytime

$10,000 anytime

$25,000 common carrier

$10,000 anytime

Cost of Policy





Island Windjammers Does Not Offer the Best Travel Insurance Value

Overall, the prices for Island Windjammers' trip insurance are reasonable. With other cruise lines, we have seen some outrageous insurance prices, up to 10-12% of the trip cost. Unfortunately, most cruise lines provide despicably low coverage at a high price.

Also, Island Windjammers' plans each provide comprehensive insurance. However, our primary concern lies with the Asset plan. Although less expensive than Bridge and Seven Corners, Island Windjammers' Asset plan falls short in Medical coverage.

AARDY always recommends at least $100,000 Medical Insurance for international travel. Since Asset only includes $50,000 Medical protection, that can leave you financially exposed if you had an injury or illness while traveling.

However, in the big picture, neither Island Windjammer trip insurance plan performs as well as Trawick First Class or Seven Corners RoundTrip Choice CFAR 75% for the money. Although Seven Corners costs more than Island Windjammers' Bridge, it provides Cancel For Any Reason for only $21 more.


Receive Reimbursement for Trip Cancellation

What happens to all the money you spent booking the trip if you fractured your ankle and could not make the trip as planned? Without Trip Cancellation insurance, you would lose all of that money.

With Trip Cancellation, you receive a 100% reimbursement of all prepaid, non-refundable trip costs if you had to cancel the trip for a covered reason.

Island Windjammers trip insurance has a great list of cancellation reasons:

  • Unexpected injury, sickness, or death
  • Weather delays
  • Bankruptcy or default
  • Traffic accident while en route to your trip.
  • Hijacking or quarantine
  • Destination inaccessible or uninhabitable from natural disaster
  • Involuntary layoff
  • Theft of passports or visas
  • Mandatory evacuation
  • Called to military service (not war)
  • Terrorism
  • Host sickness, injury, or death
  • Extended school year
  • Unable to receive vaccination that a country requires
  • Organ transplant
  • Required to attend adoption proceeding

Both AARDY policies cover nearly identical cancellation reasons except for the country vaccinations, organ transplants, and adoption proceedings. Those situations would fall under Cancel For Any Reason.

While we commend this list of covered reasons, we notice that Island Windjammers does not specifically cover hurricanes. It covers cancellation if your destination is uninhabitable or inaccessible. Still, if a hurricane is heading to your destination, it does not let you cancel before the storm hits.

Several policies at AARDY offer hurricane protection. They allow you to cancel the trip between 24-72 hours before the departure date if the NOAA Hurricane Center announces a Hurricane Warning at your destination. If you're packing for a flight to St. Lucia to board an Island Windjammers cruise, and a hurricane is on track to hit the island, it would allow you to cancel.

Similarly, Cancel For Any Reason insurance lets you cancel the trip for any or no reason at all. You would receive 75% of the trip cost reimbursed, not the full 100%. Only covered reasons listed in the policy qualify for a full refund.

Cancel For Any Reason, Receive Partial Refund

With Cancel For Any Reason benefits, you get the peace of mind that you can cancel hassle-free. You do not have to worry about whether you can cancel or not.

Because Cancel For Any Reason is the highest level of protection coverage you can buy, it costs a bit more. You maintain control of whether you can receive a refund for an unplanned cancellation.

Cancel For Any Reason has some provisions:

  • Insure all prepaid and non-refundable trip costs
  • Cancel the policy 2 days or more before your departure date
  • Buy CFAR insurance within 10-21 days of your Initial Trip Payment or Deposit
  • Receive 75% reimbursement

Although Island Windjammers' cruise insurance provides mostly good coverage, we are disappointed that they fail to offer a Cancel For Any Reason option.

Without Cancel For Any Reason, you face situations when you would need coverage but not have it, such as:

  • Sick, injured, or dying pet
  • Wedding called off
  • Outbreak of illness or pandemic
  • Travel bans, advisories, or border closings
  • Sold your home and must close the sale during trip
  • Mental illness flare-up
  • Autistic child has meltdown
  • Fear of flying or traveling
  • Dislike the new cruise itinerary
  • Financial emergency and need the money back

In this example, Seven Corners RoundTrip Choice CFAR 75% includes Covered Cancellation at 100% refund and Cancel For Any Reason at 75% reimbursement.


Cut Your Trip Short and Get Refund for Unused Expenses

Suppose you just arrived at your destination and received terrible news from back home. A close family member suddenly passed away, and the funeral is in two days. You cut the trip short and return home the next day.

Trip Interruption insurance refunds you for the unused portion of the trip, plus the extra cost of transportation home.

Most policies provide Trip Interruption protection for the same covered reasons as Trip Cancellation.

All 4 plans discussed in this article provide up to 150% Trip Cost reimbursement for a covered Trip Interruption.

Travel Insurance Also Pays for Medical Treatment

More than ever, travelers are aware they can become unexpectedly sick or injured when traveling.

However, Medical treatment overseas is not free. Even in countries with universal health care, Americans receive treatment at private hospitals and must pay full price.

Consequently, if you travel without adequate Medical Insurance, hospital bills bring a heavy financial burden. No one wants to spend their life savings on medical treatment. Trip insurance is an easy and affordable solution.

Most seniors do not realize that Medicare does not pay outside the US. Some Medicare supplements can cover up to $50,000 in emergency medical care for life-threatening circumstances. Unfortunately, you must pay the deductible and a 20% copay (up to $10,000). If your medical bills cost more than $50,000, you pay the additional charges out-of-pocket. Medical bills add up fast and can drain your retirement accounts.

Plus, don't expect the US State Department to come to your rescue. They only assist with legal and political situations, not medical ones. Even the state department urges all Americans to buy travel medical insurance.

AARDY recommends all travelers leaving the US take at least $100,000 Medical Insurance with them. We also advise travelers to get a Pre-existing Condition Waiver whenever possible. If you need treatment for a Pre-existing Condition, the Waiver assures the policy covers it.

Unfortunately, Island Windjammers' Asset falls short, with only $50,000 Medical Insurance. The Bridge policy includes $100,000.

Trawick First Class supplies $150,000 Medical Insurance while Seven Corners RoundTrip Choice offers $100,000. Both plans provide adequate Medical Insurance for a lower price than both of the Island Windjammers plans.

Medical Evacuation Home for Continued Treatment

Medical Evacuation insurance pays for critical transportation in a medical emergency. An evacuation can be as simple as an ambulance ride to the nearest hospital. Or it can be as complicated as a private medical jet outfitted as an ICU, crewed by a nursing team.

Either way, medical transportation can become expensive, very quickly. An air evacuation can run $15,000 to $25,000 per flight hour. If the flight brings you home to California from Germany, it's quite a long and costly trip.

AARDY always recommends buying at least $250,000 Medical Evacuation insurance when traveling overseas. For remote or distant places like Africa, Australia, or Asia, a $500,000 Medical Evacuation makes more sense.

Both of the Island Windjammers' plans provide a $500,000 Medical Evacuation. Trawick First Class has $1,000,000 Medical Evacuation, while Seven Corners RoundTrip Choice gives you $500,000.

All of these plans have adequate Medical Evacuation protection for worldwide travel.

Remember, it is very affordable to buy robust Medical Insurance and Medical Evacuation. If you ever need it, it can literally be a lifesaver.


Pre-existing Medical Conditions and Waiver

Many travelers, particularly seniors, are concerned whether travel insurance covers Pre-existing Conditions. What happens if your MS flares up before the trip, and your doctor says you cannot travel? It is a Pre-existing Condition, but will travel insurance let you cancel?

A Pre-existing Condition is a new or worsened medical condition in the 60-180 days before buying travel insurance. It also includes if you received a new or changed prescription medicine or your doctor recommended a treatment or test you have not yet received.

If your conditions are older than 60-180 days and unchanged, travel insurance can cover it.

However, if your condition was recently diagnosed or worsened, a Pre-existing Condition Waiver can protect your trip investment.

When you buy your travel insurance policy early, most plans include a Pre-existing Condition Waiver. This Waiver allows the policy to cover Pre-existing Conditions when you enroll within 14-21 days of paying your Initial Trip Deposit.

Both of the Island Windjammers' policies provide Pre-existing Condition Waivers when you set up the plan within 15 days of your Initial Trip Deposit. Likewise, Trawick First Class includes the Waiver within 14 days, and Seven Corners RoundTrip Choice offers it within 20 days of Deposit.

The Pre-Existing Waiver gives you peace of mind knowing that you are covered for medical cancellations, interruptions, and medical treatment while traveling.

Island Windjammers Travel Insurance Summary

Overall, Island Windjammers Trip Insurance offers comprehensive policies but lack adequate Medical Insurance and Missed Connection benefits.

Sufficient Medical Insurance is critical when you travel outside the US. Regrettably, Island Windjammers does not offer customers the opportunity to Cancel For Any Reason.

Travel plans can change unexpectedly for reasons beyond your control. CFAR provides the highest level of protection in case of political border closings, Visas that do not arrive in time, or anything else not covered by standard insurance.

We are pleased to see their prices are not outrageous, but would not recommend them due to their deficiencies.

AARDY offers plans with more benefits and a lower cost than most cruise lines. You can compare up to 30 different trip insurance options in less than 60 seconds.

Working with AARDY gives you peace of mind knowing you are well protected without overspending.

Please stop by and chat with us, send an email, or give us a call at 650-492-6298.

Safe travels!

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