How to Travel Prepared this Holiday Season, with Travel Insurance

Family enjoying Thanksgiving dinner

Summary: Holiday travel is often complex—families coordinating travel plans during a season when storms and weather can easily mess with your trip. Throw COVID-19 into the mix and travel insurance becomes an obvious consideration. We outline how our plans can help during your holiday trip, especially in the current travel climate. Or you can jump straight to our Holiday Travel Survival Strategies.

In 2019, more than 160 million Americans traveled during the holiday season, including Thanksgiving, Christmas and New Year’s.* The predictors are understandably hedging their bets when it comes to 2021 holiday travel numbers, but there will still be plenty of competition for that airplane seat or stretch of roadway – and plenty of reasons to make sure that trip is insured.

Some of the reasons for buying holiday travel insurance are relatively new, like COVID-19 sickness, and others are as old as the dawn of travel. Let’s look at some of the reasons why you might want to buy travel insurance for travel during holiday season, and how travel insurance can actually help.


Unexpected illness is an unavoidable facet of travel these days. Whether it’s getting sick before or during your trip, or a family member getting sick back home, it means travel complications are more likely and a travel protection plan might help if it happens to you.

While there are many scenarios where travel insurance can help during disease outbreaks, remember that fear of contracting a disease is not a covered reason for cancelling or interrupting a trip.

Read some of our FAQs below for details about how our travel protection plans can help if COVID-19 becomes a trip wrecker.

Trip-Wrecking Weather

Weather is more unpredictable than ever. Snowstorms are heavier and rainstorms are more torrential, and even the cold snaps are colder.

Travelers looking to vacation in coastal areas need to be prepared for the possibility that winter storms may make their destination uninhabitable. Meanwhile, people living everywhere else can be waylaid by blizzards, tornadoes, floods, and more.

Travel insurance can help in three ways when bad weather strikes:

  • By covering trip cancellation and interruption for certain weather-related issues. 
  • By paying for medical expenses due to weather-related medical emergencies if you suffer an illness or injury during travel. 
  • By providing emergency travel assistance or helping you make alternate arrangements if you’re lost, stuck, or stranded because of weather-related issues.

Read more: How Travel Insurance Works with Bad Weather

Flight Cancellations/Delays

According to data from the U.S. Transportation Department covering December 2019, the last “normal” holiday travel season, major airports Like Newark, San Francisco, and Chicago Midway struggled to get two-thirds of their flights arriving or departing on time. Having a one-third chance of having a flight delayed is not a great situation to be in, especially around the holidays.

Weather is one of the top reasons why flights are delayed during the winter, and it can manifest itself in multiple ways. In addition to wreaking havoc with flights where you are, storms can strike another part of the country and back up flights in a domino effect from Seattle to St. Pete.

The holidays only happen once a year. You have somewhere important to be, and you need to get there. Travel insurance can help make it right if you can’t, reimbursing you for covered events such as flight cancellations or delays due to adverse weather, if you need to cancel. Not to mention the travel assistance services that come with every Generali plan. Our team is just a phone call way and can help you make alternate arrangements if things go south.

I used Generali on a very stressful trip once before. That trip got even more stressful with a flight cancellation. But Generali was there to help me when I needed them most! I won't use any other Travel insurance, so now I'm back so Generali can protect me and my family while we travel abroad after Christmas.
Amanda D. from Deltona, FL

Sporting Equipment

Not every holiday vacation is a trip to see family. Sometimes you just want to get away from it all during the holidays – and when you do, it’s often somewhere where you can ski, golf, or otherwise recreate. Sporting-equipment coverage is vital to help protect your holiday-season recreation if your equipment is delayed or damaged.

Traveling with sporting equipment that you love can be nerve-wracking. Fortunately, Generali has sporting-equipment coverage baked into its Premium and Preferred plans, so your clubs, rackets, skis, and fishing tackle can be taken care of if they are lost, stolen or damaged.

If they’re delayed for a certain period of time, we can even cover your rental costs so you can make your tee time or don’t miss a day on the slopes.

Vacation Rentals

Another popular type of holiday travel is renting a vacation property with the family. Generali has a wide range of vacation rental coverage options that can help protect you not only if your trip is cancelled due to a covered event, but if you get our Travel Secure vacation rental insurance, you can also be covered for accidental damage to the rental and be reimbursed if your damage deposit is withheld due to a covered loss.

Enough things go wrong during the holidays without adding vacation rental issues to the pile. For those at least, Generali can help.

See our vacation rental insurance plans

Baggage Loss and Damage

More than 2.8 million bags were mishandled in 2019, proving that despite all the tracking technology and other upgrades airlines have made to their baggage handling procedures, bags still fall through the cracks – literally.

Generali travel insurance covers lost, damaged or stolen bags – and you can even be reimbursed if you have to buy personal effects because your bags were delayed for a certain amount of time during you trip.

Assistance and Concierge Services

Who doesn’t need help during the holidays, especially if you’re traveling?

Generali’s travel services, included with every plan, can help with everything from rebooking a flight to setting up an emergency cash transfer or finding a restaurant that’s open for Christmas dinner.

Travel assistance is particularly useful and helpful during the hectic holidays. Take advantage of it.

See all the services included with our Generali Travel Insurance plans

Rental Car Coverage

If you’re renting a car on your holiday trip, you can get Rental Car Damage coverage as part of your travel insurance plan.

Rental Car Damage coverage is available with our Standard, Preferred and Premium plans that can reimburse you up to $25,000 if your rental car is damaged through collision, theft, vandalism, natural disasters or any other cause beyond your control while you’re on your trip.

Holiday Travel Survival Strategies

So, in addition to buying travel insurance, how can you make sure your holiday travel goes off without a hitch – or if it doesn’t, that you’re prepared for the hitches? Try some of these strategies:

Be flexible about your departure airport. There are generally several alternate airports within a two- or three-hour drive of wherever you are. If you’re in New Orleans, try Mobile or Baton Rouge; in Columbus, Ohio, try Cincinnati or Dayton. Granted, if the weather’s bad no one really wants to dive into a three-hour road trip, but if it gets you where you’re going safely, it’s worth it.

Have a backup plan, and a backup to your backup plan. Know all the different ways you can get from where you are to where you need to be. Check out rental cars,  train and bus schedules, and alternate driving routes that may be able to get you where you need to go when main roads are closed.

Avoid regional air carriers. The U.S. DOT calls them “codeshare partners,” but we know them as those smaller carriers with smaller planes that fly into smaller airports.

For all that smallness, regional carriers aren’t small when it comes to flight cancellations. For instance, in December 2019 the codeshare partner of Hawaiian Air, Empire Airlines, had to cancel almost 10% of its flights.

Regional air carriers often get bumped back in priority when larger flights get delayed, which can lead to lengthy delays, especially at the end of a flying day, when all that day’s delays compound.

If you fly on a regional carrier, try to get a seat on the first flight of the day. That plane may be the least likely to be delayed.

Also read: 6 Fantastic Destinations for Christmas and Holiday Season Travel

Be prepared to spend the night at the airport, but don’t be nuts about it. Pack your carryon with stuff that can help being in an airport semi-comfortably: an inflatable pillow, lightweight blanket, toothbrush, washcloth, towel, a change of clothes, and a paper book. Budget for a pass to an airline lounge, where the couches are cushier and the snacks don’t stop.

Help Protect your health. It probably goes without saying these days, but make sure you have at the ready a mask and hand sanitizer, along with travel-sized portions of eye drops, cold medications, pain relievers, prescription meds, tissues and more.

Reserve ahead. If you’re traveling over the holidays, figure out where you want to eat and what’s open, and make reservations (our Concierge Services can help with that). Note that online menus may not be accurate over the holidays, as many dining establishments have special, set menus.

Winterize. If you rent a car somewhere warm to drive somewhere cold (think Palm Springs to Lake Tahoe), make sure the vehicle has all the cold-weather stuff you’re going to need – scrapers, chains, a shovel. Inspect the car’s windshield wipers looking for peeling rubber, insist on a vehicle with all-weather tires, and make sure the heat and defrosters work.

Stay charged. Pack a charging station (or two) for your electronics, and make sure it’s full of juice before you leave.

There’s too much at stake with holiday travel to not have added protection with travel insurance, especially this year. Consider where you’re going and what you’ll be doing, and get a quote on the right plan for you.



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