Sometimes, the chance to embrace new passions and thrilling pursuits in a far-off destination is reason enough to plan a trip. While it's a no-brainer to purchase insurance if you want to visit an off-the-grid destination to enjoy high-risk activities, other times, the answer isn't so clear-cut. Sure, you can account for rapidly approaching hurricane season, but what about unforeseen events? It's impossible to predict if inclement weather, political instability, an emergency public health scare or illness will disrupt your travel plans. And aside from choosing whether or not to buy insurance, you'll be faced with a string of caveats attached to many policies, so it's important to do your homework before taking your chances.Deciding whether or not to take the risk or buy travel insurance is up to you. To help you weigh your options, we asked industry experts to deliver practical advice and insight on travel insurance.[See: 10 Outrageous Fees Every Traveler Should Know About.]Know Where You're Already CoveredBefore deciding if it's worthwhile to buy insurance, the first step is understanding where you need coverage and where you don't. For example, some major credit cards offer some medical and baggage insurance. For example, if your travel is interrupted or canceled due to sickness, inclement weather or other conditions, you can be reimbursed for prepaid travel expenses such as flights and hotel rooms for up to $10,000 per trip with the Chase Sapphire Preferred card. And many major health insurance providers, like Blue Cross Blue Shield, cover some out-of-network medical services overseas, but make sure to read the fine print since expenses like emergency medical evacuations, which can cost hundreds of thousands of dollars, are typically not included. "If you're not sure if your medical insurance covers you while you're overseas, and for the activities you plan on doing, ask them – don't assume. Every provider and every policy may have differences," says Phil Sylvester, chief content and communications officer of World Nomads, a company that offers insurance plans online.While some major credit cards cover baggage loss, it's important to know if it's available to you and understand the specific limitations, like time required without your luggage before you can be reimbursed for replacing lost items, Sylvester says. For example, World Nomads covers a maximum of $150 per item, or a total of $750 per person, if bags are delayed by 12 hours or longer.Understand the Different Types of PoliciesThe next step is pinpointing a provider and policy that offers the type of insurance you need, based on key variables such as trip price, destination and itinerary, along with pre-existing medical conditions. "There are three main areas of travel insurance: medical costs and medical evacuation, loss or theft of belongings and thirdly, cancellation and delay expenses," Sylvester explains. "Not all policies are the same," he cautions, stressing the importance of selecting the coverage that's best for your situation. For example, if you're planning a trip where you'll be carrying tech equipment, he advises ensuring that the maximum and minimum pricing thresholds for individual items matches the amount of gear in your possession. "Policy wording matters too, as providers may define certain benefits or meanings differently, so make sure you understand exactly what is being offered," he says. If you're having trouble navigating overly complicated language, contact the provider and ask for additional clarification, he adds. According to John "Johnny Jet" DiScala, editor in chief of the travel site JohnnyJet.com, "You really need to read the fine print, because [insurance policies are] not all created equal." And if you're planning an extended trip overseas, he says it's a smart idea to consider all options and use savvy tools like InsureMyTrip, a travel insurance comparison website that helps consumers find policies that meet their particular criteria and pairs them with providers.[See: 10 Common Pieces of Travel Advice You Should Never Follow.]Consider The Type of Trip You're Planning and the Cost The key criteria to consider before buying insurance include "cost of the trip, length of the trip, your itinerary and your health," says Chris Elliott, a consumer advocate and journalist. "A simple point-to-point trip domestically probably isn't worth insuring. An around the world adventure, definitely." If you're planning to spend more than $5,000 on a trip, "that's known as a 'big ticket' purchase, and it it should be insured," he says. Another time travel insurance is a wise idea is if you have a complex or extended itinerary, he adds. "If you’re on a tour with a lot of moving parts, then insurance could be useful. When one part doesn’t go as planned, the right policy can help you make a quick recovery." Aside from your trip itinerary and price, it's important to consider airfare protection and other common perils that may arise, says Dean Sivley, president of Berkshire Hathaway Travel Protection. Historically, a little more than two-thirds of travelers do not buy insurance, Sivley explains. But rather than have travelers' frustrations come to a boil due to common stressful situations, such as missed flight connections, trip cancellations or lost or delayed baggage, the company offers immediate travel assistance. With its AirCare flight insurance coverage, if any of these situations arise, the company immediately transfers $50 to $1,000 (depending on the claim) directly to your bank account. The Berkshire Hathaway AirCare policy option starts at $34 for domestic trips.Invest in Insurance If You're Going Abroad If you're planning an international trip, you shouldn't think twice about buying insurance, Elliott says. "Medical providers outside the U.S. often ask for 'upfront' payments for medical services that can cost thousands of dollars, and travel insurance can guarantee these payments," he says, adding that this also holds true for medical evacuations, "which can cost tens or even hundreds of thousands of dollars." Also, keep in mind that if you're on Medicare and heading overseas, you should consider a policy that includes out-of-pocket medical coverage "since Medicare doesn't typically cover events outside of the country," he adds. And with cruise insurance, it's a smart idea to shop around, Elliott says, pointing out that there are often limitations and insurance could be overpriced. Depending on how often you travel, you may want to invest in annual coverage, Elliott says. "I personally recommend an annual travel insurance policy. I get mine through Allianz. If you travel more than two times a year, it could be worth it for you." It's also wise to invest in medical evacuation coverage, he adds, spotlighting Medjet as a choice provider. "Travel insurance won't always cover every aspect of a medical evacation or hospitalization, so that's worth having as well," he adds. Factor in Other Events and Calamities"A hurricane falls clearly into the definition of an unforeseen event. We know they're coming, but where and when cannot be predicted. That’s what travel insurance is for," Sylvester says. The key factors to think about if you're considering traveling to a hurricane-affected area during hurricane season include whether you'll have access to a cancellation benefit if flights are cancelled due to weather and if your hotel is uninhabitable, he explains. Still, there are some caveats. For instance, the airline must have halted flights for 24 hours to acquire cancellation coverage, he adds. It's also important to understand timing, Sylvester adds. For example, if you are planning a trip to a Zika-affected area such as Brazil for the Olympic Games, you won't be covered, because unlike an unforeseen natural event, Zika has already been declared a public health emergency and pregnant and expecting women have been cautioned against visiting affected areas. If that is a concern, ensure you've selected a comprehensive policy with a "cancel for any reason" clause, which typically cost more than other policies, but give you peace of mind, Sylvester adds. [Read: 10 Tips for Changing Your Tickets (or Postponing Your Trip).]Practice Patience If you're in a bind, and you are trying to get home due to an unforeseen weather disruption or other calamity, wait to rebook your flights, Sylvester cautions. "The airline that got you there is responsible for getting you home on their next available flight. Be patient." And if you're traveling to an area that is hurricane-prone, most reputable carriers and hoteliers have set procedures to help accommodate travelers, he adds.