How to Buy Travel Insurance on Squaremouth
Key Takeaways:
- Travel insurance is designed to protect you and your finances from unexpected trip disruptions, such as cancellations, delays, and medical emergencies
- Always check for existing coverage before buying travel insurance to avoid paying for protection you don’t need
- Having your travel details handy can expedite the process, since this will be the first information you provide when getting quotes
- Applying filters to your search results on Squaremouth can help you find the best available plans and eliminate options that don’t fit your needs
- Many travel insurance plans allow you to enhance your coverage with optional add-ons, which can be purchased during checkout
- Confirmation details and policy documentation will be sent soon after purchase. Contact our customer service team if you have any questions.
When buying trip insurance, it’s important to find a plan that’s tailored to your specific travel habits and coverage needs. At any given time, travelers can choose from dozens of providers and hundreds of plan options, each offering different levels of protection and pricing. With so many choices available, it can be difficult to know where to start.
Squaremouth helps you save time by showing all your travel insurance options in one place, so you can compare plans and premiums without hopping from site to site.
Below, we’ve created an easy-to-follow, step-by-step guide (with screenshots) on how to find the best protection for your upcoming trip on Squaremouth.
Before you buy travel insurance on Squaremouth
When buying travel insurance, a little preparation can go a long way. Taking a moment to consider your trip details can make your search for the perfect policy much smoother.
- Make an initial payment or reservation toward your trip: Typically, you can’t buy travel insurance unless you’ve made at least one payment towards your upcoming trip, such as airfare, lodging, or a cruise booking.
- Review your existing coverage: Many travel credit cards offer limited traveler protection, offering benefits like Trip Cancellation and Travel Delay coverage. This coverage is generally limited to expenses made with the respective credit card and rarely provides reimbursement for medical expenses.
- Determine your coverage needs: Consider your upcoming itinerary and the possible risks that lie ahead. For example, international trips require higher medical coverage since U.S. health insurance is not required, while cruises may call for higher Medical Evacuation coverage due to the high cost of emergency transportation at sea.
- Understand your options: Travel insurance comes in many forms, including single-trip (medical-only or comprehensive), multi-trip annual, and group coverage. Understanding the pros and cons of each type of protection makes it easier to pick the one that best suits your style.
Step-by-step guide for buying travel insurance on Squaremouth
Getting travel insurance quotes on Squaremouth takes just minutes. Use the following guide to uncover the best possible plan for your upcoming adventure.
Step 1: Determine which type of policy is right for you
The first step in buying travel insurance on Squaremouth is to determine what type of coverage makes sense for your upcoming trip(s). To help, here’s a quick look at the different types of protection that are available to you:
- Single-trip: The most common type of travel insurance, designed to protect one trip with a defined start and end date. Travelers can choose between comprehensive coverage, which protects against trip cancellations and interruptions, or travel medical plans, which focus on medical emergencies while abroad.
- Annual (multi-trip): Provides basic medical, delay, and luggage protection for 12 months, regardless of how many trips you take. Ideal for frequent travelers taking three or more trips per year.
- Group: Covers multiple travelers (a minimum of 10) under one policy when they are traveling together.
The remainder of this guide will focus on single-trip travel insurance due to its popularity among customers, accounting for roughly 97% of all policy sales on Squaremouth. Annual travel insurance follows similar steps, though it requires slightly different trip details when initially generating quotes.
Step 2: Enter your basic trip information
You can begin a quote for travel insurance on just about any page on our site, although most users tend to start the process on our homepage.
At this stage, you’ll need the following information about your trip:
- Departure date
- Return date
- Main destination
- Country of residence
- State of residence
- Country of citizenship
- Number of travelers
- Ages of each traveler
- The cost of your trip
- The date of your initial trip deposit
For annual travel insurance only: If you are purchasing a multi-trip travel insurance plan, you will be asked to estimate the number of trips you plan to take within the 12-month coverage period, as well as the approximate length of your longest planned trip.
Step 3: Decide which trip costs (if any) you want to insure
Before you get to your results, you’ll be asked to share your “Trip Cost Amount.” In this box, you’ll enter the total prepaid, non-refundable expenses associated with your trip, such as flights, hotel reservations, cruises, or tour packages.
This number represents the maximum amount you could potentially be reimbursed if your trip is cancelled for a covered reason. The more you choose to insure, the greater your premium.
If your trip is not completely paid for, it’s completely fine. You can always add more expenses as you make additional payments by contacting your provider directly, but be aware that your premium may increase as a result.
Remember, you don’t need to insure any of your trip expenses if you don’t want to. Simply select “No” under the “Cancellation Coverage” dropdown menu to find travel medical policies that don’t include Trip Cancellation or Trip Interruption protection.
Step 4: Fetch quotes for your trip
When you hit “View Quote Results,” you’ll be shown every single policy on Squaremouth that matches your trip details. As you can see in the screenshot, our search query yielded 37 unique policies from some of the nation’s top travel insurance providers!
From this view, you can quickly see basic details like provider, policy name, price, review scores, and coverage limits for important benefits.
Step 5: Sort your results

By default, your quote results will be sorted from most to least popular, which ranks plans by sales volume. However, this may not be the order in which you would like to see the policies ordered.
By using the sorting dropdown menu, you can also sort policies by price, policy rating, the number of customer reviews, or provider name.
Step 6: Apply filters, when necessary
Seeing so many options can be overwhelming. The best way to reduce clutter and narrow your search is to apply filters to your results.
When looking for single-trip coverage, you can apply the following types of filters:
- Benefit filters: If certain benefits are non-negotiable, such as Cancel For Any Reason coverage or a Pre-Existing Condition Waiver, you can select these filters to remove policies that don’t include these protections.
- Trip-specific filters: Cruises, adventure trips, and other high-risk vacations often require specialized protection. Our trip-specific filters can highlight plans that include waivers for certain activities and meet expert-recommended coverage thresholds.
- Provider features: All providers on Squaremouth are carefully vetted and reliable, but these filters can help you narrow your search based on specific preferences. For example, you can look for providers with high customer satisfaction scores or those offering perks like 24-Hour Emergency Assistance and a Free Look Period.
Step 7: View policy details
For a deeper dive into a specific policy, click the green ‘Policy Details’ button located underneath each plan found on the results page. This will open a full breakdown of the policy, including coverage limits, benefit descriptions, A.M Best Ratings, and customer satisfaction scores.
In the top bar of the ‘Policy Details’ window, you can also review key documents like the Certificate of Insurance and email the policy to yourself for future reference. Taking the time to read through these details can help ensure the policy meets your expectations before purchasing.
Step 8: Compare policies side-by-side
Squaremouth’s comparison capabilities really shine when you’re trying to decide between a handful of policies. Our side-by-side comparison tool allows you to visually see how multiple policies compete across a wide range of popular benefits.
To get to the view shown above, simply click the “Compare” checkbox next to a policy you’re considering (seen in the screenshot below).
Once you have two to four policies selected, you can hit the “Compare Policies” button at the bottom of your screen.
Step 9: Decide on a plan that meets your needs
When you’re happy with a plan, click the “Buy Now” button to head to the checkout page. Keep in mind, the best plan for your trip will be the one that meets your coverage needs and fits within your budget.
If you decide down the road that you chose the wrong plan, you may be able to cancel your policy for a full refund as long as you are within the policy’s Free Look Period.
Step 10: Review optional upgrades and add-ons (If available)
Any add-ons or policy upgrades available with your plan can be added during the checkout process stage, right before you finalize your plan. Common upgrades you may encounter include Cancel For Any Reason, Trip Interruption For Any Reason, Rental Car Damage protection, and Financial Default coverage. If you applied filters for any of these benefits on the results page, they may already be selected and applied.
As shown in the screenshot, we will show you exactly how much each upgrade will cost, and your cart total will update in real-time, so there are no surprises when you pay for your coverage.
If you don’t see any add-ons, you may not have met certain eligibility requirements and therefore did not qualify.
Step 11: Finalize your purchase
Before entering your payment information and hitting “Complete Purchase,” make sure to take a moment to verify that all the information is correct. We recommend that you confirm the following information:
- Your departure and return dates are accurate
- You entered the correct destination
- Your policy covers each destination you plan to visit during your trip
- The state of residency reflects your current home address
- You insured all current prepaid, non-refundable travel expenses (if applicable)
If this all looks good, proceed with completing your purchase. Keep in mind, travel insurance prices are regulated by state law, so the rate you see on Squaremouth is the same you would pay if buying directly from the provider.
Step 12: Save your policy documentation
Keep an eye on your email inbox for coverage confirmation and important policy documentation. This will be after your purchase is processed. If you’re having trouble finding any confirmation of coverage, please call us at 1-800-240-0369 from 8:00 AM to 10:00 PM EST daily.
FAQs: When buying travel insurance on Squaremouth
Should I always buy the cheapest travel insurance policy?
We always recommend customers opt for the least expensive travel insurance plan that meets their coverage needs, as cheaper policies do not always equate to lower quality or less effective coverage.
When searching for travel insurance, you’ll notice a wide range of pricing. This is because each travel insurance provider uses its own method for calculating premiums, often designed to appeal to a specific type of traveler. For example, some providers may offer more competitive rates for seniors by placing less weight on age when determining pricing.
Who can I call if I need help buying travel insurance?
As mentioned above, our award-winning customer service team is available from 8:00 AM to 10:00 PM EST daily. If you need any assistance or guidance, please don’t hesitate to give us a call at 1-800-240-0369.
Our agents do not work on commission, and their only goal is to help you find the best possible travel protection.
Is it cheaper to buy travel insurance directly from a provider?
No. Since travel insurance prices are regulated by law, there is no financial benefit to purchasing coverage directly from a provider. That means you’ll never pay more on Squaremouth than you would if you bought directly from the provider.
When do I need to buy a travel insurance policy on Squaremouth?
You can purchase a policy on Squaremouth any time after making your initial trip payment, up until the day before your departure. However, travel insurance cannot be purchased for a trip that has already begun.
What if I buy a policy on Squaremouth and need to file a claim?
If you purchase a policy on Squaremouth and need to file a claim, you’ll work directly with the travel insurance provider listed on your policy to settle.
After your purchase, you’ll receive your policy documents with instructions on how to file a claim, including the appropriate contact information. Most providers allow you to submit claims online, through an app, by email, or by mail.
If you need assistance during the process, Squaremouth’s Zero Complaint Guarentee team is available to help guide you, answer questions, and advocate on your behalf if any issues arise.







