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Squaremouth Travel Insurance Review — Is It Worth It?

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Ryan Smith
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Ryan Smith

Content Contributor

74 Published Articles

Countries Visited: 197U.S. States Visited: 50

Ryan completed his goal of visiting every country in the world in December of 2023 and now plans to let his wife choose their destinations. Over the years, he’s written about award travel for publicat...
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Jessica Merritt

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A long-time points and miles student, Jessica is the former Personal Finance Managing Editor at U.S. News and World Report and is passionate about helping consumers fund their travels for as little ca...
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Juan Ruiz

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Part of planning for your next vacation should include asking yourself, “What if something goes wrong?” Your answer to that question likely includes shopping for travel insurance.

Choosing the right policy can reduce your out-of-pocket expenses if you have delays, cancellations, or injuries. But how do you choose from the overwhelming number of travel insurance policies available? Enter Squaremouth: a website that provides travel insurance reviews and comparisons to help you shop for your next policy.

Squaremouth doesn’t provide insurance. Instead, it helps you shop for insurance. That can be a great starting point, but there are other elements you should understand before selecting and paying for a policy. Choosing the right policy, even on a comparison page like Squaremouth, can take considerable time and effort.

Here’s a look at the positives and negatives of Squaremouth and how shopping for a policy works at Squaremouth.

Squaremouth Travel Insurance: Positives

  • Provides comparisons of coverage and prices across dozens of insurance providers
  • Makes it easy to add favorites or choose items to compare in detail
  • Has a zero-complaint guarantee

Rather than comparison shopping on individual travel insurance websites, you can do it all on Squaremouth’s website. You’ll see prices across numerous providers and multiple plans from these providers. It’s the best free tool to start looking for insurance across the many possible plans you could buy.

When shopping for plans, you can select your favorite providers, which Squaremouth remembers for the future to help you efficiently compare plans the next time you shop on Squaremouth’s site.

Squaremouth has a “zero-complaint guarantee,” promising fair adjudication of your travel insurance claim if you buy a policy through its marketplace. While Squaremouth doesn’t provide insurance, it will take a second look at your claim and ensure it’s resolved correctly. The website describes this policy as follows:

“If your claim has been denied and you believe the determination was made unfairly, our team of licensed claims adjusters will investigate your case and mediate with the provider on your behalf. If the complaint is not resolved to Squaremouth’s satisfaction, we will remove the provider from our website and stop selling their policies.”

Contrary to the name of the policy, the company can’t guarantee there are no complaints. Still, it can advocate for you if you have problems with your insurance provider after buying a policy through Squaremouth’s platform.

Man enjoying waterfall
Image Credit: Faces of Travel via Adobe Stock

Squaremouth Travel Insurance: Negatives

  • It’s not an insurance provider and doesn’t sell travel insurance policies
  • There are mixed reviews from customers, mostly related to customer service
  • It doesn’t provide coverage details or exclusions in the comparison charts

Squaremouth isn’t an insurance provider and doesn’t directly sell or underwrite travel insurance. Having “Squaremouth travel insurance” is impossible since Squaremouth is a comparison website — not a policy provider. As a comparison marketplace, Squaremouth lets you compare policies and costs from multiple providers. In this regard, you aren’t buying travel insurance from Squaremouth but are using Squaremouth to find travel insurance.

It may help to think of Squaremouth the way you think of Expedia: You shop for flights on Expedia, but Expedia isn’t the airline you’re flying with.

Squaremouth functions as an intermediary, and many of the negative reviews of Squaremouth involve this aspect. Squaremouth can’t process your claim or explain your coverage since it’s not your provider. To be fair, some complaints also appear to misunderstand that Squaremouth isn’t the insurance provider. You’ll need to contact your policy provider for policy questions.

Additionally, some reviews complain that Squaremouth’s customer service lacks quality and availability. It has limited online chat hours and requires an email outside those times. Some customers say responses to emails are slow and aren’t helpful. However, reviews of the Squaremouth insurance marketplace don’t necessarily indicate how good or bad the providers and plans it sells are.

When comparing travel insurance providers on Squaremouth, the exact details of a policy aren’t elaborated.

You may see that Company A offers $100,000 of emergency medical benefits while Company B offers $75,000. It sounds like Company A would be better, but that can’t be confirmed without a full analysis of the policy terms. Those elements aren’t made clear when comparing policies on Squaremouth, so you’ll have to use this only as a starting point before making a final selection and paying for a policy.

Bottom Line:

You should visit the provider’s website after finding a plan that sounds good on Squaremouth’s site and price out your trip. Look for inclusions/exclusions, and ensure this is the right policy for your trip.

COVID-19 Coverage

Squaremouth has a dedicated page discussing COVID-19-related coverage on the policies available through its marketplace. Most policies cover trip cancellations, costs from quarantines, and other pandemic-related expenses, but how they do that and what expenses (or how much) can be reimbursed will vary by policy.

When reading a policy’s coverage details before buying, you can find detailed explanations. You also can use the Squaremouth page to reference current entry restrictions in various countries you might want to visit.

Optional Add-ons

Some policies have unique inclusions that others don’t — such as money you lose when a destination wedding is canceled (offered by WorldTrips) — and most policies provide add-on services for extra costs. These will cover things like extreme sports, turning your medical coverage into primary coverage, or “cancel for any reason” (CFAR) coverage. It’s important to know what’s included, what’s not, and how much it will cost to add these extras. You may fare better paying for a more robust policy than buying a bargain policy and adding numerous extras.

Squaremouth Travel Insurance Policy Elements

“You get what you pay for” tends to be true when comparing insurance plans from the same provider. More expensive plans will include more coverage types and higher maximum payouts in coverage categories. However, that saying isn’t necessarily true when comparing costs between travel insurance providers.

That’s where Squaremouth comes in, allowing you to compare travel insurance across providers, filter for what you want or don’t want, and see how similar policies stack up against each other for coverage and pricing.

To better understand the comparisons Squaremouth provides, it helps to understand the most common travel insurance categories. This way, you’ll know what these insurance benefits are and which ones are important for you.

  • Cancel for Any Reason (CFAR) Coverage: Usually an add-on for most travel insurance companies, it covers cancellations outside other coverage types. However, it doesn’t cover everything and every reason you might cancel a trip, so be sure to understand the specifics.
  • COVID-19 Coverage: If you or a traveling companion test positive for COVID-19 and need to quarantine, cancel a trip, or miss a flight, your expenses or losses can be covered. Ensure you understand how your policy treats COVID-19 because some require separate coverage while others include it as part of the medical coverage.
  • Pre-existing Medical Conditions: Your current medical conditions may be covered if you buy a plan within certain timelines. Otherwise, look-back periods tend to apply.
  • Trip Cancellation Insurance: You’ll receive reimbursement for prepaid, non-refundable costs if you cancel a trip for one of the covered reasons in your policy.
  • Trip Interruption: Once your trip starts, this coverage goes into effect, and can reimburse non-refundable costs from lost parts of your trip. It also can cover expenses to catch up with your trip, such as a tour that has already departed, if there are delays for covered reasons.
  • Trip Delay: You can be reimbursed for transportation, meals, and other expenses you incur due to delays. Timelines for when this coverage begins will vary by plan.
  • Baggage Loss or Damage: Your lost, damaged, or stolen baggage — including the items inside, with some exceptions — will be covered. Some policies are primary, while others are secondary.
  • Baggage Delay: You can be reimbursed for reasonable costs you incur when your luggage is delayed. The waiting period for when your coverage kicks in will vary by plan.
  • Emergency Medical and Dental: Illnesses and injuries are covered during your trip, plus the resulting expenses. It also can cover deductibles or unpaid expenses from your health insurance provider since this coverage is usually secondary.
  • Emergency Assistance and Transportation: If adequate healthcare isn’t available nearby, you can be evacuated to an appropriate facility. If you die during your trip, this policy covers bringing your remains to the U.S. or paying for local burial costs.
  • Accidental Death and Dismemberment: This coverage provides payments if you lose your life, a limb, or eyesight during a trip. If you die, the benefit payment goes to your designated beneficiary.
  • Rental Car Damage: You’ll be covered for collision damage, theft, vandalism, natural disasters, or damages for reasons beyond your control. Some vehicle types, such as luxury cars, are excluded from most policies, but coverage should apply to all drivers listed on your rental agreement. Coverage is up to the cash value of the car or the cost of repairs and related expenses — whichever is less. Certain countries may be excluded from the policy, so check the details.
Man walking out on pier on lake
Image Credit: Faces of Travel via Adobe Stock

Coverage Exclusions

Sometimes, understanding what’s not included may be more important than a list of benefits or choosing the lowest offer when looking at Squaremouth travel insurance reviews and prices.

Why? Exclusions are built into every insurance benefit, so you should review the details. Insurance terminology isn’t fun, but it’s essential to understand whether your trip — destination, dates, activities, and health conditions — will be covered. The only thing worse than not having travel insurance for your trip is paying for travel insurance that doesn’t cover your trip.

Common exclusions include injuries sustained while intoxicated and medical emergencies related to pregnancy. You also aren’t covered when flying a plane, hang-gliding, bungee jumping, or participating in extreme sports unless you get a particular policy with add-ons for those activities.

Most policies also exclude war zones and areas with ongoing hostilities. This could include places like Ukraine and Sudan and areas with travel safety warnings like Syria or Iran. Ensure you read your policy details to confirm it covers your intended destination.

How Much Does Squaremouth Travel Insurance Cost?

Buying travel insurance from Squaremouth costs the same as buying it directly from the insurance provider. There are no markups or fees for buying on Squaremouth’s website instead of buying directly from an insurance provider, such as Seven Corners or Generali Global Assistance.

How To Shop for Travel Insurance With Squaremouth

Squaremouth travel insurance types of policies
Image Credit: Squaremouth

You can search for several types of insurance from the Squaremouth home page. You can start in 1 of 2 ways: Click on the different types of policies or enter your trip information. The policy types (as seen above) can be found under the policy search widget on the home page:

squaremouth travel insurance home page
Image Credit: Squaremouth

You’ll see options for single-trip policies (most common), multi-trip or annual policies, cruise-specific policies, and policies geared toward adventure or extreme sports.

If you fill out the information on the home page, providing dates and destinations, the second page will ask for information about the traveler(s) to be covered:

Squaremouth insurance search page 2 traveler information
Image Credit: Squaremouth

Page 3 asks about trip costs, when you made your first deposit, and whether you have remaining payments. There’s also a yes/no option for cancellation coverage related to your trip costs:

Squaremouth travel insurance search page 3 payment details
Image Credit: Squaremouth

From here, you’ll see a list of results. My search returned 88 policies, sorted by the providers with the best review scores. You can filter your results in several ways:

  • Popular Filters: The most popular filters are listed here for easy access. These include COVID-19 coverage, CFAR, trip interruption, trip delay, medical evacuation, and pre-existing medical conditions.
  • Preset Filters: Limit your searches to policies covering cruises, COVID-19, and policies that meet the requirements to apply for a Schengen Visa.
  • Reviews: Filter by insurance provider ratings, ranging from 1 star or more to 5 stars.
  • Cancellation: Here, you can select trip cancellation reasons that you want to cover with your policy, such as hurricanes, terrorism, financial default of your travel company, losing your job, or other work-related issues.
  • Medical: You can filter for policies providing primary medical coverage, coverage for pre-existing conditions, emergency medical benefits, and even the deductible amount you want your policy to include.
  • Evacuation: You can filter for policies that include medical and non-medical evacuation.
  • Loss or Delay: Find coverage that includes reimbursement for bagage loss, baggage delay, trip delay, quarantine extension, or missed connections during your trip.
  • Accidental Death: You can filter by 24-hour policies, flight-only policies, and common carrier policies.
  • Sports: You can choose the type of sport you’re doing on a trip and indicate whether it’s part of a competition.
  • Other Benefits: Find coverage that includes rental car protections, a money-back guarantee, 24-hour assistance services, identity theft protection, or renewable policies.
Squaremouth insurance filter adventure sports bungee jumping
Image Credit: Squaremouth

After applying any desired filters, you’ll see only the policies that match your settings. In this example, I filtered for CFAR policies with emergency evacuation coverage of $1,000,000.

You will see the insurance provider’s name and the name of the plan at the top, plus key highlights of the policy listed in the middle. The review ratings are visible on the left side, and the right side holds several important elements: the price, an option to view the full policy details, an option to buy the policy, and a Compare checkbox:

Squaremouth search results page indicating feautres to use
Image Credit: Squaremouth

You can add as many or as few policies as you want to compare, but only 5 policies can fit on the screen at once:

Squaremouth comparison page details of 5 policies at a time
Image Credit: Squaremouth

You can use the Next Policy button at the top if you’ve selected more than 5 policies for comparison. If you set any filters for your search, your filters will be displayed at the top since those are likely your primary concerns. Scrolling down, you can see coverage similarities and differences in other areas, like trip cancellation benefits or lost luggage reimbursement.

Most policies also offer add-ons for an additional cost. You can view these by clicking on +More near the Buy Now button.

Squaremouth add on options pop up window
Image Credit: Squaremouth

Once you find a travel insurance policy you like, you can buy it directly from Squaremouth. There’s no cost savings for going to the provider’s page and buying the policy there. Squaremouth affirms this on its website:

Due to strict regulations in the insurance industry, it is not legal to discount or upcharge a premium. For this reason, the price of an individual travel insurance policy will be the same wherever you purchase it.

Even still, it makes sense to go to the provider’s website to view the full policy details, exclusions, and inclusions. It’s critical that you understand the specific terms of a policy before buying so that you can ensure it’s the right policy for your trip.

Hot Tip:

There’s no price difference on Squaremouth’s or the provider’s sites, but you should go to the provider’s site anyway. There, you can read the full terms of a policy before buying the wrong one.

If you click on the Buy Now button, you may see a pop-up message about important exclusions before moving forward. For instance, this policy doesn’t cover 1 airline and 4 countries:

Squaremouth pop up window exclusions notification
Image Credit: Squaremouth

Squaremouth Travel Medical Insurance Options

While many people think of travel insurance as a broad-based plan covering everything from delays to cancellations and even medical bills, it is possible to buy medical-focused and even medical-only plans. These medical insurance plans won’t necessarily help you with out-of-pocket costs from delayed flights but can help if you get sick or injured.

These policies are mixed in with the other results you see when searching for plans on Squaremouth. You can focus on medical insurance plans using filters in the Medical menu. Options include the coverage amount you want and primary policies.

Squaremouth Annual Travel Insurance Options

An annual policy may be cheaper than buying multiple policies throughout the year for each trip.

Along with standard information like the number of travelers and where you live, you’ll also choose a start date, the expected number of trips this year, and an estimate of your longest trip:

Squaremouth annual travel insurance search page
Image Credit: Squaremouth

For this example, we priced a trip starting July 1, 2023, for 2 travelers (ages 35 and 33), both U.S. citizens living in California. We estimated 5 trips this year, with the longest lasting 20 days.

You’ll notice that you don’t need to enter specifics about any particular trip, such as where you’re going or trip cost. You’ll see the same filters on the results page as you would on the standard travel insurance search results.

Compared to the 88 policies available with single-trip insurance shopping, this search provided just 6 results:

Squaremouth annual travel insurance comparison chart 1
Image Credit: Squaremouth

Price ranges are incredible here: more than $1,000 difference from the cheapest to the most expensive policy. Notice that the cheapest plans don’t cover COVID-19, trip cancellation, trip interruption, terrorism, financial default of a travel provider, travel delays, baggage delays, or CFAR. That’s quite a list of exclusions when paying $300+ for an annual travel insurance policy.

Squaremouth Frequent Flyer/Mileage Award Ticket Insurance Options

Many of us book flights with miles and hotels with points. Can these be insured? Unfortunately, it’s rare. To complicate matters, Squaremouth doesn’t have filters for policies that cover redeposit fees for your points and miles.

Some policies (a minority) may cover the fees for canceling an award redemption and putting the points or miles back in your account. To find these, you’ll need to read the full policy details. You won’t find this information in Squaremouth’s comparison charts.

Squaremouth Cruise Insurance Options

Squaremouth cruise travel insurance search page
Image Credit: Squaremouth

You can search for policies tailored to cruisers, but it’s also possible to click on Cruise in the filters after conducting a standard search.

You’ll enter your travel dates and main destination from the cruise search page. Interestingly, you can only put 1 location, despite the fact most cruises visit more than 1 country. On the next page, you’ll enter trip costs, deposit date, whether you have remaining payments, and information about the travelers.

For a sample search, we estimated a 1-week cruise to the Bahamas in November 2023. The trip covers 2 passengers (ages 60 and 58) who made a deposit in the past 24 hours but have remaining payments on their $2,000 trip. Policy costs ranged from $111 to $297:

Squaremouth cruise travel insurance comparison cheapest and most expensive
Image Credit: Squaremouth

A comparison of the cheapest and most expensive policies shows many similarities. The differences include maximum payouts for emergency evacuation, trip delay, and accidental death and dismemberment.

Squaremouth Adventure Sport Insurance Options

While it’s possible to filter for adventure sports in the standard search results, you also can go to the Adventure & Sports Travel Insurance page and begin your search with the types of activities you want to cover:

Squaremouth insurance search adventure extreme sports
Image Credit: Squaremouth

For example, there are multiple options for scuba diving, including mixed gas and multiple depth points. It’s important to choose exactly the sport you’ll be undertaking and the conditions in which you’ll participate. For example, will you be with a guide or coach? This can change your coverage requirements.

After choosing the sport(s) you want to cover, you’ll provide trip details as usual to see available policies.

Squaremouth Group Travel Insurance Options

If you’re traveling in a group (departing and returning home within 2 days of each other), a group travel insurance policy could help cost-effectively cover everyone. Some important rules must apply for a group policy:

  • Organized groups of 8 or more traveling together.
  • Travelers must be visiting the same destination.
  • All travelers must be U.S. residents.
  • Departure dates must be more than 21 days from the policy purchase date.
Squaremouth group travel insurance search page
Image Credit: Squaremouth

You can enter trip costs per traveler or overall, plus you’ll enter each traveler’s birth date. You’ll enter the home state of the majority of travelers, the earliest date anyone starts the trip, and the last date anyone will return home.

Squaremouth One-way Trip Insurance Options

Unfortunately, filtering for so-called “one-way trip insurance” on Squaremouth is impossible. One-way insurance would cover a traveler who leaves home from Texas, spends a week vacationing in Mexico, and then flies to England for a new job. These are situations where you are not returning to the trip’s starting point.

You can’t filter for these policies on Squaremouth because most policies have a start and end date based on when you return “home.” They’re also based on your state of residence for cost and legalities. Unfortunately, Squaremouth won’t show you these policies.

Companies like Expatriate Group can provide one-way insurance policies that cover you en route to your destination and provide limited coverage once you arrive until you find other coverage. Think of it as coverage just between 1 country and the next.

How Reliable Is Squaremouth Travel Insurance?

Squaremouth vs. Buying Directly From Insurance Providers

Squaremouth says there’s no extra cost when you buy insurance from its website rather than buying directly. However, it’s always good to double-check.

I priced a 1-week policy for myself to visit Italy in November 2023. Squaremouth told me the cheapest policy was the battleface Discovery Plan at $45.86. However, battleface returned a price of $36.99. Even more confusing was that the included benefits didn’t match.

On the same itinerary, Squaremouth provided a price of $103 for WorldTrips Atlas Journey Preferred. WorldTrips returned the same price on its own site, and the benefits/maximum payment amounts matched.

Squaremouth vs. Insuremytrip

Squaremouth isn’t the only site that provides comparisons as a one-stop-shop for travel insurance. InsureMyTrip has some of the same features. How do their prices match up?

We searched for a 1-week trip to Italy for 2 travelers (ages 35 and 33) who made their first trip deposit earlier today. The results across the 2 sites weren’t the same; Squaremouth showed providers unavailable on InsureMyTrip and vice versa. However, the policies available on both sites matched.

Here are Squaremouth’s search results:

Squaremouth sample search with prices
Image Credit: Squaremouth

And here are InsureMyTrip’s search results:

InsureMyTrip sample search with prices
Image Credit: InsureMyTrip

The $105 policy from John Hancock and $109 policy from WorldTrips matched when appearing on both sites, however.

Squaremouth Travel Insurance Options vs. Credit Card Insurance

While it’s nice that Squaremouth provides a simple shopping platform, buying travel insurance isn’t the only way to get coverage on your next trip. Some of the best credit cards for travelers also provide robust coverage. Cards like The Platinum Card® from American Express, Capital One Venture X Rewards Credit Card, Chase Sapphire Preferred® Card, and the Chase Sapphire Reserve® can protect your next holiday. Consider these benefits to see if they’re sufficient before buying extra travel insurance:

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The Platinum Card® from American ExpressCapital One Venture X Rewards Credit CardChase Sapphire Preferred® CardChase Sapphire Reserve®

Annual Fee

$695 (rates & fees)

$395 (rates & fees)

$95$550

Rental Car Insurance

Secondary insurance; covers up to $75,000

Primary insurance; covers up to $75,000

Primary insurance; covers up to the cash value

Primary insurance; covers up to $75,000

Trip Cancellation and Interruption

Up to $10,000 per trip

Up to $2,000 per person

Up to $10,000 per person

Up to $10,000 per person

Trip Delay

Up to $500 per trip

Up to $500 per trip

Up to $500 per ticket

Up to $500 per ticket

Baggage Loss/ Damage 

Up to $3,000 per person

Up to $3,000 per person

Up to $3,000 per person

Up to $3,000 per person

Baggage Delay 

None

None

Up to $100 per day

Up to $100 per day

Emergency Medical and Dental

None

None

None

Up to $2,500 for emergency medical expenses

Travel Accident

Up to $500,000 per person

Up to $1,000,000 per person

Up to $500,000 per person

Up to $1,000,000 per person

Emergency Evacuation

Included when approved by the Premium Global Assist Hotline

Arrangements only, no costs covered

None

Up to $100,000 with benefits administrator preapproval

Bottom Line:

Always compare your travel insurance options, whether shopping from multiple travel insurance companies or using travel insurance provided by a credit card.

Final Thoughts

Rather than selling insurance, Squaremouth provides a simple-to-use shopping platform for travel insurance of various types. You can filter results in numerous ways to help you find the right policy for your next trip — or even your next year of trips. Some details will be lacking in the comparisons, and you should always consult the full policy from the insurance provider before buying travel insurance. However, seeing numerous plans, comparing them, and understanding their relative costs with just a few clicks is fantastic.

The information regarding the Capital One Venture X Rewards Credit Card was independently collected by Upgraded Points and not provided nor reviewed by the issuer.

For rates and fees of The Platinum Card® from American Express, click here.

Frequently Asked Questions

How do I contact Squaremouth travel insurance?

You can call 800-240-0369 in the U.S. or 727-564-9203 from outside the U.S. Squaremouth also offers chat with the same hours as phone service: 8 a.m. to 10 p.m. ET daily. Outside these hours, email questions@squaremouth.com.

Who owns Squaremouth?

Specialty Program Group (SPG) LLC bought Squaremouth in early 2023. SPG is a New Jersey-based specialty insurance brokerage firm that also bought Insureon and CM&F in recent years.

Where is Squaremouth's headquarters?

Squaremouth is headquartered in St. Petersburg, Florida, and also has offices in Fort Wayne, Indiana. It was acquired by Specialty Program Group (SPG) LLC in 2023; this company is based in Summit, New Jersey.

Who is the founder of Squaremouth?

Squaremouth was founded by Chris Harvey and Matt Outten and launched in 2003.

Should you buy travel insurance through Squaremouth?

You won’t pay extra to buy a policy from Squaremouth instead of directly from the insurance provider. Due to legal requirements, Squaremouth can’t charge extra for travel insurance policies. The advantage is the ease of use; the disadvantage is that you may not see the full policy details or exclusions on Squaremouth’s website, but you can find these on the provider’s site.

Is it best to buy travel insurance direct or from Squaremouth?

Buying either way has no cost advantage — from Squaremouth or a provider directly. The advantage to buying from Squaremouth is the ease of use for comparing multiple policies. The disadvantage is that you may not see the full policy details or exclusions on Squaremouth’s website, but you can find these on the provider’s site.

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About Ryan Smith

Ryan completed his goal of visiting every country in the world in December of 2023 and now plans to let his wife choose their destinations. Over the years, he’s written about award travel for publications including AwardWallet, The Points Guy, USA Today Blueprint, CNBC Select, Tripadvisor, and Forbes Advisor.

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