Known for pink sand beaches, and crystal-clear blue waters, Bermuda is paradise located just a few hours from the East Coast. Even the most idyllic vacations come with some risk that should be protected with the right travel insurance though. Our very own Marketing and Affiliate Manager, Chelsea, escaped to Bermuda recently and came back with some new insights on 2022 travel.

The best vacations start with a great plan. I enlisted the help of a travel agency, Yes We Travel, here in Boston. Their knowledgeable staff helped me find the best deal and flights for my travel dates. Once I put down an initial deposit, I visited to purchase a plan for my trip. I knew I wanted to have the most flexibility in case I needed to cancel so purchasing a plan right away helped me secure the time sensitive benefit, Cancel for Any Reason or CFAR. With negative COVID-19 tests still required to enter Bermuda and come back to the US, a plan with Trip Cancellation and Trip Delay was also important. Trip Cancellation gives you the ability to cancel your trip before it starts to receive 100% reimbursement of your trip cost. There are many covered reasons for cancellation, most commonly when you or your travel companion suddenly become ill or injured. CFAR adds the ability to cancel for any reason whatsoever up to 2 days prior to departure for up to 75% reimbursement of your prepaid trip cost. Trip Delay adds protection if you are delayed due to quarantine required by a physician on your trip, and provides coverage for additional hotel expenses and meals. It’s a good idea after requesting a quote to click View Certificate under each plan you’re considering on This allows you to become familiar with coverages, limits, and what’s required from you for a successful claim.

Lucky for me the weather cooperated and I did not need to utilize the CFAR benefit. I also had no issues with the COVID-19 tests or travel authorization forms but did witness other travelers run into some issues. It’s very important to always review your destination’s requirements before heading to the airport. To travel to Bermuda at this time, you have to fill out an online Travel Authorization form, pay a fee, and upload your documentation including a negative COVID-19 test. Since I opted for a rapid antigen test, I was required to take it no more than 2 days prior to travel so it did not leave much room for processing. After submitting my negative result and waiting 1 business day with no approval received, I called the Bermuda Government’s COVID-19 Hotline the day before my trip. After waiting on hold for almost an hour, a representative approved our Travel Authorization applications and I immediately received them by email. Although you may want to save the paper and not print out your documents, it’s a good idea to print any important travel documents like your boarding pass (and make copies!), as well as save them securely on your phone – that way if you run out of battery, you have a backup.

I was also bringing some valuable belongings with me – my golf clubs! I opted for a travel insurance plan with Sporting Equipment Coverage. On the Plan Purchase page, you’ll find Additional Plan Options if applicable like the Baggage – Sports selection. For just a little extra, $15 total in my case, I was able to add protection in case of loss, theft, damage, or destruction of our golf clubs up to $1000/person and delay up to $500. If our clubs were delayed, the rental clubs would have cost anywhere between $60-100 per round of golf so this was well worth the peace of mind! It’s definitely a good idea to add this and similar benefits on any trip where you are bringing along sports equipment, like on a golf vacation.

On most trips, I rent a car for convenience and opt to purchase Rental Car Coverage at This saves me from paying for the exorbitant rental car insurance at the agency, and also ensures that I do not risk having an accident affect my normal car insurance. In Bermuda, there are no real car options to rent, especially those that would fit golf clubs, so we relied on taxis to get around for most of our stay. I’m not quite sure if there was a taxi shortage due to COVID-19, but we found it would take sometimes an hour to get one and we heard this was commonly experienced by other travelers too. Luckily about half way through our stay, a taxi driver recommended using a new app called Hitch. The app is available on the App Store and the one you would want to download is named Hitch Customer. Although Bermuda doesn’t have Uber or other ride share apps, Hitch works very similarly and finds a nearby taxi for you. You can also handle payment and tipping within the app and receive the receipt to your email. We found a group waiting for a taxi they called for over an hour, used Hitch and got one within 9 minutes. Although I cannot say if it works on all parts of the island, it’s a good idea to download and try yourself!

At this time, Bermuda will schedule your COVID-19 test to return to the US automatically for you the day before departure. They are currently conducting the tests at the post office in Hamilton and the cost is included in your travel authorization fee. I brought my own unopened rapid antigen tests with us and scheduled and paid for a separate telehealth service to supervise and conduct the tests for us on our last day. The little added cost was worth it to me as this way we didn’t have to go out of our way to Hamilton. Just be sure you have an approved device to do the video call test, the correct test kits, and good WIFI. If neither are options for you, I heard that some resorts may also have testing available on site for an additional cost. Whatever route you choose, it’s important to check that your test will meet the requirements of wherever you’re headed and that you take it within, no more than, the set number of days.

I had a great trip filled with lots of fun, sun, and golf! The only real hiccup we experienced was when we got back to Logan Airport and the baggage claim shoot became stuck not one, not two, but three times! About 2 hours later, we finally had our last bag back in our hands. JetBlue came through with a voucher for both of us automatically due to the inconvenience. Be familiar with what’s required for a baggage delay claim with your travel insurance plan, in my case this would not have been covered anyways so the voucher was a nice surprise.

Even the best planned trips can still be affected by the unexpected. I was able to feel much more comfortable traveling to another country in 2022 with the peace of mind I found in my plan. In just 3 easy steps, you’ll find your recommended travel insurance plan and compare it side by side with similar plans from the top providers in the industry. I was able to filter plans by the benefits most important to me, find the best option, complete my purchase, and receive the plan straight to my email. Have a question about planning your own trip? Call Yes We Travel at (617) 879-2644.

This is great info! I wish I had known more about travel insurance and how to identify which plans covered Covid-related delays before our trip to Norway earlier this year; it was like reading gibberish when I was reviewing different plans before our trip, haha. Thanks for sharing these tips. Xx Sara
Bermuda sounds like such a dream destination! Fortunately I've never had to claim on my travel insurance but it is always helpful to have a reminder of just how important it is. Thanks for sharing these great tips!
I always get travel insurance for big trips, but usually not for shorter trips. Thanks for all the advice about purchasing for ALL trips.
Thanks so much for sharing your experience of traveling to Bermuda! With all the restrictions these days, it can be helpful to read other people's experiences. Thanks for sharing!
While I have cruised and sailed in the Caribbean, I have not gone as far north as Bermuda. It sounds like a lovely island. And, I always travel with trip insurance. So much can go wrong and travel insurance has helped me out several times in the past.
Yay that you had such a nice, golf-filled holiday! It is always nice to have that insurance as a back up...and even nicer when you don't need to use it! :)
We have visited so many Caribbean Islands. But this post reminded me that we need to plan to get to Bermuda. I would definitely want those pink sand beaches. A good reminder that in these challenging times insurance has to be part of your planning process. We just went through estimating a cost and was surprised at how much planning for flexibility added to our total cost. Good that on your trip you did not need to rely on insurance.
Planning is so important these days. This was great read thanks for sharing. Insurance is very important to have (someone talking who always end up in a hospital)
Getting insurance at the car hire company is so expensive! It's great that this is a more cost effective way of doing it - thanks for sharing!
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