The US Virgin Islands is not your average beach vacation it’s landscape and alluring waters are a true oasis.  If you’re planning a trip here throw out your budget and part the seas for the most amazing USA vacay. We planned our trip in a matter of days.  I’ve received a lot of interest in my DMs about this trip, so of course I’ll share with you all the deets.  Here is your guide to traveling to the US Virgin Islands based on our trip to St. John.

Traveling during the COVID Pandemic:

With good reason traveling at this time comes with some special challenges, but after a year of being grounded, I was really looking forward to staying at an all-inclusive.  Those plans quickly became unattainable when we found out that our daughter’s passports were expired six days before our impending departure.  Now while I would like to consider myself a planner and a travel blogger, this trip was rescheduled from the casualties of 2020.  I guess I thought it was all lined up.

As we started to get closer to our Mexican siesta, I had a plaguing feeling that we needed to pull those kid’s passports out of the vault.  By the time we extracted them it was simply impossible for us to get the documents expediated in time for us to go on our spring break vacation.  We were devastated but I flipped into save the vacation mode.  

The logistic of Travel Cancellations

I told my mother apparently nothing easy will ever come to me.  I was feeling pretty sorry for myself.  Dealing with customer service for travel arrangements requires a ton of patience and determination.  Once you get through the tele prompts to talk with a human being, be prepared to spell your name four times and provide your reservation repeatedly.  You will likely then need to be transferred to another department.  

“Do  you mind holding again?  Great, give us 4-6 weeks to give you a voucher that will be valid for a year.”  It can make your blood boil, take up your entire evening and leave you with a raging migraine .  

When  you are ready to travel again, expect to wait another 60-90 minutes on an 1-800 line to redeem your credit.  Pay attention to blackout dates, read your terms and conditions, don’t be shocked if the rates change.  ‘Would you be willing to stay on the line for a quick survey?”

Spring Break USVI

Looking for a replacement trip on a tight schedule

After a full day of cancellation calls I had to quickly switch gears and start booking a rebound trip.  Although we didn’t end up booking with Shannon Rae Grunewald from Blissful Honeymoons she pointed us in the right direction narrowing our search down to USVI or Hawaii.  Both locations require a negative Covid test from travelers.  They both have ideal weather, stunning beaches and neither destinations require a passport which in our case was key.

With less than a week’s notice Shannon didn’t have availability for any of properties on the USVI.  Hawaii was appealing, but it is a very long flight so we would want to vacation there for longer than a week.  When we are ready to take that trip, I will be giving Shannon a call back.

Traveling to US Virgin Islands

Entering the Negative Test into the portal for entry into the USVI 

My husband found a direct flight from Chicago (ORD) to St. Thomas (STT) for Thursday March 18th.  We scheduled a free Covid test at Walgreens for the Sunday before our departure.  USVI requires travelers over 5 years old to submit their negative test within 5 days of their trip.  Those test results need to be uploaded into their portal.  On Monday night we found out all of our test came back with a lab error and were unreadable. 

I was started to feel like I was on some travel challenge reality show. I yanked the kids out of school and we took three additional test on Tuesday, trying to ensure that one would come back in time for our Thursday morning flight.  We tested at a different Walgreen’s location, at Jango Lab and finally at the Alliant Energy Center.   All three test came back within 24 hours.  Make sure you are aware of the accepted test for the destination you are traveling to.  

The Alliant Energy Center test results do not show the CLIA certification number, the lab and administer information.  That test came back the fastest but when I submitted them, they were rejected.  Good thing I had multiple test results coming in.  Once I submitted the proper test results the approval was emailed to me within an hour, you get a QR code  that they scan as soon as you get off the plane and enter the STT airport.

Vacation Ideas for USVI

Where to stay in the USVI St. John

One  of the issues I ran into when trying to book our last minute trip is that the island is small and many of the places I found had no vacancy.   If you combined all of the Virgin Islands they collectively are only twice the size of Washington DC (according to Frommers).  

I didn’t have any better luck renting a Villa on VRBO.   The owners have 24-hours to confirm reservations.  They list their properties on multiple rental sites.  What kept happening was that the rental would appear available, I would make the reservation and wait hours only to find out that the unit was unavailable and the reservation was not confirmed.   It was a sheer miracle we got in at the Westin St John.  As I sat up searching late on Sunday night it popped up.  I had a pending Villa rental I was waiting on so I double booked us.  The Villa fell through and the next day I called the Westin, sure enough they had our reservation for a 2-bedroom townhouse.


The Westin runs it’s own private ferry to the resort.  We chose this easy option and walked straight to The Westin counter at the St. Thomas airport after landing and covid clearance.   You can pay for a round-trip that includes your taxi to the ferry port, your ferry fare and your trip back to the airport. Alternatively you can go ala carte and find your own taxi to the red hook ferry. The red hook ferry from Saint Thomas to St. John’s is about a 12 to 15 minute ride.

Click here for the Ferry Schedule.  Many travelers choose to rent open air jeeps and to get around the island for the week.  By the time we knew we were on the way all of the jeeps were taken.  Note that the Virgin Islands is the only place in the United States where they drive on the left side of the street.  Taxis are easy to find and we used the open air Westin Taxis to get around with no problems, they are like trolleys.  Most taxi rides are $5-$8 per person, you must wear a mask each row can fit a family of 4-6 people.  The drivers like to fill them up before they leave so just be prepared to wait up to 10 mins for the taxi to fill up.

Beaches of St John

Resort Review The Westin St. John

The layout of the 2 bedroom townhouse was perfect for our family.  A full kitchen and living room space, a balcony with views of hillside villas, lush landscaping and the ocean.  Similar to our home it has a split floor plan you walk up a set of stairs that splits off to two separate bedrooms each with a bathroom attached.

We were in the 3200 building and next to our unit was a small pool with water fountain.  Most days the girls had this pool all to themselves.  Golf cart shuttles are readily available.  Many of the amenities such as the kid’s club and spa are still not open, housekeeping isn’t cleaning throughout your stay but will replenish towels as necessary.  At this price point you are paying for some of those things, my only suggestion would be that since they are not open the resort could cover the Taxis for guest staying at the property to compensate for the loss of those amenities.  The Westin was at full capacity but at no time did we have to wait for food, drinks or have a hard time finding pool seats.  

Trunk Bay St. John

Activities:  Go to the beach

It was like a bad dream getting my family to the islands but once we were there everything was so easy.  We didn’t have time to plan a lot of activities and you don’t need to.  Just go to the beach, there are several different beaches dotting the shoreline of St. John.  We wanted to see them all, each beach offers different amenities but all of them are stunning.  I found this article by Fueled by Wanderlust to be helpful.

Our favorite beaches were Cinnamon Bay, Trunk Bay, Honeymoon Beach and Maho Bay.  The breeze felt great but this chocolate mama is already the perfect shade, I need a reprieve from sun rays! Travel tip:  rent a pop up tent from @cruzbaywatersports and create your own shade.  

Giana’s favorite beach was Maho Bay you can rent snorkel gear and swim with sea turtles and sting rays.  We also recommend doing a sunset sail.  We took one with Kekoa Sailing and it was absolutely gorgeous.  The story of resilience in the eye of the storm gave the cruise depth and meaning.  Two brothers working as a team with determination to build and rebuild the vessel destroyed by the storm.  The mother of the brothers sailed on our tour with us.   Inspirational for sure, I love dream chasers.  Also impressionable for our kids, a female captain and completely female crew running it!

Check out the @yeti documentary of @kekoasailing

Remarkable Dining & Must read Trilogy

I heard that you cannot have a bad meal on the island and that’s legit we enjoyed every establishment.  One of our favorite spots to drop in was Irie Pop.  Our Bernedoodle Irie is a part of our family and the girls were missing her dearly.  Irie Pop is a super cute shop with ice popsicle treats made with fresh fruit, coconut water or coconut milk.  The owner is passionate and works his shop sun up to sun down.

Other Recommendations:

Dave & Jerry’s Island Steakhouse (The chef is from Madison, WI)

Sun Dog Cafe

Greengos cantina

Shop Mongoose Junction

Last but not least my girlfriends recommended a trilogy by Elin Hellandbrand based on the island.  I bought the paperback version before I left and it was the perfect beach read.  The day we got back I ordered the 2nd book of the trilogy, in my mind I’m still on the island.

Winter in Paradise

What Happens in Paradise

Troubles in Paradise