What is the Best Winter Island Travel Spot: Virgin Islands, Puerto Rico or Cayman Islands?

We do our best to make the case for the Virgin Islands, we also keep it honest for you to decide.

Winter weather brings with it gray clouds, cold precipitation and thoughts of escaping to a warm tropical vacation! When you are about to plan your vacation, however, some people on the mainland think that they may have only two options: Puerto Rico or the Cayman Islands. However, there is a third option that many may not realize exists— the gorgeous United States Virgin Islands! 

And, when you are looking for choices for your winter getaway, deciding between the three can be tough. You want somewhere that has a nice climate and is not too expensive to travel to: So, the Virgin Islands, Puerto Rico or Cayman Islands? In this article, we will highlight and compare the advantages of traveling to each island in 2021.

What Are You Looking For in a Vacation?

To help narrow down your Caribbean vacation it often helps to know what you are looking for. For instance, if you are in a part of a younger crowd looking for a world of hopping nightlife, Puerto Rico reigns supreme as the party capital of the Caribbean. Both the USVI and the Cayman Islands are known for their pristine beaches and historic icons, but you might want to take a look at what each island has to offer before you make your final decision.

Note: Always double-check the travel requirements with the country’s official website you are traveling to, as their protocols can quickly change. You can also reference Travel Weekly’s global travel map by clicking here. 

Puerto Rico: Best Nightlife for Young Travelers

Puerto Rico is a popular destination for young winter vacationers because it has a lively nightlife scene with lots of bars, clubs, casinos etc. The nightlife in Puerto Rico is also famous for its Latin vibe, so it can be a great opportunity to learn more about the culture of this island while having fun. There are many ways that you could enjoy your time in Puerto Rico if partying all night long was one of them.

The weather in Puerto Rico will be at its warmest between January and February with average temperatures around 80 degrees F (26C). Also, if you are a U.S. citizen, you do not need a passport to go to Puerto Rico since it is a U.S. territory. Instead, all you need to bring along is the identification you use to travel anywhere else in the country. 

The Virgin Islands: Best for Families and Honeymooners

Three islands make up the US Virgin Islands: St. Croix, St. Thomas and St. John. It's also a sublime locale for beach-lovers, with 70 miles of coastline. The islands are home to plenty of upscale resorts and hotels in case you want a little more luxury on your winter getaway. It is a top destination for honeymooners, groups and families who want to recline on gorgeous beaches and explore modern attractions.

The weather in the USVI will be warmest between December and March with average temperatures of about 80 degrees F (26C). Since it is a U.S. territory, you do not need a passport to go there either!

What is the difference between Puerto Rico and the US Virgin Islands?

Travelers who want a little bit more of an exotic feel to the Caribbean often choose the USVI over Puerto Rico. The USVI is known for its lush tropical scenery and unique culture, whereas Puerto Rico's landscape is relatively flat with not as much greenery or natural beauty. 

The Virgin Islands are also known for their picture-postcard-ready beaches, verdant hills and reefs, while Puerto Rico is known for their huge party beaches. Other differences include that Puerto Rico only has one island, while the USVI consists of three islands. Also, the average price per night for hotels on St. Thomas and St. John is about $100 less than on Puerto Rico.      

What Is So Special about the Cayman Islands?

The Cayman Islands are a British Overseas Territory, located in the Caribbean Sea only 20 miles off the coast of Cuba. Since it is further from the mainland USA than Puerto Rico or USVI, expect your flight prices to be much higher. Most people who go to the Cayman Islands are on business trips since it is one of the world's leading offshore financial centers. 

One of the Cayman Islands, Cayman Brac, is best known for its 50 dive sites, and it also has one of the largest wall diving sites in the world! Popular dive sites include “Bloody Bay Wall”, and “Eden Rock”. It's also a popular winter destination for divers because of its underwater attractions like “Stingray City” which allows you to swim with the multitudes of friendly stingrays that congregate near the shore.

What are “The 50 dive sites” in the Cayman Islands?

There is not enough time to read about all 50 of the dive sites. Everyone who has dived “The 50 dive sites of The Caymans” will have their own favorites. 

Revered Diving Spots among the 50 Dive Sites in the Caymans:

• Bloody Bay Marine Park on Little Cayman. It is considered a visually spectacular wall in the Caribbean. The wall full of colorful sponges and healthy corals, all the marine life such a set up will attract. The site routinely has 200 foot visibility.
• Devil’s Grotto and Eden Rock south of Georgetown Grand Caymans. These two shore dive sites offer similar profiles. Devil’s Grotto is loved by photographers. Eden Rock has small caverns, tunnels and swim-throughs, great sea life too. Lots of fun and great footage for underwater cameras.
• Sunset Reef at Sunset House resort Grand Caymans. This reef is reached from a pier at the Sunset House Resort. The reef is at 30 feet and sloops to about 50 feet. There are many canyons in the reef. 
• Babylon North Wall Grand Cayman. The Wall diving is outstanding in Grand Cayman and this site is said to be the best of the best.
• Captain Keith Tibbetts, Cayman Brac. Soviet-built Frigate was the property of the Cuba Navy until they gave it to the Cayman’s to use as an artificial reef.

What is the difference between the Cayman Islands and the USVI?

The main difference between the Cayman Islands and USVI is that while they both are English-speaking, there's more of a European feel to the former. The weather in the Cayman Islands will be at its warmest during December through February with average temperatures around 79 degrees F (26C), whereas it gets warmer in the USVI since it has a more tropical climate.

*(Verify if our summary below is still relevant Covid travel information, by checking our source: Travel Weekly)  

Disadvantages of travelling to Cayman Islands, if you are American:

• Cayman Islands are a British Overseas Territory, you would need a passport to travel there (assuming you are not a Brit). 
• The cost for hotels on St. Thomas and St. John is slightly less expensive than on the Cayman Islands, flights are longer to the British territory and airfare is more costly.

COVID RELATED UPDATE: Technically, the Cayman Islands has not entirely re-opened for Americans, or any other country for that matter: 

This was the following notice posted on the website for the US Embassy in Jamaica. 

Are U.S. citizens permitted to enter? Some US Citizens are permitted to enter. From October 1, 2020 until further notice, travelers eligible to visit the Cayman Islands are:

• Caymanians,
• Permanent residents,
• Work permit holders and their families,
• Persons who own residential property within the Cayman Islands,
• Students with a valid visa to study in the Cayman Islands,
• Persons with close family ties to residents or work permit holders; such as spouses, fiancés, parents, grandparents, children and siblings.
• Persons approved on the Global Citizen Concierge Program
• Other visitors approved via the Travel Cayman team.

Read more about travel to the Cayman Islands on the Cayman Islands COVID-19 website. The travel situation is changing with the data coming, make sure to double check the most current info on the Cayman Covid 19 Website.

Fully vaccinated U.S. travelers must provide results of a negative PCR test or antigen rapid test done within 3 days and show proof of vaccination. 

Even the vaccinated have to complete a 7 to 10 day quarantine (currently it is 10 day) and mandatory GPS monitoring for all travelers in quarantine, over the age of 10. 

All of this can be tedious in order to kickoff off a stress reducing tropical vacation when in comparison to USVI, any American just has to have proof of US residence or citizenship (such as a government issued photo ID or your passport).  Most current Cayman Islands Phased Reopening Plan 

Key Points to Compare them All

If you are still on the fence about where to go, here are some side by side key points to consider when trying to decide which one is best for you:

• In comparison, the USVI is averaging an approx. 3% Test to Infection rate, with 97% of the nursing home labor force being fully vaccinated. The rate of infections might appear to have increased, but in fact, that is a data anomaly related to USVI doubling testing coverage in a 4-month period of time. 
• The actual infection rate percentage dropped in that same period and the total of tests drastically grew by 100%+ in 4 months.
  
  To compare with most current Puerto Rico Covid Travel Guidelines

• Puerto Rico for Nightlife - San Juan, Puerto Rico is known as the party capital of the Caribbean and offers hundreds of bars that are open into the early hours of the morning! The nightlife in this region includes preferred venues such as El Yun que Disco, La Respuesta and Club Brava. 
• USVI for Beach Lovers and Tropical Diversity- The USVI is best known for its gorgeous beaches that are great for sunbathing, snorkeling and fishing. It also includes two national parks: the Virgin Islands National Park and Buck Island Reef. The U.S Virgin Islands has the most developed infrastructure, with fun places that are easier to navigate than in Puerto Rico or the Cayman Islands. 
• The Cayman Islands for Historical Sites - The Cayman Islands has a rich history that dates back hundreds of years to when many pirates called this beautiful destination home! “Argh we home yet?” 
  • Some popular attractions include Frank Sound Forest, 
  • George Town Heritage Site and Hell.
• Covid Travel considerations Cayman Islands vs. the USVI: The Cayman Islands are among the most vaccinated countries in the world with over 80% of the country fully vaccinated, with less than 1,000 cases, and a lower than avg mortality rate with less than 5 Covid related deaths.

Book Your Winter Escape in St. John Today

The above information should help you make an informed decision about which winter island travel is best for you. However, call us biased, but we think beautiful St. John is the best choice. We can help you book your stay at one of our many suites on St. John for your winter escape today! Simply call us at (800) 727-6610 or fill out our online form and we’ll quickly be back in touch.