caribbean winter getaway

The Caribbean is Your Best Bet for a Cheap Winter Getaway This Year

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There’s no question travel won’t be the same this year. But that doesn’t mean you have to give up all hope on a getaway in 2020.

If you’re looking to take a trip this winter, there may be no safer bet than heading to the Caribbean. From Aruba to the U.S. Virgin Islands, many islands across the Caribbean have already reopened to travelers. The region is a rare bright spot for travel as most international has shut down – or shut out Americans.

And let’s be honest: It’s never too early to start planning your winter getaway, as you can book flights as far out as June 2021 right now. Sitting on a beach sounds perfect, right?

It’s a short flight and trust us: There are cheap flights to be had for your winter escape.


Tips for Booking Your Tropical Getaway

  1. Book on an airline with flexible change and cancellation policies. Most U.S. airlines are offering fee-free changes or cancellations on all flights booked this month (though American Airlines has a few caveats). Take advantage of this flexible time to book to protect your flight’s worth.
  2. Don’t wait until the last minute to book your winter vacation. Even though winter feels far away right now, you can often save on flights – especially to warm-weather and international destinations – by booking 90+ days in advance. We find flight deals up to 11 months in advance, and are already finding deals for June 2021. Now is the sweet spot for booking winter travel!
  3. Start with a cheap flight deal and build your trip out from there. The flight is often the most expensive part of any trip, so let the cheap flight guide your tropical destination choice –  and trip dates.


When it comes to cheap flights, we’ve got you covered. Our Thrifty Traveler Premium members have been getting tons of great flight deals to Caribbean islands recently.

We’ll give you a taste…


Caribbean Islands to Put on Your List This Year

Pulling off a trip to the Caribbean this coming fall or winter requires two things: a country that’s allowing U.S. travelers; and a cheap flight.

Lucky for you, there are plenty of islands that meet both requirements.



Antigua’s borders reopened June 1. Currently, all travelers visiting Antigua must wear a mask in public at all times during their stay and complete health screenings upon arrival. 

If you’ve traveled in the past month, however, this might not be your best option. Travelers won’t be allowed to enter the country if they’ve been to Canada, China, France, Germany, Iran, Italy, Japan, South Korea, or Singapore in the past 28 days.

But getting there for relatively cheap should be no problem. This recent Thrifty Traveler Premium deal had nonstop flights from New York City to Antigua (ANU) for under $350 roundtrip!

The Bahamas

The Bahamas reopened starting July 1, with extensive health checks and safety protocols upon arrival.

American Airlines resumed service to Nassau (NAS) and Exuma (GGT) on July 7, so keep an eye out for cheap fares! We’ve found some crazy cheap fares to the Bahamas all the way through next April.
premium deal


Travelers have been welcome to visit Bermuda since July 1. Visitors must obtain a certificate for a negative COVID-19 test within 72 hours of departure and have appropriate health insurance.

These cheap nonstop fares from Boston and New York are the perfect reason to cross Bermuda off your list this year:

Dominican Republic

International flights to the Dominican Republic resumed July 1. And good news: tourism companies are scheduled to resume work then, too. This could make the Dominican Republic a great choice for a trip this year.

We sent Premium members an alert for rock-bottom pricing to the Dominican Republic from 30-plus U.S. departure cities with fares nearing $200 round-trip!


Jamaica began reopening its borders to tourists starting June 15, 2020. Expect health and safety protocols like temperature checks and additional screening at airports. Many hotels have already reopened, too.

And no, flights to Jamaica don’t have to break the bank. We found fares as low as $233 roundtrip just a few weeks ago for a trip to Jamaica all the way through May 2021!


Thrifty Tip: Use Hyatt points to book a few nights at the Hyatt Ziva or Zilara Rose Hall for under 19,000 points per night with this great promo!

St. Lucia

From June 4 through July 31, St. Lucia has opened its borders – but only to U.S. visitors.

St. Lucia plans to test how this phase of welcoming tourists goes with strict social distancing measures enforced. Visitors must have proof of a negative COVID-19 within 48 hours of departure, pass screening and temperature checks at the airport, and wear face masks during the duration of your stay.

Just a few days ago, we found an unadvertised Delta SkyMiles flash sale to multiple Caribbean destinations, including St. Lucia. You could get to paradise for as little as 11,000 SkyMiles round-trip!
st lucia

Puerto Rico

We know, we know: it’s not technically international travel. But Puerto Rico should be on your list for potential tropical getaways this year!

As a part of the U.S., Puerto Rico has not been closed to travelers throughout the pandemic, but they’re officially welcoming travelers starting July 15. They’ve had fewer than 4,000 cases on the island – less than the vast majority of the U.S. states.

The frequency of flights to Puerto Rico has been trimmed significantly, but if you’re able to snag a cheap flight, Puerto Rico is a great option for a getaway. Here’s a recent Premium deal we found for half off lie-flat business class to San Juan for the price of economy!
puerto rico

Thrifty Tip: Check out our guide to San Juan and start planning your trip.


U.S. Virgin Islands

According to The Virgin Islands Department of Tourism, the U.S. Virgin Islands began allowing leisure travelers to visit starting on June 1, 2020. Regulations and procedures will be enforced from restaurants and bars, taxis services, as well as hotels and other accommodations.

No passport? No problem! Head to the U.S. Virgin Islands for a tropical getaway, passport-free. While you’re there, be sure to visit St. Croix.

Need a cheap flight to get you there? We sent this deal from 20-plus cities to Premium members recently with fares as low as $264 round-trip.

Wondering about other destinations not on this list? Check out our country-by-country guide to see up-to-date information on destination restrictions.


Bottom Line

With travel restrictions in place for many other pockets of the globe, the Caribbean is one of your best bets for international travel this year. And while we know it’s hard to start thinking about winter trips in the middle of summer, these cheap flights we’re finding can pay off to plan ahead!

Start planning your winter getaway now to one of these destinations now open to travelers, and save a few hundred on the flight there with our flight deal alerts.


Editorial Disclaimer: Opinions expressed here are the author’s alone, not those of any bank, credit card issuer, airlines or hotel chain, and have not been reviewed, approved or otherwise endorsed by any of these entities.

Disclaimer: The responses below are not provided or commissioned by the bank advertiser. Responses have not been reviewed, approved or otherwise endorsed by the bank advertiser. It is not the bank advertiser’s responsibility to ensure all posts and/or questions are answered.

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