From beaches in the Caribbean, breathtaking gardens in South America, and stunning architecture in Europe, there are a ton of places you can visit in May  no matter your budget.

For the month of May, we are focusing our flight deals on the Caribbean since June 1 marks the start of Hurricane season.

Here’s where you can travel in May for less than $250 round-trip.

Editor’s Note: Please check all updated travel advisories and adhere to all testing requirements and mask mandates, if you decide to travel this fall.

1. San Juan, Puerto Rico

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Puerto Rico will always be a favorite location of ours because it’s an easy destination where there’s no passport needed.

It’s the perfect destination for a quick getaway when you need a break, but you don’t want to travel too far.

May is also a good time to go because, over the last few years, the island has seen a pretty active hurricane season.

Right now, you can travel to Puerto Rico for less than $200 round-trip from New York City, Orlando, Philadelphia, Washington, D.C., and Atlanta, according to Skyscanner.

May 2022 Flight Deal Round Up

The cheapest option leaves Miami on May 7 and returns on May 14 for just $82 round-trip.

May 2022 Flight Deal Round Up


2. St. Thomas, U.S. Virgin Islands

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Another gem of the Caribbean location is St. Thomas.  Like Puerto Rico, it’s the perfect destination to unwind and getaway.  Even better?  This is the second destination on our list where a passport is not needed.

May is also a great time to go because the U.S. Virgin Islands has seen its share of destruction from mother nature.

However, as we pointed out in our guide to explore the islands, there’s still a lot to indulge in from the beaches, nightlife, and excursions.

You can explore St. Thomas this May for less than $250 if you’re departing New York City, Orlando, Atlanta, Washington, D.C., and Fort Lauderdale.

May 2022 Flight Deal Round Up

Miami is the cheapest departure city on Skyscanner. Plug-in May 7 through May 9 as your travel dates for a round-trip ticket priced at $185.

May 2022 Flight Deal Round Up

3. Phillipsburg, Sint Maarten

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Now, here’s a deal you don’t see every day, let alone for the second month in a row.  If you’ve been following our monthly flight deal roundups, then you’re probably just as surprised as we are that round-trip flights to Sint Maarten’s capital city are going for less than $250 round-trip …again.

May 2022 Flight Deal Round Up

It’s the Dutch side of the island that’s shared with the French (Saint Martin) and there’s a lot to do. From art galleries, Great Bay Beach, and chilling on the boardwalk— Phillipsburg will not disappoint.

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Great Bay Beach is great for relaxing, while Little Bay Beach is perfect for snorkeling. If you’re traveling solo, the boardwalk is where you can meet people if you’re feeling social as it’s full of a ton of bars, restaurants, and stores.

Departing from Miami is the cheapest way. Use May 14 through May 21 as your travel dates in Skyscanner to get there for as low as $174 round-trip.

May 2022 Flight Deal Round Up


4. Saint John’s, Antigua and Barbuda

Antigua and Barbuda
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A trip to Antigua and Barbuda’s capital city means beaches, adventure, food, and art.

What could possibly be better than that? Our answer is nothing, too. Even though it’s a Caribbean destination where most travelers are seeking the beach, it’s one of those destinations that offers a lot both on and off the water.

You can choose from hiking, snorkeling, kayaking, horseback riding, and zip-lining opportunities to explore.

Another cool experience? Dune buggies. You can rent them from 268 Buggies for an exciting off-the-road tour.

Traveling from Miami, Washington, D.C., and Atlanta will get you to Saint John’s for the cheapest, according to Skyscanner.


Orlando is the cheapest option, though. Use May 14 through May 21 as your travel dates for a round-trip ticket for $183.

May 2022 Flight Deal Round Up


5. Belize City, Belize

Unsplash | Meritt Thomas

If you’re traveling from Denver or Orlando, then this nonstop flight deal to Belize City is for you.

During your stay, you can shop with the locals, dive into Caye Caulker Marine Reserve or go swimming with sharks at HOL CHAN CUT.

What we love about the Caribbean is the food.  Very few destinations in the world offer the spice combos, flavors, and fresh seafood the Caribbean has to offer.

At the top of your list should be Elvi’s Kitchen, known for its Mayan-Caribbean fusion cuisine that locals say is one of the best in the city.

Also, The Truck Stop and Hurricane’s Ceviche Barare favorites among tourists and locals alike.

Leaving Denver will get you there the cheapest. Use May 14 through May 21 as your travel dates for a flight deal for $170 round-trip.

May 2022 Flight Deal Round Up


source: Travel Noire

Puerto Rico is all set to welcome back tourists from July 15, but with all health and safety measures in place. It is part of the island’s four-phased reopening plan.

The vibrant island has a distinct vibe, which is the result of a mashup of cultures–African, Spanish, French, Dutch and British blood pumps through the veins of the islands’ diverse population.

With this step, Puerto Rico will join the expanding list of Caribbean islands opening up for tourism. However, Puerto Rico never closed its borders to the citizens of the United States, or foreign nationals who hadn’t been to Iran, China, Ireland, the United Kingdom, Brazil, or any of the European Schengen area in the previous 14 days.

During all this time, a 14-day quarantine rule was applied on anyone who was flying into Puerto Rico, along with other stringent lockdown measures, which meant that tourists were discouraged from visiting the island.

Reportedly, Puerto Rico Governor Wanda Vázquez recently announced that from now on, travellers who can show negative COVID-19 test results, which were obtained 72 hours prior to arrival, will not be required to undergo quarantine.

Here’s what you should know:

When You Arrive At The Airport

Arriving travelers may be asked to self-quarantine for 14 days no matter whether they have symptoms or not. The National Guard will be assisting with health screenings of all arriving passengers, including rapid COVID-19 tests.

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Getting Around

Ridesharing options like Uber have mandated face coverings for both the drivers and the passengers.  The front seat will be prohibited.

Certified transportation carriers will properly disinfect vehicles and have hand sanitizer available. In addition, drivers will wear gloves when handling doors and luggage.

Things To Do

Restaurants will open with a maximum occupancy of 25% in their dining rooms. Similar to the airport, temperature checks will be performed before entering. Anyone with a temperature of 100.3 will be denied entry.

Employees will be required to use face coverings, and buffets, salad bars, and self-serve options, as well as reusable menus, are prohibited.

Attractions, with the exception of outdoor recreation spaces, including public beaches, natural reserves, and golf courses are closed.

Shopping malls will enforce social distancing and some stores even require appointments before entering.

If you’re planning to attend a casino,  wellness checkpoints will be conducted at entryways, which includes temperature checks and hand sanitizer.

Gaming stations and slot machines will be cleaned every hour of after each guest.  Social distancing will be strictly enforced.  Face coverings by employees and guests are required.

For more information and to stay up-to-date with the latest in Puerto Rico, click here for its visitor health and safety guidelines.