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
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.
The cheapest option leaves Miami on May 7 and returns on May 14 for just $82 round-trip.
2. St. Thomas, U.S. Virgin Islands
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.
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.
3. Phillipsburg, Sint Maarten
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.
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.
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.
4. Saint John’s, Antigua and Barbuda
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.
5. Belize City, Belize
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.