May is a great time to take advantage of flight deals. It’s the shoulder season for many destinations ahead of what is usually a busy, crowded, and expensive summer travel season.
Flights to the Caribbean tend to drop significantly before the start of Hurricane Season. In Europe, popular destinations are quieter ahead of the summer months. The comfortable temperatures also make May an ideal time to explore before it gets hot and humid.
There’s much to love about traveling in May, including lower flight prices and fewer crowds. Here’s where to travel for $650 or less this May.
Managua, Nicaragua: Less Than $200 Roundtrip
May starts the rainy season in Nicaragua, but it’s a good time to visit the Pacific and central regions, where there is no shortage of sunny days with some afternoon showers. The capital city, Managua, is a springboard for the rest of the country, but it’s worth spending a day there. For adventure, climb the Masaya Volcano, one of the most active volcanoes in the world. Managua is said to be home to some of the oldest footprints in the world. Find the 6,000-year-old ancient footprints of Acahualinca at Museo Sitio Huellas de Acahualinca.
The Acahualinca footprints are ancient fossilized human footprints discovered near Lake Managua. Estimated between 2,000 and 8,000 years old, the International Commission on Geoheritage says the prints are considered some of the oldest human footprints in the Americas. They were made in volcanic mud and later preserved when ash from a volcanic eruption covered them.
According to Skyscanner, flights to Managua cost less than $200 round-trip from Miami, New York City, Orlando, Atlanta, Houston, Las Vegas, and Dallas. Fort Lauderdale is the cheapest option. Use May 18 through 21 on Google Flights for a round-trip ticket for less than $180 on Spirit Airlines.
East Coast to Saint John’s, Antigua and Barbuda: Less Than $300 Roundtrip
May is the last month to enjoy the Caribbean before Hurricane Season starts in June. As the Caribbean heads into shoulder season, take advantage of some of the flight deals in places that can get expensive, like Antigua and Barbuda. Known for its approximately 365 beautiful beaches, Antigua and Barbuda have a rich history, vibrant culture, unique landscapes, and delicious cuisine.
If you plan a beach day, head to Ffryes Beach, Dickenson Bay, or Half Moon Bay. The best way to explore the islands is through a walking tour, where you can explore historical sites while learning about the island’s heritage. Tour stops also include stops at local markets where you can shop for local produce, crafts, and other goods.
This flight deal is for East Coast travelers. Skyscanner says round-trip flights from Miami and New York City airports cost less than $300. Orlando is the cheapest option. Plug in May 23 through the 31st in Google Flights for a round-trip ticket on Frontier for less than $280. There is an 8-hour layover in San Juan, Puerto Rico.
Bridgetown, Barbados: Less Than $500 Roundtrip
Barbados is known as the birthplace of rum. Even if you don’t consider yourself a drinker, there’s no better way to learn about rum history than in Barbados. Rum was first produced on the island in 1642, and not much has changed, including producers who use the traditional local method. Take a rum tour at the Mount Gay Rum Distillery in Bridgetown or the West Indies Rum Distillery, where Barbadian Cockspur Fine Rum is produced.
As you explore history, consider visiting historical sites such as Historic Bridgetown and its Garrison. These UNESCO World Heritage Sites are an outstanding example of British colonial architecture, consisting of a well-preserved old town built in the 17th, 18th, and 19th centuries. During your visit, try the island’s national dish of flying fish and cou-cou. Cou-cou is made from cornmeal and okra and has a creamy texture.
According to Skyscanner, in May, Miami, Philadelphia, Detroit, Washington, D.C., Orlando, Tampa, Nashville, Charlotte, Dallas, and Chicago have flights for less than $500 round-trip. Travelers leaving New York City have the cheapest option. On Google Flights, use May 27 through June 2 for a round-trip ticket for less than $370 on American Airlines.
Rome, Italy: Less Than $600 Roundtrip
People who want a taste of Europe before summer madness should book a trip to Rome in May. It’s a great time to explore the most visited sites: the Colosseum, Palatine Hill, the Roman Forum, and the Spanish Steps in full bloom. Take advantage of the small crowds in May and explore the ancient city like a local. The Night of the Museums is in May. More than 60 museums and cultural venues open after hours for a festive night of art and entertainment from 8 p.m. to 2 a.m.
Some of the best experiences introduce you to the local side of Rome. Once you check off the popular attractions on your to-do list, explore the neighborhoods of Trastevere, Monti, or San Lorenzo. These neighborhoods offer an authentic Roman experience with local shops, trattorias, and vibrant street life.
On Skyscanner, round-trip flights from New York City, Seattle, San Francisco, Miami, Orlando, Fort Lauderdale, Las Vegas, Washington, D.C., and Atlanta are less than $600. Boston offers the cheapest option on Google Flights. Use May 20 through May 27 for a round-trip ticket for less than $450 on Condor Airlines.
Santiago, Chile: Less Than $600 Round-Trip
While most places on this list are transitioning from spring to summer during May, it’s the opposite in the Southern Hemisphere, where countries such as Chile are transitioning from autumn to winter. Fewer people head to Chile in May, an excellent time for people who enjoy avoiding the crowds. May is chilly, so expect temperatures in the low 60s. Visitors can venture off to wine country, where the vineyards showcase Chile’s beautiful fall foliage and plenty of grape harvest festivals.
Next, hike or take a funicular to the top of Cerro San Cristóbal for the city’s best panoramic views. Other sites worth visiting are the Museum of Memory and Human Rights, Plaza de Armas de Santiago, La Moneda Palace, and La Chascona. In 1953, the famous Chilean poet Pablo Neruda began building a house in Santiago for Matilde Urrutia, his secret love. In her honor, he named it La Chascona, the nickname he gave her because of her abundant red hair. La Chascona is now a house museum providing access to the intimate spaces where he lived and created.
Skyscanner says round-trip flights from Los Angeles, Washington, D.C., Orlando, New York City, Fort Lauderdale, and Houston are less than $600. According to Google Flights, Miami has the cheapest flights. A round-trip ticket for less than $500 is available from May 19 through May 26.
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