6 Reasons Why You Should Visit Europe or the Caribbean in May

Many travelers plan vacations during peak travel seasons, such as spring break in the Caribbean or summer in Europe. That said, visiting top destinations in the high season often means higher airfare and hotel prices, crowded attractions, and uncomfortably hot weather.

The good news is that you don’t have to visit Europe during winter or brave hurricane season in the Caribbean to have a more affordable vacation with fewer crowds.

Instead, travel during the shoulder season for better rates, milder weather, and fewer crowds at tourist attractions. There are a few months each year when traveling to Europe or the Caribbean isn’t as expensive, but not cold or rainy, either. Here’s what you need to know.

What Is Shoulder Season?

Shoulder season is the time period that “shoulders” the peak season. It’s not the busiest time of year, but it’s also not the quietest. Because of this, shoulder season often offers a balance of good weather, reasonable prices, and manageable crowds.

Shoulder Season in the Caribbean

The Atlantic hurricane season runs from June 1 to November 30, which is typically the Caribbean’s rainier and more humid low season. High season usually runs from December through April.

That leaves May as the main shoulder-season month in many Caribbean destinations. (Though some argue that the end of November is also shoulder season.)

Shoulder Season in Europe

Shoulder season in Europe varies slightly by country, but generally, the top shoulder season months are May and October. It’s not too cold or too hot, and both prices and summer holiday crowds are at bay.

Of course, this varies by country and city. September and early October in Munich, Germany, is high season, thanks to its world-famous Oktoberfest. Meanwhile, destinations like Ibiza have very defined tourism seasons, with many hotels and clubs opening from May through October.

While it may be chilly in Europe or expensive during the Caribbean’s peak season, May is the perfect time to visit either destination — before Atlantic hurricane season begins and before the crowds swarm for a European summer.

6 Reasons To Plan a Europe or Caribbean Trip During Shoulder Season

May is approaching, and it’s the perfect time for a European or Caribbean getaway. Here’s why.

1. Decent Weather

Weather plays a major role in choosing shoulder-season travel. As more severe weather events occur, such as hurricanes and heat waves, traveling outside of those periods can make for a more comfortable trip.

Europe in Shoulder Season

According to The Guardian, a study by Intrepid Travel found a 61% increase in shoulder-­season bookings to Western Europe in 2025, likely due to extremely hot weather.

Having lived in Spain for nearly 2 decades, I can confirm that summers can be intense. In Madrid, where I live, most locals escape to the beach since temperatures often climb above 100 degrees Fahrenheit. While proximity to the water helps, it can still get uncomfortably hot in months like July and August, no matter where you are in the country.

This is why May is the ideal time to visit Spain. Cities are warm but not scorching, making it easier to explore attractions during the day, and the weather is still pleasant enough for a beach getaway.

Similarly, May is a great time to visit Italy, Portugal, France, the Greek islands, and much of Western Europe. If you don’t mind cooler temperatures and possibly bringing a light jacket, destinations further north — such as Germany, Scotland, and Switzerland — can also be fantastic in May. Longer daylight hours also mean more time for sightseeing.

Caribbean in Shoulder Season

If you’re looking for a warm escape in the Caribbean, May is the perfect time to visit, when both sea and air temperatures hover around 80 degrees Fahrenheit. The rainy season hasn’t started, and the air isn’t overly humid. Since there hasn’t been much rain yet, mosquitoes aren’t usually an issue.

Just like in Europe, the weather varies by destination. For example, Aruba’s dry season stretches much further, while the Cayman Islands begin seeing more rain by mid- to late May.

2. Lower Travel Costs

Traveling in May can often mean lower airfare and hotel rates compared with peak travel periods.

Hotels in Shoulder Season

For example, the Iberostar Selection​ Bávaro Suites in Punta Cana, Dominican Republic, has the following rates:

• May (shoulder season): $233 or 55,000 IHG One Reward points per night
• April (high season): $511 or 128,400 IHG One Rewards points per night

Meanwhile, in Europe, the Conrad Algarve in southern Portugal has the following rates:

• May (shoulder season): $283 or 70,000 Hilton Honors points per night
• July (high season): $771 or 110,000 Hilton Honors points per night

Flights in Shoulder Season

Flights can also be cheaper in May. I did a quick comparison of flights to Paris (CDG) from New York (JFK) in May and July using Google Flights and the Points Path browser extension. In most cases, May flights were several hundred dollars cheaper, and many award flights also required fewer points.

A similar comparison between Chicago (ORD) and Montego Bay (MBJ) showed flights were cheaper in May than in April.

In many cases, simply shifting your trip by a few weeks can lead to significant savings on both flights and hotels.

3. Better Points Redemption Opportunities

May is often considered off-peak for many airlines, so you may be able to find affordable flights if you pay with points. Although most U.S. airlines no longer use award charts, some European airlines do, and some even use them for booking partner awards.

For example, you can find Virgin Saver awards to London (LHR) or Iberia Avios redemptions to Madrid (MAD) for lower prices in May, since it’s off-peak season. Or you might be able to fly to the Caribbean on American Airlines using Atmos Rewards, Alaska and Hawaiian’s frequent flyer program.

Although Hyatt just announced an overhaul of its award chart, sometimes May falls into the off-peak or standard categories for certain hotels in specific destinations.

Hot Tip:

Hyatt will update its award chart in May 2026, expanding from 3 pricing tiers to 5. It will be interesting to see how shoulder season dates are categorized under the new system, so stay tuned. If you want to lock in current off-peak pricing, consider booking before the changes take effect in May.

4. Fewer Crowds

Shoulder season typically means fewer crowds, making for a more enjoyable and affordable vacation. You might be able to get coveted dinner reservations, room upgrades (if the hotel isn’t full), flight upgrades, and Ubers at a better price. You may also be able to visit major attractions without being surrounded by large crowds.

Of course, none of these perks are a given, but generally, traveling when everyone else isn’t can open up additional possibilities that may improve your vacation experience.

5. Attractions Are Open but Less Busy

During the low season, some attractions may close entirely. But shoulder season often offers the best of both worlds — sites are open but far less crowded. For example, the Colosseum in Rome reported staggering numbers of visitors in August 2025: 76,860 to the Colosseum, and 50,393 to the Roman Forum and the Palatine Hill.

Visiting in months like May could mean a better experience seeing the more popular attractions. And, traveling in the shoulder season also means attractions are open.

I made the mistake of visiting Menorca, Spain, several years ago in November when I got an incredibly affordable plane ticket from Madrid. Not only did it rain most of the trip, but many restaurants and attractions were also closed.

If you plan a low-season trip, make sure the places you want to visit are actually open. Many hotels will even close seasonally, so it’s worth checking before booking a flight, no matter how cheap.

6. A More Sustainable Way To Travel

Visiting popular destinations in Europe and in the Caribbean during high seasons puts pressure on these spots and their most coveted attractions. Some attractions are taking matters into their own hands, such as the Louvre in Paris, which has recently raised entry prices to help restore infrastructure and manage overcrowding.

You can help fight overtourism by visiting these places at less popular times. Regardless of when you go, remember to follow no-trace principles for natural attractions, such as beaches and national parks. And when you’re visiting centuries-old attractions, be respectful and follow all rules.

Pro Tip: Consider Travel Insurance

Even though May is generally a safe travel period weather-wise, it’s still worth considering travel insurance, particularly cancel-for-any-reason policies. Recent global events (from political unrest to severe storms) have reminded travelers how quickly circumstances can change.

Credit card travel insurance can help, but it won’t always include every event or emergency. Still, if you’ve paid for tickets and hotels using points, you may be able to cancel at the last minute without penalty.

Do your own research based on your trip, and decide whether getting additional travel insurance is worth it for you.

Final Thoughts

Shoulder-season travel, especially to Europe or the Caribbean, is an excellent way to ensure you’ll have relatively decent weather, lower prices, and fewer crowds. As always, research your specific destination to understand its peak, shoulder, and off-peak periods.

And while May is generally a great time to travel, adding travel insurance to your plans can help provide extra peace of mind.