For families or groups planning a sailing holiday, picking the right destination is often the trickiest part. Choosing the boat is one thing — catamarans are great for space, stability, and comfort — but where to take it? If you’re planning a charter in May, three destinations tend to come up again and again: the Caribbean, Greece, and the Canary Islands. Each has its pros and cons, and the right choice depends on what you’re looking for as a family, how much travelling you’re prepared to do, and what kind of sailing experience you want.
So let’s dive into what May looks like in each of these hotspots, and weigh up which might be the best fit for your catamaran adventure.
Why May Is a Special Month for Sailing
Before we get into the destinations, it’s worth noting why May is such a good time to be out on the water. It sits in that sweet spot between the tail end of winter and the peak of summer. The weather is generally kind — warm enough to swim in some places, but not so hot that you’re constantly seeking shade. Crowds are smaller, so marinas and anchorages feel relaxed. Prices are usually lower than high season, which is always a bonus if you’re trying to balance holiday dreams with family budgets.
That said, May also has quirks depending on where you go. Some places are winding down their sailing season, while others are just getting started. Understanding those seasonal shifts is key to making the right call.
The Caribbean in May
A catamaran charter in the Caribbean has long been at the top of many peopl'es bucket lists, and with good reason. Flat seas, predictable trade winds, and hundreds of islands make it the perfect playground for sailors. In May, you’re at the very end of the Caribbean sailing season, which runs roughly from December to May. That means the weather is still generally excellent, with warm seas, steady breezes, and plenty of sunshine.
The big plus is that May falls before the official start of the hurricane season, so you can still count on good sailing conditions without the storm risk. Anchorages and marinas are much quieter than in January or February, and you’ll often find lower prices as local operators look to wrap up the season. The flip side is that some restaurants, beach bars, and even charter companies start winding down in May, so you might not get the full high-season buzz.
For families, the Caribbean has a lot going for it: calm waters, big roomy catamarans, and plenty of family-friendly activities both onshore and afloat. The challenge, though, is distance. If you’re Europe-based, the long-haul flights can eat into your holiday time and energy. For younger kids, a transatlantic trip can feel like a mission. If you’ve got older children or teens, however, the adventure of heading somewhere so exotic can add to the excitement.
Greece in May
Now, if the Caribbean is winding down in May, Greece is just waking up. The sailing season there kicks off in late spring and runs right through to October. By May, the islands are starting to come alive. Temperatures are pleasant — usually in the mid-20s Celsius — and while the sea can still feel fresh for swimming, it’s not unbearable, especially for kids who seem immune to cold water.
The beauty of Greece in May is that you beat the summer rush. Marinas aren’t jammed, tavernas are welcoming without being swamped, and the islands still feel authentic before the mass of tourists arrive in July and August. Sailing conditions are manageable too. The notorious Meltemi winds that rattle the Aegean in high summer haven’t kicked in yet, so May tends to mean lighter, more predictable breezes — perfect for families who don’t want every day to feel like a survival challenge.
A Greek charter in May gives you that intoxicating mix of culture, food, and scenery, and if you're on the right boat, some real luxury. One day you’re exploring ancient ruins, the next you’re eating freshly grilled fish in a harbour-side taverna, and the next you’re anchored in a deserted bay with turquoise waters. For kids, the chance to hop from island to island feels like an adventure, and the short sailing legs mean no one gets bored stuck on deck for hours.
The only downside is that the water isn’t bath-warm yet. If swimming is a big deal for your family, you might find yourselves doing more land-based exploring. But for most people, the balance of good weather, light crowds, and affordable prices makes May in Greece a real winner.
The Canary Islands in May
The Canary Islands are an intriguing option for May because they don’t really follow the same seasonal rhythm as the Caribbean or the Med. Thanks to their location off the coast of Africa, the Canaries are a year-round sailing destination. Temperatures in May are very comfortable, usually hovering in the low 20s, with plenty of sunshine.
The islands themselves offer a different vibe: more volcanic landscapes, dramatic cliffs, and black-sand beaches rather than the white sands of the Caribbean or the postcard-perfect harbours of Greece. If you’re into rugged beauty and something a bit off the beaten track, they tick a lot of boxes.
From a sailing perspective, though, the Canaries can be a mixed bag. The winds tend to be stronger and more unpredictable than in the Med or Caribbean, and the distances between islands are bigger. That can make for exhilarating sailing if you’re an experienced skipper, but it’s not always ideal for families who want shorter, gentler passages. Catamarans handle the chop better than monohulls, but you’ll still want to think carefully about how much sailing your kids will tolerate.
On the plus side, flights from Europe are short and cheap, the infrastructure is solid, and prices for chartering are often lower than in the Med. For families wanting a reliable climate and a bit of adventure without long-haul flights, the Canaries can be a great choice.
So, Which Should You Choose?
When it comes to choosing the right destination for a May catamaran charter, there’s no one-size-fits-all answer. It really depends on what your priorities are.
If you want warm seas, classic sailing conditions, and you don’t mind the long-haul flights, the Caribbean is still a fantastic choice in May. You’ll enjoy calmer anchorages and lower prices than peak season, but you may find the buzz a little quieter as things wind down.
If you’d prefer something closer to home, with a balance of culture, history, and relaxed sailing, Greece in May is hard to beat. You get the romance of the Greek islands, the charm of quiet tavernas, and the comfort of knowing you’re sailing in a shoulder season where everything feels more manageable.
And if you’re after sunshine without the long haul, and don’t mind a bit of brisker sailing, the Canaries offer something different: rugged beauty, year-round sailing, and affordability. They’re not as classically idyllic as the Caribbean or as romantic as Greece, but for families after adventure and reliability, they’re well worth considering.
Ultimately, the best choice is the one that matches your family’s style. If your kids want to splash in warm seas all day, go Caribbean. If they’re up for exploring ruins and eating their bodyweight in ice cream, Greece is the winner. And if they love the outdoors and you fancy something different, the Canaries might surprise you.
Whichever you choose, May is a brilliant time to be out on a catamaran. The crowds are thin, the prices are fair, and the sense of adventure is the same wherever you drop anchor.
