How to Plan a Seamless Group Escape to Costa Rica this May

Planning a group trip sounds fun… in theory. Everyone says yes. Everyone’s excited. Everyone’s already picturing the beach days, the shared dinners and laughter, and the long overdue conversations.

Then reality hits. Dates don’t line up. Budgets vary. Someone wants adventure. Someone else wants total relaxation. Everyone wants their own private bathroom. And absolutely nobody wants to volunteer for the role of “planner”… but someone has to do it, right? 

If this sounds familiar, you’re not alone. And if you’re starting to think about a May escape with friends, here’s the good news: it doesn’t have to be complicated. With the right destination and the right support, a group trip can be smooth, energizing, and surprisingly easy to pull off.

And no one has to be the planner. 

Las Catalinas was designed for exactly this kind of travel, and at Las Catalinas Doorway, we love being the planners. In our walkable coastal town, where everything is close, where villas keep your group together, and where your partner concierge crosses the Ts, dots the Is, and coordinates all the logistics so you don’t have to. Pair that with May’s lighter crowds, better pricing, and the significant perks of early green season, and you have the perfect moment for a group escape.

Why May Works for Group Travel

May is one of Costa Rica’s most underrated months for friends traveling together. It’s the beginning of the green season, which means you’ll enjoy bright mornings, warm temperatures, and only the possibility of short afternoon rains that cool everything down. The weather is still great for the beach and water sports, and mornings are especially beautiful.

Even better, May sits between Spring Break and summer vacation, which means you’ll miss the school-age crowds. The coast feels relaxed and open, and rates are often lower than in high season. That combination of great conditions and shoulder season timing makes it easier to find the right villa, the right travel dates, and the right rhythm for your group.

This is also when spontaneous trips work. Found a screaming deal on airfare? Great news: With shorter booking windows for May, February is when many groups start saying, “Should we just do it?” 

Yes, you should. You definitely should.

The Truth About Group Travel: People Want Connection, Not Complexity

Every group has different interests, different energy levels, and different ideas of what a perfect day looks like. That’s normal. What matters is choosing a place where all of those differences can work together instead of against each other.

In Las Catalinas, your group isn’t scattered across town or reliant on cars. Once you’re here, everything flows. You walk to the beach. You walk to dinner. You walk to your morning coffee. You meet on terraces, in plazas, on the beach, and at your villa’s private pool. You naturally come together because the environment makes it effortless.

And with Las Catalinas Doorway, you’re not the one coordinating any of that togetherness. Your concierge becomes the built-in problem solver who handles the moving parts and meets your group where you are.

Let Your Concierge Do the Heavy Lifting

Most group trips fall apart because someone gets stuck managing logistics and planning conflicts. Here, that pressure disappears. With Las Catalinas Doorway, your concierge helps with:

• Choosing the right villa based on group size, layout, and preferences (a.k.a. Private bathrooms for all? We got you!)
• Organizing airport transfers with seamless airport pickup for your whole group, even if you’re arriving on different flights
• Making restaurant recommendations and reservations, fully accounting for your group’s dining preferences
• Planning daily activities that match your group’s energy, skills, and travel style
• Scheduling excursions around weather patterns
• Coordinating special at-home experiences, from massages to mixology classes

Think of it as removing the stress from the group chat. Instead of debating options for days, you send your concierge a few notes, and they tailor everything around what your group actually wants.

Stay Together in Group-Friendly Villas

The easiest way to keep Costa Rica group travel simple is to stay under one roof. At Las Catalinas Doorway, we have a curated collection of villas designed for groups who want shared spaces, privacy when needed, good kitchens, and plenty of room to gather.

You’ll find:

• Large terraces with ocean or town views
• Private pools
• Indoor-outdoor living spaces
• Multiple bedroom suites for comfort
• Easy access to the beach, plazas, and trails

For smaller groups, select flats work beautifully for two couples or a small group of friends traveling together. They offer the same walkable convenience and comfort, just in a cozier layout.

Wherever you stay, you’ll never need a car to get around town. Everything is walkable, and the car-friendly streets in our downtown core make it natural for groups to meet, wander, and explore together.

 Activities That Groups Actually Love

Group travel gets easier when the activities naturally fit your range of personalities. Here are some of the guest favorites that work especially well for May:

 Group SUP or Kayaking

Calm morning water sets the perfect tone. You can head out together, paddle at your own pace, and enjoy coastal views without needing lessons or special skills.

 Mountain Biking on World-Class Trails

Las Catalinas is a global draw for riders. Over 22 kilometers of single-track trails wind through tropical dry forest with flowy curves, shaded valleys, and Jurassic Park-style scenery. You can rent bikes in town or join a guided ride. It’s a memorable adventure for beginners and seasoned riders alike.

 At-Home Chef or Taco Night

Some of the best group travel moments happen at home. Your concierge can organize a private chef, a casual taco night, or even a bartender who creates cocktails while you relax on the terrace.

Tennis and Pickleball

Las Catalinas’ courts are an easy place to gather and play. You can take a group lesson, split into friendly matches, or start your morning with a high-energy cardio session.

A Sunset Boat Day

One of our most popular group experiences, a boat day blends connection, adventure, swimming, coastal views, and sunset moments that your whole group will remember.

Plan a Group Escape That Feels Effortless

When you choose the right destination, planning becomes the easiest part of the trip. And May is the moment when Las Catalinas feels open, vibrant, affordable, and ready to welcome groups who want to travel without complication.

This is a place where connection happens without effort. Where people who haven’t traveled together in years find their rhythm again. Where conversations stretch long into the night because nobody’s rushing off or dealing with complicated transport plans.

So if your group has been talking about a getaway but hasn’t found the right time or the right place, this is your sign. Do it. This year. Right now. Get the ball rolling! Start the group chat. Coordinate your calendars. Book your airfare. And start dreaming about those late-night conversations, shared laughter, and an epic trip that will have you reminiscing for years to come.

Then, lean into effortless group travel planning. Share your travel dates, and our concierge will create a seamless group itinerary for your 2026 escape.