How to Plan a Multi-Generational Family Vacation in Costa Rica 

Three generations, one private estate on Costa Rica’s Pacific coast, and a week the whole family will talk about for years. Getting there takes a little more planning than a typical getaway, and the payoff is worth every bit of it. 

Anyone who’s planned a multigenerational trip knows the real challenge isn’t choosing Costa Rica. It’s getting three generations, three schedules, and one very busy spreadsheet to cooperate. 

A multi-generational family vacation in Costa Rica comes down to four decisions: who sleeps where, how each day is paced, how meals are handled, and who does the planning. Get those right, and grandparents, parents, and kids each enjoy the trip on their own terms. 

This guide covers how to make that work, from arranging the rooms to building a daily rhythm everyone can enjoy, and how a private estate like Villa Firenze takes most of the effort off your plate. 

What makes a multi-generational family vacation work? 

A multi-generational vacation works when every generation gets both shared time and time on their own. That usually means a few fixed moments each day, such as breakfast and dinner together, with flexible time in between for different energy levels and interests. 

More families are discovering this firsthand.  

According to AARP’s 2026 travel research, 26% of family trips planned by travelers aged 50 and over are multi-generational, and 76% say strengthening family bonds is a top benefit of traveling with family. 

Those bonds grow in small moments. A grandmother and grandchild spotting a toucan together. A father teaching his son to swing a golf club. A long dinner where the stories run late. A well-planned multigenerational family vacation simply makes room for them. 

Plan the rooms before you pack 

The rooming plan is the first decision that shapes the whole stay. Base it on sleep schedules and mobility first. Here’s an arrangement that works well at Villa Firenze, though every family can adapt it. 

Space	Works well for	Why
Lower Master Suite + adjoining convertible room	Parents with young children	Ground level and facing the pool, with a connecting door to a second sleeping space
Dome Suite	Grandparents	Opens onto the Italian-style courtyard, close to where meals happen, on a step-free route
Upper Master Suite	Parents or a couple wanting a retreat	Raised above the courtyard, with its own terrace
Upper Patio Suite	Teens or young adults	At the far eastern edge of the villa, a little apart from everyone else

With this setup, little ones nap in peace, grandparents stay close to the heart of the house, and teenagers get the independence they crave.  

Take a closer look at the Villa Firenze luxury suites for the full layout. 

Build a daily rhythm with together time and your own time 

The most relaxed family trips share one quality. They don’t try to do everything together. Two or three fixed moments each day bring everyone back together, and the rest of the day stays open. 

Here’s how a single day might unfold. 

Time	Grandparents	Parents	Kids and teens
Morning	Coffee on the terrace, birdwatching from the garden benches	Optional yoga on request	Sleep in, then the pool
Together	Breakfast in the courtyard	Breakfast in the courtyard	Breakfast in the courtyard
Midday	Rest in their suite	Off-property trip, like a boat outing or fishing	Join the trip or play X-Golf
Late afternoon	By the pool	By the pool	Golf cart rides with an adult driving, games
Together	Chef dinner in the courtyard, then the fire pit	Chef dinner in the courtyard, then the fire pit	Chef dinner, then a movie night

Each generation follows its own rhythm, and the day still ends with everyone around the same table. 

One table, every appetite 

Mealtimes are where a family reunion comes together, and also where it can unravel. At Villa Firenze, you share dietary needs and preferences before arrival, and our chefs plan meals around the whole group, from children’s meals to gluten-free requests. 

Expect fresh local fish, tropical fruit at breakfast, and mostly organic, local ingredients. Learn more about our private chef experience. 

The estate is also fully staffed throughout your stay, with two managers, two housekeepers, and two maintenance staff on-site. That means no one in the family has to play host. 

Experiences every generation can share 

On the estate 

Days at the villa offer something for every age. The 50-foot infinity pool, an X-Golf simulator tournament across generations, movie nights, and evenings by the fire pit all bring the family together.  

Golf cart rides around the grounds are a favorite, with a licensed driver over 18 at the wheel, as Costa Rican law requires. Families with young golfers will enjoy these tips on golfing in Costa Rica with children. 

Beyond the gates 

A private boat excursion, included in the Elite package, is one outing grandparents enjoy as much as the kids. Teens and parents can add ziplining, which typically costs around $75. 

The concierge team can also book a sportfishing charter from nearby Los Sueños Marina. Most operators recommend children be at least 5 years old, though private charters can be shortened or customized for families.  

Charters range from roughly $750 to $4,000, depending on trip length and how far offshore you go. Our guide to Los Sueños fishing has more detail. 

Good to know for young children and older relatives 

Villa Firenze is a gated, secured estate with cameras and a private entrance. It isn’t a childproofed home, however, so plan supervision as you would in any multi-level home. 

• There are stairs inside and outside the villa. 

• The pool isn’t separately fenced. 

For grandparents, the space was designed so that every generation can enjoy it together. 

• The route between the suites, pool, courtyard, and dining area is step-free. 

• The golf cart is available to take guests around the grounds. 

For families with babies, a little planning goes a long way. 

• The villa doesn’t provide cribs or high chairs, so plan to bring your own. 

• The concierge team can arrange a babysitter or nanny on request. 

Find out more about why Villa Firenze is a family-friendly villa. 

Let the concierge team do the planning 

On most family trips, one person ends up organizing everything. Remember the relative with the spreadsheet? Consider them officially retired.  

Here, the concierge team takes that role, handling excursions, transport, chef menus, and special requests. 

The Signature package adds itinerary planning and a dedicated concierge, which is especially useful for a group of 8 to 10. Read more about planning a Villa Firenze family reunion. 

Which package suits a multi-generational group? 

Think of our three stays as Costa Rica family vacation packages built around one private estate.  

Most families find their fit in the Firenze Escape or Signature package, while Elite suits groups who want the helicopter transfer and the private boat excursion.  

Every package starts at four nights, and the villa sleeps up to 12, comfortably hosting 10. 

Every generation, one courtyard table 

A multi-generational trip works when there’s enough space and flexibility for everyone, with a few fixed moments that bring the whole family back together.  

Years from now, those are the moments your family will remember. The sunrise coffees, the poolside afternoons, and the long dinners in the courtyard. 

When you’re ready to bring every generation together at a family reunion villa built for exactly that, Plan Your Family Reunion at Villa Firenze. Check availability or contact the concierge team at concierge@villafirenzecr.com. 

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