50th Anniversary Trips to Costa Rica: Best Ideas, Itinerary & Luxury Villas for a Milestone Celebration
Some vacations are relaxing. Others are exciting. But 50th anniversary trips—the kind that honor five decades of love—are in a category of their own. These aren’t just vacations. They’re legacy experiences. And they deserve a destination that feels as remarkable as the life you’ve built together.
If you’re starting to plan a once-in-a-lifetime wedding anniversary trip, chances are you’ve considered the usual suspects: Hawaii, Paris, the Amalfi Coast, maybe even an African safari. But if you want a destination that’s equal parts luxury, adventure, and soul—Costa Rica offers an anniversary escape unlike any other.
Whether you’re planning a romantic trip for two or a week-long luxury villa experience with your entire family, this guide reveals why Costa Rica is one of the best places in the world to celebrate a 50th wedding anniversary—plus exactly what to do, where to stay, and how to make it unforgettable.
In this post, you’ll uncover:
- Why Costa Rica is one of the best destinations in the world for a 50th wedding anniversary trip
- The top anniversary trip ideas that combine relaxation, connection, and luxury
- Where to stay: a behind-the-gates look at Villa Punto de Vista, Costa Rica’s premier private villa estate for family celebrations
- What to do in Manuel Antonio, from sunset catamaran cruises to rainforest adventures and hands-on cultural experiences
- How to create a seamless multi-generational vacation with tips for planning, pacing, and personalization
- A full 7-day luxury itinerary for celebrating your 50th anniversary with style, intention, and unforgettable moments
Why Choose Costa Rica for Your 50th Wedding Anniversary Over a River Cruise or the Amalfi Coast?
Costa Rica is a masterclass in contrasts: untamed rainforest and pristine beaches, decadent dining and barefoot simplicity, meaningful experiences with family and serene moments alone. It’s this natural duality that makes it a brilliant canvas for a wedding anniversary celebration.
Compared to other popular destinations like Greece, Mexico, Cape Town, even Baden-Baden, Costa Rica feels alive in a different way.
You don’t just look at beauty here. You touch it. Taste it. Move with it. And best of all, it’s an easy flight from North America, with no need for long-haul logistics or endless flight connections. You can use that time to spend with those you love and have built this life legacy with, instead of days of travel.
It’s a place where every generation can thrive: small kids can splash in waterfalls or play in the surf, while adults indulge in spa treatments, sunset cruises, and five-star cuisine.
Whether your idea of a great trip involves jungle hikes or poolside cocktails, you’ll find it here.
Where to Stay: The Ultimate Setting for a Family Milestone
Skip the all inclusive where you’re sharing space with other travelers and rent a private villa with breathtaking views, wonderful service, and enough space for all your nearest and dearest.
Villa Punto de Vista: Private Estate, Infinite Possibility
For an occasion this special, nothing compares to having your own private estate. Villa Punto de Vista, perched in the hills above Manuel Antonio National Park, is a luxury villa estate that redefines the group travel experience. This is not a hotel stay. This is your own private world.
Accommodating up to 54 guests across two fully staffed villas, the estate includes private pools, an elevator, ocean-view terraces, game rooms for the kids (and kids at heart who love a little fun), and butler service that anticipates your every desire and blows the butler service at resorts out of the water.
It’s the kind of place where your mom, your brother-in-law, and your grandkids can each find their own rhythm and come together effortlessly.
Whether you’re gathering a few loved ones or the entire family, this is where good suggestions become great ones and where “happy anniversary” is more than a toast. It’s a lifestyle for the week (without the pricetag of a private island).
What to Do in Costa Rica for a 50th Anniversary Trip
Here, every day holds a different kind of magic.
These are the types of anniversary trip activity ideas that create connection, laughter, and a deep sense of presence—whether it’s your first time in Costa Rica or your fifth.
Private Catamaran Cruise
Set sail from the nearby Marina Pez Vela in Quepos, just minutes from Villa Punto de Vista, for an unforgettable sunset catamaran cruise along Costa Rica’s Central Pacific Coast. As the boat glides past jungle-covered cliffs and hidden coves, you’ll sip chilled cocktails on deck and watch for dolphins dancing in the wake.
Manuel Antonio National Park
Take a private tour through this wildlife-rich coastal jungle where monkeys leap from the trees and sloths nap overhead. Whether you’re 8 or 80, the park is endlessly enchanting. Check out this post for our naturalist guide’s favorite finds in the park!
Coffee and Chocolate Tours
Costa Rica’s coffee and cacao traditions are woven into the soul of the land. When you’re driving in from San José through the Central Valley to reach the villa, we can help you organize a visit to a high-elevation coffee estate for a tasting experience en route to the coast.
Once settled at Villa Punto de Vista, a day trip to Villa Vanilla Spice Farm, just 25 minutes away, offers a sensory deep-dive into organic cacao, vanilla, and spice production. Walk shaded trails, sip fresh-brewed coffee, and sample decadent chocolate as you take in views that stretch from rainforest to sea. It’s a delicious way to slow down and savor the richness of place.
We can also organize a private coffee and/or cacao experience for you at the villa.
Spa and Wellness Experiences
Cacao ceremonies, aromatherapy massages, oceanview yoga sessions infused with reiki and massage—Costa Rica is an ideal setting to slow down, breathe deeply, and reconnect with your body and soul. We have cultivated a list of world-class wellness providers that help elevate any villa stay with ultimate relaxation.
Cultural Cooking Class
Make arroz con pollo from scratch with a local chef in a hands-on cooking experience that ends, naturally, with a feast. It’s one of the most greatly appreciated moments for families who love great food.
Tips for Planning a Meaningful and Easy 50th Anniversary Trip
Hire a Travel Agent or Book Accommodations with an Included Private Concierge
Planning for multiple generations? Enlist an expert to coordinate tours, transportation, dining, and surprises. At Villa Punto de Vista, your pre-arrival concierge handles everything from airport transfers to anniversary cake orders so you don’t have to hire any external travel planner or concierge—we take care of all of it for you, no added expense!
Design with All Ages in Mind
Add variety to your itinerary: animal sanctuaries like Kids of the Rainforest for the kids, beach downtime for tired travelers with an epic beach picnic setup and chairs already laid out and waiting, and solo free time for couples to reconnect. You don’t need to do everything together to have the perfect trip.
Build in Ritual and Celebration
Set aside one night for a formal dinner, vow renewal, or family toast. It doesn’t have to be extravagant—just intentional.
Your Luxury 7-Day Itinerary at Villa Punto de Vista, Manuel Antonio
Here’s what one week of memory-making could look like at Villa Punto de Vista, where every detail is customized for your celebration.
Day 1: Arrival + Champagne Welcome
Your anniversary journey begins the moment you land. A private driver whisks your group to the estate, where chilled champagne and tropical florals await.
After check-in, explore the villa’s oceanview terraces, let the kids dive into the infinity pool, and unwind over a chef-prepared welcome dinner on the open-air rooftop, lit by flickering candles and the warm Pacific breeze.
Day 2: Jungle Serenity + Playful Joy
Mornings begin slow here. Sip Costa Rican coffee as toucans chatter nearby. Adults enjoy a sunrise yoga session or rooftop massages, while younger kids venture to the animal sanctuary for sloth sightings and butterfly gardens.
In the afternoon, the entire group heads to the beach for swimming, sandcastle competitions, and coconut drinks before returning to the villa for a casual barbecue dinner and rooftop stargazing.
Day 3: Sunset Catamaran + Champagne at Sea
After a leisurely breakfast and time to relax by the pool, your group boards a private catamaran. Set sail along the coast, cocktails in hand, spotting whales, dolphins, and dramatic cliffs.
As the sun sinks behind the horizon, you raise your glasses to 50 years of love and legacy. Dinner back at the villa is light and relaxed, ending with locally made chocolate and laughter under string lights.
Day 4: National Park Adventure
Today is for exploration. Choose your pace: a naturalist-led tour of Manuel Antonio National Park, ziplining through jungle canopies, or snorkeling at a nearby cove.
Lunch in town offers a taste of authentic Costa Rican fare—grilled fish, plantains, and fresh juice—before returning to the villa for a chef’s paella dinner served family-style.
Day 5: Culture and Cuisine Immersion
Dive into Costa Rica’s rich culinary culture. Begin with a visit to a coffee plantation or cacao farm, then return to the villa for a hands-on cooking class. Everyone—from grandkids to grandparents—joins in the preparation. Dinner is the reward: a shared feast created with your own hands, paired with curated wine and lively stories from the day.
Day 6: Celebration Night to Remember
The morning is open—some nap, some journal, some walk the nearby trails.
In the afternoon, a professional photographer arrives for a family portrait session on the estate’s grand staircase and sunset terrace.
As evening falls, the final anniversary dinner begins: a five-course tasting menu, private guitarist, candlelight, speeches, and a custom cake. You toast not only to the last 50 years—but to the joy of being here, together.
Day 7: Farewell Brunch + Departure
On your final morning, a farewell brunch is served on the villa’s rooftop terrace, with fresh pastries, pico de gallo, a sprawling tropical fruit platter, and, of course, views of the glistening sea. If you visit from July to October, you may even see whales during whale season!
Frequently Asked Questions About Planning 50th Anniversary Trips
What are the best destinations for a 50th anniversary trip?
Top picks include Costa Rica, Hawaii, Greece, the Amalfi Coast, and river cruises through Europe. Costa Rica stands out for its blend of luxury, nature, and ease of travel.
Is Costa Rica good for a 50th anniversary family trip?
Yes. With private villas like Villa Punto de Vista, Costa Rica offers an ideal setting for multigenerational groups, with activities for kids, adults, and couples alike.
How much does a 50th anniversary trip to Costa Rica cost?
Pricing varies by group size and season, but private luxury estates like Villa Punto de Vista offer inclusive packages with concierge planning, staff, and unforgettable views.
If you get in contact with us, our concierge and sales team (yes, real people!) will put together a formal quote for you based on your desires.
What’s the best time of year to visit Costa Rica for an anniversary?
December through April is the dry season and ideal for beach weather, while July–October is best for whale watching in Manuel Antonio.
Celebrate the Legacy of Your Love
In a world where time often slips by unnoticed, marking your 50th wedding anniversary with a destination like Costa Rica is a bold and beautiful declaration: that love is worth celebrating, always.
It’s easy to be swayed by the glitter of cruise lines, the charm of theme parks, or the history of France and Greece. But what Costa Rica offers is presence. Depth. Connection. A reminder that the best places aren’t just beautiful—they’re soulful.
So whether you’re traveling with your kids, friends, or just each other, let your anniversary be more than a milestone. Let it be a movement. One that honors your past—and plants seeds for all that’s still to come.
Here’s to love. Here’s to Costa Rica. And here’s to you.
Would you like help planning your 50th anniversary at Villa Punto de Vista?
Let our concierge curate the entire week for you. Because you’ve spent 50 years building something beautiful, it’s time you were celebrated.
Explore rates and dates and book your 50th anniversary trip today!
