20th Anniversary Vacation Ideas: Costa Rica Edition

• July 16, 2026
• Christien
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Some anniversaries call for a nice dinner out. But your 20th anniversary?

That calls for an experience. The kind that blends romance, adventure, relaxation, and a setting worthy of two decades of building a life together. Of trials and tribulations, joys and struggles, highs and lows. It all deserves to be celebrated.

If you’ve been going down a Google rabbit hole searching for 20th anniversary vacation ideas, you’ve probably already seen the stereotypical go-tos like the Amalfi Coast, Banff National Park, the Greek Islands, Key West in the Florida Keys, maybe even a private island or an African safari.

They’re stunning, yes.

But if you’re looking for a romantic getaway that feels intentional, adventurous, and deeply restorative, Costa Rica is one of the most meaningful anniversary trip destinations in the world.

Speaking from personal experience, Costa Rica has a way of slowing you down enough to awaken those butterflies in your stomach that you had at the very beginning of your relationship.

The guests who come to our villas in Manuel Antonio to celebrate their milestone anniversaries always share how deeply connected they feel after escaping the rat race for a week and indulging in the simple things that are true luxury: time with family and friends, culinary delights, vibrant culture, adrenaline-pumping adventure, and the opportunity to create memories, stress-free.

In this guide, you’ll find the best anniversary trip ideas in Costa Rica, romantic experiences, and where to stay for your 20th anniversary celebration. 

Plus, we’ll share decision tools, sample itineraries for travel inspiration, and the most common FAQs travelers ask before staying with us for their anniversary trip.

Why is Costa Rica a good place to go to celebrate your 20th anniversary? 

equally magical for milestone anniversaries. 

Couples come for the beautiful beaches, the wildlife, the adventure, but they leave grateful for the connection and ease that lead to the perfect trip. 

Here are a few reasons why couples love Costa Rica:

It’s romantic without trying.

You don’t have to search for beauty; it surrounds you. 

Golden sunsets that turn to purple over the Pacific, quiet coves draped in warm ocean breezes, and rainforests that come alive at all hours of the day with wildlife you’ve never seen before. 

Everything slows down here, making it easy to reconnect, linger, and actually feel present with each other.

It gives the best of every world: adventure, romance, relaxation, and culture.

Whether you’re celebrating your anniversary just the two of you or traveling with friends and family, there’s a little something for everyone in Costa Rica. 

When guests stay at Villa Punto de Vista, they make their celebration of love a week-long affair with friends also celebrating or family they’ve built along the way. 

Not everyone always wants to do the same thing, so the villa’s pre-arrival concierge will help organize excursions, spa treatments, cultural classes, and more, depending on what your group is looking to do.

It’s easy to get to with plenty of direct flights from the U.S. to Costa Rica.

Travel to your final destination is never the fun part of the trip. But Costa Rica makes it easy. 

There are plenty of direct flights from hubs throughout the United States to both San Jose’s Juan Santamaría International Airport (SJO) and Liberia, Guanacaste’s Daniel Oduber Quirós International Airport (LIR). 

Anniversary trip ideas: Where should you stay?

Choosing the right home base sets the tone for the whole celebration. After 20 years together, most couples want something more private, more meaningful, more “this is just for us”.

Below is a decision guide to help you choose what type of accommodation suits your style:

Should you book a private fully-staffed villa or a resort in Costa Rica?

Ask yourselves:

Our honest take:

After seeing dozens of couples celebrate their milestone anniversaries in Costa Rica at our villa, we can confidently say that private villas create a level of intimacy and personalization that even the most intimate resorts and luxury hotels simply can’t touch. 

Guest Matt P. shared: 

“I can speak for all our guests when I say the week we spent at Punto de Vista was magic. The villa, the setting in the jungle, the proximity to the awesome beach, the wildlife, the natural beauty, and last but not least the service was ALL well above exceptional and much better than any 5-star hotel I’ve ever stayed at. 

We had our anniversary dinner on the villa’s panoramic rooftop with live local music. The dinner and setting made the night magical. 

I also wanted to say both the villa’s 24 hour concierges – Oliver and Jossue were huge contributors that made our stay perfect, these two make any wish come true.”

What should you do on an anniversary trip to Costa Rica?

Here are a few of the activities our guests love, whether they’re looking for romance, quality time to connect with family, active adventures, or authentic experiences that share the essence of pura vida.

1. Charter a private catamaran for the day or go ziplining

Gather your entire family on a private catamaran for the day. 

The team will bring you over to Marina Pez Vela to greet your private vessel to take you out on the Pacific. Spend the day slipping into hidden coves and watching dolphins skim the bow. During whale season, you may even spot a few baby humpbacks. 

A chilled bottle of something celebratory at sunset is a necessary end to the experience, of course.

If your family prefers a bit more adrenaline, go ziplining or canyoning in the lush treetops of the local jungle! 

2. Indulge in an in-villa spa day

Is there anything more romantic than a rooftop couple’s massage during a thunderstorm, listening to the sounds of the jungle and the patter of the rain on the shingles? There’s no need for spa music when you’re getting a massage in Costa Rica. 

At Villa Punto de Vista, we offer private spa experiences throughout the villa, whether on the open-air rooftop or in the spa room with Pacific Ocean views at Villa La Isla. 

Your pre-arrival concierge will ask what style of treatment you want and what your preference is to ensure it’s a romantic, soul-stirring, luxury spa day experience, without having to set foot outside your private villa. 

3. Enjoy a private beach picnic with a personal photographer

While Costa Rica is much more than a beach vacation, it’s not complete without a beach day! Our team will set up beach chairs and service for the ultimate beach day just down the hill from the villa.

We work with talented local photographers in Manuel Antonio and the surrounding area who can join before the day begins to take romantic photos of you and your partner or family photos. Better yet? Both! 

4. Learn the art of Costa Rican cacao and coffee

Costa Rica is one of the most iconic destinations in the world for coffee and cacao, and that part of our culture is meant to be explored! 

If you want to stay at the villa, we can bring in Mama Cacao for an intimate workshop, like an introduction to chocolate making, including the rich history of cacao in Costa Rica, or a guided pairing with chocolate and coffee or wine tasting.

If you want immersive exploration, we can bring you to Villa Vanilla Spice Farm, where you can walk the farm, sip fresh brews, taste artisan chocolate and ice cream made with fresh vanilla harvested from their trees, and learn about rich Costa Rican history.

5. Take a waterfall hike before a private dinner

Our guests love excursions to Nauyaca Waterfalls, which are just an hour’s drive from the villa. A professional guide will lead you and your family and friends through lush rainforests with hiking trails where you may spot frogs, sloths, tens of bird species, and more, before you reach the cascading falls for a refreshing dip. 

Drive through charming towns that give you a feel for Costa Rica before arriving back to the villa later in the day with a chef ready to prepare your favorite meal. 

6. Renew your vows with your nearest and dearest in attendance

While some just want the memories and adventure, others want to make it more sentimental by renewing their vows. 

Your villa team can organize an intimate beach vow renewal or a large party, complete with a DJ and dancing in the ballroom until the sun comes up; it just depends on your unique vision for commemorating 20 years and committing to the next stage of life together! 

7. A day of nothing but poolside lounging and snacks

The simplest idea, but often the one couples remember most. Especially when you’ve raised kids, built careers, and finally have a moment to breathe together.

Our team puts together a pretty incredible pool day, complete with bartender-crafted cocktails with fresh tropical fruit, floating fruit trays with exotic sweet treats, catered tapas to nibble on, and floats galore for all ages. 

A sample 5-night anniversary trip itinerary: Beautiful beaches, culinary delights, and adventure

Below is a curated six-day, five-night anniversary itinerary that blends romance, adventure, culture, and a few indulgences you didn’t know you needed.

Day 1: Arrival and Rooftop Welcome

When you and your loved ones get off the plane in San José, a private driver is waiting with water and chilled towels for the adventure to the coast.

As you drive down the rolling hills to reach the villa, you see a slice of the Pacific. The doors to the villa open to your butler team waiting with a welcome cocktail made with passion fruit, mint, and a hint of tropical rum.

After your bags are brought to your villa suite, you relax by the pool, jets relieving any tension you acquired on the flight. 

A chef-prepared dinner awaits beneath the swaying rooftop lanterns. 

Erick, our in-house sommelier, joins you to lead you through a flight of Latin American wines paired with each course. Each chosen to honor places your love has traveled over the last two decades.

After dinner, you rest early, ready for a week of love and adventure. 

Day 1 Highlights: 

• Private transfer
• Welcome cocktails
• Chef-prepared dinner under the stars
• First toast of the trip with sommelier-led wine tasting 

Day 2: Romance and Relaxation

Some decide to sleep in, while others wake up to join a rooftop yoga class with Mei, or one of our talented instructors. She infuses her yoga classes with massage and Reiki, if desired, for ultimate relaxation so that you can start your day in a zen state. 

After a chef-prepared breakfast, head out for a morning to explore local hot springs before returning for your in-villa spa day, complete with a long afternoon of spa treatments. Think botanically infused oils and the kind of unhurried care you rarely give yourselves at home! 

After, head to the beach for a dip and sunset.

While the rest of your group heads into town for dinner, a candlelit table is set just for the two of you on the open-air rooftop. A linen tablecloth, fresh seafood, and a crisp white wine. Just you, the sound of waves below, and the familiarity of someone who’s known your heart for 20 years.

Day 2 Highlights: 

• Morning yoga
• Hot springs and spa treatments
• Afternoon beach lounge time
• Romantic dinner just the two of you, while everyone else goes out in town

Day 3: Private Catamaran Adventure

A private catamaran awaits at Marina Pez Vela, gleaming under the late-morning sun.As you head out along the coast, the cliffs turn into green velvet draped over stone, and the Pacific shifts into shades of azure that feel almost unreal.

You’ll see playful dolphins racing the bow of the boat, tropical fish and sea turtles flitting just under the surface, and you will bask in the golden rays of sunshine in pure bliss. Lunch is a smorgasbord of Costa Rican specialties like plantains, gallo pinto (a rice and bean dish), BBQ chicken or pork, and of course, all the tropical fruit.

By sunset, you’re tired from swimming in the weightless water, wrapped in towels, sipping champagne as the horizon changes hues. Eat dinner at one of the amazing restaurants in the marina, like Runaway Grill right on the water, and have the team pick you up just in time for a late-night swim.

Day 3 Highlights: 

• Dolphin sightings
• Sunset champagne
• Costa rican lunch on board
• Diving off the boat into clear blue waters 

Day 4: Cultural and Culinary Immersion

After a slow morning at the villa, you head inland toward the hills for a coffee and chocolate experience that feels far more intimate than a typical tour. Villa Vanilla Spice Farm is a fully working farm. 

You’re greeted with a spiced hibiscus drink made with the rich spices and fruits grown right on site, then walk you through the plants and drying racks, sharing stories that make you appreciate your morning cup in a new way. You reach a special overlook where they pull out chocolate and ice cream made with all the goodness you just saw growing on the land right before your eyes. 

Everything tastes beyond description, unlike anything your taste buds have experienced before. 

Back at the villa, the kitchen comes alive. A local private chef sets up for an afternoon cooking class built around Costa Rican staples and your own favorite flavors. Aprons go on, wine is poured, and soon the whole group is chopping, stirring, and laughing.

Dinner that night is a nod to where it all began: your honeymoon. The chef interprets the flavors of that place into a multi-course meal. A beautifully thoughtful way to weave your past into the present.

Day 4 Highlights: 

• Coffee and chocolate tour
• Cooking class
• Dinner inspired by your honeymoon

Day 5: Anniversary Celebration Night

Leave the morning open intentionally. Some of the group will spend it by the pool, others wander down to the beach, and a few opt for a massage or a long nap after shopping in town. 

Just before sunset, everyone heads up to the rooftop for your vow renewal. 

The photographer captures a few portraits while the sky moves from soft gold to coral and purple hues. Then, with the ocean below and your group gathered nearby, you renew your vows. 

It’s simple and relaxed, exactly the way most couples prefer it.

As the evening continues, a guitarist begins playing while dinner is served: a five-course tasting menu designed around the season’s best ingredients and your favorite wine or cocktails.

Day 5 Highlights: 

• Vow renewal
• Private guitarist
• Five-course tasting menu
• Photos at sunset

Day 6: Departures

A final breakfast on the terrace, a last swim, or a few minutes sipping coffee while watching the jungle wake up.

Your driver arrives to take you to the next leg of your adventure or to the airport to fly home. As the coastline disappears behind you and the banana plantations lead the way to San Jose, you’re already talking about the next trip, the next chapter, the next reason to return.

Day 6 Highlights:

• Farewell breakfast
• Private transfer
• Smooth, easy departure

FAQs: 20th anniversary in Costa Rica 

Is Costa Rica a good place for a 20th anniversary?

Yes. Couples choose Costa Rica for milestone celebrations because it offers privacy, year-round warm weather, and activities suitable for every travel style.

What is the most romantic place to stay in Costa Rica?

Private villas provide the highest level of personalization for anniversary trips, offering chef-prepared meals, concierge support, and total privacy.

What should we do during a 20th anniversary trip to Costa Rica?

Private catamaran cruises, spa treatments, hot springs, cooking classes, wildlife tours, beach days, and luxury dinners.

Is Costa Rica a good destination for couples who want relaxation?

Absolutely. Between the spas, secluded beaches, boutique hotels, and rainforest hideaways, it’s one of the world’s most relaxing destinations.

When is the best time to visit?

There’s no bad time to visit Costa Rica! 

For beach lovers who don’t like a rainy afternoon, aim for dry season between November and April. During the green season from May to August, you can expect sunny mornings with a quick afternoon shower. And if you’re looking for a great deal and don’t mind adventuring with some raindrops, visit in September or October during rainy season.

Here’s a full breakdown of each season.

Do we need a car?

It depends! If you stay at a luxury villa like Villa Punto de Vista, transportation is typically included to a certain extent. Most villas will offer a private driver throughout your stay and help you arrange transportation to/ from the airport, as well as for excursions throughout your trip.

Roads in Costa Rica aren’t always the easiest to navigate without prior experience, so for the most effortless trip, we always recommend hiring private drivers or selecting accommodations that provide transportation. 

Is Costa Rica safe for couples?

Yes. The tourist regions, especially Manuel Antonio, are known for safety, friendliness, and excellent tourism infrastructure.

Celebrate your 20th anniversary at a luxury villa in Manuel Antonio, Costa Rica

Twenty years deserves more than a vacation. It deserves memories you’ll talk about for the rest of your lives. And that’s what we’ll help you create at Villa Punto de Vista. 

Costa Rica is one of the top 20th anniversary vacation ideas because it blends romantic beaches, rainforest adventure, and luxury villa accommodations into one seamless experience.

Here’s to your next adventure. Here’s to 20 years. And here’s to everything still ahead.

Our luxury private villas in Manuel Antonio, Costa Rica, tend to book 12-18 months in advance. So, to ensure you’re able to secure your anniversary dates, get in touch today to start planning your milestone celebration! 

Christien

Christien Johnson is the Co-Founder and Managing Partner of Villa Punto de Vista Estate, an award-winning private resort in Manuel Antonio, Costa Rica. With nearly 20 years in luxury hospitality, he has helped make the estate a benchmark for private villa experiences, earning 700+ five-star reviews, 13 consecutive WeddingWire Couples’ Choice Awards (an achievement only secured by the top 3% of venues worldwide) and a vote as the #1 wedding venue in Costa Rica, as well as recognition from Architectural Digest, Condé Nast Johansens, and the Global Choice Awards as the Best Villa in Central America. 

Christien also founded and manages Vista Destinations Luxury Travel Agency, Costa Rica Weddings, and Costa Rica Chefs, and advises brands worldwide on automation and AI in luxury hospitality, shaping the next era of high-touch, personalized travel as a trusted voice in private-estate and transformational travel.