Booked: Multigenerational Family Trip to Costa Rica

If you’re looking for an adventurous vacation filled with lush rainforests, stunning beaches, and abundant wildlife, then Costa Rica’s a great choice for your family.

My family and I spent some time in the country to take advantage of the kids’ Christmas Break and to escape the chilly Canadian winter.

The five of us love spending the holidays with extended family, so we decided to bring them along with us on this trip. With my parents and my sister’s family, we had a total of six adults and six kids ranging in age from 4–68.

Planning group travel is always a bit challenging as you have to try to work around everyone’s schedule and their points/miles balances or, sometimes, lack thereof.

Since we were travelling with three generations of family, we also had to find activities suitable for everyone. My parents aren’t the adventurous types, and my sister’s family likes to take it easy, whereas I personally like to hop around and see as much as I can.

With these factors in mind, read on to find out how we planned it all.

The Trip

Costa Rica is a country in Central America blessed with natural wonders. Being close to the equator, it’s hot and humid year-round, and it has a dry season and a wet season. The dry season runs from mid-November to April, and the wet season runs from May to November.

Areas within the country also have their own microclimates. Even if you’re travelling during the dry season, make sure to pack rain gear as you can still experience short periods of rain randomly.

The dry season coincides nicely with Christmas Break and March Break for school-aged kids. The only disadvantage to travelling at this time is that this also coincides with Costa Rica’s peak travel season, so flights and hotels often cost more.

For this reason, and for additional reasons I’ll explain later in the post, my tip is to book hotels and flights early.

Costa Rica is a big country, with several hours of driving between some destinations, so plan your time there accordingly. With 11 nights in the country, we decided to divide our time between the rainforest and the beaches.

After landing in Liberia to start our trip, we headed to the small town of La Fortuna, where we spent three nights.

Nestled at the base of the Arenal Volcano, it serves as a great base to visit Arenal Volcano National Park, where you can hike trails to catch breathtaking views.

If long hikes in the humidity aren’t quite your thing, then visit the hanging bridges instead. There are several of them in the area that allow kids to be immersed in the heart of the rainforest while overlooking the canopy and traversing a network of suspended bridges.

It’s a fun way to observe the flora and fauna of the region and still catch great views of the volcano. For a more in-depth visit, you can also hire a guide to go with you.

To beat the heat, there are many water-based activities in the area, including water rafting and river tubing. If your kids are thrill-seekers, then book a canopy tour to go zip-lining through the rainforest or an off-road ATV tour through rivers and hilly terrain.

For something more toned down, visit a chocolate or coffee plantation for a tour, or join a tour to a local farm to learn about their traditional farming practices.

For the animal lover, take a guided sloth tour to see these iconic creatures in their natural habitat, or sign up for a night tour if your kids enjoy frogs, snakes, and other creepy-crawlies. Consider visiting the Costa Rica Wildlife Sanctuary for a great hands-on learning and volunteering experience.

After a day of adventuring, you can relax in one of many hot spring parks or resorts in the area. Better yet, book a hotel that includes one on-site so you don’t have to pay a separate entrance fee to experience it, or alternatively, you could just visit a river downstream from a hot spring on your own.

If time permits, visit Monteverde for a day or two to see the cloud forest, a unique ecosystem that comprises only 1% of global forests.

Monteverde is often seen as the quieter, more rural and rustic alternative to La Fortuna. It is a three-hour journey to get there from La Fortuna. If you choose to go for more than a day trip, look into a jeep-boat-jeep option to break up the drive.

After our first three nights in inland Costa Rica, we continued our trip with a move to the coast to spend four nights in the Playa Conchal area and relax at one of the all-inclusive resorts there.

While in this area, our goals were to see some nesting turtles, try our hand at surfing, and maybe join a crocodile boat tour.

After this, but before heading back to San José, we visited Playa Herradura near Jaco for a few nights.

This served as a good base to explore Manuel Antonio National Park, often considered one of the most biodiverse parks in the world, and to take a day trip to the bohemian Montezuma Beach or visit Tortuga Island for a taste of paradise and some of the best snorkelling in the region.

Even the journey to the latter two destinations can be exciting, as you may be able to see dolphins, whales, and manta rays while crossing the Gulf of Nicoya.

Of course, our itinerary is just one example of what can be planned. There are so many additional destinations in Costa Rica worth visiting that a single post couldn’t come close to covering them all.

Many of these destinations also offer similar attractions and activities, so if you don’t have enough time to do something while you’re in one location, just make arrangements to do it at another location.

Given the diversity of amazing opportunities and activities, do some research and see what will suit your family best.

The Flights

There are two major airports in Costa Rica: Juan Santamaría International Airport in San José (SJO), and Daniel Oduber Quirós International Airport in Liberia (LIR).

Knowing this, rather than just looking at round-trip flights, consider flying into one airport and out of the other if you’ll be moving around the country, as it may save you time on the road.

If you’re flying from Western Canada, it’ll require at least one stopover to get to Costa Rica. If you’re coming from Eastern Canada, Air Canada and WestJet both offer regular non-stop flights from Toronto, and Air Transat offers non-stop flights from Montreal.

Flights can be expensive, costing an average of $800 (CAD) for a round-trip fare.

Thankfully, there are often flight deals, and these can bring a round-trip flight down to $400 (CAD).

If you find yourself in the unfortunate situation of needing to book a flight during Christmas Break when there’s unlikely to be a flight deal (much like my situation), then there are a few options in the award redemption space.

Flying from Toronto, the best options for point redemptions are through Aeroplan, WestJet Rewards, and American Airlines AAdvantage.

A flight from Toronto to Costa Rica comes in at just over 2,300 miles, which puts in the third distance band for Aeroplan redemptions within North America.

While finding flights on Air Canada within the listed point range is possible, during peak travel times, the redemption costs were going for double this amount of points.

Thankfully, if you don’t mind a short stopover, you can still redeem through Aeroplan for multiple tickets on Avianca for 12,500 points one-way from Toronto to San José. This takes advantage of fixed pricing with partner airlines through the program.

Also, if you book early enough, you may luck out with an involuntary schedule change. This was something I was banking on when I booked our tickets this way, and it’s what actually ended up happening.

In the end, we were able to swap onto Air Canada’s direct flight back to Canada for 12,500 points per passenger instead of the 30,000 points it would have otherwise cost us.

Other award options include redeeming through American Airlines AAdvantage program for 11,000 miles one way from Toronto to Liberia, or if you have enough WestJet dollars and a companion pass, you can leverage those to bring down the cost of your flights.

The Hotels

There’s an array of accommodation options in Costa Rica, with many that are economically priced and several options that can accommodate families of five in one room.

Outside the coastal regions, you’ll mainly find local stand-alone hotels, some of which are five-star properties that can be booked through our in-house luxury travel agency, Prince Collection.

In La Fortuna, we booked our stays at a couple of independent hotels: Noah’s Forest by Tifakara for $414 (USD) per night and El Silencio Del Campo $413.50 (CAD) per night before taxes.

Since I wasn’t booking with a hotel chain that I had loyalty status with, I booked the first property through Expedia for TD and used my TD Rewards points to offset the cost by 50%.

I booked the second property through to make use of a couple of my free night vouchers to reduce the cost of my stay by 65%.

For the rest of our trip, we booked at a couple of Marriott properties.

We decided that an all-inclusive would fit the needs of my extended family perfectly, so we booked at The Westin Reserva Conchal, an All-Inclusive Golf Resort & Spa, for several nights, followed by Los Suenos Marriott Ocean & Golf Resort.

For these bookings, we made our reservations close to when the booking calendar opened and pricing was the most optimal. Since then, cash rates have only increased, thought this isn’t always the case. Plus, given the option of free cancellation, I always try to book early for this reason.

For our nights at Los Suenos Marriott Ocean & Golf Resort, we booked for $227 (USD) per night before taxes & fees; I later saw the rate at $379 (USD) per night.

I also looked at using Marriott Bonvoy points as an option, but the rates weren’t favourable at all, with the rooms costing 42,000–76,000 points per night.

Redemption rates at the Westin Reserva Conchal weren’t any better, ranging from 77,500–122,500 points per night for up to two adults and two children.

Given that we value Marriott Bonvoy points at 0.6 cents (USD) each, and I secured a room for $567.20 (USD) per night I opted to save my Bonvoy points for a better redemption in the future.

One of the benefits of travelling with a large group is that you can sometimes shuffle the number of guests amongst the families so that larger families can fit in a cheaper room type.

For example, on Marriott’s website, I can book two adults and two children into their Deluxe Junior Suite for $1,017 (USD) plus taxes and fees.

However, adding a third child automatically bumps the lowest bookable room category up to a Family Junior Suite for $1,307 (USD) plus taxes and fees.

Comparatively, placing an extra child in the grandparents’ room only increased their room cost by $79 (USD) before taxes and fees, compared to the $280 (USD) it would have cost to move up a room category.

Getting Around

If you’re moving from place to place in Costa Rica, the best and most convenient way to get around is by renting a vehicle. If you’re staying in one area, however, you could definitely get away with not having a vehicle as many attractions offer transportation to and from hotels.

Uber operates in Costa Rica as well, but only in the major cities. Many of the smaller coastal towns won’t have Uber available, and taxis may be difficult to find as well.

Since we’re travelling as a party of 12, I opted to hire a shuttle transfer service. To arrange transfers for our group from the airport in Liberia to La Fortuna, Playa Conchal, Playa Herradura, and finally to San José cost us $1,500 (USD) total, including fees for extra time spent during stops and meals enroute.

Although you may not save a ton of money using paid shuttles, they are a comfortable and easy way to travel with air conditioning, water, and sometimes even free Wi-Fi.

With the shuttle service, you don’t need to worry about car insurance, navigating unfamiliar roads, or refilling the gas tank. Also, I’ve been told that navigating the roads going into La Fortuna in particular is not for the faint of heart.

Keep in mind that all children under the age of 12 require a car seat or booster seat. Most shuttle companies will include them free of charge; however, some will charge extra for them. If you can, bring your own.


If you’ve got a nature lover and thrill-seeker in your family, and you don’t mind the heat, add Costa Rica to your bucket list. You’ll have endless opportunities for fun, learning, and relaxing that you won’t find anywhere else.

We’re looking forward to our upcoming trip, and will be sure to report back with some more specific recommendations and property reviews once we’re back.

1 Comment
  1. Rebecca R

    I’m inspired

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