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Our 6 best family award trips -- ever

Jan. 08, 2020
20 min read
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All trips are not created equally. Some go just the way you hoped. Some don't. Still others throw you for loops you never imagined. Leveraging points and miles while taking into account school schedules, kids' illnesses, activities (and moods) can make it a challenge to pull together the "perfect" award-fueled family getaway.

But then there are special trips that exceed your expectations.

Over the past decade of traveling with my own family, some award trips simply worked out better than others -- and they aren't always the ones you might expect. With kids, the trip with the best dollar return for your points isn't always the trip that works the best. Using points and miles for extremely luxurious redemptions to fly Lufthansa first class or Singapore Suites, or to stay at the Park Hyatt Tokyo, can be great, but sometimes a good pool, an ocean or a thrill ride does the trick just as well.

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Bora Bora

As my youngest kiddo grew out of the hardest age to travel, it was time for a bigger family adventure. Maldives was a bit too far, but Tahiti and Bora Bora sounded just right at eight hours of flight time from the West Coast. We could cash in some Hilton Honors points to stay in a big suite next to some of the calmest and most breathtaking water we'd ever seen.

(Photo by Summer Hull/The Points Guy)

Why we loved it

Bora Bora feels like a world away even though it's only a portion of the world away. An eight-hour flight from the West Coast isn't exactly a hop to the next state, but it's only a little farther than flying to Hawaii. What you get in return is a postcard-perfect island paradise that feels decidedly different from anything in the U.S.

As long as I live, I'll remember my children snorkeling in the crystal-clear water with schools of brightly colored fish and even some (friendly) sharks.

(Photo by Summer Hull/The Points Guy)

It didn't hurt that the spa at the Conrad Bora Bora was exceptional and our Hilton elite status (which you can get with just a credit card) translated to free, full breakfast to keep expenses relatively in check.

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(Photo by Summer Hull/The Points Guy)

How to get there

To get to Bora Bora, you'll likely fly from the West Coast to Papeete (PPT) on United, Air Tahiti Nui, Air France or French Bee. Most of those flights, other than the United flight, connect Paris to the West Coast, as Bora Bora and French Polynesia are ... French. Cash fares can be pretty competitive with rates commonly starting at about $300 per direction in economy. If you want to fly on miles, expect economy awards to be much easier to come by than business-class awards, though business-class awards can happen, especially on Air Tahiti Nui (book with AAdvantage miles).

Related: Booking Bora Bora for a family using points and miles

Conrad Bora Bora. (Photo by Summer Hull/The Points Guy)

From PPT, you'll need a short flight on Air Tahiti to get to Bora Bora. If you don't want any more flights, you can skip Bora Bora and take a ferry to nearby Moorea. Either way, we encourage you to experience more than just Tahiti, although it's more than fine for an overnight at the Intercontinental Tahiti near the airport. The flight from PPT to Bora Bora (BOB) will require cash and/or using fixed-value points.

Air Tahiti flight from Bora Bora. (Photo by Summer Hull/The Points Guy)

In Bora Bora, you have many points-friendly hotel options. Availability is tight, but you can use Hilton points as we did at the Conrad Bora Bora (from 89k Hilton points per night), or at the St. Regis Bora Bora (from 70k to 100k Marriott points per night), the Le Meridien Bora Bora (50k to 70k Marriott points per night), etc.

Exploring at the Andaz Costa Rica

If you like a perfect blend of a new passport stamp, outdoor adventures, swimming and beach time, you will be hard-pressed to find a better family destination than the Andaz Costa Rica.

Infinity pools at the Andaz Costa Rica. (Photo by Summer Hull/The Points Guy.)

You'll find a complimentary kid's club, private beach house, multiple infinity pools, easy access to the jungle, horseback rides, waterfalls, nature tours and incredible food and coffee. The coffee itself can't be oversold.

Why we loved it

Your family can be as active or mellow at the Andaz Costa Rica as you want. The complimentary kid's club for children ages 4 and up means that you can mix adult time with family time within the same day without spending hundreds of dollars on childcare. The coffee, drinks and ceviche at the Andaz Costa Rica were enough to make us want to return, but the lush jungle setting, complete with monkeys, sealed the deal and made us repeat visitors.

Taking the Andaz Costa Rica nature tour. (Photo by Summer Hull/The Points Guy)

How to get there

At 20,000 World of Hyatt points per night, you can secure a sleek room at the Andaz Costa Rica without paying the going rate of hundreds of dollars per night. You can transfer points to the World of Hyatt program from Chase Ultimate Rewards and cards such as the Chase Sapphire Preferred Card. Alternatively, you can earn them with the World of Hyatt Credit Card.

Andaz Costa Rica. (Photo by Summer Hull/The Points Guy)

The best value for award flights into Liberia, Costa Rica (LIR), can often be found on Southwest or JetBlue, though the airport is also served by the major U.S. airlines. However, because it is an international destination, traditional airline award charts may require more miles to travel to that zone than the carriers that tie the award price to the cash price of the ticket.

The Magic of Disney World

We did not set out to be Disney people. I only went to Disney World once as a kid myself, but there's no denying we evolved into Disney people as parents. Disney World isn't the only place we go but it sure makes having fun easy.

From the Baby Care Centers in the parks that made diapers and nursing a breeze to Magic Bands and FastPass+ reservations, we go there and just play. I have been to Disney World with a child at just about every age and development stage from 2 months old through the tween years and every single trip has been special and unique.

Fun at every age at Walt Disney World. (Photo courtesy of The Points Guy)

Why we love it

Disney Magic is real -- at least to us -- and as long as you know how to plan to secure your dining reservations at 180 days out and FastPlass+ reservations at 60 days from check-in (30 days if staying off-site), then Disney works. In fact, the Type A planner in me does really well with planning a Disney trip.

Related: Guide to planning a trip to Disney World

A dinner in Cinderella's Castle may sound like a cliche to some who prefer exploring real castles in Europe, but for my 4-year-old being greeted by Cinderella, Aurora, Jasmin, Rapunzel and Tiana ranks higher than a stuffy tour of a real castle ... for now.

(Photo by Summer Hull/The Points Guy)

If anyone in your family has dietary restrictions (and we did for a while), then Disney World jumps even higher on my list as it manages those challenges like the professionals that they are. And Disney's not just rides and princesses. A recent "camping" trip we took to Disney World was also pretty great and showed just how different each trip to Disney could be. We enjoy the heck out of some of the best restaurants at Disney World too.

Yup, this one is at Disney too. (Photo by Melissa Ann Photography for The Points Guy)

How you can get there

Orlando International Airport (MCO) is served by all the major U.S. airlines, so you have your pick of miles and awards to get you there. If you can fly to Orlando on an American Airlines-operated flight of 1,151 miles or less that has saver award availability, then you could book those flights from just 7,500 British Airways Avios. Southwest and JetBlue often have low-priced awards into MCO because of their revenue-based award-pricing models.

Recently we have started to use the Kids Fly Free promos on Frontier Airlines when we head to Orlando.

Related: How to save money on a Disney vacation by renting points

For your hotel stay, you can use Marriott points to book nights at the Walt Disney World Swan or Dolphin and enjoy most of the Disney Resort perks. There are some additional points-friendly hotels available in the Disney Springs area that now also convey many Disney Resort perks.

(Photo by Summer Hull/The Points Guy)

If you don't need the Disney-specific perks, you can use Hyatt points to stay at the nearby Hyatt Grand Cypress. On our last few trips, we have gone all-in and booked stays at true Disney Resorts such as the Polynesian, Contemporary, Wilderness Lodge, Animal Kingdom Lodge and the brand-new Disney Riviera Resort. This allowed us to enjoy all of the Disney World perks, including the Magical Express Bus transportation to and from MCO and the Disney Skyliner gondolas -- and be fully immersed in Disney as Walt imagined it.

We often use our Citi ThankYou points for Disney park tickets and have also used fixed-value points from the Capital One Venture Rewards Credit Card or Barclaycard Arrival Plus® World Elite Mastercard® at a value of 1 cent each to cover the cost of our Disney Resort hotel stays. The Barclaycard is not taking new applications at this time.

The information for the Barclaycard Arrival Plus World Elite Mastercard has been collected independently by The Points Guy. The card details on this page have not been reviewed or provided by the card issuer.

Indulge in a fancy trip to Paris

About a year before we welcomed our second daughter to the family, I took my oldest daughter for a girls-only fancy trip to Paris. We flew in lie-flat business-class seats, stayed at the Park Hyatt Paris-Vendôme, tasted macarons everywhere we went, played in the parks and even met up with Grandma Points and her sister for a three-generations Parisian experience.

(Photo by Summer Hull/The Points Guy)

Why we loved it

This trip was just about doing what the "girls" wanted at our own pace. We enjoyed springtime weather in Paris, shopped for paintings and books along the Seine, and enjoyed the classic rides at Disneyland Paris.

(Photo by Summer Hull/The Points Guy)

We experienced Paris in a very luxe way thanks entirely to points and miles. Otherwise, lie-flat seats and stays at Park Hyatts would have never happened. Heck, even our delightful room-service breakfast would have been out of range at nearly $200 were it not for my Hyatt elite status that made it essentially free. Six years later, I still remember how incredible and fluffy those eggs were.

How you can get there

You can fly to Europe round-trip in business class as we did from just 88,000 Amex Membership Reward points earned via cards such as the American Express® Gold Card or The Platinum Card® from American Express transferred to Star Alliance partner ANA at a 1:1 ratio.

Another idea is to brush up on the Air France Flying Blue program and keep your eyes open for a business-class award flight to Paris available from about 66,500 miles per direction plus taxes and fees. You can transfer points to Flying Blue from all of the major credit card programs, including Chase Ultimate Rewards, Amex Membership Rewards and the Citi ThankYou program.

To stay at the Park Hyatt Paris Vendôme as we did, it will now cost you 30,000 World of Hyatt points per night that you can earn with the World of Hyatt Credit Card or transfer from Chase Ultimate Rewards and cards such as the Chase Sapphire Preferred. Be aware that the maximum occupancy for a standard room at the Park Hyatt Paris-Vendôme is typically just two people, though some deluxe rooms can accommodate two adults and a child. The recently renovated Hyatt Regency Paris Etoile may be a more family-friendly option at just 15,000 points per night with standard rooms available that sleep up to two adults and one child. Here are points-friendly hotel options in Paris.

Related: Paris on points and miles

Hawaii -- on repeat

Unless you live on the West Coast, Hawaii is a pretty distant destination. There are likely beaches much closer and less expensive to enjoy than those in Hawaii. But for us, Hawaii is so, so worth it. As long as you don’t just spend your time on Waikiki, you are in for the treat of a lifetime in this small group of islands in the middle of the vast Pacific.

Explore beyond Waikiki for a rich Hawaiian experience.

Why we love it

I've been to Hawaii numerous times and love everything about it. From the poke, the shave ice, the music, the waterfalls, the plants, the surfing, the green mountains of Kauai, otherworldly geography of the Big Island and the picture-perfect resorts, it is all just perfection for our family. When I try to describe how it feels to be in Hawaii, I say it's like you're floating because the air and temperature feel so perfect that you don’t feel anything. That is one of the many reasons that Hawaii is a top destination for our family.

How you can get there

If you live in a city with nonstop service to Hawaii on Alaska or American Airlines from the West Coast or as far east as Phoenix, you can fly to Hawaii in economy from 13,000 British Airways Avios each way. Those with Citi ThankYou points can transfer them to Turkish Miles and Smiles and book economy awards on United-operated flights to Hawaii for just 15,000 miles each. I'll admit, I'm also a sucker for Hawaiian Airlines' lie-flat seats as a great way to start the vacay a bit early.

Related: Best ways to get to Hawaii on points and miles

(Photo by Summer Hull/The Points Guy)

Related: The best ways to get to Hawaii on miles

If you don’t want to mess with award availability, the companion certificate that comes with the Alaska Airlines Visa Signature® credit card can knock down the total cash price for your family. I also recommend subscribing to @TPG_Alerts on Twitter, as the team does a great job sharing Hawaii airfare deals when they drop to around $300 round-trip.

In terms of points-friendly resorts, we've our loved stays at the Hyatt Regency Maui (25k Hyatt points), Grand Hyatt Kauai (25k Hyatt points), Westin Princeville 50 to 70k Marriott points), Hilton Waikoloa Village (60k Hilton points) and the Westin Moana Surfrider (50 to 70k Marriott points).

Grand Hyatt Kauai. (Photo by Summer Hull/The Points Guy)

Viva la Mexico

Since we live in Texas, Mexico is just a short plane ride (or cruise) away. The easily accessible location, postcard-perfect beaches, friendly people and vibrant culture make Mexico a fun destination for a short school break. Our family has especially enjoyed vacations in Punta Mita and Cancun.

Why we love it

In addition to being convenient for those in the southern or western portions of the United States, Mexico offers tremendous family-friendly resorts and some solid award values. The level of service we enjoyed at the St. Regis Punta Mita with our then-two-month-old baby was both indulgent and attentive, yet not stuffy or overly formal.

(Photo by Summer Hull/The Points Guy)

The gated resort of the St. Regis Punta Mia is located on the Pacific Ocean about a 50-minute drive from Puerto Vallarta. There is a complimentary Kid's Club for children ages 5–12 and nannies you can hire on an hourly rate. I still miss the nanny who helped us for those few days in paradise as we were adjusting to life with two kids. Outside of the available childcare, we loved the deep blue ocean, multiple infinity pools and the fresh-caught seafood served by the water.

If your family is looking for an all-inclusive option in Mexico that you can book with points, I recommend the Hyatt Ziva Cancun. At the Hyatt Ziva Cancun, we felt free to just enjoy our time together because everything was already covered by our award reservation, including the kid's club, margarita bar, oceanside shrimp tacos and all of the surprisingly good restaurants.

At this family-friendly all-inclusive resort, we were able to say yes to a visit to the dessert store, second breakfast, playtime at the kid's club, an evening show and poolside smoothies without stressing about the cost. It also didn't hurt that the clear, turquoise water was mesmerizing.

(Photo by Summer Hull/The Points Guy)

How you can get there

The St. Regis Punta Mita ranges from 70,000 to 100,000 Marriott points per night. The all-inclusive Hyatt Ziva in Cancun can be booked with 25,000 World of Hyatt points for double occupancy, but be aware that children ages 3 and up cost an additional 12,500 Hyatt points per night.

Related: Best ways to earn Hyatt points

Bottom line

Our favorite family trips don't stop with these six memories. If I were to go on (and on) you would hear about our family trips strolling through Buckingham Palace in London with a sleeping baby, exploring the alleys of Edinburgh, taking horseback rides through Alaska, swimming with the stingrays in Grand Cayman, ice skating in Bryant Park and skiing through powder in Canada.

Horseback rides through Alaska. (Photo by Summer Hull/The Points Guy)

Points and miles have quite literally opened up the world for us, but we aren't unique in that. Points and miles can open cities, countries, destinations and experiences to any family ready to learn how to let rewards do the hard work for them.

Editorial disclaimer: Opinions expressed here are the author’s alone, not those of any bank, credit card issuer, airline or hotel chain, and have not been reviewed, approved or otherwise endorsed by any of these entities.

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