Family of Five Travels Using Points, Deals, and Lots of Advance Planning

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While I am always happy to share my own traveling stories with my family, there are tons of other great traveling families out there with kids of different ages, different numbers of kids, and who have had different experiences than me.  As part of my “Little C’s Traveling Friends” series, I am thrilled to share different families’ stories so we can all learn from their experiences.  If you would like to be a part of this series just shoot us an email info at

Travel with one kid is a big game changer, but when numbers 2 and 3 come along in rapid succession family travel is forever changed!  Or at least dramatically changed for the next 18 years or so…  Here is how one family adjusted accordingly and continued to travel with their family of five by taking advantage of deals and advance planning while supplementing with miles and points along the way.

S and her husband J have three beautiful daughters who are now almost 15, 10 and 8. She is an accountant and her husband is an engineer. Between working full-time and having three children their lives never seem to have a dull moment. They like to make the most of their free time by making memories traveling all over the world.  Here is their traveling story as told by the mom!


I consider vacation a necessity to reward us and recharge our batteries, but traveling as a family of five can be very costly. Purely free travels using miles and points is impossible as we don’t apply for multiple rewards credit cards and never have enough points to do it all that way. So from the very beginning my goal has been to keep cost as low as possible, which often means “plan ahead”!

To say I am crazy about travel planning is probably an understatement. I am always looking for deals. I search resort availability 12-18 months out, and airline tickets 11 months out. Most people cannot plan their trips this far ahead. We are able to do so partly because our ability to travel is limited by girls’ school breaks, our work schedule and in recent years our oldest daughter’s summer sports competition schedule. The limitation has really worked in our favor as it narrows down my research.

When our oldest daughter was little we traveled frequently, but when the family suddenly grew from 3 to 5, we took a break from flying and focused on road trips to the beach or mountain. It wasn’t until L (their youngest daughter) was 2 ½ years old that we started flying again. We tested the water by taking the girls to Puerto Vallarta as it was a short 3 ½ hour flight. We exchanged our Christmas week timeshare in Orlando for a week at the Grand Mayan resort. The resort was perfect for our girls – a huge water park, a giant water slide, a wave pool, a lazy river, and numerous connected pools!  The kids club charged only 150 pesos a day with lunch included! Everyone loved it and we have been back every year since.



The success of our first Mexico trip boosted our confidence and Puerto Vallarta and Cabo San Lucas became our frequent designations for one-week trips. We slowly extended the distance to Hawaii and the east coast. One year we got brave and took the girls to China for two weeks over Christmas! Unfortunately we discovered painfully on the long 18-hour flight that K (their middle child) gets sick on planes some times.  Since then we set up a “5-hour rule”, which means that any trip that requires 5 hours of flying in one day will be a minimum of two weeks long.

We spent most of our vacation at beach resorts where the girls will entertain themselves for hours in the pool or at the beach. We try to do one major activity every other day. Over the years, the girls have enjoyed many fun activities, such as releasing baby sea turtles, parasailing in Cabo, snorkeling in Hawaii, fishing in Puerto Vallarta, feeding giraffe in China, and meeting the Mouse in Disney World.



They also discovered many interesting foods that they really like, including water bugs and crispy pigeons in China, Malasala (traditional Portuguese donut) on Big Island, shortbread cookies from Honolulu Cookie Companies, chocolate dipped churros from Mexico, keylime jelly beans and conch chowder from Key West, and most importantly the pineapples in Hawaii – according to K, it is the best in the world!

While most of our trips were planned over a year in advance, some were not, such as the two-week Florida trip we took last December. When we decided to do this trip, it was already June and airfare was well over $700. I wanted to use up our 200,000 Delta SkyMiles and was thrilled to find five award seats at 40,000 each (they are SkyPesos after all), but there was one small problem .  We had to take either three 3 flights into the town J’s parents live, or two flights into Tampa which is two hours away. Three flights in one day was really not an option considering K’s situation, so we opted for Tampa and decided to use the opportunity to visit J’s aunt who we haven’t seen for a while.

With the flight to Tampa booked, we started to brainstorm with the girls where to spend the second week. They wanted to visit Atlantis, but the hotel cost was insane during the holiday. I wanted to see San Juan but airfare wasn’t cheap and required a connection in Miami. In the end, we picked Key West, as we could take the high-speed ferry from Fort Myers beach for $86 per adult and fly one-way back to Tampa for $79 per person.

It was a challenge to find an affordable place to stay in Key West during the busy New Year’s week. Most hotels do not accommodate five people in one room, and booking two rooms would be too costly. The few Hyatt timeshare rentals I found were asking over $2,000 for the week. In the end, I settled on Sheraton Suites, which had two queen beds plus a sofa bed in the sitting area. Instead of paying $400 per night, I redeemed 16,000 SPG points per night for four nights and received the fifth night free. The hotel worked out really well for our stay with a convenient free shuttle into old town, and a location that is across from Smathers Beach.  This isn’t a great beach, but it satisfied our craving for sand and ocean. The girls enjoyed kayaking and building seaweed sand beds. K went parasailing for the first time and had a blast!



We needed three nights in Tampa and we opted to stay with Marriott properties, even thought they were more expensive than other hotel chains. I needed the stay to complete the Gold challenge, which I signed up for last November as part of my planning for the China trip later this year. I made one reservation each for J and I, so that we both earned one free “Mega Bonus” night, which we could use in China. I called the hotels one month before arrival and asked for connecting rooms, and we got it.

The Renaissance International Plaza fit our needs perfectly for the first two nights: free airport shuttle, hotel restaurant with good yelp-rating (perfect for feeding hungry kids), next to a big shopping mall with food court and nice restaurants including Capital Grills. J and I are foodies and we never pass up the opportunity to try out a new steakhouse. The steak and lamb chop both turned out ok, but the coconut crème pie was really fantastic!

For the night before our flight home, we opted for Marriott Tampa Airport, which is located inside the terminal. We walked straight in after arriving from Key West. The hotel even left a little surprise for J!


The final piece of the trip planning was where to stay while visiting J’s parents. There really weren’t many nice choices in the small town, so we opted for renting a condo in the waterfront Cape Harbor development, which has a marina, a coffee shop, some boutique shops and a few nice restaurants. Through VRBO, I was able to find a two-bedroom two-bath condo for $130 per night! The condo was great and had fantastic views of sunset from the lanai. It provided us a comfortable base for day trips to nearby beaches. We even went shell hunting on Sanibel Island.


Key West exceeded our expectation in so many ways that to this day the trip is the favorite topic over dinner! There was simply so much for our kids to do! We saw the six-toed cats in Hemmingway House, climbed the 180 steps in the lighthouse, rode trolley around the island, and dazzled by hundreds of butterflies in the conservatory, not to mention feeding fishes and birds on the wharf! The highlight of the trip though was the hot sauce tasting at Peppers, the only bar in town that kids are allowed! Two hours of free tasting led to the purchase of 13 bottles of hot sauce to be shipped home!!


Key West is great, even with kids.  After all, where can you find a dozen oysters for six bucks?! We will be back and maybe we would even go fishing!

As the girls are moving into higher grades in school, I find it more difficult to go away during the short one-week winter or spring break. So I adjust our strategy to focus on making two-week trips. Currently our itinerary includes two weeks in Hawaii this summer, two weeks in China this Christmas/New Year, and two weeks in Mexico over Christmas 2014! We are using some miles and points to keep the cost down. Between big trips we try to add in some weekend getaways to the coast or the mountain, and just recently the Napa and Sonoma Valley! Who says there isn’t anything to do with kids in the wine country? J K will be first in line to debate with you!


The biggest challenge in our travel is K’s motion sickness. We do everything possible to make the long flight less painful for her, including:

  • Reserve seats in the front and a non-window seat for her;
  • A good meal before leaving home;
  • Take the motion sickness pill 30 minutes before boarding;
  • Board early, usually during elite boarding. Gate agents are usually sympathetic.
  • Opt for a layover so she could have a break and eat some food;
  • During flight, use electronics to keep her mind off her discomfort;
  • Remind her to close her eyes during takeoff and landing.

The list changes as we learn what works and what doesn’t. We convinced her to try ginger ale and she liked it. Maybe she would be willing to drink it on the flight to Hawaii.

I checked in with the family since last talking with them quite a while ago and learned that this past Christmas the family successfully took a 3 week trip to China (via Cathay First Class) to visit S’s family, which took S a whole year to plan! The family is currently on a 2.5 week east coast trip including visiting family in Maryland, and catching some sights in Philadelphia and DC.  They are looking forward to two weeks at their favorite resort in Mexico at Christmas and February 2015 to Taipei and China for the Chinese New Year.   This is a great story of how kids may necessitate a change in how you travel, but they don’t have to cause a permanent full-stop on travel.

Thank you so much to this awesome family for sharing their story and we look forward to hearing about more about their traveling adventures!

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  1. It’s more difficult to plan a trip for big families, but not impossible. I also plan my family vacations (for my family of 6) way in advance to get the best deals and try to maximize the miles and points in the hotels.

    On the spring we traveled to Hawaii and for next spring I already book our flights to Paris and Switzerland (both using miles and points). It is very rewarding to be able to give our kids those experiences – I write about our travel adventures with the kids in my blog.

    • I love the family travel stories! In fact, I find the “couples” stories to often be something I can’t relate to, with regard to points/miles, schedules, etc. We are a family of 4 with 2 teen daughters, with the oldest heading to college in 3 weeks. We have just returned from 8 nights in Switzerland, which I started planning last Fall. We had to have 2 rooms for each of the hotels, and all our rooms were free for 6 nights. The other 2 nights we did have to pay for because there were no point hotels in Zermatt. We got a huge “family room” in a chalet, facing the Matterhorn. Anyway, early planning is the key. Had I gone a step further with each of us getting the Barclays cards, we could have reduced our expenses even more. Our greatest expense was our Swiss Passes for travel for 8 days (~$1500). In the end, our family of 4 was able to have a fabulous “out of our league” holiday for only a fraction of the cost most people pay.

  2. I’m sitting this moment on the French Riviera with my three kids and husband. We are here a week, then Paris, then South Africa for three weeks. Saved up points for business class flights and using some airbnb and bed and breakfasts for lodging. Booked nine months ago. I love that I can give this experience to my children. They will grow up thinking the world is an open, accessible place.

  3. I agree we have been travelin4free for a while now. I have 4 girls 5-11 years old. The past year the girls have bee on 21 flights for free. We did Hawaii the big island and Oahu(marriott). Tokyo (Conrad), Shanghai (woldorf astoria), Beijing (grand Hyatt), macau ( grand Hyatt), Taipei (grand Hyatt), Bali (grand Hyatt, intercontinental hotel), Istanbul (marriott), Rome (bolivar/hilton), florence (vrbo -arrival card), Venice (vrbo -arrival card). We have had fun. We need to take some things slower but always fun. Today I think they walked 4 miles in Rome. We stopped for 2 hours in the hotel and watched iPads and rested so we could get out and play some more. Spend as much time before hand researching to make it easy on your family and don’t wait in lines by buying tickets online when possible.

  4. Really enjoy these real-life family travel adventures. With our family of 8, our kids are still young enough that we don’t think it’s really necessary to take them to super fancy resorts.

    I always like to joke that the only things my kids seem to care about are a) is there a swimming pool and b) is there a waffle maker for breakfast 🙂

  5. Thank you! My wife and I run a blog for millennial couples who want to travel more. The more and more we think from going from a two to travel family to three, it’s great to see posts from families who are out and traveling, when so many people love to remind us that “our travels will end once we have a kid.” So to MommyPoints, and other bloggers defying the stereotype- thank you all!

  6. This is such a great article and and the comments are terrific also. Our family of 5 have been doing road trips mainly but really want to fly more. The vacations have been fantastic but the driving can be torturous due to fighting by the kids! We live near Niagara Falls in Canada and it is pretty common for people to travel out of Buffalo as it’s usually cheaper than Toronto. I only wish I could get hold of those American credit card bonuses but I’m figuring some Canadian options out a little at a time.

  7. I love these family travel articles. While it definitely takes more planning, it is absolutely possible to travel the world with children. We backbacked in South America for three weeks this summer with our five children (ages 8-18), and over Christmas vacation we are going to Australia (with a 13-hour layover in Beijing on the way, complements of United points, and a 3-day stopover in Hawaii on our return, compliments of American’s old award rules)!

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