Family travel looks completely different at every age — these are the trips that stood out most along the way.
One of the things nobody really tells you about family travel is that the way you experience the world with your children changes constantly as they grow. I have always made travel a part of my kids’ lives. Both were on airplanes before a year old, and both of them (who are now teens)still travel with me multiple times a year.
I never quite understood why parents wanted to wait until their kids were older to take them on a trip. I was lucky to travel with my parents and have such fond memories of family vacations, and saw how much my brother (who was 10 years younger than me) experienced them also!
Now that I am firmly into teen travel (with two boys who are 15 and 13) I can tell you that traveling with toddlers feels completely different than traveling with elementary-aged kids, tweens, or teenagers. Every stage comes with its own challenges, surprises, and moments that shape the kinds of trips that work best.
When my boys were little, our travels revolved around a morning or afternoon activity, then pools or playgrounds, and unstructured play. We did a lot of classic holiday destinations as they led well to having everything we needed. We did Hawaii and California often, as they were both nonstop from Vancouver, Canada, but it did not take long to see that it was possible to survive long haul with preschoolers!
Once I knew I could do it (often alone with the boys), I knew I wanted to go everywhere, and I could bring them too! That meant we could seek adventure, the culture I craved, and active itineraries as long as we worked in snacks and downtime to play!
Currently, my kids have a lot to say about the kinds of trips we take. Currenly their favorites are family sports trips (usually one-on-one with me) that give them more independence and ownership over the experience itself.
Looking back now, I can tell you that anywhere can be a destination to explore as a family. But with that being said, some destinations work better at different ages. Not because one stage was better, but because what excited and engaged my kids evolved so much over time.
Some trips were magical because they were simple. Days at the beach or an all-inclusive resort where everyone’s needs were taken care of! Others challenged us in the best possible ways. Sometimes it was me who was challenged to get through the day (it is often parenting in paradise, not a vacation), and sometimes it was challenging the boys with a long hike or having to behave in a museum. Some of our favorite memories came from small moments in destinations I never would have predicted would resonate so strongly with my boys at the time.
These are the trips that stood out most through every stage of parenting, from the toddler years all the way through the teen travel era we’re navigating now.
Travel with Little Kids (5 and under)
When my boys were little, the best trips were usually the ones that allowed for slower afternoons, more flexible schedules, and plenty of downtime (which meant playtime) built into the itinerary.
At that stage of parenting, travel never revolved around seeing everything and more around finding destinations where we could comfortably settle into a rhythm that worked for the entire family (especially as a single mom). Swimming pools were a hotel must at this age. Many of our trips revolved around places where we could access pools, playgrounds, beaches, stroller-friendly streets, and accommodations with space to relax.
Some of our favorite trips during the little kid years were the ones that balanced simplicity with just enough adventure to keep things interesting. We mixed easy resort destinations with far-flung adventure, because the things that would keep the kids happy can be found just about anywhere in the world!
Looking back now, some of my trips seemed very ambitious, but I am here to tell you that we all survived all of them. There were tough moments thats for sure (but there are tough moments at home too), and the memories from our trips near and far make those hard moments worth it!
Trips that worked well for little kids:
- Hawaii, USA – Hawaii worked especially well during the toddler years because it combined manageable flights from the West Coast (we have lots of nonstops from Vancouver) with calm beaches, outdoor spaces, and plenty of downtime. It was one of the easiest destinations for balancing adventure, culture, and the familiarity of restaurants and shops. Read More: Oahu with toddlers & preschoolers, Hawaiian souvenirs
- San Diego, USA – San Diego was one of our favorite preschool-friendly city breaks thanks to its beaches, parks, family attractions, and relaxed atmosphere. It felt easy to navigate with young kids and enough pool time for parents to relax, too.
- Jordan – Traveling through Jordan with a 3 and 5-year-old may sound ambitious, but it ended up being one of the most memorable trips we took during those early years and is the reason I am now a full-time travel writer. Between the warm hospitality, desert landscapes, outdoors, and cultural experiences, my boys (and I) were constantly engaged by the experience. Read More: Amman with Kids, Jordan travel guide, Best Hotels in Petra for families, Amman hotels for Families, Dead Sea tips.
- Egypt – Egypt was difficult, but the destination is difficult for all ages. There is well developed tourist infrastructure due to its incredible history, but with that comes the constant haggling and street sellers. I actually found I was bothered less than others because my hands were full with two kids, and we also had arranged local guides to make our days a little easier.
- Disneyland, California, USA – The toddler and preschool years were probably the phase where Disney magic felt the most real. At that age, the rides, characters, and excitement genuinely matched the stage of imagination my boys were in at the time. Now, Disney intimidates me with its ride strategy and lineups.
- Vancouver Island, Canada – Vancouver Island worked beautifully for slower family travel when my kids were little. Its a road trip for us, which meant we could bring as much as we wanted, and the cities (and towns) have everything you need.
- France – France for us was a mix of big city vibes like Paris and smaller towns in Provence. We mixed our days with sightseeing and then playing on playgrounds or afternoons in the pool. The kids did great with slow outdoor meals and we managed with busy city vibes!
- Greece – Greece was one of those destinations that balanced both relaxation and adventure perfectly for our family. We visited Meteora, where the kids could move around and explore, and then the Greek Islands, where we enjoyed beach time, ferry rides, fresh food, and exploring small towns. Finding a meal was not hard when we ate earlier than everyone else in town.
Travel in the Early Elementary Years
- Jordan – Jordan has plenty of outdoor spaces and places to explore.Kids can enjoy floating in the Dead Sea, exploring Petra, seeing the desert on the back of a 4×4 and riding camels all alongside unmatched cultural hospitality. Read More: Amman with Kids, Jordan travel guide, Best Hotels in Petra for families, Amman hotels for Families, Dead Sea tips, 5 days in Jordan Itinerary.
- New Zealand – New Zealand was perfect for active kids who loved being outdoors. Easy hikes, wildlife, beaches, and constantly changing scenery made the entire trip feel adventurous but with the comfort of an English-speaking country.
- Turks and Caicos – This is for the all-inclusive vacations. Stunning beaches, everything you could ever want to eat or drink can be found at the properties in the Turks and Caicos. My kids still say Beaches is the best resort in the world (we went twice).
- Vietnam – Vietnam kept my 9 year old constantly curious with busy streets, incredible food, and sensory overload in the best possible way. The culture is friendly and hiring a local guide makes seeing the country a piece of cake! Read More: What to buy in Vietnam, Tips for planning a trip to Vietnam, 10 days in Vietnam with kids
- Whistler, Canada – Whistler works beautifully for elementary-aged kids because it balances outdoor adventure with easy, family-friendly activities year-round. At this age, they can bike or ski, so a visit at any time of year works for families! Read More: Whistler with Kids in Summer, tips for skiing in Whistler with kids,
- Cabo San Lucas, Mexico – Cabo was an easy warm-weather getaway with beautiful resorts, pools, and enough outdoor activities to keep younger kids entertained without overcomplicating the trip. This is the kind of trip parents can relax as the kids enjoy the many amenities of an all-inclusive resort.
- Banff, Canada – Banff felt like stepping into a real-life nature documentary for my boys, with turquoise lakes and easy access to outdoor adventure. The dining is approachable, and there is enough active adventure for all types.
- Costa Rica – Costa Rica was one of our favorite destinations for adventurous elementary-aged kids, thanks to wildlife, beaches, adventure, and nonstop outdoor activities.
- Fiji – Fiji combined relaxation with cultural experiences and incredibly welcoming hospitality that made traveling with younger kids feel easy and memorable. You can do a lot, or a little and it feels a lot more culturally foreign than the Hawaiian islands. Read More: Fiji with kids, tips for planning a trip to Fiji
Tween Travel
- Joshua Tree National Park, USA – Joshua Tree worked especially well during the tween years because the unique desert landscape felt adventurous, different and surprisingly fun for kids who were beginning to crave more active experiences and can handle longer hikes and hot climates.
- Whistler, Canada – During the tween years, Whistler became less about family activities and more about outdoor adventure, independence and active days together. Read More: Whistler with Kids in Summer, tips for skiing in Whistler with kids,
- La Paz, Mexico — La Paz offered a more relaxed and authentic side of Mexico with soemthing you can only do in a few places around the world: swim with whale sharks. Younger kids would not be big or quick enough to keep up in the water which is why I put this in the tween category. Read More: Whale Sharks in La Paz with kids
- Jordan – Jordan became even more rewarding with older kids because they could better appreciate the culture, history, food, and adventure elements woven throughout the trip. Read More: Amman with Kids, Jordan travel guide, Best Hotels in Petra for families, Amman hotels for Families, Dead Sea tips, 5 days in Jordan Itinerary.
- Alaska cruise – Alaska cruises worked incredibly well during the tween years because they balanced built-in entertainment with outdoor adventure and wildlife experiences. Smaller ships mean the kids can have some independence to explore on their own. We sailed with Holland America. Read More: Holland America Alaska Cruise Review
- Costa Rica – Costa Rica remained one of our favorite tween-friendly destinations thanks to surfing, wildlife, jungle activities, and nonstop adventure.
- Tokyo – Tokyo completely fascinated my tweens with its arcades, food culture, transit system, and nonstop energy around every corner of the city.Read More: Tokyo for Anime Loving Tweens
- Buena Park, California USA – Buena Park worked well as a Southern California base during the tween years because it offered easier access to attractions while still feeling manageable and relaxed. Buena Park is where Knott’s Berry Farm is located and it felt a lot less busy than Anaheim and the Disney Park system. Read More: Buena Park with Kids
- Tanzania – Tanzania created some of our most unforgettable family memories through safari experiences and the chance to see wildlife up close. Tweens are able to manage long game drives much better than younger kids.
- Miami, USA – Miami became an exciting sports-focused trip during the tween years thanks to the chance to see Lionel Messi play while also enjoying the city’s beaches and nearby nature in the Everglades.
- Pittsburgh, USA – Pittsburgh surprised us as one of the best sports-focused city breaks for tweens, especially getting to experience the atmosphere around Sidney Crosby and the city’s passionate tailgate culture Read More: Three days in Pittsburgh with teens
- El Salvador – El Salvador combined beaches, volcanoes, and adventure in a way that felt exciting and immersive for older kids. Tweens are old enough to try surfing and can manage an all-day hike to summit a volcano without complaint! Read More: El Salvador with Kids
- Invermere, Canada – Winter trips to Invermere worked beautifully for active tweens who loved snow, skating, and outdoor mountain adventures with a hot springs as an added bonus. Read More: 5 days in the Columbia Valley with kids
- Mexico City, Mexico – Mexico City was one of the most unexpectedly engaging trips for my tween thanks to Lucha Libre, incredible food and bikable city.
Teen Travel
- Pittsburgh USA – Pittsburgh became one of our favorite teen city breaks thanks to sports culture, walkability, good food, and an atmosphere that felt genuinely exciting for older boys. Read More: Three days in Pittsburgh with teens
- Tampa, USA – Tampa worked especially well with teens because it combined professional sports, warm spring weather and enough independence for my boys to feel more grown up while traveling. Read More: Three days in Tampa with teens, what to buy in Tampa, Where to eat in Tampa with kids
- Mexico City, Mexico – Mexico City challenged and fascinated my teens with incredible food, huge cultural experiences and neighborhoods that felt endlessly interesting to explore.
- Jordan – Jordan is one of my favorite places in the world and teens canfully appreciate the culture, conversations and adventure elements that make the country so memorable. Read More: Amman with Kids, Jordan travel guide, Best Hotels in Petra for families, Amman hotels for Families, Dead Sea tips, 5 days in Jordan Itinerary.
- Whistler, Canada – Whistler evolved into a destination centered around outdoor adventure, independence, and active experiences that worked especially well with teens. In the winter it is skiing and in the summer it is hiking and biking and lake days. Read More: Whistler with Kids in Summer, tips for skiing in Whistler with kids,
- Tofino, Canada – Surfing in Tofino became one of those quintessential teen travel experiences that combined adventure, independence and the laid-back atmosphere older kids naturally gravitate toward.
- El Salvador – El Salvador worked incredibly well for teens because it balanced surfing, adventure, and cultural immersion in a way that felt exciting rather than overly “family-focused.” Read More: El Salvador with Kids
- Morocco – Morocco offers sensory overload in places like Marrakesh, cultural immersion, markets, food, and experiences that are unfamiliar from home.
Lindsay Nieminen hails from Vancouver, Canada and shares her love of travel on this website. She is passionate about showing others that they should not put off traveling the world just because they have children or are single parents. She aims to encourage them to seek out adventure, whether it is at home or abroad by providing information on how just about everywhere can be a destination to explore as a family.