A Journey of Roots: Planning a Multi Generation Vacation

“Family, like branches on a tree, we all grow in different directions, yet our roots remain as one.”


Four Generations Celebrate as Grampa Turns 80!  Oahu, Hawaii

We live a very fortunate life, not only for our ability to travel, but simply to be part of a four generation family with extremely close bonds.  Every time I watch my daughters interact with my grandparents, it’s pure nostalgia of some of the happiest memories of my own childhood, a step back in time as I watch my most special people bond in a way that I remember so well myself.  It’s a bridge across generations; pathways connecting our roots, our stories, our pasts and our futures.

Generational gatherings around an extended table of food are an age old tradition, but multi generational travel is something few families have the opportunity to experience.  Time, distance and the ever dropping value of a dollar can easily keep families from gathering together as often as hearts desire.  But the core of families, and the necessity to bond remains a constant.   We live in a continually evolving world, and there is nothing to solidify a family unit than to bridge the decades through stories, laughter, tears, many bottles of wine and ultimately, the formation of new memories as a whole.

My grandparents at the Beach House, Oahu

Most importantly, generational bonding is about the effort.  Time has the unfortunate ability to both scatter and shatter.  Our stories make us who we are, and fortunately our tragedies have brought us together rather than tear us apart.  We not only realize the importance of making the effort to come together as often as we can, we are active in ensuring it happens.

I am blessed to have a family with such a passion for exploring and adventure, willing to take the time and energy to be together.  We’ve had the privilege of experiencing four generation vacations on two occasions now, one to an All Inclusive in Mexico for Christmas, and the other a beach house rental on the North Shore of Oahu, Hawaii, to celebrate my Grandfather’s 80th birthday.

Both were completely different experiences that connected us, each coming with pros and cons.  If you are looking at planning multi generational travel to bring your family together, I celebrate your efforts!  Here are helpful tips and important things to consider based on our personal experiences:


This is ultimately the key decision in any travel itinerary, but when you have a vast variety of ages and interests, it can be a bit more challenging.  You need to consider:

  • Travel Time:  You need to calculate airport arrival, flight times, layovers and destination transfer times. For example, some resorts can have a 3 hour transfer time if being done on a large coach that drops passengers along the way.  Additional travel hours add up, and very quickly become simply too much for some travelers, especially if a flight delay is part of your experience.  You need to consider time zone changes and factor in any serious jetlag that may eat into precious vacation days.
  • Time of Year:  What will the heat and humidity be like for the time of year you are planning?  Are there any seasonal issues such as major rainfall or hurricanes to be aware of?  Different areas of the world have different high and low seasons for weather and tourists.  Did you know that in the Mayan Riviera, the week that contains both Canada Day and Independence Day is one of the busiest next to Christmas??  Or that June thru November is typically the rainy season in the Caribbean?
  • Safety:  An absolute key.  Not only for the destination itself or the area surrounding a resort, but water safety and knowledge of any undertow issues is vital.  While much of it is common sense, all members need to be aware of any safety concerns prior to travel. Travel smart, travel safe.


Chances are, not everyone in your group has the same travel budget.  Figure out the realistic budget per person before you even begin looking at destinations. The discussion of comfort level and affordability that comes along with the various destination options needs to be clearly discussed, understood and respected.  If you won’t be doing an All Inclusive, you’ll need to factor in all of the additional expenses beyond airfare and lodging. Food, alcohol, airport transfers and rental cars, cleaning fees, parking, resort/hotel fees and taxes will be above and beyond the price per night, and add up quickly.


  • Stairs and walking distances: Resorts can be huge and have long stretches between amenities, rooms and the beach.  Some destinations that are hillside based can have more stairs than your loved ones wish to handle.
  • Does anyone require a stand up shower for accessibility reasons?
  • Will anyone require a wheelchair or other transfer service?  Can your destination provide this service if and when needed?
  • Are rooms accessible by stairs only, or are there elevators?


This will vary depending on the age of your children. Parents with small children will need to have access to any necessary infant/toddler items they will require such as playpens, strollers, ability to sterilize bottles, etc. Look into whether the resort has a kids club and what ages it allows.  Is there a children’s pool or water park?  Ensure anyone with small children will have what they need to be comfortable and safe.

***If staying at a resort with late night entertainment, ask to have families with little people stay in a room away from the hustle and bustle.


  • How close is the nearest doctor or hospital?
  • Does everyone have travel medical insurance?  What is the deductible?
  • Are there any shots/vaccinations required prior to your departure?
  • Are there any medical risks associated with your destination you should be aware of?


This has come up on numerous occasions as we have traveled.  If you have a late departure, you need to have a plan in place for the hours between checkout and leaving for the airport.  Some places will allow for a late check out at an additional fee, based on availability.  Often it is necessary to pay an additional night on a room.  In Hawaii, we had to check out by 10 am from our rental house, meaning we had to then rent a hotel room that would allow early check in (at full price) in Honolulu until our 11 pm departure.  This will need to be factored into your budget as well as be planned in advance, a necessary consideration for luggage storage as well as the members of your party.


Part of the fun of traveling are the unexpected things you come across, and those impromptu stops for adventure.  However, when you are planning for a large group covering different ages and interests, you need a general idea of a few things:  What types of adventure does the destination offer?  Tripadvisor.ca can be a great tool for checking what is popular.  Find out any “must see/do” for members of your group, factor in the costs involved and decide if the excursions need to be booked in advance.  Who wants to snorkel?  Who wants to visit a historical site?  Who wants to swim with sharks, parasail or learn to surf?  Ensure that everyone in your groups has the freedom to embark upon the adventure of their choice, and that no one feels obligation to do them all. 

SO ULTIMATELY:  All Inclusive, Hotel or Home Rental?

Do you plan to cook or eat out every meal?  Is everyone wanting to completely relax and be budget worry free at an All Inclusive?  Is everyone on board to pay restaurant bills every night at a hotel?  Is everyone willing to pitch in for groceries, as well as the efforts of cooking and cleaning at a house or condo rental?  Ensure you are aware of the options and that everyone attending is on the same page as far as expectations.

The All Inclusive:


  • Everyone receives their own rooms, and distinct separation can be vital for some families to co exist.  No matter how close your family is, all members need a place to get away for a reprieve.  Resort rooms offer more privacy and are a major consideration in varied times for bed/quiet time.
  • No one has to lift a finger when it comes to cleaning or cooking.
  • All inclusive means less budget stress.  You know ahead of time a basic total cost outside of tipping, excursions and souvenirs.
  • There are a multitude of excursions at your fingertips with staff to help guide you.  You can snorkel, zipline, explore ruins, parasail or deep sea fish all by simply booking with the concierge desk.
  • Kids Clubs:  While Multi Generational travel usually means someone can take the kids while Mom and Dad take a break, having a kids club is an option that is super fun and geared for youngsters, a great opportunity to play with other kids and make friends.
  • There is something for everyone and every taste.  Not everyone prefers their toes in the sand in the same way not everyone loves to be poolside.  Those who want to party it up at the disco and sleep until 3 in the afternoon can, just as early risers can find that perfect ocean side spot at 6 am with a coffee in hand.


  • If the resort has poor food selection, you may not have a lot of options.  Consuming water or fruit can be an issue, and traveler’s diarrhea is a common problem.
  • Many travelers choose not to drive in foreign countries, meaning you can feel a bit secluded on a resort, and excursions for large groups get quite costly.
  • Because of the separation of rooms, pool, beach, nightlife, etc, family can begin to feel segregated and it can begin to defeat the purpose of being together.



  • Everyone is together under one roof.  It’s the epitome of bonding, eating and wine drinking.
  • Full kitchens mean that food is catered to whatever your party desires, and is an excellent way to be cost effective as a large group.
  • Rental cars mean freedom.  Having roads in Hawaii very similar to Canada meant we were completely comfortable exploring the entire island.
  • There is nothing that will ever top waking up to this.




  • Such continual close proximity can work for or against members of your family.  It is a lesson in respecting boundaries and shared bathroom time.
  • The additional effort of grocery shopping, cooking and cleaning.  With shared efforts among the group, this one is quite simple to manage, but it still requires more work than an All Inclusive.
  • Costs can quickly add up with the addition of rental cars, food and alcohol, especially if your family plans to eat mostly at restaurants.  We shocked ourselves with how well we did on this one by cooking for ourselves.  One word. Costco.


If you are traveling for a special occasion, plan a few items in advance: 

Gifts:  For my Grandfather’s 80th birthday we decided on a group gift, a beautiful watch that we had engraved.  It represents our family standing the test of time, a single gift equally special from everyone.  It was also compact to transport.

Special Menu Items:  We needed a cake!  So I spoke with our home owners who were able to make a recommendation as to the best place to get a cake (a Chocolate Haupia Pie from Ted’s to be exact)  If you plan to dine out, make a group reservation in advance.

Hire a Family Photographer:  We’ve learned some hard lessons in loss, and because my heart is wrapped around photographs, it is important to me that we capture the moments we are all together and I consider it one of the greatest gifts I can give my loved ones. You can also use the opportunity to honor loved ones traveling with you in spirit.  We chose to represent my brother with his red converse shoes and my Uncle with his yellow hat.  It will make for tears, but is an incredible way to pay tribute.

All Inclusive Resorts normally have their own professionals, and it is quite easy to set up an appointment.  If you are renting a home or hotel room, speak with the owner or concierge to discuss options in the area that suit your needs.

Multi Generational vacations are all about mindset, respect and embracing the individuality of our most special people.  It is a time to share in each others lives, to learn about where we come from and where we want the future to take us.  It’s about supporting one another along our separate journeys and simply enjoying the fortune of being together.

Oh, and wine….but I may have already mentioned that.




Read it? Loved it? Share it!

18 thoughts on “A Journey of Roots: Planning a Multi Generation Vacation

  1. Great post! So much good information. I agree 100% with everything. This info also applies to traveling with friends, other couples or any type of group really. You always have to take into account the interests, physical abilities, and budget of your fellow travelers.

    1. Thanks Melissa! It is a great effort combined with a great amount of respect, patience, wine and laughter for sure! There is no “perfect” place, but with proper planning, you can come pretty close.

  2. What a special thing to do – love the idea of 4 generations spending relaxing time together, sounds wonderful. We don’t have 4 generations now (sadly) but always have a summer holiday with 3 generations – always fun and really important.

    1. We eve also gathered on occasions as three generations and I agree whole heartedly that it is equally important and so much fun! And it definitely still requires the extra considerations when you travel for it!

  3. Great post Amy! Spending quality time with your extended family is so important and being able to share memories so wonderful as an 80th birthday together is awesome! The memories that all of you gained on this trip will last a lifetime and be told around many dinner tables with many wine bottles 😉

  4. Another great post! I’d love to have four generations of family that were actually interested in traveling together. Our family is super young, and I’d be the third generation – but only my parents and my generation would be interested. Maybe someday my own children will interact with my parents, the way I wish I could with theirs. Alas!

    1. Thank you! I am so fortunate to be able to have these experiences and I hope that it is a tradition to carry on thru the future. Whatever form, family get togethers are always a time to celebrate!

    1. Thanks for taking the time to read! I think the “cons” of all inclusives are minimal, but there are cons to everything in life. Some people simply don’t enjoy an AI, but we love them for the absolute relaxation attached.

      1. I see your point. I think that sometimes we just have this vision that All Inclusive means “perfect”–that’s probably what AI marketers would like us to believe, and it may be perfect for some, just not all. I think what i get out of your post is it’s important to think about what you need in a vacation–then compare your needs to the type of vacation. Thanks!

  5. We take a multi generation family trip every Christmas. There’s definitely a lot that goes into planning but it’s so, so worth it. Hawaii has been one of my favorite trips we’ve taken because there’s something to do for everyone. Thanks for sharing!

Leave a Reply