For the Love of Travel: How to Successfully Vacation with Family & Friends

by Noreen Kompanik

“We didn’t realize we were making memories. We just knew we were having fun.” This quote by an unknown author describes the perfect vacation. And can that really happen when we travel with extended family and friends? It certainly can, if we are willing to follow a few helpful guidelines.

On our most recent trip to Cabo San Lucas, Mexico with my husband, brother, sister-in-law, and teenage nephew, we had some great laughs about events that occurred on past vacations that would give comedians some pretty good stage humor material. Co-family or co-vacationing travel isn’t necessarily everyone’s forte. Thankfully, for us, we’ve learned some great tips over the years, and putting these into practice have resulted in some wonderfully memorable vacations together.

Good communication leading up to and during the trip is one of the most crucial elements of a successful multi-family adventure. We found that making a list well before the planned trip, and addressing all aspects, options, and variables of the upcoming vacation sets the bar for success. And making a calendar for the group highlighting the upcoming activities and reservations is extremely helpful for those of us who are by nature “visual planners” as well as to address the diverse interests of the group.

Planning the Destination. Whether it’s a beach vacation or ski vacation, it’s important that everyone in the group is in agreement with the location. Nothing is worse than arriving at a beach resort only to find that one member of the party isn’t “really into the beach thing.”

Length of Vacation/Time of Year is of great importance, especially if children are involved and working around school schedules is a must, or adult vacation time limits have to be considered. Often we plan our trips around paid holidays to maximize our days off.

Transportation Plans. If the destination is not drivable, (i.e. there’s a big ocean between here and there), transportation once we arrive at our destination has to be considered. If a rental car is needed to optimize destination experiences, the decision to rent one or two vehicles will need to be made. On the occasions we’ve rented just one vehicle, we’ve learned to limit the number of suitcases each individual brings to avoid making two trips to and from the airport to accommodate all the luggage. Yes, this has happened. Or, even more incredibly, having to tie two of the suitcases to the roof of the car with bungee cords and pray it doesn’t rain. We have learned to discuss the luggage issue ahead of time. Another important consideration is who will be the designated driver (or drivers.) Not everyone is keen on driving on the “left” side of the road in the Virgin Islands, or in a foreign country!

Activities. Having everyone on-board with planned activities is absolutely crucial, especially when events need to be booked ahead of time, like sunset sails or zip lining tours. Age and health considerations may necessitate alternative venues for those seeking a little less adventure than the more daring members of your party.

Dining In and Out. When staying at a vacation rental as we often do while vacationing with family and friends, the choice of dining in, whether it is breakfast, snack, or dinner is a consideration. Often times, hitting Costco or other grocery stores gives the option of having food and beverages on hand when needed. Then, we discuss ahead of time how we’ll equitably share the cost of the food. Often times we end up just splitting the checkout bill in half. Choices for eating out in town can range from fast food to casual family restaurants or even fine dining.  Selection is often driven by each family’s budget. If “hard to get reservations” for that perfect table at sunset need to be made ahead of time, this is an early planning consideration. So is how to handle the dinner bill. We make it a point to ask for 2 or 3 checks as appropriate, so, the expectation is clear at the beginning of dinner. This avoids any possible misunderstandings on who’s responsible for picking up the tab.

An “Everyone Does Their Own Thing” Day. No matter how much family and friends love one another, we have found that taking breaks from the group is a healthy, refreshing practice. We often plan one or two days where everyone has the chance to do their own thing. This is particularly beneficial when the avid adventurers want yet another adrenaline-filled day, while others prefer to just lounge by the pool- their idea of a relaxing vacation. This also works well for dinner reservations- the chance for Mom and Dad to have a romantic dinner out while Grandma and Grandpa enjoy their special one-on-one time with the grandkids.

Staying Flexible. While good planning is essential when vacationing with family and friends, it is possible to have too much structure built into your vacation with every minute of every day firmly scheduled. With family activities that don’t require reservations, we leave multiple openings in our vacation with options that allow the group to democratically decide activities they feel like doing together in those opportune times. Work is stressfulvacations shouldn’t be. Sometimes new opportunities present themselves, and it’s fun to deviate from the schedule as long as we are all on the same sheet of music. 

We must also remind ourselves that sometimes factorsbeyond our control may come into play necessitating a change in plans. On a recent trip to one of the Hawaiian Islands, a storm forced cancellation of our planned sunset sail. We were able to collectively recoup, come up with alternate plans and reschedule the sunset sail for later in the week. As a result, we still had a fun day, everyone was happy, and we ended up with the most beautiful sunset views of the trip.

Though taking trips with extended family and friends may require some extra work and communication up front, one thing is for certain- seeing smiling faces, sharing those special moments and re-living memories made, are worth the upfront planning. It makes us realize that the best things in life are the people we love, places we’ve been, and the many memories shared along the way. And the highest compliment ever is when we all look at each other at the end of the vacation and say “let’s do this again.”


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Read more about Mexico

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Food and Fun: Cabo San Lucas Style

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La Palapa – Dining with an Alluring View

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Zihuatanejo Mexico: For Children of all Ages


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  1. says:

    Great post.


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