Planning a family vacation is always a difficult task. How much can you spend? Where will you stay? How will you get “X” number of people to the destination? Those are questions that must be answered for just about any trip, but when teenagers are a part of the equation, the struggle increases with each teen added to the mix.
A vacation with teenagers is an active venture. They rarely are happy just spending a week lounging in a beach chair around a pool while reading a good novel. They want to be doing things and seeing things. This causes a challenge for families that have a mixture of ages. Often parents are just looking for a relaxing holiday. Younger kids often are fine with days splashing in a pool or playing on a playground. Teenagers, however, want to go, go, go. Finding that sweet spot where everyone is happy is tough.
Here are two quick and easy solutions if you are planning a vacation with your teenagers:
- Take a cruise. There are several cruise lines that really cater to families with children and teens. Look for cruises that offer kid camps for the younger children – they will be kept busy doing all kinds of crafts, recreation, and sciency stuff – and teen-oriented activities – they will be kept busy doing all types of physically-challenging activities, such as learning to surf in the surf pool or participating in an improv show. Meanwhile, parents are left to do or not do whatever they want, guaranteeing that everyone will get the vacation of their dreams.
- Look at all-inclusive resorts for families. These resorts, like family cruises, specialize in activities for a variety of ages, keeping the teens and children entertained and parents relaxed.
But what if you don’t want a cookie-cutter vacation. What if you’re looking for something more adventurous and unique? There are a few things you need to consider as you make your plans:
- What are the ages of the people going on the vacation?
- How many people are in the party?
- What are the interests – music, sports, hobbies – of each person going on the trip?
- How active is each person and what is their fitness level?
- What kind of location does each person prefer? Beach? Mountains? City? Country?
- What kind of weather does each person prefer? Cold? Hot?
- Are they adventurous or more reserved?
- How are you traveling? Driving? Flying? Train?
- How far away can you go?
- How much can you spend?
All of the answers to these questions will help you to determine where you’ll go and what you’ll do on your trip. My husband and I have six sons. Two are working adults, two are college students, and two are high school sophomores. Having a two- or three-year gap between the boys has made planning vacations a real challenge in the past. When the oldest two boys were around 9 to 11 in age, the youngest were just babies, and a lot of activities were hard to do with babies in tow. When the older kids were teens, they didn’t want to participate in the “baby stuff” that was appropriate for their elementary age brothers.
It was very frustrating. It is equally frustrating now. My oldest four boys are over 21, which opens up a lot of options for us, but the youngest two are 16, which eliminates many of those options again. Despite these problems, we have managed to take some pretty spectacular trips the past couple of years. So where do you start?
First of all, just know that one or more of your children (no matter their age) are going to indicate they don’t want to go and do whatever you are planning. That’s okay. Proceed. They don’t know, really, that they are going to have a good time. My boys always think my ideas for trips are “boring,” but they always come away saying, “Thanks, Mom, I had a great time.” The trick is to plan a trip that has a balance between intellectual growth, physical activity and relaxation.
A Balance of intellectual stimulation, physical activity and relaxation is the key to a successful vacation when traveling with teenagers.



So armed with the information from the questions above and an overall budget for your trip, start by making a list of three cities or locations that sound promising. When we were searching for our summer vacation destination, I picked Washington D.C., Savannah, Ga., and Miami, Fla. Right off the bat, I eliminated Miami since we were driving, and we didn’t want to spend the entirety of the trip in a van.
I knew Washington D.C. is a happening city so that is where I began my research, with my first internet search being “Things to Do in Washington D.C.” I made a list of places and activities I thought would interest various family members who were going on the trip and included the admission prices of each activity. Then I began plotting an itinerary to see what was feasible to do in the time we had allotted. (Washington D.C. has so much to do, much of which is free.) Then we had a short family meeting to discuss the options for activities if we went with a D.C. trip.
We had pretty much settled on D.C. and had even booked our hotel rooms through Booking.com which offers the “pay-when-you-stay” option. However, in order to stay within our budget, we had to book a hotel in Manassas, Va., which meant a lot of driving through D.C. traffic. We looked at taking the train into the city at least one time, which sounded kind of fun, but that was pretty expensive with six people in the group. By the time we crunched the numbers, D.C. had grown way out of our comfort zone as far as budgeting was concerned.
Also, the trip was leaning heavy on intellectual growth, but I figured all the walking from one attraction to another would provide enough physical activity for balance. However, I was concerned that there was not enough down time for those of us who needed some relaxation included in the itinerary. So it was back to the drawing board, with another round of research.
Then I started researching options in Savannah and Tybee Island in Georgia, and things just started to fall together. It didn’t take long to determine that this was the perfect destination for my family. There was something for everyone: sightseeing, activities, and beach time. At the end of the trip, everyone agreed that Savannah and Tybee Island were amazing destinations for our group. (See my stories on those two destinations in my blog listings.)
Now the family wants to celebrate the holidays with a trip instead of the traditional gift-giving routine, so I’m back to researching. My oldest son has requested beach time, so southern coastal destinations are the main focus. This time we have 10 or 11 people in our group so it’s going to be an even bigger challenge to please everyone, but I feel confident that my method will again result in a successful vacation!
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What vacation destination has been your family’s favorite? Also, if you have any suggestions for a Christmas vacation destination (with beaches), I’d like to hear from you. Share in the comments below!

