How to Plan a Big Family Vacation: 9 Tips From Real-Life Experience

“This is probably the last time we’ll ever all be together,” my mom said when she was telling me why she wanted to have all 13 of us in the same location. I wondered if we both were thinking the same thing – finishing that sentence in our heads with “except for the inevitable funerals.” With that thought I was determined to make my mom’s wish happen – it was her one request for her 80th birthday; to have everyone together in the same place for a family vacation. She told me how all of her friends send Christmas cards every year with their entire family gathered, but she wondered why we could never seem to be all together at once as a family.

I told her that she raised us to leave home and family – to be independent and go start and live our own lives – and she and my father were quite successful at that parenting style. And thanks to their ‘grow up and take care of yourself parenting’, we’d never be like her friends’ families….until this summer.

It had been 10 years since we had all been together; the last time was their 70th birthday right before I left on my career break to travel. In fact, I even wrote about the 70th birthday experience as one of the first-ever blog posts on Ottsworld! Getting all 13 of us together under the same roof is about as likely as me ever finding a boyfriend who will put up with me. In the last 10 years, my 6 nieces have grown up into busy teens and college students who now have jobs, sporting careers, and lives of their own. So now we have nearly 13 adults (5 in my sister’s family, 5 in my brother’s family, my mom, dad, and little ole single me) all going in different directions.

After a lot of coordination of schedules, we came together in Breckenridge Colorado this July, a perfect location for a family reunion vacation and celebration. However, I’m used to traveling alone, and planning travel for just me; taking on the planning of a family vacation was a whole new challenge for me. We are a pretty diverse family, everyone moves and thinks at different speeds and we have very different priorities. Most people love the idea of getting a big house somewhere beautiful and having everyone stay together under one roof. But as fun as it is to get together – it can also be a bit stressful too as we all have to get along under the same roof.

Having survived the week together, I took away a few learnings from what worked and tips on how to travel and stay in a big villa as a family group and make it a great experience for everyone.

9 Tips for Planning a Big Family Vacation

1. Location: Choose a Rental/Housing that Will Hold Everyone

My mom chose Colorado since it was pretty easy for us all to get to and she likes the mountains. Plus, we had tons of big rental properties to choose from. Since Breckenridge is a ski destination in the winter there were plenty of properties to choose from that would sleep 13 or more easily. There were a number of rental companies to choose from – like the big worldwide ones such as Airbnb, FlipKey, and Home Away, as well as some local ones that really specialize in the area. We went with a local company called Summit Rentals which had lots of options and an office in Breckenridge.  Colorado delivered with its beautiful scenic views!

2. Location: Activities for Everyone

Choose a location that has lots of things to do for all ages. Most family trips like this mean you’ll have multiple generations involved so it’s important to have things grandparents and grandchildren can do.

Remember that not every activity has to be done as a big group. Sure it’s nice to have some family-wide things to do, but realistically you want to let people decide what they want to do based on their interests. During the week we often found people going in different directions – some people hiking, some kayaking, and some shopping. Then we’d all come back together in the evening for a big group dinner and games.

Our Favorite Family Adventures in Breckenridge:

White water rafting with River Runners:  This was something we all did together! However there is no rafting real close to Breckenridge, it’s a 90-minute drive away but the drive there to Buena Vista is beautiful and worth it. It was a great way to see more of Colorado and we all loved the rafting…even my 80-year-old dad!

Vail Pass Biking: This is an activity that most of my family went on, however, my parents opted out of this one. Rent bikes for the day and have Alpine Sports Rental drive you and your bike to the top of the Vail pass and then coast back down 14 miles to Frisco through woods, lakes, and mountains! We stopped in Frisco for lunch and most of us did the rest of the bike trail back to Breckenridge – which was more challenging than simply coasting!

Explore Piney Lake – a side of Vail you’ve never seen before

Hiking abounds in Colorado of course:  We found a hiking app, All Trails, that had a number of great hikes on it for all levels. People could do harder, high-altitude hikes or just simple flat hikes. As everyone else took off on a moderate hike my mom and I did an easy loop with a trailhead right in Breckenridge.

Lake Dillon Adventures:  In the Breckenridge area, you not only have mountains, but you also have one big, beautiful lake – Lake Dillon. My brother went fishing around the lake while my dad and I attempted to go kayaking until the winds cancelled our trip. You can also rent pontoon boats on the lake.

The important thing here is variety – something for everyone.

3. Take Turns Cooking

Split up the cooking duties, don’t make one person do everything. We had each family agree to plan a meal one night, which meant they shopped for what they needed and did all of the cooking that night while everyone else relaxed. We got plenty of groceries for ‘help yourself’ breakfasts and lunches but for dinners, we made it more of a sit-down meal and enjoyed the opportunity to have all 13 of us at the same table.

4. Have a Plan for Who’s Paying for What

Before we got there we discussed how we would handle groceries. As families did the grocery shopping we kept all of the receipts and in the end totaled everything and split it among 13. You can also easily designate one person to pay for all of the groceries and keep track so that you can pay them back at the end. It’s just good to have the conversation before the trip if possible.

5. Get a Discount Card at the Local Grocery Store

The local grocery store was new to us, but all the sale prices around the store required a local store card. Even though none of us were from Colorado, we quickly signed up for a discount card and saved hundreds of dollars just in a week! It was worth it even though we’ll never use it again.

6. Find a Farmer’s Market

It’s always great to support the local community where you are staying. We found local produce being sold near the Frisco Marina around Lake Dillon every day and there is also a larger weekly farmer’s market held every Friday in the summer in the central part of town. Just do a quick search of your vacation area for farmer’s markets before you go to see what days they run.

7. Shop Local

It’s great to support the local community in which you are staying whenever possible. I got hooked on a local sparkling tea called Bhakti while I was there. You know about the big craft beer scene in Colorado – they also have a big craft juice/tea scene! I couldn’t believe how many juices and teas there were in the markets. But Bhakti was like a little flavor of India in Colorado so it won me over immediately! The flavors were inspired by the owner’s trip to India. After all, summer is a time for exploring and trying new things, and that’s exactly what Bhakti is all about. The best thing is, I learned that this little local company is expanding across the US. You can find their sparkling teas in any Whole Foods Store. Oh – and the best part, you can also use the sparkling teas as a mixer with gin, vodka, or rum; making it appropriate for kids or adults on a multi-generation family trip!

8. Record and Share The Memories

Pictures are the lasting memories from a family trip so make sure that you capture the moments. Since my mom was hoping for a big family picture we were sure to do something a bit more formal and traditional. I brought a tripod and we did a number of family photos – (expect to get this pic on my mother’s Christmas card this year if you know her!)

But it is also great to get a lot of candid captures of all of the activities! Make sure you have an easy way to share all of those images among the family by setting up cloud sharing or a Dropbox folder before the vacation. I set up a Dropbox folder and invited everyone in the family to it. Most of us already had the Dropbox app on our phones, so we could easily share all of the images right from our phones to the shared folder so that everyone had access to them immediately.

9. Turn Off The Digital Occasionally

Since there are multiple generations, it’s easy for some to just be attached to their phones and forget that this is a special time for the entire family to be together. It’s a good idea to set aside some time and make sure that everyone puts down their phones or laptops and just connects face-to-face. I often think we have lost the art of simply talking to one another. One night after dinner we all sat around the table and shared a personal memory of my parents since we were in Colorado together celebrating their 80th birthdays. It was by far the most memorable and touching moment of the whole trip.

One of the key things to take away from these tips on how to plan a family vacation: think about being local whenever you can. Even though you are away from your homes, you can support the local businesses where you are traveling.

Hopefully, you can use some of these tips when you plan your next family vacation or reunion and keep everyone in the family happy!

Have you ever planned a big family vacation?  Where did you go?  Share in the comments below!