Picture this: 16 family members, eight of them kids under eight, embarking on a two-week adventure through Greece. Sounds chaotic? It was—but it was also one of the best trips we’ve ever taken! With the right planning, a mix of relaxation and adventure, and a willingness to embrace the unexpected, we made it work. If you’re planning a big family trip, here’s how we did it and what we learned along the way.
Planning for a Large Family Trip
Organizing a trip for multiple families is no small feat. Thankfully, with event planners, marketing professionals, and seasoned travelers among us, we had a solid strategy. After many zoom calls and in-person powerpoint presentations, we settled on a 15-day itinerary that balanced sightseeing, relaxation, and activities for all ages.
Key Takeaways:
- Limit Destinations: With young kids, island-hopping was unrealistic. Instead, we chose three locations: Athens, Naxos, and Mykonos.
- Accommodations Matter: We booked family-friendly hotels and villas with large common areas and pools to keep kids entertained.
- Build in Downtime: Over-scheduling leads to meltdowns, so we planned quiet afternoons for naps, swims, or meals made by in-home chef services!
Choosing the Right Greek Islands
Since we had 8 kids in tow, we knew this was no backpacking trip or honeymoon vacation. As much as we wanted to pick our favourite party-hopping spots, this trip was about culture, relaxation, and kid-friendly experiences. Here’s how we broke it down:
Athens: Culture & History (2 Days)
Athens was our first stop. We stayed at Divani Palace Acropolis, a comfortable and centrally located hotel. The biggest highlight was visiting the Acropolis early in the morning before the heat and crowds became unbearable.
Tips for Athens with Kids:
- Stay near major attractions to avoid long commutes.
- Visit the Acropolis first thing in the morning.
- Plan for snacks, water, and shade to survive the heat.
Additionally, we took a short trip to Varybobi, where the kids helped water trees planted in honor of my husband’s Greek roots through the We 4 All organization.
This experience not only connected us to nature but also added a meaningful touch to our journey.
Naxos: Quiet & Family-Friendly (7 Days)
After two busy days in Athens, Naxos provided the perfect contrast. It’s a laid-back island with beautiful beaches, charming villages, and amazing food. We stayed in two private villas—both with infinity pools—giving the kids space to run and play.
Why Naxos Worked for Us:
- The beaches were quiet and shallow, making them ideal for kids.
- We enjoyed home-cooked, farm-to-table meals from a private chef.
- Old Town Naxos offered a scenic stroll without overwhelming crowds.
Mykonos: Bustling & Iconic (5 Days)
Next, we headed to Mykonos. Known as a party island, it wasn’t our first choice for a family trip, but we found ways to make it work. We stayed in a large villa with enough space for everyone and spent our days at Konstantis Beach, where the shallow water and soft sand kept the kids entertained.
What We Learned in Mykonos:
- Avoid peak party spots and instead find family-friendly beaches.
- Shopping in Old Town was fun but best done in short bursts.
- Gelato is an excellent incentive for kids on long walks.
Final Thoughts: Making It Work
Traveling with a big group takes patience, flexibility, and a solid plan. Despite the inevitable challenges—tantrums, delays, and occasional chaos—this trip gave us memories we’ll cherish forever.
Our Best Tips for Large Family Travel:
✅ Book accommodations with large kitchens and outdoor space. Hotels are great, but villas give kids more freedom.
✅ Choose a mix of structured activities and free time. Overscheduling leads to burnout, so balance is key.
✅ Make dining easy. Find restaurants with outdoor seating and, when possible, book private chefs for a stress-free experience.
✅ Accept that not everything will go as planned. Rather than stressing, go with the flow and focus on enjoying the moment.
Ultimately, planning a trip with multiple families requires effort, but the rewards are immeasurable. By choosing the right destinations, allowing for flexibility, and keeping expectations realistic, you can create a vacation that is both fun and memorable. Here’s to more adventures!
