7 Tips for Planning a Small Group Trip to Italy

group trip

Whether it’s friends, family or members of an organization, small group trips to Italy are becoming a popular – and super fun way – to create the vacation of a lifetime for like-minded travelers. Because the participants of the group have something in common, traveling together just makes sense. But that said, anyone who has traveled together with others knows that it can be tricky too! That’s why it’s important to start with a solid plan.

Having created and hosted small group tours for years (which I love, by the way!), here are 7 of my favorite tips for planning a successful small group trip to Italy.

1. Choose one leader right from the beginning and make it clear which person (you, perhaps) will be the primary planner. Too many cooks in the planning kitchen and things can get sticky fast. If you end up as the leader, be prepared to gather ideas from all members of the group and regularly share them collectively.

2. Delegate jobs, like gathering travel information or logistical details. “Sarah will be arranging our flights, Dan will be looking into smart phone plans for our trip”, etc. There is an endless list of details when planning a small group trip to anywhere, so sharing the load is a must. It’s also nice to include everyone in the planning in some way, so you might want to delegate a pre-trip job to each member of your group.

3. Be specific when you ask for input. For example, if you’re planning a group trip to Tuscany and someone suggests that you take a tour of ruins in Sicily, that’s just not relevant. The more specific you are, the more helpful and relevant the input with be. “We’ll be organizing a side trip into the wine county – no more than an hour’s drive from our villa in Tuscany. Does anyone have a winery suggestion?”

4. Include group experiences in your trip itinerary that suit all members. Rock-climbing might not appeal to your great Aunt Agnes, however the pasta rolling lesson will be a hit with everyone. When in doubt, take a vote.

5. Build in plenty of on-your-own time. Too much togetherness can be … well … too much. Even if you dearly love those with whom you’re traveling. One of the easiest ways to include time for people to do their own thing is to schedule in a side trip to a hill town. Once you’re there, simply choose a spot in the center of town and decide on a time to meet. Then encourage everyone to fly free for a while.

6. Hire local guides. Being the designated leader of a small group of friends or family doesn’t mean that you have to be an actual guide throughout the trip. That would be exhausting! Nothing beats hiring Italian guides or taking guided tours. Plus you support the local economy and get to benefit from their expertise. It’s a win win.

7. Include down time. If I had a pick the biggest mistake that people make when planning trips to Italy, it’s this one. Down time is crucial to prevent stress, irritability and exhaustion, and nothing puts a damper on a trip like exhaustion. Every day should include down time, whether it’s rest time, free time or just plain on-your-own time, members of your group need to be able to take a breath and recharge their batteries.


DSC_0034Pamela Haack creates and hosts boutique-style, small group tours that are a combination of the very best of Italy: the exciting and the peaceful, the popular and the secret, the talked about and the never-heard-of-before. From art experts and operettas to authentic cooking classes and ancient Etruscans, Pamela helps visitors experience the spectacularly beautiful, endlessly interesting cities and countryside of Italy in an up-close and personal way – off the beaten strada.

Pamela is also the author of Top 10 Favorite Etruscan Sites. She lives with her husband, Lou, in Umbria, Italy.

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