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What it’s like as a first-time group traveler

May 27, 2016 by Jamie Burke

When my coworker Paula and I learned we’d be traveling on the Grand Tour of Italy, we didn’t really know what to expect. What would our tour group be like? Would we have enough time to see everything we wanted? Well, we’re back and happy to report: We loved it. Keep reading to learn more about our first group travel experience.

Rose garden in Florence, Italy

As travelers, Paula and I both had different experiences. I’d been abroad before, either with my family or traveling alone, but this was Paula’s first time leaving the country. We were both really excited to visit Italy. It’d been on my wish list for a while, and traveling on a Grand Tour meant we’d get to see so much of the country.

Jamie's group in Assisi, Italy

After landing in Milan, we met up with our Tour Director and a few members of our group (one was even on our plane!). We quickly exchanged names, where we were from and how our flights had been. A bus ride from Milan to Como was spent getting oriented, and staring out the windows at incredible mountain scenery and castle ruins. It wasn’t until we got to our hotel in Como and opened up our French door-style windows out onto a view of the village and lake that it hit us: We made it.

At our welcome dinner that night, we soon found ourselves laughing and sharing stories with our tablemates. I had been a little nervous about how we’d all get along, but I quickly realized that we all had something in common—a love of travel. We had so much fun spending time with everyone in our group, not just because everyone was so nice (they were!), but because we were all feeling lucky to spend two weeks in such an amazing place.

Guided sightseeing in Capri, Italy

As for visiting everything we wanted, our guided sightseeing tours helped us do that and more. I’d taken myself around places like Dublin and Berlin and thought I did a good job of seeing the sites and learning about the city I was in all by myself. But having a local guide by our side or our Tour Director sharing her insights (like where exactly George Clooney’s villa is along Lake Como), was so eye-opening. We got to see and learn all about the “big hits” like the Colosseum, but some of my favorite moments were when we explored something unexpected, like street art in Capri or a hidden courtyard in Venice.

Even though our itinerary was action-packed, we also had plenty of time to explore on our own. I had a few “musts” to cross off my list in Florence, like getting a sandwich at Al’Antico Vinaio and admiring the view from the top of Piazzale Michelangelo. Everyone in our group had their own wish list items to cross off, so I was happy we all had the chance to spend a free day in the city. When we met up again for dinner later that evening, we swapped stories of strolling Boboli Gardens, seeing David at the Uffizi and discovering the Mercato Centrale. It was great hearing about everyone’s day and learning more about the people in our group by talking about the things they love doing most.

Street art in Capri, Italy

As far as being able to travel as part of my job? Well, let’s just say, sometimes I pinch myself to make sure I’m not dreaming! Setting out on one of our tours was even better than I expected. From watching the sunset along the port in Sorrento to raising a toast at a wine tasting in San Gimignano, it’s hard to pick a favorite moment from our trip. But one of the best parts of visiting Italy with 20 other people I’d never met was that I got to share that experience with 20 travelers—just like me.

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Traveler stories
About the author | Jamie Burke
Always on the lookout for the next best meal ever, Jamie loves exploring the world—and all the great food in it. When she's not working to inspire new travelers, you'll find her biking around Boston, eating at her favorite sushi place, or hanging out at home with her family (and cat).
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