What happens when you round up three friends and your boyfriend of seven years to spend two weeks in one of Europe’s most prolific countries? Vannessa of Adventure with V decided to do just this when she planned a return trip traveling around Italy this past summer. After all, on top of all that Italian culture has to offer, she has family there as well.

While Vannessa did most of the planning in terms of figuring out flights with Sky Scanner, everyone gathered together to both book flights and browse the internet, particularly AirBnb, for places to stay during their trip. “The planning process went extremely smooth; I don’t think it could have gone any better,” she remembers.

When all was said and done, the group would spend three days in Milan, three days in Venice, three days in Pescara, and four days in Rome, allowing one extra to take a day trip to Capri. They would fly out of Toronto to Milan, allowing for a layover and quick trip to Brussels in between, and then fly home from Rome. They chose Milan as one of the them wanted to see where her family had come from, and they “were curious if the fashion lived up to the reputation.”

While Rome and Venice were for obvious reasons, Pescara was added to the trip because this is where Vannessa’s family lives. “It benefited my friends too because Pescara has some of the most beautiful beaches in Italy, and it offered a nice 3-day break from all the walking we had done,” she says. “We were able to just relax and enjoy the Italian sun.”

She does admit to feeling a bit anxious before departure simply because she had never traveled this long with her friends, and she was concerned about how trying this might be to their various relationships. “The most challenging was dealing with everyone’s different personalities,” she says. And while there was some head butting, it was luckily fleeting. “For the most part we were able to make compromises or come to the same decision, which was great.”

Over all, Vannessa recalls this trip extremely fondly. She now has four other people who can share the stories and memories for years to come. “We still talk about this trip even though it has been about five months. We still laugh about it and cringe at stories and none of this would have happened if we hadn’t have gone all together.”

“This is cliche, but I felt so blessed [after]. Not a lot of people take the time to go on such an amazing trip with their best friends, and I am forever grateful.”

On her tips for traveling around Italy? “Definitely look at options on AirBnB. Stay near a metro. Keep an eye on your bags. Try new food. Drink the house wine, it’s the cheapest but it’s delicious as well. ALWAYS say yes to dessert. Buy tickets ahead of time for any attraction you can, it can help you avoid lines at the ticket counter. Don’t be afraid of a stopover; ours may have been extremely long, but we were able to see a different country that we’d never planned on in the beginning.”

And on advice she’d give to those who want to travel with friends in the future?

Be patient.

“If you and your friends butt heads, stop arguing; it’ll all blow over once you sit down to eat (or get back to some air conditioning like us). Make compromises; everyone won’t want to do the same things all the time, so give your friends some space and encourage time to split up and meet back together at a later time. ENJOY. Don’t worry too much about whether your friends are enjoying the trip as much as you are; it’s your trip too, and you’ll regret worrying.”

You can check out Vannessa here:

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Interview by Samantha, Photographs by Vannessa

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