Going Places is a series from TripIt that highlights frequent travelers to showcase their unique travel styles and insider tips.
Picture this: You’re on a road trip around Iceland and your rental car breaks down. Fellow tourists come to your rescue. The rest of your trip plans sync. You spend the next several days exploring a new country with new friends—friends who, years later, you still keep in touch with.
“That’s the beauty of travel,” quipped Raimee Iacofano, travel expert and digital content creator. (And yes, this really happened to her.)
Raimee’s love of travel began when she was just 14 and her parents took her to Central and South America. Years later, she studied abroad in The Netherlands and Germany, taking weekend trips to visit as many European cities as possible.
“That was the ah-ha moment that there was a whole world out there that I needed to see.”
On chasing deals and appreciating the details
Whether it’s a road trip with girlfriends through the south of France or hiking in Peru, Raimee is always planning her next trip—and helping others do the same. She hosts group trips as well as shares tips for how to afford to travel with her community of social media followers.
Her advice? “Don’t be picky. Chase the deals over the destination. There’s always a deal to get you somewhere and experience more of the world.”
So, what parts of the world will Raimee be experiencing this year? “I just returned from skiing in Japan thanks to an incredible flight deal,” she said. “The cost of skiing in Japan is a fraction of the cost at a U.S. resort—this trip was a no-brainer.”
And later this year, Raimee plans to check a bucket-list destination off her list. “I’m a huge Lord of the Rings fan, so New Zealand has been number one on my list for years. I’m finally going this October.”
ICYMI, pop-culture trips are a major travel trend this year. According to a recent TripIt survey, 40% of Americans are planning a trip inspired by pop culture—think: Taylor Swift’s Eras Tour or TV shows like Game of Thrones or Emily in Paris.
Related reading: 4 Trends Shaping Pop-Culture Travel in 2024
Setjetting aside, Raimee plans to explore the natural wonders of New Zealand’s countryside by car. “I love a road trip. It allows you to slow down, appreciate the details, and experience a place like a local.”
Tips for planning ahead—and getting off the beaten path
<Counts months until October> Raimee reads my mind: “Yes, I’m a big fan of planning ahead. And that’s where TripIt comes in.”
“I’m always planning multiple trips and always months ahead of time. Sometimes I’ll forget I’ve booked something, like a food tour, because I’ve planned it so far in advance. But I don’t have to sort through months of emails, because all of my plans automatically sync to TripIt.”
And that way, all of her plans—no matter where or when she booked them—are in one place.
Tip: Want to automatically add your travel plans to TripIt? Turn on Inbox Sync so you never have to remember to forward your booking emails again.
As a Virgo, Raimee enjoys looking back just as much as she enjoys planning ahead. “Travel stats is another one of my favorite TripIt features,” she said. “I love being able to see—and show off—where I’ve been at the end of each year.”
Reflecting on where she’s been also helps her dish advice to her friends and followers.
“As for destinations, there are two under-the-radar places I always recommend. First, for anyone heading to Switzerland, I encourage you to add Brienz to your itinerary. It’s a charming—and often overlooked—little lake town. It’s stunning. Just trust me!”
And for those looking to get off the beaten path? “Tunisia. I planned a trip there with no expectations and was totally blown away. The food, the people, the beach towns—everything was amazing. And everyone I’ve told to visit has come back and said the same.”
Any advice for getting to those (or other) places? “Set flight alerts and subscribe to newsletters that send you cheap flight deals. And always try to offset the cost of flights with credit card points or airline miles. They’re a great way to bring costs down if you can’t catch a good deal.”
Her final tip: “Always book a walking tour on your first or second day. You’ll get a feel for your destination, build confidence in navigating it on your own, and learn tips from local guides who know the place best,” she said. “And the best part: you’ll meet new people. You never know who you might meet—and become friends with for life.”
Want more of Raimee’s tips? You can follow her on Instagram or TikTok for advice on planning smart and affordable trips. And catch up on all Going Places features to learn new travel tips, discover underrated destinations, and more.
