Wine • Food • Culture

See Europe differently.

Private European journeys & hosted small-group trips designed around the places, flavors and experiences that make you want to stay a little longer.

Italy • France • Spain • Portugal • Greece • Croatia

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Hi, I'm Jenn

I plan the kind of trips I love to take.

Great food, local wine, beautiful places to stay, and meaningful experiences are always at the heart of what I do. I design private trips and host small groups throughout Europe, pairing a well-planned itinerary with authentic experiences and enough free time to actually enjoy where you are.

Meet Jenn

Where I Specialize

Some places I know especially well - and love sending my travelers.

Italy

Spain

France

Portugal

Greece

Croatia

Have Somewhere Else in Mind?

My specialties are rooted in Europe, but my travel planning doesn't stop there. I also work with clients traveling to destinations around the world.

Explore Travel Beyond Europe

Come Travel With Me

Small Groups. Great Wine. Even Better Company

Barcelona & Beyond: A Taste of Catalonia September 2027

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Sep 06 - Sep 13 , 2027

Girl's Trip: Puglia & Matera's Dolce Vita September 2027

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This Month's Featured Journey

Greece: A Food, Wine & Island Escape

Experience the best of Greece with a thoughtfully curated journey through Athens, Santorini, and Mykonos. Stay in beautiful boutique and luxury accommodations, explore the Acropolis...

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I feature a new ready-to-book private itinerary each month.

Wine Cruises

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Kind Words From My Travelers

Our girls trip with Jenn Hilchey was absolutely phenomenla! Me and my sister wanted a getaway to Italy, so when we saw an all girls Tuscany wine trip we knew it would be perfect! And goodness did it deliver! Jenn... read more

Kaitlyn D

The vacation of a lifetime! My wife and mine's first international trip to Europe and we are so appreciative of Jenn Hilchey from Travel Box International for helping us to plan and execute our trip. Our cruise excursions to Mykonos, Kusadasi, Santorini,... read more

Randy F

I loved the women’s trip Jenn hosted on Virgin Voyages. It was my first cruise and she answered all my questions. I met amazing people and made new friends. The excursions were spectacular and unique. I will be booking another... read more

Sarah S

The Travel Journal

Wine, Food, Places & Ideas For Your Next Trip.

Tuscany vs. Piedmont: Which Italian Wine Region Is Right for Your Trip?

Slow Travel, Done Properly: Why Boutique Stays Change Everything

Why I Love Hosting Girls’ Trips—and What I’ve Learned Along the Way

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