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...

Explore The Itinerary

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

Wine Cruises

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Kind Words From My Travelers

If you like discovering what a Women’s retreat means in Europe choose Jenn. I chose her for my Italy retreat and it was epic. What a best choice! From welcoming lunch at Florence and doing a little site see, everything... read more

Bethlehem A

We just returned from our cruise and Jenn helped us book our excursions in Nassau and Amber Cove. She did lots of research and vetting that saved us time and landed us 2 AMAZING VIP experiences! She was in constant... read more

Jennifer J

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

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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