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Journey With Jen
Wander-Worthy Plans
From weekend getaways to multi-city adventures, find detailed itineraries packed with must-see sights, hidden gems, and travel tips to make your trip unforgettable.


The Ultimate Family Guide to San Diego: A 7-Day Itinerary for Fun & Adventure
San Diego is a dream destination for families, offering everything from sun-soaked beaches to world-renowned attractions. This 7-day...
Jennie Vandegrift
May 25, 20254 min read


A Magical Family Christmas in New York City: A Long Weekend Itinerary
There’s something truly magical about New York City during the holidays—the twinkling lights, the snow-dusted streets, and the contagious...
Jennie Vandegrift
May 11, 20253 min read


Finland & Estonia Itinerary: A Magical Snowy Adventure
If you’re dreaming of a winter wonderland filled with twinkling lights, Arctic adventures, and fairy-tale charm, this 9-day Finland and...
Jennie Vandegrift
Apr 27, 20254 min read


Exploring the City by the Bay: A Kid-Friendly Weekend Itinerary
Here’s an idea to kick your week off with a little wanderlust: have you been dreaming about planning a trip to San Francisco? With its...
Jennie Vandegrift
Apr 13, 20253 min read
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