Travel Tips/Advice Archives • Jessie on a Journey

Taking you beyond the guidebook

Inspiring you to live your best life through travel

Looking for the best travel medical insurance for digital nomads? Here is my in-depth review of SafetyWing, a company offering a new kind of coverage.

Wondering what to wear in NYC in winter? This guide with packing list can help you stay warm yet stylish while visiting New York City December-March!

This woman’s cancer journey led her to quit her job, sell everything and travel. Learn why you shouldn’t wait to travel + how to plan a long-term trip.

Wondering how to entertain yourself on a long bus, train or plane ride? Here are some fun and productive ideas for your next trip.

Intercultural learning can cultivate immersive travel and a kinder world. Here is how to develop your cross-cultural skills for more meaningful trips.