Jessie on a Journey

Solo travel guides and active adventures, helping women explore NYC and the world confidently.

Visit jessieonajourney.com

Written By

Jessie

Travellers

Solo

Focus

Female Solo

Popularity

29 / 100

Running Since

2011

Posts

975

Every few weeks

Last Updated

Oct 2026

About Jessie on a Journey

Jessie on a Journey is run by Jessie, an NYC-based solo female traveler who launched the site after a life-changing solo trip and study abroad experience. The blog has been active since 2011 and now hosts more than 975 posts and 1,306 pages covering trekking, immersive cultural experiences, NYC tips, and travel business advice. Jessie writes first-person trip reports, detailed trekking and packing guides, and offers free email courses and planning printables. The site also operates NYC Photo Journeys for tours and trip planning. Posts are long-form and richly illustrated with many photos, though some articles use stock imagery or sponsored content.

Jessie writes like a confident travel-savvy friend who plans your solo trip with you. The site delivers long, practical deep-dives - think multi-thousand-word guides, exact gear lists, and honest trekking reports - alongside local New York City tips and resources for travel creators. The voice is encouraging and precise, aimed at women who want active, immersive adventures beyond typical sightseeing. We appreciate the abundance of actionable how-to content, clear safety and packing advice, and the regular cadence of new posts, roughly a couple of guides each month. The blog is also transparent about partnerships and includes lots of photos to illustrate routes and experiences.