Hello I am Cassondra. This is where I share my tips, tricks and tales from the road.

I have a 4 year old son and he travels with me, wherever we go, so far he’s been to 14 countries and counting. We’ve done a lot of island hopping, road trips and round-the-world travels. As well as, exploring my home state of Michigan, it’s a gorgeous place to live!

Toronto CN tower view canada airbnb

The Back Story 

In 2014, I set a new life goal. I wanted to see the world and my 9-5 job wasn’t allowing me the freedom to travel. In two weeks time, I sold everything that didn’t fit in my car, paid my lease off on my apartment, resigned from my job and set out to explore the world!

This lead to nearly 5 years of full time travel. Covering 3 continents, 20+ countries and half of the United States. 

For nearly a decade, I lived and worked seasonally on Mackinac Island, from April to October. I spent my summers on the most magical one-of-a-kind island in Northern Michigan. For the other 6 months of the year, like a Snow-bird, I went south to my winter home in Jamaica.

The seasonal jobs on Mackinac Island, gave me the ability to travel full-time every winter. It was really an amazing opportunity, I would always recommend it to anyone itchy to try something new! Unfortunately, I retired from Mackinac Island in 2018.  I always miss waking up on Mackinac Island and working at the amazing hotels.

I’m an open book when it comes to travel – I’ll drive, fly, cruise, dive – whatever it takes to get there. I feel the world is there to be discovered.

I’m glad you are here and I hope you find something useful to help you on your journey. If you have any questions, let me know, I’d love to help however possible.



Where I’ve Wandered

There isn’t a place I wouldn’t go. I have a mile long bucket list and keep adding to it every day.

I’m not big on counting countries, I actually prefer to take it slow, wander a little and hopefully get to know some locals. Each year my goal is to see at least 1 new country and I’m working on visiting all 50 states in the USA. 

So far, I’ve been to:



  • Bahamas 
    • Freeport, Nassau
  • British Virgin Islands 
    • Tortola
  • Cayman Islands 
    • Grand Cayman
  • Cuba 
  • Jamaica 
  • Puerto Rico 
    • San Juan
  • Saint Martin & Sint Maarten
  • US Virgin Islands 
    • St. Thomas

Central America 

  • Mexico 
    • Cancun, Cozumel, Tulum


  • Andorra
  • Austria
    • Reutte, Ehrenberg
  • England
  • France
    • Strasbourg, Ax Les Thermes 
  • Germany
    • Frankfurt, Speyer, Gottmadingen, Munich
  • Iceland
    • Hella, Reykjavik, Vik, Jokularson
  • Spain

North America

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