Travel Advisor

Black and white portrait of the travel advisor

Matthew Cashman



  • Canada,
  • United States,
  • Digital Nomad Travel,
  • Arts & Culture

Based in


Profile details


Addicted to the feeling of being somewhere new. Entertainment and events background.

Travel style

Comfortable in a rundown hostel with only a backpack or on a luxury yacht after a spa treatment.

Favorite hotels

Previous slide

Freehand Chicago

This stylish Freehand outpost is housed in a classic 1927 building in Chicago’s vibrant and artistic River North neighborhood.

The Drake

Upscale hotel built in a landmark building from 1920 with lake views and traditional rooms.

Next slide

Get in touch with Matthew

Reach out to customize and book your own experience. Or, just to chat about travel in general.

You can normally expect a response from Matthew within a business day or so. You'll also be subscribed to our travel newsletter (you can unsubscribe at any time).

Black and white portrait of the travel advisor

Travel Advisor

Matthew Cashman