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Life and Work with Sheila Drakeley and Chris Caswell

Today we’d like to introduce you to Sheila Drakeley and Chris Caswell.

Sheila and Chris, please share your story with us.
We are a Boston based couple who are constantly looking for a way to escape our day jobs. We are not only best friends but each other’s favorite travel buddy! We’ve seen so much of the world near and far in the short time, we have been together and get yourself into unique situations… and yes, they are quite unique…

We began dating in July 2016 and since then have managed to travel near and far, experiencing some of the most amazing cities in the world. We have been to five countries, twenty states, and over thirty cities in just two years!

We started The Traveling Massholes to share all the interesting situations we get ourselves into on our getaways. We wanted to share the beauty of the world, we have been so fortunate to explore, with those via our photography and blog. Our biggest advice is never to turn down the opportunity to travel; near or far; short or long – every trip will teach you something and broaden your horizon.

We’re always bombarded by how great it is to pursue your passion, etc. – but we’ve spoken with enough people to know that it’s not always easy. Overall, would you say things have been easy for you?
Starting up your own business, blog or hobby is never easy. Of course, nowadays with social media, everyone has the power to be one of these three things with the touch of a button. Being travel bloggers and travel photographers has its own challenges. While we had already been traveling for over a year when we launched our site – we have found much success in being consistent. That means consistently posting and engaging with our followers. Reach out to brands and companies that aline with our beliefs and never passing up an opportunity to try something new!

Our biggest advice we try to implement is never tried to reinvent a wheel that is already successful. If something works for someone else try that! Tailor it to your brand or business and make it unique but no one is asking you to do a complete 180. But ultimately, it is what sets you apart and what is unique about you and your drive and passion towards your work, which will allow you to be successful.

So, as you know, we’re impressed with The Traveling Massholes – tell our readers more, for example, what you’re most proud of as a company and what sets you apart from others.
The Traveling Massholes strive to provide travel advice, tips, and tricks, about our worldly travels while including a sense of humor and enlightening our readers with the real-life details of the situations we have found ourselves in. Of course, traveling with your significant other always has it adventures but one thing is for sure, traveling the world with someone you love strengths your relationship; and if you can survive that you can survive anything.

We target our audience to those who want to feed their wanderlust while working full-time jobs. Both Sheila and Chris work more than one job but still make it a priority to get out see the world, even if sometimes it is quick weekend trips or a spontaneous go out on a whim adventure.

Unlike many other travel bloggers, we try to keep it real – showing you that yes it is possible to see the world and all that it has to offer without spending all your life savings. Some of our best trips have been those we spent the least amount of money on. We also try to provide a realistic view of each place we’ve visited. Keeping our itinerary open and showing our readers how to achieve the same type of travel we did. Our biggest target is 20 to 30-year-olds, like ourselves, who are still finding themselves and travel helps us as humans to do that.

Contact Info:

Image Credit:
The Traveling Massholes

Getting in touch: BostonVoyager is built on recommendations from the community; it’s how we uncover hidden gems, so if you know someone who deserves recognition please let us know here.

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