Tag Archive for: vacation

Working Remotely from Anywhere in the World

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For the past six years, travel planner Cassandra Santoro has split her time between New York and Italy. She spends summers on the Amalfi coast, travels throughout Italy in the fall, and then returns to the U.S. for the spring.

Sounds pretty great, right? 

Cassandra isn’t on vacation 24/7/365, though. She’s a successful entrepreneur and CEO of Travel Italian Style. She’s become an expert at working remotely from all over the world.

Now that the pandemic has opened up remote work opportunities for so many people, this lifestyle is more and more feasible. But to make this work, there are more than a few logistical challenges to address. 

Cassandra joined me on my live-streaming show Inside Scoop to share how she does it:

Bring your own WiFi

You might think there will be internet access wherever you go — but Cassandra says that’s actually not the case. She says bringing your own WiFi can help the transition to go smoothly, ensuring you can always log on when you need to. Cassandra recommends buying a Skyroam hotspot.

If the home rental where you’re staying advertises WiFi, Cassandra says you should always check with the host to make sure the internet connection is strong and reliable. Better safe than sorry!

I have lots of other remote office tips in my LinkedIn Learning course “Organizing Your Remote Office for Maximum Productivity” as well. 

Making the space work

Even if you’re in a beautiful part of the world, huddling up in a dark room to work will kill your mojo.

When you’re working remotely from somewhere new, Cassandra recommends buying fresh flowers or even a basil plant to make the space feel homey. She also prioritizes light-filled rentals. 

Consider time zones

When you’re figuring out the logistics of working away from home, Cassandra says it’s important to consider time zones. Will you have to get up in the middle of the night for client meetings? It’s important to ensure that you can do your job without having crazy hours.

When in Rome…

When you’re working from someplace new, Cassandra suggests really immersing yourself in the local culture. For her, that means an aperitivo!

If you want to hear the rest of Cassandra’s suggestions, you can watch our full conversation here!

Checklist to Take Your Remote Office on the Go

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BONUS FREEBIE: Want even more ways to stay organized, productive and less stressed? Click here to get access to my List-Making Starter Kit. It will boost your efficiency and get you back to doing more of the things you love.

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If you’ve been working remotely because of the pandemic, by now you’ve probably got some of the basics down — where in your home you work, what your hours are, and what you wear. (Although I have my opinions about the Zoom shirt…)

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How to Have a Mindful Vacation

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BONUS FREEBIE: Want even more ways to stay organized, productive and less stressed? Click here to get access to my List-Making Starter Kit. It will boost your efficiency and get you back to doing more of the things you love.

When I was on vacation in Cancun, Mexico recently, I took lots of pictures of my friends, my husband, and the beautiful landscape.

Whenever one of us took a great picture, we shared it with the group. 

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Wouldn’t it be nice to make some money off delayed flights?

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I belong to a mastermind group for entrepreneurs and business owners and they meet twice a year in a great locations. This time it was in Tucson, Arizona.

Of course the day I was leaving NYC there was a snowstorm and I was connecting through Atlanta. Because of a tiny bit of ice…the whole city of Atlanta closed down 🙂

I was stuck in O’Hare airport for 5 hours. It wasn’t fun but since I’ve started meditating I found that I was a little less upset than I’d normally be.  Plus I went directly to the Delta Sky Lounge. I have a Delta Amex card and you can get in for $30. Well worth it!  I recommend getting a day pass if you ever get stuck! It’s a much more civilized way of hanging around an airport. Read more

A Trick to Make Traveling So Much Simpler

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Jay and I at the Colosseum.

I’m feeling refreshed and reinvigorated after returning from Italy and Switzerland last week with Jay and a few of our friends. Jay and I went to Rome on our own — taking a tour inside the Colosseum and the Roman Forum plus having our favorite pizza in the world at Baffetto.

We also ate our way through through the Testaccio neighborhood. If you go to Rome definitely take a food tour with Eating Italy Tours — it was a highlight. And I’ve recently had to follow a gluten free diet as a complication of my appendix rupture and they were so sweet and accommodating about it! Don’t worry if you go somewhere like Tuscany instead of Rome, they still have Tuscany Tours that show off all the food that Italy has to offer. You won’t miss out on the amazing food of Italy!

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Eating my favorite pizza at Baffetto.

Then we were off for Geneva to meet up with our traveling friends Peter & Nicole and Nancy. We hopped in an SUV and drove an hour to Montreaux for the 50th annual Jazz Festival there.

The jazz festival was lots of fun with wonderful gourmet food, wine and lots of cool music. The town of Montreaux itself is really adorable with lots of shops and restaurants. Plus it’s right on a lake so the views are amazing. A note if you’re ever in Switzerland – it’s super expensive. Think 35 dollar cheeseburgers and 15 glasses of wine (and the pours are miniscule.)

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In the adorable town of Montreaux, Switzerland.

Off to Lake Como from there with a 4 hour drive through the Swiss Alps. Such a cool experience to drive through nearly untouched mountainsides. We saw snow capped mountains and lots of animals on our twisty travel. Those roads are all over the place and obviously very high up. It was a bit unnerving at times but we made it through with good music and snacks!

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The beautiful Lake Como!

We stayed in a small town called Varenna and absolutely loved it. It was so charming and picturesque. We were in love. We stayed at a villa called Casa Stacy and I highly recommend it. Not only did Stacy make sure we had everything we needed but she also hooked us up with some fun excursions. We went on a boat tour of the entire lake and had a private wine tasting that was amazing.

On a boat with our friends Peter and Nicole

On a boat with our friends Peter and Nicole.

Then it was off to finish the trip in Milan where we got a full tour of the city and got to see The Last Supper thanks to Milan Day Tours. It’s so interesting to see ancient art up close. When I saw the Mona Lisa I was a bit underwhelmed because it’s so tiny. Not like you’d expect. But this piece by Leonardo di vinci is huge. It takes up an entire wall and I thought it was in very good shape. We learned all about the restoration and history. I’m glad we did that tour.

My vacation was full of amazing food.

My vacation was full of amazing food.

Trick to Make Air Travel More Bearable

Our travels throughout Italy and Switzerland went off without a hitch. Air travel is usually the biggest headache for me when I’m on vacation. But here’s the trick I promised — get Global Entry. It’s amazing how much time you save.

Global Entry gives you several benefits for 5 years and a $100 price tag. First you are eligible for TSA Precheck within the United States. That means you get to basically skip the line at security, keep your laptop in it’s bad and forego taking off your shoes and sweaters.

Then when you travel internationally there’s another perk – you get VIP treatment when you return home and go through customs.

We just had to scan our passports and fingerprints. We got a printed pass and brought it to the customs officer. It took us about 7 minutes to do this. So from the time we landed to the time we were in a taxi at JFK heading home — just 37 minutes went by. That is a far cry from the usual experience we have when coming home internationally.

Other than the cost — the other catch is that you have to go for an in person interview to get access to Global Entry. It’s a pain to carve out the time in your calendar – I totally get that. But I have to tell you – not having to wait in line and prolong an already long trip was key for me. I’ve been trying to mitigate stress in my life and this is definitely one way to do it while traveling.
If you go for Global Entry let me know how your experience is. I’m giving mine two thumbs up!