Dropbox, Slack, Square, and Twitter.

These are all popular online tools and services that help millions of Americans do their jobs faster, easier, and better. And many workers have something else in common with these companies: being untethered from a cube, office, or even a specific ZIP code.¹

While these are the companies making headlines for giving their employees the freedom to work from anywhere — with some strings attached — thousands of other small businesses and larger enterprises alike are also turning the workplace inside out.

Some employees are content to strap into their home office. But others aspire for a bit more adventure than troubleshooting their wireless router. These are the workers who see an opportunity to bring their work on the road, exploring new destinations and visiting familiar ones for business and pleasure.

And there’s another factor making it possible to combine work and travel: the money people are saving by skipping the commute. From gas costs and vehicle maintenance to eating at home and the simple fact that time is money, a third of workers reported saving $51 to $100 per week, according to a FlexJobs poll. An astounding 21% said they saved $200 per week, which could build an annual travel fund of more than $10,000.

That’s more than one trip; that’s a working getaway for every season.²

The opportunity to work from anywhere isn’t for everyone. But if it’s for you, we have some tips and advice to make sure your performance

What Does It Mean To Work From Anywhere?

First off, let’s clear up some confusion. While working remotely simply means you’re not working in the cubicle bearing your nameplate, working from anywhere implies adventure. It could be one trip, but it’s often a series of getaways balanced out with time at your home base. When you work from anywhere, you’re not simply set up in your kids’ playroom with a headset and coffee mug. No, you’re galivanting around the country (or globe), balancing work while exploring exciting new destinations.

Got it? Good.

Before You Decide to Work from Anywhere…

What you’re about to read may seem obvious. But we’ve heard about enough would-be mobile workers who didn’t see this next step as essential before making the move to work from anywhere that we thought it was worth sharing.

Here it is: Ask first. Ask your regional manager, department director, or company president.

While seemingly every week we hear about more companies that are making the decision to allow telecommuting permanently, or at least for a good while longer, it doesn’t mean your company is following suit. If you’re unsure what your policy is or aren’t positive that management will give you the green light to take your job on the road, don’t make any big decisions until you’ve presented your case and have a solid answer.

If and once you get the big OK, it’s time to start planning. Do you have a laptop, bag, and smartphone built for life on the road (and in the air) — or is this the right time to cash in some of those WFH savings? One accessory you won’t want to skimp on is a mobile hot spot. Sure, free WiFi continues to pop up more in unexpected places, but it’s far from ubiquitous — especially when you stray from population centers. While your smartphone may double as a hot spot, it can drain the battery and limit your productivity. If you’re looking for suggestions to make sure you always have an option for connecting to the ‘Net, top-rated tech product review site Tom’s Guide includes the Skyroam Solis Lite among its picks. The mobile hotspot works in 130-plus countries with service options ranging from a $9 day pass to a $99 monthly subscription that includes unlimited data.³

Planning for a “work from anywhere” lifestyle isn’t always about planning for every foreseeable event. It’s about planning for all the events you could never imagine happening. That’s pretty much why people pick up travel insurance in a nutshell. And the more you travel, the more likely you are to encounter random twists of fortune that can be remedied with a solid travel insurance plan.

Allianz Global Assistance’s AllTrips plans are an ideal choice for digital nomads and all travelers seeking to work from anywhere. These annual plans provide protection for a full 365 days of travel for individual trips up to 45 days. Best of all, you don’t need to travel every week or even every month to make these a wiser financial decision than purchasing a separate travel insurance plan for every trip you take. That’s because it only takes three trips to make an annual plan the more cost-effective choice. Plus, with benefits including Trip Cancellation and Covered Emergency Medical Care, your peace of mind can be immeasurably boosted. Right now is a great moment to find the AllTrips travel insurance plan that fits your “work from anywhere” setup and your budget.⁴

Sweet Spots & Hot Spots

So, where do you go? Maybe you have bucket list destinations to cross off or friends who are also working on the road you plan to connect with. But if you need a muse to get started, we have a few ideas.

All of the following destinations come with this caveat: be sure to check local travel guidelines and restrictions. This is especially true of our first work from anywhere landing spot…

• Get Connected in New York City: While there are a million reasons to include the Big Apple on a list of potential destinations, we’re including it for one: it’s connected. In fact, no U.S. city boasts close to the amount of free WiFi pumping through NYC. We’re not just talking about cafes and hotels. Thanks to Link NYC, New York has free WiFi kiosks all over the city — from parks and green spaces to underground subway stations.⁵

• Plan A Destination For Every Season: Maybe you don’t want to hang out with 8 million people yet. We get it. We have somewhere that may be a bit more your pace: Lake Metigoshe State Park in North Dakota. Never heard of it? Great! There you can rent a cabin to kick back after your canoe ride or hike — we recommend Osprey Cabin — and be sure to bring a notebook and paper. You see, there’s no WiFi here. Or electricity. Just a wood-burning stove and a propane-fueled lantern. If you’re a creative professional who needs some inspiration, you can find it in the Turtle Mountains among beavers and moose. And if you really need to connect with Corporate HQ, bring along that hotspot we mentioned earlier.
  
  For the true Lake Metigoshe experience, plan your trip for the winter.⁶
  
  Now that you have carte blanche to work from anywhere plus an annual travel insurance plan, why not plan a different trip for each season?
  
  For spring, why not return to civilization, traveling back across the country to our nation’s capital just in time to catch the Cherry Blossoms blooming. While in D.C., do some sightseeing for free. The National Zoo and U.S. Botanic Garden — plus a host of other museums, monuments, and attractions — are all free. Just because you’re saving money by telecommuting doesn’t mean you need to spend it all.
  
  When summer hits, how about a road trip back west to Newport, Oregon? This coastal city is famous for its picturesque lighthouses, whale watching, kite flying, and simply beach bumming around. Pack some crab lines and chicken necks, as the area is famous for its Dungeness crabs. Why order them when you can catch them fresh?⁷
  
  Our seasonal travel loop is almost done. Since this itinerary has already tallied north of 4,500 miles, let’s keep our fall travel leg a bit shorter. How about pulling onto the Las Vegas Strip just in time to pop in the sportsbook for the opening of the NFL season? With Vegas reawakening after hibernating for a year, the deals and discounts will be plentiful to jumpstart the local economy.

• Make it a Field Trip: The work from anywhere lifestyle is an ideal scenario to visit family around the country while still making sure that paycheck is deposited every two weeks. We don’t know where your family lives, but we do know that seeing your kids is a great place to start. There are fewer spots with more college-aged kids and young professionals than North Carolina’s Research Triangle, which is formed by the University of North Carolina at Chapel Hill, Duke University, and North Carolina State University. (This makes a great college visit trip, too, if you have high schoolers. Add Wake Forest for bonus points). Encompassing the cities of Durham and Raleigh, we’re actually going to have you head to the southernmost angle of the Triangle to Cary. Here’s you’ll find the Umstead Hotel & Spa, a modern hotel with a welcoming, outdoorsy vibe. James Beard semifinalist Chef Steven Green will take of you, picking and preparing the freshest ingredients from 14 area farms.

The ability to work from anywhere gives you freedom like you’ve never experienced before. But it also comes with great responsibility. Remember, you only get to work from anywhere as long as you continue to work. Plan your trips carefully, slotting them after big deadlines and before your industry’s peak season. Do that and we’re pretty sure all your happy hours will be unforgettable forevermore.

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