Top 7 vacation destinations for small business owners to unwind


One of the most difficult aspects of running a business is having the ability to keep your creative juices flowing (didn’t being creative seem so easy when you first set out to start a business?!). Having the ability to think creatively can you help you solve problems and enhance and optimize processes. From coming up with new ways to keep employees and customers happy, to determining areas to save money, to dreaming up new business developments, your business success depends on your ability to continuously come up with innovative and creative ides.

One way to inspire creativity is to immerse yourself in new places. This could be as simple as taking a walk in the woods.  Or, it could mean going on a year-long round-the-world sabbatical.

For most business owners, reality means that a year-long trip is unfeasible. However, a week or two away from work can be a happy medium. Here are some of the top vacation destinations for small business owners to unwind:

San Francisco, California

There’s a reason why so many successful companies are started in and around San Francisco. This is a place with a “Yes” culture. Have an idea? Yes, there are people here who want to help you. A trip to San Francisco can feel like a trip five years ahead in the future; people here are today using the apps and gadgets that people around the world will use in five years time. Thus, it is a market researcher’s paradise. Plus, the beautiful surroundings in every direction mean that no matter if you’re going south to Santa Cruz, east to Lake Tahoe, or north to Muir Woods, you’re bound to get a heavy dose of Mother Nature’s goodness to stoke your mindset.

San Juan, Puerto Rico

In September, 2017 Hurricane Maria decimated the island of Puerto Rico. But since then, Puerto Rico has come back strong. In early 2018, The New York Times reported, “Dozens of entrepreneurs, made newly wealthy by blockchain and cryptocurrencies, are heading en masse to Puerto Rico this winter.”

Beyond the planned-but-not-yet-realized-crypto-utopia, tax incentives also have caused entrepreneurs to flock to this island. Whereas other places have coffee shop cultures as gathering spaces for entrepreneurs, in San Juan the entrepreneurs set up camp in hotels along the beachfront. Two of the most popular hotels for entrepreneurs are the Condado Vanderbilt Hotel and the AC Marriot, both located on the beach in the Condado neighborhood of San Juan. There’s no better place to mix business with pleasure.

New York, New York

If you’re an entrepreneur who has never been to New York, go there now. This is a city that was built for hustlers. People in NYC are always creatively thinking of the best ways to make their fellow citizens part with their dollars. The diversity of people from so many backgrounds gives New York a constant source of fuel on the fire. Each of New York’s five boroughs (Manhattan, Brooklyn, Staten Island, Queens, and The Bronx) has its own unique flavors, all driven by entrepreneurs, many of them immigrants or the children of immigrants. There are many popular hangout spots for New York City’s entrepreneurs to unwind at, but among the most popular are Toby’s Estate, a coffeeshop in Williamsburg, Brooklyn, and the Ace Hotel Lounge, located in Manhattan’s Flatiron District. If you’re looking to escape the city for some solitude, try the nearby Catskill Mountains.

Detroit, Michigan

In 2013, Detroit became the largest U.S. city to file for bankruptcy, which it exited in December 2014. But Detroit is a city that was built on the backs of entrepreneurs, most notably in the auto business. Yet it is the city’s musical underbelly where arguably even more innovation has occurred. From Motown and techno to jazz and punk, not to mention hip-hop, music entrepreneurs have long turned to Detroit for new ideas. With some of the best art museums in the country, from the Detroit Institute of Arts to the Charles H. Wright Museum of African American History, Detroit’s institutions were built to inspire you. And when you need a little R&R, visit Detroit’s excellent waterfront restaurant scene.

Cape Town, South Africa

If you’ve got frequent flier miles to spare, consider Cape Town. As the second largest and most Southern city in South Africa, Cape Town is in many ways the hub of where the rest of Africa gets its ideas from. Once you arrive, you’ll be shocked by many things.  First, the gorgeous scenery leave you in awe. Second,  the bargain basement prices on everything is something you’ve rarely encountered in other places. Third, the kindness and generosity of nearly everyone who you will meet along the way will be so refreshing. Africa is a continent that is on the brink of many major positive changes.  It will likely be able to leapfrog other continents, countries, and cities because it lacks existing infrastructure. Cape Town is the hub where much of the planning for a brighter future (literally, with electricity now spreading across the continent) for Africa is now taking shape. With high quality locations to lounge just about everywhere, try Clarke’s or the Loading Bay for both food and coffee that will inspire.

San Diego, California

You can get access to everything you need to make relaxation a priority, while still being inspired in San Diego.  San Diego is a small city with universal appeal.  San Diego boasts a comfortable climate (70 degrees all year long, so you can visit during any season!) and an abundance of nature.  No matter where you go in the city, you’ll find small business creating the backbone of the neighborhood, keeping each area unique…and full of inspiration.  From Old Town, which serves up great Mexican food along side a helping of California history to North Park’s ethnically diverse neighborhood full of indie coffee shops and art galleries. San Diego is also just a stone’s throw from Mexico, so shuttling across the border for the day is super-easy.  The local residents are laid-back, casual and extremely friendly.  All of this combined, makes it a lot easier to allow yourself to unwind – it’s simply the culture here!

Montreal, Canada

With a population of just over 4 million residents, Montreal is Canada’s second biggest city (second to Toronto). And, it is a hub for business, art, and culture.  It is the business center of Quebec and was named by Lonely Planet Travel guide as one of the “10 happiest places in the World”. As a metropolitan area, Montreal is refreshingly multicultural and its diverse mix of ethnicities are reflected through the city’s neighborhoods, each having it’s own flavor and unique aspects that can get those creative juices flowing.  A highlight of Montreal is its arts and culture scene.  Throughout the year, Montreal hosts the world’s largest comedy festival, film festivals, jazz festivals, firework festivals and more.  You can also find, throughout both downtown and in residential areas, art installations which pop up regularly.  Unique in Canada in that it is the only French metropolitan city, it will give you the opportunity to practice speaking a new language.  It also allows you to meet individuals from all around the world. It has even been described as being half Paris, half Brooklyn – making it (for some) the perfect city.

Remember, there are so many inspiring places on this earth, and these are just a handful. Wherever you decide to travel, make sure you don’t turn your vacation into a business trip! Put your phone down!  Make sure that you’re living in the present.  Absorb new cultures, ideas, and innovations to get yourself on the right track when you return from your journey.

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