The Top 35 Vacation Ideas For Entrepreneurs

Guest post by Greg Boudonck

Entrepreneurs need a vacation too!

Sometimes it is so easy to get caught up in our work, and making sure the business keeps flowing smoothly that we neglect our own sanity and peace of mind.

Sometimes we just need to turn off the phone, laptop and tablet and go to a zone where we can relax and forget about the stress and pressure of business.

I know, some of you (like myself) will say that we just cannot take the chance of everything falling apart while we are gone.

But is it worth having your body and brain falling apart while you are here?

There is surely someone you can trust to keep control while you take that much needed vacation.

Besides, you really should be training someone to run the show.

What if you had to have major surgery or you were forced to leave for an emergency?

Or what if you did what we all will do someday, die?

Maybe you will say something like it really won’t matter then because I will be dead, but is that fair to your family?

Well, that is enough playing psychologist.vacation

Just take a vacation!

You need it!

Here are the top 35 vacation ideas for entrepreneurs… You should consider 1 or more.

These are in no particular order, so research them all.

Some are low cost, while others may be slightly expensive.

So let’s take a look.

1: Pan for gold in Alaska

I just knew this first one would immediately grab your attention.

After all, you are an entrepreneur and gold is a very valuable substance.

There are various gold panning tours offered in Alaska and who knows, maybe you will discover a nugget that will allow you to stay on a permanent vacation.

Nearly every area with humans in Alaska has had a history of gold mining.

Some tours even guarantee that you find gold.

So purchase your equipment and get “gold fever” in beautiful Alaska.

2: Puerto Rico

Okay, maybe I am being slightly dramatic, but you will truly love the Caribbean island I reside on.

And I happen to know of a great place to stay which is called El Escondido guest house.

Not far from where I live, you will love the place as you are near the rain forest and it is peaceful.

You may even want to check out some of the books I have published on Puerto Rico.

3: Marrakech, Morocco

Just below the Atlas Mountains, this city is a popular destination for tourists who want to see something new.

But by no means is this city new; the architecture is amazing and the shopping is a dream.

Marrakech would be an excellent choice.

4: Myrtle Beach, South Carolina

If a beach is your idea of a great vacation, Myrtle Beach is an excellent choice.

It has a long strand of beach line where you can take a comfortable chair, your bathing suit and a book.

Just sit back and relax watching the tide.

5: Refuga

Refuga is a program that was started in 2012.

You can travel with other entrepreneurs on exciting adventures.

It is my understanding that this year, the trip is to Thailand.

You can get more information about Refuga here.

6: Backpack Europe

Why not just get a backpack and a flight to Europe and start backpacking it?

Just pick a course and enjoy the European hospitality.

This is an adventure many dream of but never do.

You should.

You can see all you want to see in Europe and it is a cheaper way to do so.

Here is a good step by step guide.

7: Costa Rica

This Central American country is another huge favorite.

Much of Costa Rica is dense rain forest with delightful wildlife.

It is a trip you will remember for a lifetime.

8: Geeks On A Plane

Maybe you have a lot of issues with leaving your work completely.

I understand.

Most entrepreneurs love what we do so essentially, when we work, we are on vacation.

Geeks On A Plane is just for you.

Tour with other entrepreneurs to start-up locations worldwide.

See their website here.

9: Siem Reap, Cambodia

This is a highly popular Asian tourism destination.

With amazing architecture and wonderful shopping districts, Siem Reap has so much to see and admire.

10: Las Vegas, Nevada

I just could not leave out the city that never sleeps.

You can gamble, take in some shows and just have a grand time.

Remember, what happens in Vegas stays in Vegas.

11: CocoVivo

Shhh, this is a secret get away.

In the Bocas del Toro, it is Isla San Cristobal.

You can only arrive by boat, and electricity and water are precious commodities.

You will love CocoVivo, so see the website here.

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12: Take a Cruise

There are excellent deals on cruises.

We often have cruise ships docking here in San Juan, and ships cruise all over the ocean.

So just use your search engine to find a cruise you will love.

13: Climb Mount Kilimanjaro

How about a taste of adventure?

The highest mountain in Africa is waiting for you to climb it.

Just travel to Tanzania and get ready for a fun time.

Here is a link telling you all about it.

14: Istanbul, Turkey

The history of Istanbul goes back for ages, and you will be able to see that when you enter this city.

You can see where many kingdoms once ruled and see a culture so much different than you know now.

It will do you good to visit Turkey.

15: New York City

It only makes good sense to take a vacation to the Big Apple.

See the Statue of Liberty and other landmarks that has made this city so great.

The only thing that may stop you is if you are an entrepreneur that now lives in New York.

16: Coboat

Are you that entrepreneur that absolutely cannot allow someone to have complete control of your business while you vacation?

Coboat may be your answer.

Jump on this boat with other like-minded people and work while you vacation on the high seas.

Don’t worry, you will have internet and everything else you need to have a working – boating vacation.

This link tells you more.

17: Habitat For Humanity

Why not help others while you vacation?

It can do our hearts and minds a lot of good when we help needy people.

Habitat For Humanity is worldwide, so why not sign up to help build or remodel a home for less fortunate people?

You can volunteer and vacation at the same time.

Visit the Habitat For Humanity website here.

18: Golf The Master’s Course


I challenge you to travel to Augusta, Georgia and golf the Master’s Course at the Augusta National Golf Club.

Be sure and come back here and tell us what you scored.

It is a tough course, so be prepared and practice.

19: Hanoi, Vietnam

Once a war torn country, you can visit now without fear of Vietcong trying to capture or kill you.

You will be amazed by the architecture and the way the Vietnamese people live.

This will surely take your mind off work and allow you to see another side of life.

20: Destin, Florida

Destin is in the panhandle of Florida on the Gulf of Mexico.

If you like fishing, they say that Destin is a fisherman’s paradise.

Destin has some beautiful beaches and I am sure you will enjoy your stay at this popular location.

21: Surf Office

Here is another one for that entrepreneur that cannot completely leave work.

Surf Office has accommodations that you can stay a few days, a month or even a year if you like.

You also can use the in-house co-working areas and when you need a break, go out and surf the waves.

There are 2 Surf Office locations:

  1. Lisbon, Portugal

  2. Gran Canaria which is a Spanish island off Africa

Check out Surf Office here.

22: Prague, Czech Republic

This large city in Europe is full of museums and history.

Unless you take a 1 year vacation, you surely will not be able to take in all that Prague has to offer.

This is a great idea for a vacation.

23: Ocean City, Maryland

This beautiful city on the Atlantic Ocean has so much to offer vacationers.

Stroll the boardwalk or simply lounge on the beach.

Amazing shopping and great food awaits you.

See here.

24: London, England

It only makes perfect sense that London is on this list.

After all, you need to see Big Ben and Westminster Abby.

Stroll the streets where John, Paul, George and Ringo walked.

Are you too young to know who I speak of?


25: Orlando, Florida

This is another must be on this list.

The city where Walt Disney World is located, along with many other attractions is a perfect idea for the entrepreneur vacation.

Say hi to Mickey Mouse for me please.

26: Rome, Italy

There is so much to see and do in Rome.

Don’t even attempt to work while there; just go out and sight see.

Be sure and eat some great pasta too.

27: Virginia Beach, Virginia

Maybe you want to stay close to home, but still have a delightful vacation.

I would say that Virginia Beach is the answer.

Miles of beaches, and many other attractions makes Virginia Beach a popular tourist destination.

28: Buenos Aires, Argentina

This is a great idea for a South America traveling adventure.

You will see some neat architecture and you can purchase items very inexpensively.

Just keep an eye on your purse or wallet as crime is rampant.

29: San Francisco, California

See the Golden Gate bridge and all the other attractions San Francisco has to show.

This is a great vacation destination and quite cost effective.

30: San Diego, California

San Diego is a wonderful city to vacation at.

The beaches are wonderful and there is a hopping night life in this city.

Plus, you are real close to Tijuana, Mexico if you want to see some craziness.

31: Paris, France

This is another location that just could not be left off this list.

You must see the Eiffel Tower, and the museums located in this French city.

Be sure and send us a postcard.

32: Shanghai, China

Not only is there many things to do and see in Shanghai, this is considered the financial hub of mainland China.

So as an entrepreneur, you just may be able to strike some good business deal or relations while you are on your Asian vacation.

33: Cape Town, South Africa

You will absolutely love this city.

With the mountains behind and the ocean in front, you have a wide range of choices in what you will do each day of your vacation.

And, if you enjoy surfing, some of the best surfing in the world happens here.

Just watch for sharks.

34: Beijing, China

The most populated city in China, you will gain an understanding how lifestyles are different in China compared to here.

You will also see both modern and ancient architecture.

The biggest recommendation is to wear a mask as pollution levels are high in Beijing.

35: Key West, Florida

This Florida southernmost island is a very popular tourist destination.

Take some flippers and a snorkel and go diving.

Or just sit and have a drink and watch the waves.

Relaxation and fun is the Key West way.

Along with Jimmy Buffett.

Final Thoughts

It is time to take a vacation.

Which of these choices will you go with?

Maybe you should just print it, put it on a wall and throw a dart and let the dart tell you where to take your vacation.

You can leave all comments and questions below.

Thank you.


  1. 11 Perfect Vacation Ideas for Entrepreneurs


About the author

Greg Boudonck is a freelance writer and the author of over 50 books. He writes on many different topics, but business subjects are one of his primary areas of writing expertise. See Greg’s biography here.

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