Where Do Business Owners Vacation? — Experts Weigh In

Owning a small business is exhausting. Ask any entrepreneur and they’ll tell you that the CEO never really gets a “day off,” but it’s still nice to get away every now and then. We asked our small business experts what they look for in a vacation spot. From the fastest WIFI available to fine dining, here’s what they had to say…

“Living in San Diego is to some, a vacation in and of itself, so when I do travel, I look for places that are as different to my hometown as possible. Most recently, I traveled to Bacalar, located at the very tip of Mexico and bordering Belize. We stayed in an eco turism hut, where environment consciousness is primary, and at night, you are truly surrounded by the still wild jungle.

I look for places where the culture is rich, the food is great and the people are warm. I look for destinations where I can leave feeling inspired, renewed and having learned new lessons. I really don’t like all-inclusives or other places where the commercialization and globalization is too obvious… I look for a change, for a place that will change a little bit of who I am, and create a better person when I leave.” –Thomas Bryer, Bryer Leather

“I love to travel (and became an entrepreneur specifically so I’d have freedom of time). However, there’s never really an off day in the life of an entrepreneur. Therefore, a *must have* feature of anywhere I go is reasonable Internet. Even if I spend the whole day sightseeing, I need to catch up on emails in the evening. Web-based businesses can’t go dark for days at a time. Customers will revolt.

The WORST place to use Internet (who claim to have Internet) is cruise ships. OMG. They are soooo SLOW and soooo EXPENSIVE. Unless you want to send/receive text-only emails once per day then it’s not even usable. Forget about megabyte attachments. I think they have 2000 people using a tiny little pipe designed for 1 person. It’s so bad that often times I have to find a land-based Internet cafe (or just a regular cafe that has free wifi) as soon as I get to shore. I can understand why they’re slow when out in the middle of the ocean, but why the heck don’t they switch to some shore-based fast connection when in port? Drives me nuts. We’re sitting at a dock for 12 hours right next to some super high tech city (like Singapore) and I’m dealing with a 300 baud modem connection. Ugh.

A couple years ago I hiked to base camp of Mt Everest. Surprisingly, you get decent cell reception when you’re on a ridge (but not so much down in the valleys). There’s lots of up and down on the 40 mile trail to base camp, and every time we’d get to a high point our group of tech-savvy hikers would break out the electronics to catch up on email or send a few text messages. Yes, it wasn’t great from a get unplugged stand point but it was great because it allowed me to take a 3 week hike that I otherwise would not have been able to do because of the lack of connectivity.” –Mike Scanlin, Born to Sell

“You would think a busy entrepreneur would want a nice, relaxing vacation. Yet, for me I like adventure, learning and seeing new things. This may also match the curiosity of an entrepreneur. It also gives me the time to feed my other passion which is horses. Therefore, I often take horseback riding trips around the world. My favorite was in South Africa and Botswana. Wow! To ride next to elephants, wildebeest and zebras was exhilarating. Plus you meet people from around the world and learn the local culture. I’ve taken two trips to Spain and one in Ireland too. I book my trips through Https://www.equitours.com/ I think travel builds creativity and ideas and do quite a bit of it.

Founded in 1991 and located in Rantoul, IL, Taylor Studios collaborates with visitor centers, museums, nature centers, universities, and corporations to plan, design, build, and install exhibits. Their experience encompasses interpretive planning, exhibit design, graphic design, immersive environments, outdoor signage, scenic work, interactives, models, murals, and dioramas. They are the first and only exhibit design and fabrication company to back their work with a ten-year warranty. In 2000, Inc. Magazine named Taylor Studios among the 500 fastest growing companies in America. In 2007 and 2009, they were listed among the 5000 fastest growing companies. This growth can be attributed to their outstanding quality and their ability to complete projects on time and within budget.” –Betty Brennan, Taylor Studios, Inc.

“Mandatory being that we’re a startup is a facility that has free Wi-Fi both in the hotel and around the grounds of the hotel. When you’re looking to truly expand your startup you’ve got to assure you have the ability to still keep your company running efficiently and continuing to provide the best customer experience.

This is the #1 thing I’m looking at followed by is this a family friendly facility.” –Mike Kawula, Social Quant

“As a small business owner I work nonstop for seven days a week. Whenever I get a chance to take a vacation with my family I always make sure we find a location that has cell phone reception and wifi. These two things are very important to me because I need to answer calls and send out emails. With those two things checked off my list it’s a lot easier to pinpoint which locations would be a great vacation. I like going somewhere that has a laid back vibe without the hustle and bustle of a city. Beautiful landscapes and a small friendly city are always a bonus. When I’m on vacation I like exploring the restaurants and what the city has to offer. Family bonding time is equally as important because I want to create new experiences with my kids. Vacation with my family is an important part of my life. It helps me rewind, relax and renew my passion for my business.” –Lisa Chu, Black N Bianco

“My husband and I own a couple businesses together and we regularly take staycations– we go to cities near enough to LA that we would be able to come back if there’s an emergency, but far enough that we don’t have constant reminders about our business. This means we’ll stay at a hotel in Santa Barbara or drive down to Long Beach with our dog or head into the mountains of Big Bear– places with a slower pace so we can be outdoors and unwind. We like to have wifi reception, but we’ll turn our phones to Airplane Mode for several hours at a time to get a little peace and quiet!” –Diana Lamon, Peaches’ Smokehouse & Southern Kitchen

“I look for three things:

1. Great views of an ocean or body of water. Why? I’m in NYC and see buildings and streets all the time so I want some sun, sky and surf!

2. A hotel with conveniences like free wifi, a gym, someplace to hang out away from the room but not a bar, cool amenities and trendy lobby’s.

3. Some no name hotel without a big flag or brandname?

And if all else fails I just use hotels tonight to give me a list of trendy and hot places to stay. It just makes it super easy to find a shorter list of great hotels not easily filtered out by other sites.

On hotels tonight I also search by smaller neighborhoods in big cities, like lower east side or soho instead of just new york city to get a more targeted result.

Some of my favorite hotels are SOHO House in NYC, The Standard, and NYLO.” –Anthony Girand, VoyagerMed

“I look for free wifi (I am a web designer, so I can work while on vacation), a quiet place and dog friendly. My husband and I usually drive to the Florida keys (Key Largo) for a month (winter) bringing our Black Labrador. Plenty of sun, water and good restaurants.” –Catherine Simms, Web Dezine It

“As a small business owner who operates in an urban area with high population density (NYC) I always look for vacation spots that are relatively secluded with quiet atmospherics. I still enjoy the company of people but just less of them. To that end, I usually take my summer vacations around the lake areas in upstate New York or New Hampshire. Spending a vacation around water gives me and the family time to do some outdoor watersports and I also try to find some personal alone time for some fishing which is a must on any vacation in the summer.” –Matthew Reischer, Esq., Attorney & Owner Legal Marketing Pages Corp.  

“When I go on vacation, I look for a place that has a variety of nature activities. Cape Cod is one such vacation spot. There are so many gorgeous beaches to go to, each very different in appearance including those with sand dunes, cliffs or marshes, such as Race Point Beach and Marconi Beach. Cape Cod also has beautiful hiking trails such as White Cedar Swamp Trail. The peninsula is truly the perfect outdoor vacation where I can clear my head, get away from busy city life, and enjoy quality time with my family. What tops it all off are the incredibly serene bed and breakfasts that take you back to a simpler time. One great bed and breakfast I like to stay at is the Brewster by the Sea. The owners makeyou feel like family, and the hospitality is incredible.” –Avishai Weiss, Apartable 

“I have a wife and 3 young children. Whenever I’m not working, I’d like to spend time with them. My business provides emergency service, so I rarely take long vacations.

My wife and I love to take the family for a weekend getaway. Our favorite spots are within 2 hour drive of Los Angeles: Santa Barbara, San Diego, and the Santa Monica mountains. We can go to the spa, visit museums, local shops, and attractions if we want to. There’s also plenty of hiking and surfing and playing in the sand for the kids.

I’m pretty low-key when it comes to vacation. I avoid crowded places and like to stay close to nature. There’s something about the quietness and solitude of nature that relaxes me. I feel like I really get to spend time with my family that way, away from all the noise.” –Idan Shpizear, 911 Restoration

“We are a family of 4 who have 2 children under 5 years old. We are looking for a vacation that gives us something for everyone. Our favorite go to place is South Beach, FL to a Hotel called The South Seas. It’s a quiet and family friendly hotel, right on the beach and in the center of everything. Not to mention they’re clean and affordable. The only downside is while its family friendly outside of the pool and beach, there’s really nothing for children in South Beach as a whole. So to solve that problem we call Carnival Cruise. This is where everyone in our family can really cut loose. Especially the children with all of the activities available. The ship gives us everything we could possible ask for and then some, including an area to work. The wifi isn’t free but that’s even more of an incentive to either stay off the grid or work quickly if there’s an emergency. But I always say, if you’re on vacation then there should be no reason for anyone to be working, otherwise what’s the point. Enjoy the moment!” –Valerie Pierre, Mommy R+R  

“When I vacation, I like to pull out all the stops – I fly first-class (with free upgrades thanks to elite status) and stay five-star. I need to have a beach, gym, and a place to do some active sports such as hiking, kayaking, kite surfing, etc.” –Dan Nainan, Comedian

“Whenever my family and I look to go on vacation, we typically try to rent a condo or a house. We find the easiest way to travel with a little one is to have your own sanctuary. Having a kitchen and a place that feels more like home is also a great plus! Also for me, since I work in the hospitality industry, I actually prefer to stay away from hotels because I start inspecting things, examining how they greet guests, etc to see if there are things I can incorporate into the hotels we operate.

Free WiFi is always a must too! Even though I’m on vacation, I still like to spend my early mornings going through email to ensure I’m not overloaded with work when I get back. Plus, it’s just nice to be able to surf the web and explore things to do around you while you’re in a certain town.

I prefer to take a vacation once a year somewhere in the Caribbean for a week to just relax, snorkel, and chill out. Then, we also take another vacation somewhere in the world to see someplace new and immerse ourselves in culture, history, and/or wildlife. My favorite place to vacation thus far has been on safari in Kenya/Tanzania. Sitting in an open jeep, staring out in the plains of the Serengeti, and watching all this magnificent wildlife… NOTHING beats it. It’s a place I recommend to anyone and everyone.” –Manu Lail, RMG Hospitality

“I tend to want the complete and utter lack of internet. Seriously, there’s always something that comes up, but rarely does it actually need to be dealt with within a day or two. I find that seeing the customer complaints or regular activity the way I do normally, isn’t as much a vacation…as it is doing work remotely.

I think it’s important to really get away-even if it means simply turning my phone off and leaving the laptop, at home.” –Mark Aselstine, Uncorked Ventures

“For me it is Italy.  I have rented a 17th century farmhouse with no wifi or internet access, stayed at villas with no computers, etc.  It is the perfect way to unplug and let your batteries recharge.  I highly recommend it.  Taking a technology vacation is underrated for people who live it every day.  My contact info is below as well as a link to my site.” –Paige Arnof-Fenn, Mavens & Moguls

“What do I look for in a vacation spot? A place that has every possible amenity for me to access my business office, but also has so much to enjoy that I have no desire to access my business office while there. My preference? High end resorts, spas, and luxury private getaways.” –Stephanie Adams-Nicolai, GODDESSY and GODDESSY Organics

“When I go on vacation I look for places that have several activities (hiking, zip lining, etc.) near the beach. Typically I do an activity one day and the next day lay by the beach and continue the pattern for the rest of the trip. The activities distract me from thinking about my business and laying by the beach allows me to rest.” –Kyle Ems, SeniorCareBox.com

“What I am looking for in vacation: to UNWIND. Nothing is better for me on vacation than total relaxation and no wi-fi (even if it’s hard to become unwired). We operate from Tulum, Mexico, which is one of the most beautiful vacation spots in the world with gorgeous beaches, yoga, spas and gourmet restaurants. So sometimes, a weekend at one of the gorgeous boutique hotels on the beach is all that it takes to rejuvenate. However, this summer we are planning a far more exotic trip: Pemba, Mozambique. We will be staying at a beachfront African lodge Il Pirata, surrounded by empty gorgeous beaches and warm Indian ocean, where I hope to learn to kitesurf.” –Raminta Lilaite, Riviera Maya Property Consultants

“While it may sound crazy, solid wifi is on the top of my list for a vacation requirement. The ability to get online and work in the morning while people are still sleeping, or when the kids go down for a nap is key for me, but also gives a bit of peace of mind. Having to hunt around for an internet connection is quite annoying especially on vacation when you want to spend the vast majority of your time with your family. We like to vacation at The Homestead in Michigan, which has always been great. On the flip side, I’m a huge Disney fan, but we recently went on a Disney Cruise and the wifi was terribly expensive and just about non existent.” –Bill Fish, ReputationManagement.com

“When I am looking for a good vacation spot it depends on the time of year. I like to make one trip during the summer for a work/play vacation like this summer I am exploring the Green Rush in Colorado and looking to bring back information to apply it when it becomes legal in my State but also while I am there, I will have rest and relaxation by exploring the mountains and during the winter time the only thing I care about is that it has warm beaches and a place I have never been to before. When you work as hard as an entrepreneur has to work and as many hours as you have to put in, you have to give the mind a break and hit it hard the minute you get back.” –Matt Dolly, AirFilterOnDemand.com

“I’m a big fan of Agua Caliente Casino in Palm Springs. It has beautiful desert scenery, a golf course and a great pool and cabana scene. For every vacation, It’s important to me that there are things to do for both me and my wife, together and on our own. This place amazing spa that my wife can go to when I’m golfing or in the casino. When I want to get away from the all stress of running a business, I head to Agua Caliente to clear my head and focus on having fun.” –Craig Shacklett, UrComped.com

“I look for a place where I can both work and play. This means reliable Wifi, a quiet place to take work calls, and plenty of accessible fun! Royal Caribbean’s Liberty of the Seas was a great ship for a quick getaway. I also look for great food when I go away. Portland, Maine has an amazing food scene. Street and Co. never disappoints.” –Todd Horton, KangoGift

“When it comes to a vacation spot, I need Wi-Fi. It doesn’t matter if I have to pay for it or not. To stay connected with my business, which is an online marketing company, I need the internet.

When vacationing with the family, we like to find a place that can accommodate everyone. My wife and I tend to choose vacation spots that have a little bit of something for everyone. That way, the kids can have their fun and the adults can too. Personally, my family is a big fan of Royal Caribbean Cruises. They have tons of activities, and the family can split up on the ship without fear that someone will get lost or left behind. We leave the ship together, but try to do something everyone wants to engage in.

When it’s just me and my wife on a vacation, we like to optimize our time alone. That means no kids, whether their ours or somebody else’s. When it’s just the two of us, we look for adult time, so we’re looking for places that cater strictly to adults.” –Rich Kahn, eZanga.com  

“My company is a Member of the Extreme Customer Service Directory created by the Experience Pros. Founders Angel Tuccy and Eric Reamer, Co-Hosts of the Experience Pros Radio Show created a radio contest which resulted in several business owners going on vacation in April. We visited The Dreams Sands Cancun Resort & Spa where we experienced extreme customer service, the best reward for working hard as a small business owner!!

For me, personally, a vacation is meant to be enjoyed on a beach. Last year, I visited Dreams Cabo San Lucas and this year, Dreams Cancun. This company understands customer service and relaxation. I met with their Pool Concierge who told me, We think of everything so you think of nothing on vacation.. I really like their attitude as I believe a vacation features sun- soaked beaches, an array of foods to enjoy, comfortable luxurious accommodations, a spa, free WIFI to stay in touch with the office every now and again, drinks with umbrellas and new activities to enjoy with many options for RELAXATION.

After a week in paradise, each business owner returned to Denver Colorado relaxed and ready to thrive! We traveled with 12 guests who found all of the above and more – and we loved it so much, we are returning to the same location in 2016.” –Kimbirly K. Orr, Knock Out Performance

“I really enjoy vacations to places with scenery that is very different from what I experience every day. I live in the desert, so I look forward to visiting the ocean, particularly in the summer when it is so hot where I live. The Cliffs Resort, near San Luis Obispo in central California, is one of my favorites. The scenery is breathtaking — the hotel is literally on a cliff overlooking the Pacific Ocean. When you arrive and feel those cool ocean breezes, you feel instantly refreshed.

It is in a quiet area but is not far from excellent restaurants. The nearby beach is relatively uncrowded. The hotel is also dog friendly, which I appreciate because I hate to leave my four-legged companions at home. After all, they deserve a vacation, too.” –Brian Hill, Profit Dynamics Inc.

“My wife and I really enjoy vacationing to places where the cost of living is low. This allows us to really cut loose and enjoy our time without worrying about our overall spending.

We are doing a few weeks this winter in Chiang Mai and Bangkok, Thailand. The weather is the best around our Christmas holiday, and the food is incredible. You can find great meals for around $1 throughout Thailand.

Similar destinations include Vietnam, Mexico, and quite a few smaller countries throughout Central America. You can live well in these places for around $1,000/month, which is much cheaper than most places in America.” –Jacob Lumby, Cashcowcouple.com 

“One of the things I look for in a vacation spot is free Wi-Fi. I usually need to check in with work electronically at least a few times, and I do not see the need to have to pay for that. It’s been my experience that most reputable hotels now feature this benefit. I also look for a fitness center. Staying on track with my exercise routine is important to me, even if I’m on vacation. But most hotels normally have some sort of exercise facility as well. A vacation spot with a healthy listing of rooms for rent on Airbnb is also nice, that way I know I have the option to choose cheaper lodging if I need to save money. I also usually try to vacation at a destination with a wide and varied list of activities, so I have a lot to choose from as far as entertainment. I know that Charleston, SC and Virginia Beach, VA fit into this category.” –Andrew Schrage, MoneyCrashers 

“When I go away on vacation I like to completely disconnect. Any access to WIFI or phone means I’m not really on vacation. The human brain needs downtime to properly function at a high capacity so I discourage any “connected” vacationing. My last vacation was in Cuba where it was difficult to even make a simple phone call. It was totally relaxing and just what I needed!” –Hajmil Carr, TrueLine Publishing