How to Get Tax Deductions for Part of Your Vacation

July 26, 2018 by · Leave a Comment 

One thing I’ve learned as a small business owner and a freelance writer is that you can take tax deductions on certain parts of your vacation, but it has to be done very carefully.

Previously, I’ve talked about “bleisure travel,” which is the practice of tacking a small vacation onto the beginning or end of a business trip. Then, if you’re visiting a city you’ve always wanted to explore, you can take a couple days off or stay over the weekend, and pay for your added hotel and food expenses yourself. It’s a great way to get to see a part of the world you might otherwise never visit.

But this is a little bit different. Taking tax deductions on your vacation means tacking a little bit of work onto your leisure time, not the other way around.

Before we go any further, let me issue two warnings:

  1. This is not professional tax advice. Talk with your accountant before you actually do this to make sure you’re deducting the right activities and so forth.
  2. You’re not going to be able to deduct your entire vacation, so don’t get ideas of taking a world cruise on the government’s dime.

1. Part of your vacation has to be work-related, like a conference or business meeting.

A trade show floor. You need to do some work on vacation if you want any tax deductions.To begin with, taking a vacation closely related to your work qualifies. This is sometimes referred to as a busman’s holiday, which is a vacation spent following or practicing one’s usual occupation. In the days of bus conductors and bus drivers, a busman might spend a day off riding on a pal’s bus or even take the bus to get to his holiday, hence the name.

A professional writer could visit a writer’s conference or research a particular location or city for her book; a house builder might spend a holiday week repairing and building houses for his church’s missions trip; a museum director would spend her holiday visiting museums in other cities or countries. Even a theater teacher heading to New York to watch Broadway plays could count that as professional development. In essence, if you are doing an activity that helps you improve your business, your work skills, or expand your knowledge, that can be tax deductible.

2. Schedule any business appointments before you leave.

According to Quickbooks,

. . .you must have at least one business-related appointment set up before you leave. It’s not possible to deduct any expenses if you leave with the idea that once you arrive, you will meet contacts and conduct business on the fly. The IRS expects you to establish a “prior set business purpose,” and keep a copy of your correspondence and books showing the scheduled appointments.

So, schedule your meetings and events before you ever leave. Mark them on your calendar, and save all the emails related to scheduling. This way, you can show you set the meetings before you left, if there’s ever a need to prove your deductions.

3. If you travel on a weekday, that can be deducted as business travel.

If you’re attending a conference or setting business appointments, travel during the week to get there and back. If your trip is being used primarily for business (i.e. you’re not taking a two-week vacation with one day of business meetings), you can deduct your transportation costs, whether it’s airfare or mileage. You can also deduct expenses on business days, like lodging, taxis/ride sharing, and 50% of your food.

4. Keep track of everything.

According to the IRS, you don’t need to keep receipts for anything under $75, but you do need to keep track of when everything happened. Whatever you do that’s work related, keep track of it in a diary or on your electronic calendar. Appointments, travel times, meals, conference sessions, you need to keep track of anything that ties into your business travel. That way, if the IRS wants to check, you can prove that you have legitimate charges and aren’t just counting handing out business cards at the hotel’s happy hour.

You can also get by with electronic copies of your receipt. I use Receipts by Tidal Pool Software to take photos of all my receipts, regardless of the amount. You could also use Evernote or just take photos of everything and upload them to a designated folder. I like Receipts because it keeps track of the amounts and I can export reports for the year’s taxes.

5. Just remember, you can only deduct your portion, not your family’s.

If you fly to get to your vacation, only your ticket is deductible. But if you drive, the mileage is deductible, and you still managed to get everyone there. Just remember, if you take the tax deductions, you can’t claim the expenses too (e.g. gas costs). You can only do one or the other.

It’s the same with food (only 50% of your cost is deductible), the hotel room (if you need two rooms, yours is deductible), and you certainly can’t deduct any entertainment expenses (unless that’s your actual job, and this is a research trip).

Finally, remember, your family wants to take this vacation with you, so don’t spend all your time working in an attempt to make this vacation as cheap as possible. They’ll accept a day or two of you working while they go off and have fun, but the whole reason for the vacation is to get a break for a while. Take advantage of it.

While you won’t pay for your entire vacation, you can at least see some tax benefits from tacking a little work onto your time off. Just remember to talk to your accountant or other tax professional before you book that three-week Hawaiian “business trip.”

Have you ever taken a busman’s holiday or deducted business expenses on a family vacation? How did you do it? Share your tips and tricks on our Facebook page, or in our Twitter stream.

Photo credit: ADunwoody07 (Wikimedia Commons, Creative Commons 4.0)

How to Make Vacation Costs Less Painful

March 29, 2018 by · Leave a Comment 

Before we moved to Florida two years ago, my family of five took an annual vacation down to Orlando every year for six years. It wasn’t always a Disney World trip, but it was a chance to get a break from the cold and snow of Indiana and to bask in the warmth of Central Florida.

And we didn’t always have the money for an expensive trip, but we were certainly able to have a fun time, all without breaking the bank or putting ourselves in terrible debt. It started with a little pre-planning the year before, which lightened the load. Here’s how we did it.

1. Driving is Cheaper than Flying

It may be a huge pain, but we would drive from Indianapolis to Orlando in about 20 hours. For a while, we did it in a single day, which was awful. After a while, we switched to two days which was fine, but usually added $250 to the trip, including the hotel nights and extra meals.

Still, it certainly beats five tickets at $400 apiece (although I certainly envy the two-hour flight time). We could drive 1,000 miles, visit the grocery store for breakfast and lunch, and then hit a decent restaurant for dinner, all for around $150. If we wanted to stop in a hotel, we would stay at the Holiday Inn Express near Macon, Georgia. We weren’t going for comfort and luxury there. We wanted something clean, comfortable, and safe. All told, the 2-day trip cost between $250 –$300 each way, and was still cheaper than flying. Plus we had our car once we were in town.

2. Buy gift cards throughout the year

Epcot in Orlando, Florida during the Flower and Garden Festival in May. One of my favorite vacations.

Epcot during the Flower and Garden Festival in May

One strategy we had to cut travel costs was to buy gift cards during the year and keep them in an envelope. My wife would buy $25 gift cards for Shell gas or Outback restaurant once a month. We had traveled enough times on this route that we knew where to stop to use them.

While it didn’t save us any money, we didn’t have to come up with a fistful of cash all at once just to cover the drive. By getting the gift cards, we were able to sock away some savings without actually putting the money in a savings account. (We tried that a couple times, but always had some emergency or other that required us to “borrow” from the savings and never put it back.)

3. Plan your activities, book ahead when possible

If you’re watching your vacation budget carefully, this is where you have to be hard-nosed. You will be sorely tempted to “just this once” add a new activity to your itinerary. It could be a tour or show, or some other amazing attraction that caught your eye, but it inflates your total costs. It’s worse if you show up without any plans at all, because you won’t really keep track of what you’re spending, and you can easily go overboard.

Instead, schedule out your activities and book the tickets in advance throughout the year. That way, you don’t have to cough up the cash right at that moment (see #2 above). Then, when temptation rears its ugly head, you have to stick to the schedule, and either refuse to be tempted or be willing to give up another activity (or activities) so you can pay for the new one. And if you’ve already bought the tickets, you’ll be even less tempted than before.

4. Plan for rest days

There’s a lot of truth to the old joke of “needing a vacation from our vacation.” When we would return home from Orlando, we would be exhausted, and not just because we drove 20 hours straight. We had spent days and days walking around the theme parks, visiting friends, or popping over to the beach for a day. We were exhausted. Plus, it’s expensive to do something every day.

We finally got smart and started blocking in rest days into our schedule. Those were the days we stayed around the rental house, spent time in the pool, or visited different parts of the city. We didn’t have anywhere to be, and best of all, we didn’t have to spend any money.

Even that one day of not doing anything gave us a chance to sleep in, take a nap, or just recover from the drive and last few days of activity. It also helped us reduce our costs, because we were just able to eat at home instead of going out.

How do you reduce your vacation costs without reducing the enjoyment? Do you have any cost-saving measures you can recommend? If you’ve got any tips, suggestions, or ideas, please share them in the comments below, on our Facebook page, or in our Twitter stream.

Photo credit: Erik Deckers, used with permission

Four Spring Break Ideas for the Whole Family

January 11, 2018 by · Leave a Comment 

The new year has begun and we’re already thinking about Spring Break ideas? Well, if most of you were hit by the sudden bomb cyclone weather last week, I’m sure you’re dreaming about warmer weather. Plus, I know a lot of people from New Orleans flee the city during Mardi Gras, while many Bostonians head south during the week of President’s Day, since they get the entire week off.

If you just want to get out of Dodge for a little while, but you maybe don’t want to hit the typical college hot spots, here are a few Spring Break ideas for you. There’s something to do for the whole family, but these are also great places to eat and experience the local culture.

1. Portland, Oregon

If I had to move anywhere else in the country, I’d head to Portland. It may rain quite a bit, but it’s usually a light rain, and not the major storms we get in the Midwest. It also has low humidity and surprisingly few mosquitoes. It’s a great place for excellent food and craft beer, as well as plenty of festivals, theater, and the arts.

There are several museums, including the Oregon Museum of Science and Industry (OMSI, pronounced AHM-zee), the Portland Art Museum, the Portland Children’s Museum, and the Oregon Maritime Museum. There’s also the Oaks Amusement Park and North Clackamas Aquatic Park for some fun.

Plus you’re a couple of hours away from the beach (I especially love Lincoln City), and Mount Hood if you want to go hiking. If you like outdoor activities, Oregon has a lot to do, and you can do a lot of it within a couple hours of Portland. And the rainfall is less between winter and summer, so a March spring break trip wouldn’t be as rainy as, say, May or September.

2. Nashville, Tennessee

This city is great if you have older kids. While you probably can’t go cruising the bars with them, there are several restaurants that have musical acts in the late afternoon and early evening. Take them out for some music and dinner as you check out some of the sights around the city.

There’s also the Country Music Hall of Fame, the Nashville Zoo, the Parthenon, and Opryland (which also has an amusement park). If you want to pay homage to the entertainment pioneers of the south, there’s the Johnny Cash Museum and Cafe, Willie Nelson and Friends Museum, Patsy Cline Museum, and of course, Cooter’s Place in Nashville, a museum dedicated to the Dukes of Hazzard. Or if Spring Training is over, you could catch a ball game with the Triple-A Nashville Sounds baseball team, or a Nashville Predators hockey game.

Finally, if you’re a rock and roll fan, don’t forget to check out Third Man Records, Jack White’s record store and recording studio. He’s doing some interesting things with vinyl records, so it’s worth a look if you’re into vinyl at all.

3. Dallas, Texas

Actually, anywhere south of Nashville is going to be a lot warmer than the Midwest and Northeast at this time of year. But Dallas is a large enough city in one of the biggest states in the country, which means there’s a lot to do, and it’s going to be plenty warm.

You can visit the Dallas Museum of Art, the Perot Museum of Nature and Science, the African American Museum, and Dallas Heritage Village, which is like Colonial Williamsburg in Virginia or Indiana’s Conner Prairie.

If you’re looking for some fun activities, there’s Six Flags Over Texas or the smaller Zero Gravity Thrill Jump Park. But if you’re interested in sports, check out the Dallas Mavericks for basketball; the Texas Rangers will open at home against the Houston Astros on March 29th; and the Dallas Stars have a few games at home in March.

4. St. Augustine, Florida

Aviles Street in St. Augustine - one of my favorite Spring Break ideas

Aviles Street in St. Augustine, Florida

It’s right on the beach, but it’s not one of the college hotspots. As the United States’ oldest city, it has too much educational and historical significance to be of interest to college students. Or your kids, but who says Spring Break has to be all about amusement parks and kiddie fun time?

St. Augustine was originally a Spanish outpost and colony, so it’s known for its Spanish colonial architecture. Anastasia State Park is a protected wildlife sanctuary and you can check out the St. Augustine Wild Reserve, a nonprofit animal sanctuary. There are also plenty of old sites to check out, including the Fountain Of Youth Archaeological Park, Castillo de San Marcos, the St. Augustine Pirate & Treasure Museum, and the El Galeon Ship.

Walk around historic St. George Street, and you can see the oldest wooden school, the old jail, and plenty of interesting shops. You can also ride around on the hop-on-hop-off trolley tour to get around town and hear a little about the place while you’re riding.

The last time we were there, my family and I ate at The Conch House Restaurant, which is right on the main pier overlooking the Bay. But if you’re in the mood for seafood, there are more restaurants than you’ll be able to visit in a single week. And since they’re right on the water, the seafood is always going to be fresh.

Where do you go for Spring Break? Do you have any good Spring Break ideas? Share them with us in the comments below, on our Facebook page, or in our Twitter stream.

Phoo credit: paulbr7 (Pixabay, Creative Commons 0)

Take Vacations During Off-Peak Travel Times

November 30, 2017 by · Leave a Comment 

One of the greatest joys I have as a traveler is going to a normally-busy place sometime in the off-season and feeling like I have the entire place to myself. Mackinac Island, Disney World, overseas trips to Germany and The Netherlands. They all feel like a private playground when I visit while everyone else is at work or school.

It’s like I’ve discovered a secret location that only a few people know about. We all stroll casually around, smiling at each other, knowing we’re in on the same secret. You can walk up to rides, there are no lines for museums and exhibits, there’s no one on the beach, and you can get seated within minutes during normal meal times And you’re spoiled for choices when choosing a hotel room at an inexpensive rate. It’s glorious!

I’ve also been in Disney World, Chicago, and several resort towns during peak vacation times, and it’s — well, let’s just say I didn’t feel so special on those days. Hotels are expensive, traffic is evacuate-before-a-disaster heavy, you’ll wait for a week at a restaurant, and the crowds are so big that even an extrovert like me just wants to crawl under the covers for a week.

As a result, my family has been a regular practitioner of traveling during off-peak times. Hotels cost a lot less, there are often discount packages available for some destinations, and you can get a more personalized experience as the staff can focus more attention on you, or at least not be so harried when they try to help you.

So I’m very interested in Offpeak.io. It’s a website that analyzes the travel times in major cities and give you an idea of what’s a peak travel time versus an off-peak time in a chosen city, so you can book your travel plans accordingly. The site is still in beta, but what I’ve seen so far is pretty spot on.

You can use Offpeak.io to find out if there are any major events going on in your chosen city — sporting events, festivals, and holidays — what the weather should be like, and even check the average hotel rates and number of available hotels.

The results appear in a bar graph showing occupancy rates. The smaller the bar, the more rooms there are; the higher the bar, the more crowded everything is going to be. The hotel room rates follow the median price for a hotel room too: higher bars mean higher expected rates.

The occupancy/room rate graph from Offpeak.io will let you know about peak and off-peak travel times.

The occupancy/room rate graph from Offpeak.io will let you know about peak and off-peak travel times.

The end of January and early February are always off-peak travel times because there are no major holidays, and everyone is back at school (which makes running around Disney World a dream!). You can find hotel rooms for a median rate of $78 on a February weekday in Edinburgh, Scotland, but then the weather is cold and rainy at that time. A comparable hotel in Boston will cost $189, which is pretty cheap for Boston, but the city is going to be most likely buried under a foot of snow.

Offpeak.io has information on 111 cities, including Amsterdam, Mexico City, Osaka, Cape Town, and Melbourne. But no Indianapolis, Offpeak? Seriously? You’ve got Cleveland in there, but not Indianapolis? (Hint: The end of May is horrible for finding a hotel in Indianapolis, especially on the west side. If you’re not going for the Indy 500, stay on the northeast side.)

Be sure to pay attention to the weather in your area, and plan your travel methods accordingly. You may find a cheap hotel rate in Boston and Chicago in January or February, but you can almost count on the weather being a factor in any cancelled flights, highway closures, and hotel availability. On the other hand, when are you going to find hotel nights that cheap in Boston and Chicago at any other time of the year?

When do you like to travel? Do you go the same time as everyone else and just fight the crowds? (You’re a better person than I am!) Or do you like to go when no one else is around? Share your strategies with us in the comments below, on our Facebook page, or in our Twitter stream.

Family Vacations: Airbnb Versus Hotels?

October 26, 2017 by · Leave a Comment 

How do you feel about staying in someone else’s home during family vacations? I don’t mean visiting family during your holiday break (which is no picnic, let me tell you). I mean renting someone else’s house for a night, a week, or even a few weeks?

If you’re traveling somewhere for a few days on one of your family vacations, would you rather rent a hotel room with a brand you can trust so you can get an experience you can expect? Or would you rather be adventurous, stay in a place that lets you experience the real part of a city, and have a lot more space than you would in a cramped hotel room?

I’ve had a chance to stay in both Airbnbs and hotels over the years, and I’m actually having a hard time deciding which I prefer. Not my wife though. She’s insistent: no staying in other people’s houses. She’s only done it once, and then only because it was way cheaper than a hotel room. Otherwise, she doesn’t like it.

She just doesn’t like the idea of sleeping in a stranger’s bed, using their sheets, occupying their space. I’m less worried about it. For one thing, they always put clean sheets on the bed. For another, they’re never around (I always get the “whole house” rentals, never an “own room”).

Airbnb is a great way to find an inexpensive place to stay during family vacations
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Does Your State Have a Tourism Trail?

July 27, 2017 by · Leave a Comment 

If you’re ever looking for a short vacation you can do close to home, but don’t know where to start, try a tourism trail. A tourism trail typically focuses on food, alcohol, history, or sports, and is usually created by tourism boards or local businesses.

For example, Indiana has six separate wine trails, all created by the Indiana Wine Grape Trail. Covering different parts of the state, you can spend a day or two each on trails in southeastern Indiana, northeastern Indiana, or Indianapolis.

But if you don’t want Indiana wine, there are wine trails in nearly every state. Check out America’s Wine Trails to pick a wine trail in your favorite part of the country or something close to home.

When I was a travel writer in Indiana, I even devised an Indiana Microbrewery Trail. It’s a fantasy beer trip around the Hoosier state, in three parts, each taking two days.

The Woodford Reserve Distillery is part of the Kentucky Bourbon Tourism Trail

The Woodford Reserve Distillery is part of the Kentucky Bourbon Trail


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Consider Visiting Quirky Places on Your Next Family Vacation

July 13, 2017 by · Leave a Comment 

I’ve got a weird sense of humor and always appreciate the unusual and quirky. I collect typewriters, I listen to radio theater, and I love stories about little-known historical events. My tastes in travel and family vacation run a bit unusual as well. I’m fascinated by cities that have unusual histories or have odd attractions that no one else in the world has.

When I visited Washington D.C. years ago, I made sure to visit my friend who ran the Bead Museum (now closed), a museum dedicated to artistic beads throughout the world. I was intrigued by the way different civilizations had all discovered putting holes in pretty objects to wear around their necks and wrists, but I was more intrigued that there was a whole museum about it.

When I lived in northern Indiana, I lived about 40 minutes from Mentone, Indiana, home of the world’s largest egg. It’s a 10 foot high concrete egg that weighs 3,000 pounds in the middle of town, and I occasionally drove to see it just to say I did.
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How to Travel Light On a Family Vacation

February 24, 2017 by · Leave a Comment 

I’ve been a long-time proponent of traveling light because I hate carrying a lot of stuff. I’ve gotten to the point in my work life that I never carry paper, and it bothers me when someone hands me a piece of paper. (I even scan business cards with my phone and hand the card back to the owner.)

Minimalism is the key to travel, and I’d rather do without something not-so-important than lug it along “just in case.” That’s how I keep my business backpack so light.

The Atlantic Ultra Hardside luggage collection

The Atlantic Ultra Hardside luggage collection

My family has been bitten by the minimalist bug as well, and we’ve spent the last several years shedding unwanted stuff in our lives. So it’s only natural that we adopt this approach to our travel, and we’ve gotten pretty good at it. Here are a few things we’ve learned over the years.
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Five Apps You Need On Your Next Road Trip

February 3, 2017 by · Leave a Comment 

As a frequent driver, I love what my mobile phone can do. It’s a mini computer and camera that lets me make phone calls, and thanks to the various apps that are available, I could leave my house right now, and drive all the way across the country without a laptop or pre-planning, and navigate the entire trip.

But I couldn’t make it without my phone.

That’s because I use certain apps just to find my way around anymore. Whether it’s ordering coffee, booking a hotel, or finding somewhere to eat, there’s an app that’s sure to help any traveler on any trip. But there are a few that are perfect for road trips. Here are my top five.

Siri/Android Virtual Assistant

First, let’s get this out of the way: I don’t text and drive (and you shouldn’t either). Instead, I use Siri to send and read my texts.

If you have your mobile phone plugged into a power source, you can call out “Hey Siri” and she’ll answer. I plug the phone into the AUX jack on my stereo, so I can hear everything going on. When I say “Hey Siri, read my texts,” she’ll read any new texts, then ask if I want to respond. I dictate a short response to her, including all punctuation (because I’m a geek that way) and she sends it for me. There will be occasional errors, based on my pronunciations, like “will” instead of “we’ll,” but the people I text understand when I’m dictating, and will figure it out.
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Should You Drive or Should You Fly? A Vacation Formula

January 27, 2017 by · Leave a Comment 

When heading out on vacation, the biggest decision you’ll make is how to get there. Do you drive or fly? If you fly, you can get there sooner and spend more time at your destination. Driving is more budget friendly, but it takes a couple of extra days out of your vacation time.

In my travels, I’ve driven and flown to dozens of destinations. On some airplane trips, I would have been satisfied with driving, and on some car trips, I wish I’d been born with wings. But for the most part, we made the best decision we could with the information and resources we had. If you’re trying to decide, here’s a handy 3-step formula you can use to help make your decision.

How far is your destination?

Kids on a planeI typically won’t fly anywhere if I can make the drive in less than six hours. If I fly, I get to the airport two hours early, and it takes me at least 45 minutes to drive, park, and get inside. My flight will take at least one hour. Then I have to disembark, walk to the rental car counter, get my car, and drive to the hotel, all about two hours after the plane touches down. And if I take the hotel shuttle, then I’m without ground transportation.

This all takes at least 5.5 hours.

But if I drive, I can take the same amount of time, and have my car with me in a new city, which lets me explore on my own. I’m in control of my progress and circumstances.
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