How to Plan for Vacation: 7 Ways to Pack More Relaxing Travel into Your Over-Scheduled Life

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According to the U.S. Travel Association, in 2019, Americans left 768 million vacation days unused. Wasted. That amounts to $65.6 billion in lost benefits or an individual average of $571 in donated work time. Workers earned nine percent more vacation time in 2019 than they did in 2017, yet they used even fewer days. Maybe workers aren’t sure how to plan for vacation?


You want to use your vacation days to travel. But with uncertainty in both your personal and work schedules, it’s challenging to plan a vacation. Then coordinating time-off with a partner adds to the complexity. Finally, considering the kiddo’s programs and extracurricular activities, and it’s just impossible to find the perfect time for a traveling vacation.


At work, faced with finding a backup or coming back to a mountain of work, the whole idea leaves you overwhelmed. You feel like it’s easier to forget those vacation days. Don’t.


Here are seven approaches I’ve used to pack more leisure travel into my hectic life.



Tall Ship Sailing on Grand Traverse Bay in Traverse City, Michigan


Prioritize Travel


Make travel your priority. Prioritization helps in the planning process. You’ll need to prioritize both your time and your money to reach your travel goals.


If travel is your priority, but you think you can’t afford it, try this. Write down your expenses for a week and see where your money is going. Then decide, is it more important to spend $5 on a daily Starbucks’ venti full-fat pumpkin spice latte or is it a higher priority to use that week’s $35 from Starbucks to take a whale watching tour on your next vacation.


You’re prioritizing your vacation days for travel. First, realize no time will be perfect, so settle for a time you can make work. Ask yourself what you can miss at work and on your social calendar? Undoubtedly you will miss something, so you need to figure out what your priorities are and what you are willing to lose in exchange for what you will gain on that fun-filled trip.


Don’t leave your vacation to chance; schedule your vacation time early in the year. The last Tuesday of January is National Plan for Vacation Day. When planning, mark more extended vacations on the calendar first. Like Stephen Covey recommended, in The Seven Habits of Highly Effective People, fit in the big rocks first, then the medium ones, and finally, let the gravel fill in around the larger rocks and stones.


Using your vacation days for travel doesn’t mean you can’t just take a day off when you need it. If you need a day off, take a one-day vacation or a day trip. Just because a destination is near, doesn’t make it any less of a getaway.


View of Put-in-Bay, Ohio from the Perry’s Victory and International Peace Memorial


Plan Your Vacation


People who plan their vacations used an average of 12 paid-time-off days to travel compared to the five days off used by non-planners.


To start planning, you need ideas. Read travel websites and blogs to find recommendations on where to go and what to do. Get input on where in the world you should go next. Read general travel sites like Nomadic Matt to get ideas for your next vacation. If you’re a foodie, read foodie sites, if you are a hiker, seek out information on great trails.




Keep a list of places that interest you and decide how much time you would need to take that vacation. From the United States to Australia you might need two weeks, for a city in Europe, maybe ten days. Perhaps a long weekend in Las Vegas. A new restaurant in your town, perhaps just an evening.




Once you have a destination and amount of time required, decide what’s feasible. When could you take that trip? Will it be this year, next year, or a trip you need to save for over several years?


Make a list of the kinds of activities each person in your family enjoys. When in doubt, ask them. You might be surprised to learn that your granddaughter has an escape room experience on her bucket list. Then match the travelers’ interests to the destination.


Consider the best time to visit a destination. Compare calendars to determine what week will work best. Schedule time off work. Will the kiddos be out of school? Does the timing work for all those going on the trip? Consider planned activities and weather? Check for hotels and flights. Be sure all the elements of the journey work together.


Determine what you’re willing to compromise on and what you aren’t. If there’s something you especially want to do, like have breakfast at Tiffany’s, make sure their restaurant isn’t under renovation.


China Town in Washington, D.C.


Be Prepared


Plan a list of vacations, with activities and restaurants so that you can take advantage of spur of the moment opportunities.


Be ready. If it takes hours to get ready to go on a spontaneous trip, the opportunity evaporates, but if you’re packed, you can seize the moment. Always have a travel bag packed, prepared for at least a three-day weekend, like the concept of an emergency bug-out bag. Have the bag always at the ready, in case there’s some emergency fun required.




Create a packing list and keep it in your suitcase, ready to be checked off. If you have enough clothes, keep a bag packed ahead of time.


Prepare a toiletry bag and keep it in your suitcase. You’ll always need that when you travel, so have it ready, packed, and in your weekend-sized suitcase. The same goes for a first aid kit. I have one assembled and prepared to go in my bag.


Piper’s Pro Planning: Create kits–Beach Kits, Snow Play Kits, Snack Kits, ready to grab and go with the paraphernalia already packed in a container. When my child was small, I kept a tote in the garage to throw in the car with everything we would need for the beach–sunscreen, beach towels, bug spray, swimsuits, sand toys, and beach balls. When we had a day where the weather was excellent, and everyone happened to be free, we didn’t need to search the house and use precious time finding things we needed. We could grab the tote, jump in the car, and head to the beach. We were ready in 15 minutes instead of an hour and 15 minutes.


Figure out what your family likes to do and make a kit with all those items packed. Your chances of going will increase exponentially.


Lioness and Cub in Tanzania


Set Aside Vacation Funds


Set up a vacation bank account separate from your other funds and have the money added directly from your check rather than putting all your earnings in one account. Some save for Christmas in a Christmas Club fund; use the same concept to create a Vacation Club fund. When it comes time to take your vacation, your budgeted funds will be available. This practice reduces the stress and worry of not having funds available for your vacation.




To save money on hotels, car rentals, and activities, call ahead when reserving and find out about any special discounts available with AARP, AAA, veteran discounts, or student discounts.


Check out destination websites and look for coupons or call a destination’s Visitor’s Center to see if they have coupon books available. They often do.


Keep a list of free things to do in your town or your planned vacation destination, so that when you have the time but don’t have a lot of money, you can still go. In Lansing, Michigan my home town, my list of free things to do includes tours of the Eli and Edythe Broad Contemporary Art Museum and the State Capitol Building. During summer, they perform free concerts in several parks, and a bike ride on the River Walk is yet another possibility. So, if funds are limited, see what’s available to do for free in your town or a neighboring city.


Stay Flexible


Create a one or two-day itinerary for a cheap staycation. You won’t need a hotel or airfare.


Flexibility is critical to be able to switch your plans when it’s raining on beach day – always have a Plan B.  Keep a couple of options in mind, in case it rains, and you still want to have a micro-vacation. Substitute that bike ride on the River Walk for a tour of the State Capitol Building. Sometimes it doesn’t matter what you do, and it’s the change of pace that makes the difference.


Dirty Fries at EnVie Restaurant in Lansing, Michigan


Combine Pleasure with Business


The trend to extend a business trip into a pleasure trip at your own expense makes sense. When you go for business, the city can remain mostly unexplored. If you are at a destination all week or the days are adjacent to a weekend, planning a vacation night or two at your own expense may benefit the company. Flights on Saturday are usually less expensive than flying out on Fridays, for example.


I had been to New York City twice and had never seen more than the inside of a windowless conference room. I decided that the third time would be my chance to change that. The leadership said, fly on Sunday, and our meetings will start first thing Monday morning. Rather than take the last flight from home to New York City, I took the first one. I landed by 10:00 a.m. and had the whole day and evening to take a tour and see a Broadway show.


Work within Your Constraints


Depending on your business constraints, look for pockets of time. Are you free for lunch? Grab a quick lunch at a museum café. Are you open in the evenings? Research what’s available after 5:00 p.m. Perhaps a tour of the Las Vegas lights or an evening at the Winnipeg ballet.


You must eat on a business trip, so to experience the local culture, look for local restaurants rather than national chains. I remember a business trip to Kentucky; I had my first Hot Brown. On a business trip to Asia, I had a Singapore Sling in the Raffles Hotel in Singapore, the hotel where they invented the drink.


If your business trip covers two weeks, rather than flying home for the weekend, stay, and explore the destination for the weekend. It saves the company money on airfare and gives you some leisure time that will feel like you planned a vacation.



Go it Alone


You aren’t planning Noah’s Ark; you can travel alone. Getting your partner, spouse, friend, or family available for a trip at the right time can be difficult. Getting everyone to agree on the same destination might be impossible. Maybe you have different interests, or you need some alone time to rejuvenate. Work with your family to agree on separate vacations.


If you don’t want to go to it alone, join a tour. Others with the same interest will be on the trip, yet you can still have your alone time.


Decide on that one thing you would enjoy that others wouldn’t. That’s the trip or activity to plan when you go it alone.


Iguazu Falls


Take Shorter Trips More Often


Research local destinations within an hour or two drive of your home. Think of destinations near home that might seem like a far-away place; for example, I live in Michigan. Lake Michigan can remind me of the California coast; so, it seems like I got farther away than I did.


Travel locally by planning day trips that don’t include a hotel. Trendy micro-vacations make you a tourist in your own town. You don’t have to go far – how many times have you walked by that art museum and never stopped to go in? Google your town’s tourism site to find new things to do. I know I have lived in Lansing, Michigan, my entire life, yet there are dozens of places I have yet to explore. Plan a vacation day during the week when the crowds are fewer than on the weekend, making it a more enjoyable experience to explore that new museum exhibit in your city.


Decide what you need, a more extended period to completely disconnect, or more frequent breaks. You can use your week-long vacation in one five-day stretch or use those same five workdays off as a series of five three-day weekends. Maybe short weeks, long weekends are the answer.


Make it a three-or-four-day weekend; add a holiday to extend the weekend to a four-day weekend. Sometimes traveling on the holiday, itself is cheaper, because others want to get where they’re going before the holiday.  


I flew from Detroit to San Diego on Independence Day for less than $200 roundtrip, because we were willing to fly on the actual holiday. We left early, and with the time difference, we landed in time for lunch in San Diego. We were able to pack a lot into the three-day holiday weekend, at an affordable price.


India’s Backwaters


How to Plan for Vacation and Go


Imagine what it’s like to use all your vacation days. How much fun could you have if you made travel a priority and planned your vacation days to re-energize through travel, rather than donating that time back to your company?


In addition to planning more extended trips, prepare to carpe diem with spontaneous trips. Formulate your budget so that you can enjoy your trip.


Are you already traveling for business? Add on an extra day and explore the area.


And don’t give up because you can’t coordinate with other’s schedules. Solo travel is trending for a reason. Get to know yourself.


Stretch your weekends by a day or two, so that you can have more frequent getaways.


But, don’t leave those vacation days on the table. Get started planning your next vacation on the last Tuesday in January; it’s National Plan for Vacation Day.


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Let’s get something on the calendar! Here are some of Piper’s Pro Planning links to help you book your trip.

Plan your flight and book your airline ticket with these links:

Plan your overnight accommodations anywhere from national chains to private homes with:

Plan to save on all of your activities, from tours to attractions. These links will help:

Visit my resources page for more planning help.


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  1. Shawn donley

    Great stuff, love your post. Saw you today on Happy trails Hiking Stream today, nice to meet you.

    • Piper

      Thank you Shawn Donley! Are you planning your next vacation yet? I hope some of these tips help!

  2. BrianSwify

    Cool internet site you have going here.

  3. Jamie

    Juggling all of life’s obstacles can be difficult when you love travel, but I think you’ve highlighted some really good points here to make it happen. Prioritizing it is the key, by far, and with the other elements offering good foundation. I’ve used similar techniques of forgoing the take-away coffee to save for a trip, it’s remarkably effective.

  4. Nina Bosken

    It is absolutely crazy to me how much vacation time goes un-used. We really do get the stereotype for being workaholics. I’ve been living in Spain for the past 5 years and I know that this statistic would shock spaniards. almost everyone takes a few weeks to a month in august. Lots of other european countries are the same. Your tips are great. I think people should take advantage of 3 and 4 day weekends more! You can do and see so much!

  5. Agnes

    I’m surprised by the statistics that people are not taking their holidays. So many vacation days are unused. It’s a pity because everyone should find time to rest. It’s great that you are giving so many Great tips on how to plan a successful vacation!

  6. Kavita Favelle

    I’ve never not used all my leave allowance, it’s what I live for (a slight exaggeration but I know you know what I mean!)
    I agree with the point about prioritising – when I had colleagues who moan about how lucky I am to travel and they can’t, it’s nearly always people who earn the same or more than I do / did at the time, but who drip drip drip their money away on nights out drinking, on make-up and fashion, on music and newest phone and so on. All of which is OK but it’s their choice to spend it that way, and their choice to then have not enough left to use for travelling!!!



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Welcome to Follow the Piper! Discover interesting destinations, and practical planning tips for packing more travel into your everyday life.

Our founder and author, Amy Piper, is a freelance travel writer, blogger, photographer, and author specializing in luxury and multi-generational travel. She is a native Michigander who travels through the lens of a food lover and has been to 41 countries and 45 states.


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