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

Travel Tips

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 average of $571 in donated work time. Workers earned nine percent more vacation time in 2019 than 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, planning a vacation is challenging. Then, coordinating time off with a partner adds to the complexity. Finally, considering the kiddo’s programs and extracurricular activities, finding the perfect time for a traveling vacation is impossible.

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When 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. Travel planning doesn’t need to be a lot of work.

Here are seven approaches I’ve used to improve my trip-planning process and pack more leisure travel into my hectic life.

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

Prioritize Travel

The first step is to make travel your priority. Prioritization helps in the planning process. You’ll need to prioritize your time and money to reach your travel goals.

If travel is your priority, but you think you can’t afford it, try this. Write down your weekly expenses and see where your money is going. Then, 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 same amount of money from the week’s $35 spent at 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 your priorities and what you are willing to lose in exchange for what you will gain on that fun-filled, perfect vacation.

National Plan for Vacation Day

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. As 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 needed. You don’t always need a long time. 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
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 for a travel destination. 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 perfect vacation. If you’re a foodie, read foodie sites; if you are a hiker, seek information on great trails. Research is critical to making travel plans for the perfect family vacation. 


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 A new restaurant in your town, perhaps just an evening.

Keep a list of places that interest you and decide how much time you need to take that vacation. From the United States to Australia, for international travel, you might need two weeks; for a city in Europe, maybe ten days. Perhaps short trips, like a long weekend in Las Vegas are a good idea for the time you have—a new restaurant in your town, maybe just an evening. You don’t always need much time to explore a new place.


Once you have a destination and the required time, decide what’s feasible. What time of year could you take that trip? Will it be this year, next year, or a trip you must save for several years? You’ll want to establish a travel budget line in your overall budget.

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

Consider the best travel dates to visit a destination. Get something scheduled by looking at specific dates on the calendar. You may get a better deal at one time of year than at another time. 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 hotel rooms 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 you especially want to do something like have breakfast at Tiffany’s, make sure their restaurant isn’t under renovation.

China Town in Washington, D.C.
China Town in Washington, D.C.

Be Prepared

Plan a list of vacations, with activities and restaurants to take advantage of spur-of-the-moment opportunities. Be ready for last minute plans. It doesn’t need to be a long trip. If it takes hours to prepare for 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 an emergency bug-out bag. Have the bag always at the ready, in case there’s some emergency fun required.


Create a list of things you’ll always need, no matter your destination. Keep it in your suitcase, ready to check off. If you have enough clothes, the easiest way is to pack a bag 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 when the weather was excellent, and everyone was free, we didn’t need to search the house and spend precious time finding things we needed. We could grab the tote, jump in the car, and head to the Beach — ready in 15 minutes instead of an hour and 15 minutes. We were prepared for those last-minute plans.

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

A lion cub and mother in Tanzania
Lioness and Cub in Tanzania

Set Aside Vacation Funds

Set up a vacation bank account separate from your other funds and add the money directly from your check rather than putting all your earnings in one account. Some save a little bit 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 having insufficient funds 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. No matter how much money the trip costs, you’ll find ways to shave off some extra cost. A tight budget doesn’t mean you have to stay home. Avoid high season for the best price.

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 you can still go when you have the time but don’t have a lot of money. My list of free things to do in Lansing, Michigan, my hometown, 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 another possibility. So, if funds are limited, see what’s free in your town or a neighboring city.

Stay Flexible to Plan a Vacation

Create a one or two-day itinerary for a cheap staycation. You won’t need to book flights or book an accommodation. Flexibility is critical to switch your plans when it’s raining on beach day – always have a Plan B.   Keep a couple of options in mind if 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 the change of pace makes the difference.

Dirty Fries at EnVie Restaurant in Lansing, Michigan
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. It may be the best way to see those some destinations for the first time without a lot of additional cost. When you go for business, the city can remain primarily 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. For example, flights on Saturday are usually less expensive than flying out on Fridays.

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 to fly on Sunday, and our meetings will start on 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 to make you feel like you planned a vacation.

Important Documents

When traveling internationally, remember to plan in the amount of time you need to secure certain travel documents. Look into visa requirements. Be sure that you have an ATM card or debit card that will work in a local bank at your destination. Documentation is as important a cheap flights when traveling and you’ll want to have enough time to obtain all the important things you need.

Plan for a vacation on South Manitou Island Michigan
Lighthouse on South Manitou Island, Michigan

Go it Alone

You aren’t planning Noah’s Ark; you can travel alone. Getting your partner, spouse, friend, or a family member 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 need some 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 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.

How to Plan for a vacation in Argentina or Brazil

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 far away; for example, I live in Michigan. Lake Michigan can remind me of the California coast, so it looks like I got farther away than I did. Maybe a road trip is just the ticket to a relaxing, inexpensive get away.

Day Trips

Travel locally by planning day trips that don’t include a hotel. Trendy micro-vacations make you a tourist in your 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.

Weekend Trips

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 the same five workdays off as a series of five three-day weekends. Maybe short weeks and 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 is when you’ll find the cheapest flights because others want to get where they’re going before the holiday begins.

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

How to Plan for a vacation in India's backwaters - a canoe fishing boat with a fishing net

India’s Backwaters

How to Plan a Vacation and Go

Imagine what it’s like to use all your vacation days. How much fun could you have if you prioritized travel 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 to 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.

Pin this to your favorite travel planning Pinterest Board to read later!

Amy Piper
Author: Amy Piper

While Piper is a lifelong Michigander, she’s had adventures worldwide. Bomb-sniffing dogs chased her in the middle of the night in Bogota (working late), gate agents refused her boarding to Paraguay (wrong visa), and US Marshals announced her seat number on a plane while looking for a murder suspect (she’d traded seats). It’s always an adventure! She even finds exciting activities in her home state of Michigan, where she lives in Lansing with her husband, Ross Dingman, her daughter, Alexis, and two granddaughters.


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 traveling through a food lens 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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