We all could use more vacations. That should go without saying. But as far as planning our next great trip goes, well, let’s just say sometimes we end up needing a vacation from planning our vacation.
And let’s face it, some of us have been out of the vacation planning game for a long time now.
Between travel restrictions, being married to work, or simply being a terrible planner, you’re here because you’re struggling to put together a solid plan for your next vacay.
But there’s no need to stress. We’ve put together 12 helpful tips to take you from troubled to triumphant and leave you with a foolproof plan for how to tackle your vacation planning one step at a time.
Table of Contents
- 1. Choose Your Destination
- 2. Pick Your Travel Partners
- 3. Determine Your Budget
- 4. Decide When You’ll Go
- 5. Research Travel Deals
- 6. Ask for Time Off
- 7. Find a Great Place to Stay
- 8. Research the Area
- 9. Plan Your Itinerary (Or Don’t)
- 10. Get Your Documents in Order
- 11. Decide on Travel Insurance
- 12. Minimize Travel Risks
1. Choose Your Destination
When planning a trip, the first step is one of the most fun … deciding where you want to go for your vacation. The options here are endless, from vibrant and energetic cities to magnificent national parks and palm-studded islands.
Whatever you’re looking for, you can find the perfect travel destination to make your dream vacation a reality.
It doesn’t even have to be a specific place to start. If you find yourself too spoiled for choice, try narrowing it down first by region to give yourself multiple destinations to choose from.
Suppose you know you want to have a boozy getaway in wine country. Then you can start narrowing down your travel destinations to include places like Napa Valley, Bordeaux, and Tuscany.
Or maybe you want a relaxing vacation in the tropics. Then you know you can cross off most of the continental US and start looking to places like the Caribbean for your ultimate getaway.
You don’t have to start off married to a specific destination just yet.
In fact, it may be better to start with only a vague idea instead.
This way, you can adjust your plans to allow for changes in your budget and your time-off schedule and score the best deals possible for your trip.
2. Pick Your Travel Partners
We’ve all heard the saying: “It doesn’t matter where you’re going. It’s who you have beside you.”
Well, when it comes time to plan a trip, that couldn’t be more true.
Trips—and how you plan them—are defined by the people who take them, from family vacations to epic bestie adventures.
Sometimes, other travelers aren’t a requirement at all.
Solo travel is on the rise, and more and more women are doing it by themselves, from planning a quick weekend trip somewhere close by to traveling abroad and visiting a foreign country solo.
And, of course, the answer to how to plan a vacation will differ immensely if you travel with family, plan a trip with friends, or even go it solo.
With a family, you may need a more disciplined plan, with precise itineraries for what you’re going to do and when. Whereas with friends or alone, you may be more inclined to go wherever your feet take you. You also may be less picky about where you stay and not mind traveling off the beaten path when something catches your interest.
These are all things to consider as you make your travel plans.
3. Determine Your Budget
Now that you have at least a basic idea of the where, why, and who of your how-to-plan-a-vacation master blueprint, we can start talking budget.
This is usually the worst part of trip planning—at the very least, it’s in the top three.
Don’t worry, it isn’t nearly as bad as it sounds.
Okay, yes, this is the part where most of us have to start saving money and figuring out how much we need to afford our next trip and what that’ll cost in terms of time and effort. You have to start asking yourself questions like, will you need to work more hours, set aside more money each month, or cut back spending in other areas to afford your trip?
But most people think of their travel budget as an obstacle to their dream trip. Of course, there’s bound to be some bad blood in the mix if you think of it like that. Instead, think of your travel budget as the little piggy bank or money jar you kept as a kid.
Remember the incomparable joy you felt at adding more money to your stockpile, whether Christmas money, weekly allowance, etc.?
Think of your travel budget just like that piggy bank and know it’s going to need filling before you can start booking all your plans. Use that to incentivize your decisions and give you that little boost of joy as you put each dollar away, knowing the cause is a worthy one.
And this is where having a more general destination comes in handy, too, as you can plan a trip around your budget. Set on an escape to wine country but looking for a less expensive option than Tuscany? Maybe Napa Valley will do the trick instead.
4. Decide When You’ll Go
When you’re going to go is almost as important as where because the timing can affect just about everything in the trip planning process, from how much money you spend to how you spend your time.
This is one of our key takeaways for how to plan a perfect vacation: travel during your destination’s shoulder season.
The shoulder season is that time between peak season and low season. And this sweet spot is the gift that keeps giving, with cheaper flights, lower hotel rates, smaller crowds, and more.
On the other hand, if you plan your next trip for a holiday or peak travel time, prepare for inflated prices and larger crowds. If it takes place at a specific time—like during a famous festival or peak tourist season—then start your planning process early.
5. Research Travel Deals
Savvy budget travelers know that having a solid budget in place before you start your planning process is key to getting the best deals and saving money.
- You want to look for specific ways to save money, not go overboard because you found “deals” that you didn’t want to pass up.
- It’ll be that much more satisfying to see how much money you save—and how much you come in under budget—from all the deals you nab during your travel planning.
Take advantage of countless online resources to help you compare prices and score the cheapest deals. Here are just a few to get you started.
- Google Flights – for comparing flight prices from multiple airlines
- Kayak – for finding cheap hotel room bookings
- Airbnb – for locating fantastic vacation rentals
While accommodations can take up a sizable portion of your budget, airfare tickets are arguably one of the most expensive parts of travel. To make matters worse, finding and booking flights can often be a nightmare.
If you want to be sure you never miss out on great flight deals in the future, try signing up for Next Vacay! You may even find yourself with some new travel inspiration, as NV sends you all the best airfare deals to domestic and international destinations available right out of your home airport.
You can even book directly through the airline to use travel points for a discounted or even free flight!
With a budget in place, you can search for the deals that’ll keep you at your budget thresholds or below. So, when a great deal from Next Vacay comes in several hundred dollars under budget, you’ll know it’s one you won’t regret snatching up right away!
6. Ask for Time Off
If you’re not planning this trip because you already have time off approved, schedule time in your calendar to speak with your boss or submit your time off request as soon as you’ve nailed down the dates you want.
Try not to schedule your request off during your busiest time at work or when you have a lot of unfinished projects awaiting completion.
The earlier you get your request in, the better positioned you are to have your time off approved. Then you can start cementing your travel dates and itinerary.
Also, make sure you get the confirmation of your time off in writing. This way, if something happens, you can refer your boss back to the written confirmation and dispel any confusion.
7. Find a Great Place to Stay
Booking accommodation for your trip shouldn’t be complicated. We touched on this a bit earlier when talking about how to score the best deals on your travel, but plenty of search engine websites exist to help you compare prices on accommodations and get the best rates. We recommend starting with a few at a time:
Who you travel with could also affect your accommodation plans, so keep the needs of your travel group in mind.
Are you looking to stay in boutique hotels, secure a whole vacation rental for yourself, or simply book a single bed in a hostel? Do you need to make meals or wash clothes during your trip?
Approach how you plan a vacation with this mindset of asking questions to hone in on what will work best. This way, you ensure you’ll find something to accommodate your group and fit your travel budget.
8. Research the Area
There’s more fun to be had in your travel planning. One of our favorite parts of planning a vacation is detailing the trip! That means once you’ve gotten some of the particulars, like budgeting and finding deals, out of the way, you can start researching where you’re going!
This research can be as brief as or in-depth as you want. However, we always vote to do a bit more research than not here, especially if you’re visiting a foreign country. We can think of fewer things worse than finding out about an incredible sightseeing destination or local eatery on the last day of our trip. Trust us, it’s happened before, and it’s not fun.
Not to mention, doing some recon on your destination is a great way to drum up excitement for your trip. It can also help you iron out an itinerary—if you’re into those.
Here are some helpful travel tips to get you started:
- Look up famous sights or experiences at your destination (research travel blogs, recommendations from locals, and Google’s handy Things to do feature).
- Note the average length of any activities you’re interested in.
- Check out distances between activities and your lodgings (try checking out multiple locations with Google Maps).
9. Plan Your Itinerary (Or Don’t)
Once you’ve got a list of things you’re interested in seeing and doing, you can narrow it down further. Consider this intro lesson 101 for the itinerary portion of our how-to-plan-a-vacation breakdown.
Start with the things you:
- Want to do most
- Fit in your budget
- Are easiest to get to
Then you can purchase tickets or time slots based on how busy you want your day to be and travel times between different attractions.
If you’re not the itinerary type, don’t feel like you have to be just to check this off your travel planning list.
Instead, try making plans for must-see attractions and purchase those tickets. Then leave the rest of your schedule free to wander down random streets, linger somewhere with a scenic view, or slip into other attractions that have same-day ticket slots open.
And for those by-the-book travelers, don’t stick to an itinerary at the cost of your enjoyment.
Just because you’ve planned to visit something one day doesn’t mean it can’t be moved around or struck from your itinerary entirely if needed. Sometimes, you just need a day to sit and do nothing but enjoy the fresh air or have a drink with a newly made friend.
Make plans, but don’t be afraid to break them.
10. Get Your Documents in Order
Okay, now that you’ve gotten a chance to have some fun, it’s time to wrap up the last few details of your trip planning.
First and foremost, that means getting all your documents in order.
A quick and relatively painless way to make sure nothing gets left at home is to create a checklist for all your essential documents and confirmations:
- Passport or visa
- Drivers’ license/ID card
- Flight booking confirmation
- Accommodation booking/order confirmation
- Tickets to attractions
- Vaccination record or negative COVID-19 test result
- Travel insurance
The more digital options you have, the better, as that’s fewer physical documents to carry around. You’re also less likely to forget your phone on a major trip. But a checklist will do the job of making sure you get everything you need together, so you don’t have any last-minute panic attacks at the airport.
11. Decide on Travel Insurance
Travel insurance isn’t always necessary when you decide to hit the road. Still, it can help relieve some stress knowing that you’re covered if something happens before or during your trip.
Different types of travel insurance will ensure coverage in different situations, so it’s crucial to familiarize yourself with the primary forms of coverage available:
- Trip cancellation, interruption, or delay insurance
- Travel medical insurance
- Emergency medical evacuation coverage
- “Cancel for any reason” coverage
- Baggage and personal belongings
- Car rental collision insurance
You may find that some of these are covered already through things like your credit card, renters or homeowner insurance, or even your current health plan, so double-check before adding on the expense of travel insurance.
Keep in mind there are benefits and drawbacks to adding travel insurance to your trip, so give time to consider all of them and determine if travel insurance is right for you.
- Provides peace of mind
- Offers compensation for lost items
- Covers medical expenses
- Helps save money if something drastic does occur
- Can be expensive
- May not cover pre-existing conditions
- Claims could be rejected due to technicalities
Whether or not you need travel insurance will be up to you and if you’ll feel comfortable traveling without. Take the time to do your research and find out what you may already have covered!
12. Minimize Travel Risks
At this point, we’re so close to being ready to fly you might be inclined to zip up your suitcase and call it a day. We’re almost there, we promise. Before you fly out, there’s just one last check you need to do in your travel planning: prepare for the worst.
It’s the last thing we want to imagine, especially on a trip abroad, but taking a few precautions ahead of time will doubtlessly save you lots of anxiety and dread should you run into trouble on the road.
So, how can you prepare for the worst when you’re not sure what the worst might be? Here are a few things you can do ahead of your travels to make sure you’re not caught unprepared.
- Sign up for the Smart Traveler Enrollment Program (STEP) – helpful for getting in touch with your local embassy and friends and family during emergencies
- Make copies of your essential documents – keep a physical copy of your ID and passport with you and keep electronic copies of documents like travel insurance, credit cards, etc.
- Research common scams – familiarize yourself with typical scams at your destination to avoid risky situations and tourist traps
- Inform your credit card companies you’ll be traveling abroad – ensure your credit card companies know you’ll be out of the country so your accounts aren’t frozen
- Bring backup credit cards – try carrying one card on you and leave another at your accommodations in the event one is lost or stolen
- Secure your valuables – ensure your valuables are locked up tight at your accommodations or kept in hard-to-reach places on your person to reduce the chances of theft
It’s never fun to imagine all the ways your trip might go wrong, but taking the time to make a few plans for what-if scenarios can help you avoid these situations during your vacation. And if they do still happen, you can minimize their impact on your travels and hopefully still enjoy what remains of your trip.
Which helps make all the planning, checklists, and scheduling worth it!