Have you ever scrolled through the picture-perfect images on Instagram or Pinterest and thought to yourself “sweet baby Jesus I just need a vacation”? *Hands up emoji*
Or have you started planning a trip and all of a sudden became so overwhelmed with options that it was no longer fun and in a fit of a rage swore off traveling for the rest of your life?
Maybe you have so. many. destinations. you want to visit that it is literally impossible to choose just one so instead of going anywhere you go nowhere?
*Gasp!* The horror!
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ESSENTIAL GUIDE TO TRIP PLANNING
I have been in every one of those above scenarios more than once and I’m sure many of you have as well. You can often find me aimlessly scrolling through my Instagram or Pinterest feeds stopping on any photo that has impossibly blue water, snow-capped mountains, or winding cobblestone streets with adorable cafes that serve food I’ve never heard of. All of this lends itself to having a list a mile long of places I want to visit.
Vacation planning can be quite stressful and I think it’s because as Americans we have so little time off from work that when we do take a vacation we want everything to be ab-sa-lout-ly pinch me perfect. It puts a lot of pressure on us, no?
If you feel the same way keep reading for my ultimate guide to trip planning and save your sanity 🙂
Step 1: Brainstorming your destination
I’ve found that when planning a trip there are several guiding questions you should first ask yourself/others you’re traveling with before making any other plans. So pull out that list of must-visit destinations or make one if you don’t already have one!
Where on Earth do you want to go?
This is obviously the most important question, but it’s arguably the toughest to answer. Don’t think about time constraints or budget right now, literally just write down everywhere you think you wanna go.
Is it somewhere that’s less than 3 hours away on a direct flight? Or will you tolerate multiple connections and jet lag to land yourself on some remote island in French Polynesia?
Think about what sort of feel you want for your vacation.
- Is it the dead of winter and you’re dying for a quick trip with some sunshine and all you wanna do is sit on the beach drinking cocktails?
- Or do you want to do something exotic like riding camels in the desert?
- Maybe you’ve had one thing on your bucket list for years and years and now is finally the time to check it off?
- Do you wanna luxuriate in a five-star resort with daily massages?
- Do you wanna go to the beach or the mountains?
- Center city or somewhere remote in the countryside?
- Are you trying to do as much as you can for as cheap as you can?
- Is the family going or are you going solo, with your spouse, or with girlfriends?
- Is this going to be a non-stop adventurous vacation or do you prefer days spent drinking seven margaritas, eating tacos, and laying on a beach?
Jotting down the answers to these questions will start you off on a good course to planning the perfect vacation! If you’re having a brain freeze and need help thinking of fun destinations, thumb through some inspiration on Pinterest and start a vacation board for yourself. Then make it rain with pins until you find something that really sparks your interest.
Now if that doesn’t work for you and you’d rather browse by price, Sky Scanner and Kayak both allow you to enter your departure airport and then search everywhere. They’ll serve you up a list or a map of the price for flights everywhere in the world.
These two things are usually enough to get the mind going and come out with a list of five or six places that are appealing. If you still need some help, consult Facebook, Instagram, hashtags on Twitter, friends/family, blogs, guidebooks etc. Or message me! Planning vacations is like my favorite hobby ever.
Resources full of wanderlusty inspiration:
Step 2: What does the time frame look like?
When do you want to travel?
- Are you bound by the constraints of your children’s summer vacation so you must go during the high season of June-August?
- Or do you have more leeway and can squeeze the trip into the shoulder seasons?
- Do you only have a long weekend or maybe just a week?
- Or are you taking two to four or more weeks off of work?
Vacations should be about relaxing and getting away from that day to day grind and stress. You can plan the perfect vacation but if you cram too much into a tight timeline your trip is going to be rushed, stressful, and will likely leave you feeling unfulfilled. Ever hear people say “I need a vacation from my vacation?” Yeah, don’t do that.
So if time is your limiting factor, then I suggest starting here and then working backward to choosing a destination.
If you only have a long weekend then traveling to Tahiti is out of the question, obviously. But maybe you can catch a quick and cheap flight to Washington D.C., Las Vegas, New York City, Chicago, etc?
On the other hand, if you have a few weeks maybe now is the time to take that dream trip to Australia, New Zealand, or Bali.
If you must travel during the summer either because of kids or your work schedule then look into cities/countries that aren’t as well known and overrun with tourists. I don’t know about you, but I don’t want to spend my hard earned vacation time standing in lines the length of three football fields and listening to other people’s bratty kids whining while I’m trying to enjoy the Eiffel Tower.
So, I definitely don’t recommend doing Rome or Paris or London in July, but maybe checking out Finland, Croatia, or a safari in Botswana?
If you have the freedom to travel whenever you like please please please check into the shoulder seasons of whatever destinations you’re looking at. I LOVE traveling during this time because
- Things are so much cheaper
- No tourists = no lines = better pictures = more exploration = more fun had by all
- The weather is usually a bit cooler, but still nice enough to be out exploring
A quick search on Google will give you the shoulder seasons and most popular times to travel to your proposed destination.
Step 3: Researching and booking your flights
The first thing I always do once I’ve selected a destination is to check out the flight offerings. Learning how to find cheap flights will help reduce your spending tremendously because flights are more often than not going to be your biggest expense.
It’s really helpful when sites like Kayak and Skyscanner allow you to view several months in advance for trends in prices. You can set a watch list and receive push notifications or emails when prices drop as well as their recommendation on when to buy the tickets. There is literally nothing more annoying than purchasing flights only to have them drop in price a week later.
Also, don’t take what they offer as concrete. Once you find the best price with best travel time and layovers head directly to that airline’s website and see if they have it listed for cheaper- often times they do. And while you’re at it, sign up to their rewards program and start building up some miles. It’ll be a slow boat to China building miles without their credit card, but every bit helps.
Or, if you don’t mind a little bit of finagling, you can always travel hack your own set of flights together for sometimes significantly cheaper. Take the city you have in mind and look at neighboring cities and check those flights.
Often times flying into capitals like Rome or Paris can be expensive, but flying into a smaller city or a less popular city is sometimes cheaper. Then just take a car or ride the train to wherever it is you want to go. Or spend some time exploring the new city and then moving over to the original city a couple days later. Bonus vacation for the win.
Another fun thing to do is build in layovers. Icelandair has a thing now with the Iceland stopover. If you’re flying to Europe you can choose to stay in Iceland for a few nights. You can essentially do the same thing if you piece together a couple one-way flights.
Ever wanted to visit a city that’s on the way to your destination? Book a flight there and spend a day exploring before heading off to your final destination! An intentional 24-hour layover in a city of your choice far beats a 9-hour layover laying across the chairs in Heathrow.
Keep all of this organized by keeping a spreadsheet with various flights/cities/prices etc and cost compare across the board until you find something that you’ll be happy with. There is some talk about which days of the week are cheaper and how far in advance you should book, but I’ve never really found any of that to be true. One thing that you absolutely should do is always search flights in a private window on your browser – this will keep prices cheap. Airlines know when you’re searching repeatedly and often jack up the prices.
Step 4: Researching and booking your accommodations
What do you want your accommodations to look like?
- Five-star hotel with incredible pools and showers?
- All-inclusive resort with as many drinks and food as you can handle?
- Or do you want to rent out someone’s house, grocery shop, and live like a local?
- Maybe you’re into hostels or couch surfing?
- Cheaper, more budget-friendly hotels?
- If you’re traveling with kids, does the place have a daycare for date nights?
After flights, accommodations are the next most important thing. You must have a plan and book these as soon as you’ve secured your flights. There have been some instances that I’ve booked accommodations first, but this is usually for big events like Oktoberfest (which I’m finally doing this year!).
But do secure somewhere to sleep, otherwise, you’ll end up like me with nowhere to stay.
Like everyone, I try to get the best value for my money, but I won’t “rough it”. I would never stay in a hostel, couch surf, or a budget hotel – but if that’s your thing then by all means, book that $25 a night room and then make it rain with your savings.
I like to do a nice mix of higher-end hotels, resorts, and Airbnb. I think hotels are really nice if you only have a couple days to spend in a city before you move on to the next one. It doesn’t make too much sense to me to book an apartment and have groceries and laundry facilities if you’re only there two or three nights.
On the other hand, if you’re parked in one area for quite some time it’s so helpful to have a kitchen and at least a washing machine. And if you’re traveling with others you can arrange separate bedrooms which after several days spent together is a godsend.
I booked my first ever Airbnb when I went to Ireland and absolutely loved having a home base to come back to each night. Also, nothing makes you feel more like a local than lugging bags of groceries up 4 flights of stairs to your apartment.
I’ve only ever stayed at an all-inclusive resort once. It was fun and convenient to have nearly everything you need right there on campus. And you get “free” drinks and food so after you’ve spent a full day exploring the town it’s nice to come home and not have to go out for dinner.
You can search for accommodations on sites like Tripadvisor, Expedia, Airbnb, VRBO, or Booking.com Also, large hotel chains sometimes offer cheaper rooms than the search sites do, so if you have a reward card for Marriott, Hilton, etc then check out their websites. And if you’ve never booked an Airbnb you can sign up here and save $40 on your first stay!
Step 5: Transportation
- Are you planning on driving once you arrive at your destination?
- Or are you looking to do public transport?
- Or is it a small enough place that you think you’ll walk everywhere?
If you plan on driving while at your destination it is better to go ahead and book your rental car in advance. You’ll have a better selection and will get the car for cheaper than you would if you waited until you arrived at the airport. You can find rental cars on the usual suspects like Expedia and Kayak, as well as Enterprise, Avis, Hertz, Alamo etc. If you are going abroad, don’t worry, you can search rental cars over there, too.
Make sure to research license requirements in your home and destination country. You can’t always drive legally with your US drivers license abroad. Some countries require you to obtain an IDP which is an international driver permit and other countries allow a US license for up to one year. So, just Google that and look for reputable sites like government or embassies.
If the idea of driving abroad freaks you out as well, most big cities have public transport. You can search for metro cards or purchase tickets to the hop on hop off buses, which are a really fun and convenient way to get around town.
Step 6: Food and things to do
This is the best part of trip planning! After all the boring stuff like choosing flights and accommodations is out of the way you can finally start researching the best cafes, pubs, and sights in your proposed location.
What sort of activities would you/your group like to do?
- Wine tours?
- Any particular tourist sights that you have to see?
If you’re traveling with children look up things like zoos, aquariums, parks, theme parks etc. Take into consideration their tolerance for heat/cold, walking, change in time zones/jet lag etc and don’t plan too much for your days.
To start your activities research you’ll want to know what the “must visit” attractions are and then plan other free activities, restaurants/cafes, and tours around this. And if you’re going somewhere popular during peak season then you’ll want to secure tickets to the most popular things as soon as you can as they are likely to sell out well in advance.
My favorite sites to browse are Tripadvisor and Viator. Tripadvisor is great because you can just hit the “things to do” tab up top and type in your destination and voila! All sorts of ideas about activities and the best sights your destination has to offer.
Viator is a Tripadvisor company, but their site includes various small group tours all over the world. You can read thousands of reviews and see the price of tours and compare those with other sights that you’re looking at as well. When I went to Ireland I booked a few tours through Viator and loved them. Also if you book the hop on hop off tour buses they always include discounted rates for city attractions so you kill two birds with one stone.
Pinterest is super helpful when planning things to do and you can create destination boards and keep everything nice and organized.
Keep checking back, this will be constantly updated with more information!