27 Tips To Plan An Amazing Trip Itinerary For Any Destination
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Creating a travel itinerary for an upcoming trip is at once a very fun and very overwhelming experience. If you are going somewhere you have never been before, you may be starting from scratch. If you are going international, there are a host of foreign factors to take into account. It is exciting to prepare for a travel adventure, but also—where on earth do you even start?
How do you organize your time to make everyone happy? Will you be able to check off the bucket list of everything you were hoping to see and do? What did you forget?
After all, I am sure you value your time and money, so taking the preliminary steps to create a realistic and researched trip itinerary will ensure the amazing vacation experience that you were hoping for.
Below are the guidelines and questions that you can apply to any trip and any destination to maximize your vacation time. A great travel itinerary is your key to a great travel experience, so you can begin right here, with us!
How Do I Choose A Destination?
Usually, travelers have a destination in mind before even beginning their travel research, but if you have an open mind and are looking for inspiration on the coolest travel destinations, the best advice is to start looking early, read around, and take a look at travel blogs to get excited about certain places.
Think about what time of year you are thinking of taking your trip, and which destinations are suitable for that season. For example, North America’s summertime is Australia’s winter. For another, if you look at skiing trips during your holiday time off around Christmas and New Year’s Day, be aware that every other skier is doing the same, so prices will be high.
What To Consider When Planning Your Trip Itinerary
Budget
Time of year
Trip duration
Size of traveling party (their ideas, abilities, and budgets)
Weather
Lodging
Dining
How To Research Your Destination To Find The Best Attractions And Activities
The best way to start researching your destination is cross-checking multiple websites that list the area’s top attractions and activities. Don’t rely or subscribe to just one website’s recommendations; aka don’t stop after scanning Tripadvisor.
Read a few travel blogs and sample itineraries of previous travelers’ experiences in that destination, and get a feel for how they broke down their trip. It is worthwhile finding out what they did not find worthy of their time and money, seeing their unprofessional photos (not the marketed photos of a commercial attraction), and getting more of any everyman’s viewpoint of the area.
Always read reviews—but with a grain of salt—not just taking for granted the one-star review that totally rips into every single negative.
You could try Wanderlog to help build out an organized trip itinerary in one place. You can link dinner and hotel reservations; it provides information and inspiration. You may enjoy this assisted creative process in creating your trip itinerary. Hi, Type A travelers.
If you want to dive into some hearty information resources, I whole-heartedly recommend Rick Steves, Frommer’s, and the like. I used these kinds of guides when road tripping southern France.
I usually start making my own itinerary by copying others! I open a new Google Doc and start copying and pasting links and relevant information, so that it is all organized in one place for me (and potentially for my traveling companions to view and edit). I almost always use Google Maps to “star” attractions, pit stops, and sites I know I won’t want to miss, and I reference this map often on my trip. That way I have sites listed on a physical map, and I can see the distance from A to B without hassle.
How To Create a Custom Travel Itinerary That Fits Your Schedule And Interests
Raise your hand if:
You find travel stressful
If a trip has turned into a fiasco
If you have found yourself wishing you had made more time to just freaking relax
If you get back from “vacation” more tired than you were before
A great trip is about walking the fine line between adhering to a well-rounded and informed itinerary, while also keeping close to mind the intention behind this trip. It is always harder than you think to maintain a mental awareness and flexibility that you are taking this trip for fun.
First of all…. What are you traveling for?
Comfort, relaxation, some pampering? Excitement? A crazy adventure to fire up your blood? Quality time with loved ones? First things first, know why you are traveling. This will impact everything (honestly!): how long you want to travel, where you stay, where you eat, how you spend your time. Your trip is entirely in your hands, and that looks different for every traveler.
We all travel for different reasons; we are all looking for different kinds of experiences. Do you care about cuisine, the outdoors, the local arts, the scenery, the architecture, the history, the museums, the sports? Some travelers are happy to pick up dinner from a street vendor after a long day of adventure and call it a night. Some travelers want their day’s activities to wrap up around 4 so that they can recharge and get ready for a nice dinner reservation at a popular restaurant they’ve heard a lot about.
Decide when and how long your trip will take place
How much time are you taking off of work? How long is too long with your travel companions? What duration is within your budget? Look into how much time other people spent at this destination and how well-satisfied they were with their trip length.
What time of year are you going? Research weather so that you can pack accordingly and plan your itinerary accordingly. If you wanted to hike on your trip during your destination’s rainy season, adjust your expectations and pack clothes/shoes you are fine with dirtying.
Quality, not quantity
Decide what activities and attractions are important to you, prioritize those, and plan your day around them.
Travel destinations normally hold more opportunities and options than you can realistically—or comfortably—fit into one trip itinerary, so you will have to pick and choose. Try delegating one or two major attractions or activities per day; then, have back-up options for amusement if you find that you have time and energy to spare!
Look at the length of the trip as a whole, and try to realistically envision yourself going about all these hoped-for activities in real-time. Take into account time, distance, transportation, weather; you are better off over-estimating than under-estimating all of these factors. Most travelers overfill their trip itinerary, imagining bouncing from here to there to there. In reality, travel is tiring and can often be over-stimulating.
Take It All In
Try to experience some of the area’s top attractions and spots, but do not limit yourself to solely those popular sites, and do not waste away in anxiety if you are unable to see each one, whether due to full bookings or high cost.
Most likely, your destination holds hidden gems and offers plenty of lesser-known, but equally-fascinating, opportunities to experience, rather than just checking off major attractions from Yelp and Tripadvisor.
Try something out of your comfort zone
This, my friends, is maybe the most important and rewarding part of travel: experiencing something you cannot—or would not—at home in “real life.” Traveling to a new destination has already placed you in unknown territory, and it is strange and exhilarating to let yourself do something you (under normal circumstances) choose not to do. That’s why people come back from trips with “crazy” travel stories! They found themselves suddenly doing something they truly had not anticipated or experienced before, and it leaves a lasting impact on them. They remember it fondly; they feel stronger and bolder because of it. Trying new things keeps us human beings alive. Take that and run with it when you travel!
Embrace Local
Look for local experiences and phenomenons, not “home-y” experiences, like The Cheesecake Factory.
Search for what activities and sites make this destination unique and different from anywhere else. Challenge yourself to find the well-kept secrets and small spots, not just the huge, widely-marketed, and money-making attractions.
Many travelers spend high amounts of money on really nice lodging accommodations, only to either (a) not leave the hotel and miss out on the amazing destination all around them, or (b) don’t set aside time to enjoy the lavish accommodations that they spent a good deal of their budget on.
Communicate
Make sure your travel companions are on the same page.
Everyone should have complementary expectations on budget and itinerary. This always proves to be difficult, doesn’t it? The best way to prevent tense and conflicting situations during the trip is to manage expectations and have any uncomfortable, but necessary, conversations beforehand. Take everyone’s opinion into account, respect each other’s wishes, and make allowances for mistakes. There is hardly a better opportunity than travel to test your patience and understanding with others.
Do The Research
Research what factors could impact your safety—physically, financially, and more.
Do some research on what to avoid and common scams that may be lurking in your specific destination. If it is a popular travel locale, the economy and environment is most likely very established as such—for better and for worse. For example, in Rome, street peddlers will often be calling out to you from every street corner…and not all of them are honest.
Plan Ahead
Book and make reservations for popular restaurants and attractions ahead of time.
In busy travel seasons at popular destinations, some reservations can fill up months in advance. If a specific experience is important to you, then get tickets far in advance, in order to avoid disappointment when on the trip.
Make a packing list
Necessary items first, then extraneous and comforting items last. On the night before or day of travel, run through the list and make sure you check off each necessity.
Make a to-do list in the days before the trip
Have a physical checklist of things that need to be done before go-time. Having things in writing will always work to your advantage; a mental checklist is about as useful as a mental plane ticket.
Important Questions To Ask
These are a few important questions to ask yourself (and your travel companions) when creating a travel itinerary.
What do I want out of this experience? What kind of trip am I hoping to have?
Do I know the local language?
What local customs should I be aware of?
In case of emergency, who would be available to step up to help, and who do I know is physically closest to me?
What is the budget?
Do I want to pay in money to stay closer to the heart of things, or pay in time and convenience to stay farther away from the center of your destination?
How much down-time do I want to have?
How busy do I want this trip to be?
Have I accounted for the time for transportation between sites of attraction?
Do I want an Airbnb or hotel for lodging?
Am I being flexible for my travel buddies’ ideas and wants?
Tips For Navigating Airports and Public Transportation Systems in Other Countries
Planning out transportation is one of the most crucial steps to preparing for a trip.
If you plan to use public transportation, be generous with your timetable. There are an immense amount of unanticipated and unknown factors working into the equation here: not being able to find an Uber, long lines at the train station, not being able to find the bus station in the city, road traffic on the way to the airport… The list goes on.
Do not wait last-minute to know how you are getting to and from the airport when traveling internationally; make careful calculations. When I think of stressful situations that cause me to literally break a sweat, this is mine, hands down.
Tips On Setting a Travel Budget
Here’s how you can save money on travel expenses while still enjoying every moment of your vacation.
Travel is not off-limits to you if you are on a budget, and your travel experience does not have to be tainted in any way. Your expectations need to be realistic and aligned to your budget, but there are a variety of ways to make travel more feasible for you, while still keeping an eye on the wallet.
Sometimes lower expenses is a trade-off for your time and energy, so decide which is more important to you. Oftentimes to save, you will be opting for the more time-consuming, inconvenient, and less-than-luxurious option. But for some travelers, that doesn’t really matter!
Plan Transporation
Transportation nearly always ends up being one of the most expensive parts of travel. If you can, base your trip around affordable flight prices. Sign up for alerts from airlines, as they will email deals, or from sites like Kayak and Scott’s Cheap Flights.
If possible, walk. Skip the Uber, Lyft, or taxi. Save money, get your steps in, and see your travel destination slowly and in real-time on your own two feet. Or, rent a bike or scooter.
Plan Ahead
Book things ahead of time. You can find deals online that get you crazy discounts; some attractions even incentivize travelers to book ahead time by offering lower prices. You can often get hotels to price-match; you can shop around for the best rental car option, instead of taking the most convenient (and expensive!) option of those at the airport. Online research will also display more options and allow you to compare more prices, as opposed to just choosing whatever option presents itself to you in the moment of travel. Not planning in advance can really cost you money if you don’t pay attention to and plan out details.
Keep it To A Minimum
Travel light. The more stuff you have to carry, the more inconvenient and costly it ends up being (bigger car, paying for to check a bag on an airline). Travel for the experience, not the stuff.
What to Do if Something Goes Wrong While You're Away From Home
In order to prevent disaster—or even just inconvenience—when traveling, do everything in your power before the trip to eliminate these possibilities. While you are still in the pilot seat, fact-check, research, dot your i’s and cross your t’s. Knowledge is power when traveling.
I tend to repeatedly come back to this point when talking about travel, but if you fail to prepare, you prepare to fail. Going on a road trip and don’t have AAA or how to change a tire yourself? Well…hope for the best.
An itinerary is fun, but the primary purpose of an itinerary is also to ensure the smoothest vacation. Yes, you want some unexpected adventure, but you also want to say no thanks when it comes to a medical emergency or to being the victim of crime or scam.
Ways to prevent travel disaster
Someone should always know your location, especially when traveling internationally. Update your loved ones at home or share a copy of your itinerary with someone you trust so that your journey could be roughly tracked if you need to be found.
Carry extra cash, in the currency of value, of the country you are in. Also carry a back-up credit or debit card, in case one is lost, stolen, or denied.
Have a physical map (but do not openly display that for everyone and their grandmother to see in public spaces).
Bring a lock for your valuables and carry your wallet in a secure spot, so that you don’t position yourself to be a victim of petty crime.
Know how to get back to your lodging at all times.