How to Plan an Awesome Trip!

Depending on the type of person you are, you may love or hate making travel plans. Whether you’re a budget or luxury traveler, this comprehensive travel planning guide walks you through the entire process.

Personally, I love poring over travel guides and imagining all the great things we’re going to do. However, I have also learned the ease and freedom of not over-planning. I still worry sometimes about missing out on something really cool, but you discover plenty when things are unplanned, as well.

The best part, though, is the excitement. You’re going to get to go somewhere new, and different! You’ll be discovering new things. Even if you’re staying in your home country, travel opens you to a wider range of experiences, and that’s always fun.

We’re going to cover some different approaches to planning so you can find the one that suits you best.

Then there are the logistics. I don’t think this part is fun for too many people, but there are things you can do to make this part of travel planning easier. Preparation is key, and digital tools go a long way to helping keep your records straight. Doing this right will save a lot of headaches and make for a more relaxed trip.

Plan things right, and you, too, might meet a goat in front of a radio station – or not.

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Choosing Where to Go       

**If you’re absolutely certain about where you want to go, feel free to skip this section.**

So, what kind of trip do you want to take? Are you an adventurer, antique shopper, or maybe a beachcomber? Do you want luxury, or are you willing to rough it? Do you want to unplug, or will this be a working vacation? Hot or cold climate? What kind of activities do you enjoy? Do you want to travel with a theme, like Best Neon Signs in the US or Game of Thrones Shooting Locations? Are there goats in your future?

Colorful Travel Sign for Travel Planning

Of course, these are questions only you can answer.

It used to be that I’d go to a travel bookstore, or the library and browse for hours, looking at information on different destinations. While these are still fun things to do and we highly recommend them, you can also do your preliminary research online. Why wait? Daydream now. (Just don’t let the boss catch you.)

Don’t fall into the typical travel planning search trap. Sure, it’s okay to search for the 10 Best Beaches in the World, but so often the sites all say the same thing, or are trying to sell you a tour.

Try searches like: the most underrated beaches, or the most interesting beaches, or secret beaches or even haunted beaches. Get creative. This will help you discover some truly unexpected destinations and keep you off the over-worn tourist track. Atlas Obscura is especially good for finding unique places.

As you’re searching, bookmark any destination that lights a little fire inside of you. When you see something that makes you go, “ooh!” – save it.

Compile a list of your top choices. Whether you do it in your word processor, on your Notes App, or by having ten tabs open in your browser, just sit down with all of them in front of you.

Now you have some juggling to do.

Narrowing Your List

If you only have a week, you might not want to go somewhere that takes 24 hours to get to. Remove any destinations that are too far away based on travel time vs time at destination.

Of what remains, which places excite you the most? If anything has dropped down to a meh for you at this point, remove it from the list.

Is there somewhere that sounds interesting, but you’re scared to go? Unless it’s a true safety issue, like terrorists and bandits, LEAVE IT ON THE LIST. Often the places that scare us are the most rewarding.

Don’t let fear remove a destination from the list.

Now’s a good time to consider budget. I’ll talk about it more in depth, later, but if money is a concern, you shouldn’t ignore costs at this point in the process. Keep search tabs open on SkyScanner and your favorite hotel app so you can do a cursory check of flight and accommodation pricing for a region. If any place is too expensive, nix it.

By the way, we have a FREE eBook: How to Save Money for Travel – on Almost ANY Budget! Click the link for your copy.

You probably have five or fewer destinations by now. Start comparing things like activities, interesting sights, culture, climate, timing (local festivals), etc.

And once again, we come back to fire. Which one gets you the most excited?

If you still can’t decide, join some Facebook travel groups. There’s a Lonely Planet Traveller’s group, where you could discuss multiple destinations and choices, and there are more regional groups, like Southeast Asia Backpackers, or West Africa Travelers. Find one, or several, that match your choices and join them. Ask questions. Get opinions. They’re good for later stages of planning as well.

By now, you’ve probably chosen the perfect destination – but wait! Is there something you forgot?

Including Everyone in the Travel Plan

**If you’re traveling solo, more power to you. Skip ahead to the next section.**

Who else is going with you? Your significant other, best friend or the whole family?

The biggest thing when travel planning as a couple, or for a group, is to make sure there are plenty of activities that everyone will like. If you want to go to a surf beach in Morocco but there’s weak internet and not much else to do, you might want to make sure your hubby is okay being a beach bum for a week or two, if he doesn’t surf. Or, you can search for alternate activities he might enjoy in the area. Nothing says you need to be glued together. You can surf while he goes looking for goats in trees. (Yes, really.)

Actually, once you’ve narrowed the choices, it’s time to talk to your travel-mates. Depending on the size and personality of the group, you probably want to offer 3-5 choices. Have a list of activities at each destination that you think each person will be interested in, as well as a few basic details like weather, terrain and comfort level – and costs, if appropriate.

When you’re discussing the possibilities, listen to everyone’s concerns. If a destination is going to make someone miserable, take it off the list. You can encourage people to grow and try new things, coax them a little with other highlights they might enjoy, but don’t force it. This is easiest if you choose destinations with a large variety of activities and options.

Once you’ve wrestled everyone into agreement, you have to determine how you’re going to travel. Oh, and buy the latest guide book for the location. We’re partial to Lonely Planet.

Travel Planning: Tight vs Loose

Do you prefer to schedule everything in advance, packing each day with as much as you can? Unless you’re doing a tour, this can be hard to pull off. There’s always something to throw the schedule off, and everything takes longer than you think it will.

Still, sometimes you have a lot you want to do and see, and a short time to do it in. So you need some tight travel planning. Just…leave some breathing room. Know that you might have to remove some things from your list. Don’t let getting off schedule ruin your vacation. Plan for it. Sure, have an optimal list of everything you’d like to do, and plan your route. But earmark some activities or sights as ‘disposable’. They’re the first to go if/when things start to go haywire.

If you just like to travel loose, landing somewhere and not having any special sights or activities in mind, well, you’re probably not the one reading this. Though it would behoove you to do a little research to find out what the highlights are for wherever you’re going. Don’t get on a FB travel group once you’ve arrived and expect them to do all the itinerary work for you.

Generally, the best solution is a mix of fast and slow, tight and loose. That brings us to our next section.

Taking Breaks

If you’re planning any trip of two weeks or longer, you’re going to need to include some breaks.

The first thing to consider is travel time and arrival. How tired will you be? Will one good night’s sleep put you right, or will you want to use the first day for rest and relaxation?

Tim and I usually plan for a day off after we arrive. That works out better for him than me, because even if we’re not going sightseeing, I still have to scout our new area, learning where the convenience/grocery stores are, checking the terrain (to see how difficult it will be for him to handle), and figuring out where we’re going to get meals. But that’s okay. I generally feel better about a place once I’ve done this. Giving Tim a recovery day after travel takes a lot of stress off.

Should you schedule your breaks when planning a longer trip?

The truth is, you don’t know what might slow you down. A bout of tummy issues, a canceled bus route, hotel problems or even just being tired after a long day of sightseeing might have you calling for a day off.

We recommend, overall, not scheduling your breaks. Let them happen when you need them. When I took Tim to China for six weeks in 2007, his first trip out of the country, we traveled on a fast, tight schedule. I knew we wouldn’t get to everything, so when we needed a break, we took it. It amounted to about one day off per week. Though, we ended up having one of our favorite adventures on a so-called rest day, because a walk in the park in China is not a simple thing.

Hotels and Booking Ahead

Do: Research hotels in the towns you’re going to. This is where the hotel apps, like Agoda, help. You can save lists for each city of the places you like, then review them and choose one when you’re sure of which day you’re going to arrive. Look for places that offer free cancellation in case your plans change.

Don’t: Book everything ahead on a so tight of a schedule that an unexpected delay causes a ripple effect, ruining all of your reservations and causing you undue stress.

This one is tricky and really depends on how, and when, you’re traveling.

If you’re going to some event, or are traveling in high season, you probably want to book your hotels ahead. Big events require a lot of advance planning. Don’t underestimate this.

Other than that, in most situations you can book as you go, maybe a day or two ahead, especially if you have several hotel options available. This gives you the flexibility to deal with unexpected occurrences and problems. It also gives you the freedom to move at your own pace. If you find somewhere you love and want to stay longer, you can, and vice versa.

We do recommend having your first hotel booked. After you get off a long flight, the last thing you want to deal with is figuring out your hotel. Book ahead, see if they offer airport pick-up, or can at least tell you how much the taxi should cost.

Also, if you hate any hotel, don’t hesitate to leave. We’ve done that a few times, when conditions were poor.


Have you decided to go for luxury, or are you backpacking? Or do you fall somewhere in-between? Make sure you have the funds you need so you can enjoy your trip and not spend it worrying.

Cup of Money for Travel Planning

If you want a rough estimate without doing all of the work, we’ve found Lonely Planet Guidebooks, and their website, do a good job of estimating for budget, mid-range and top end. Actually, I think they estimate a little high in the mid-range sometimes, but they’re good numbers to use. Look up your destination, then go to the In Detail tab. Under Planning Tools there’s a section for Money and Costs.

I’d back this up with a little search on your hotel booking site For instance, in researching Namibia, Lonely Planet puts mid-range hotels at $50 and up, but a search on several other sites I quickly found several in the $30/night range, in a major city. So there’s definitely some in-between choices that LP’s guides just can’t cover.

While you’re figuring out your budget, don’t forget about airfare, eating out and transportation, not to mention activities. All of this info is pretty available online. If you’re having trouble finding it, you can ask in those Facebook travel groups I mentioned earlier.

In fact, remember when you’re choosing your hotel that a lower per night fee might be offset by taxi costs to get to the interesting things. Unless you’re renting a car, we highly recommend choosing a hotel near the center of the action when possible. It makes everything easier and it’s generally fun to be in the thick of it. It’s nice to be within walking distance of local restaurants and street food, as well. (Of course, if you’re distinctly looking for peace and quiet, this might not be the way to go.)

Once you’ve determined your budget, add 20%. This will let you stay relaxed when you have to cover those unexpected things, good and not-so-good, that are bound to come up.

I’m going to pitch our FREE eBook: How to Save Money for Travel – on Almost ANY Budget! again, for people that need to save up for this trip. I mean, it’s a free eBook, and full of good, real advice and things we did ourselves. No catch. We’ll send it right to your inbox, (just click on the link).

Oh, and whatever you do, make sure you include travel insurance in your budget. Good policies cover trip interruption, medical evacuation, and much more. You can check to see what kind of protections your credit card company might offer, but make sure you’re covered. One mishap may or may not ruin your trip, but don’t risk a major financial setback. Whatever the cost, it’s worth it. If you can’t afford travel insurance, you can’t afford to travel.

Make a Packing/To Do List

However, definitely have a list. We recommend keeping it on your phone so you can add things the moment you think of them. Never say, I’ll remember that. It’s a lie. You’ve got too many things on your mind when you’re planning for a trip and if you don’t write it down, you’re going to forget something. So write it down!

Get Your Documents in Order

Having your travel paperwork at your fingertips will make your life soooo much easier.

There are a few ways you can do this, most involve apps. First, let’s take a quick look at the things you’ll need a little more in depth.

International Travel

PassportAlmost every country requires you to have 6 months of validity past your travel dates, so make sure your passport isn’t about to expire. If you need to apply for one, do it as soon as you can in case there are delays, or you need it to get your visa. Yes, you can rush a passport, but it costs a lot more money that way. SCAN YOUR PASSPORT and email it to yourself. Also make several photocopies to carry with you, they can come in handy in a lot of ways.

Passport and Map for Travel Planning

Visas – The best way to get current visa information is to go to the immigration page of the country you’re going to visit. They’ll tell you everything you need about getting your visa. If you’re having trouble finding that page, check your home country’s State Dept. In the US, make sure you’re on a .gov site.

There are also third-party visa sites. They’ll also give you correct document information. If you choose to use their services they are efficient and generally a fair deal. These sites can make your life easier if you’re trying to get a difficult visa, or if you just don’t want to hassle with ins and outs of immigration paperwork. At the very least, they’re a good resource, give them a look (after you finish reading this post).

*Note: Some countries can be especially difficult to obtain visas for, and some are just slow. Don’t put this off until the last minute. At the very least, research their requirements as soon as you decide on the destination and leave plenty of time to get this bit of paperwork done.

ATM/Credit Cards – Call your bank and check what their foreign transaction and ATM fees are, and whether they have any branches in the country you’re visiting. Foreign withdrawal and transaction fees can be outrageous. We highly recommend finding a bank, like Aspiration or Radius, that don’t charge ATM fees. These two banks, and there are others, even reimburse any fees imposed by other banks’ ATM’s. Keeping your travel funds in an online bank like this only makes sense if you do any foreign travel.

Also, don’t forget to put a travel alert on your account so your transactions don’t get tagged as fraud. Not all banks require this anymore, but check with your bank before you go.

Having Cash When You Land – A lot of people will tell you that the exchange rate at the airport is horrible, or that you won’t need cash, or to use the ATM at the airport. Personally, we like arriving in a country with about $100 worth of local money in our pockets. Let me tell you why.

You land at the airport late and the money exchange isn’t open. Or, the ATM decides it doesn’t like your card, or it’s out of money, or the network is down. Yes, all of these things can happen. But you need to get to your hotel. You need money for the taxi or shuttle. You need a SIM card. Maybe you want a snack or drink, or any number of other little expenses. This is why we like to have cash when we land.

You can use the Forex (foreign exchange) at your departure airport, but if you’re in a hurry, this can be difficult. We just discovered that Travelex, one of the most trusted and widely seen currency exchanges, will actually let you purchase the currency you need online and deliver it to your home. This could make your life a lot easier. It’s one less thing you have to worry about.

Check them out.

Vaccinations – In some locations you’ll need a Yellow Fever Certificate. You need at least 10 days between the shot and your arrival (though check country requirements). The good news is that you only have to get this shot once in your lifetime. The WHO no longer requires a booster every 10 years.

As far as other vaccinations, you’ll need to refer to information for each location. If you can, talk to your doctor about which vaccinations are wise, or necessary. Some come as ‘recommended’ but are expensive and obscure. If your doctor can’t help, there are travel clinics; though they tend to be expensive, they’re sometimes necessary.

You can also try some pharmacies (like the ones in Costco (US)) that work with online travel advisors. You fill out information about your trip, pay a fee to the advisory medical website, and they send you a report of what they recommend. Then, you can get your vaccinations from Costco which is usually reasonably priced, and you don’t need to be a member.

*Note: Some people traveling to Southeast Asia wait and get their vaccinations on arrival somewhere like Bangkok because it can be much cheaper. This is a good question to search for in a Facebook travel group.

Domestic and International Travel

Airline Tickets – Surprisingly, we’re not going to try and give you a bunch of cheap airline ticket buying tips. There are a ton of sites that do that better than we can. Sure, we’ve bought plenty of air tickets, but usually on short notice, with very small local carriers (one still hand-wrote their boarding passes), and no consistency with companies for upgrades and frequent-flyer miles. Just make sure you read airline reviews before booking. Sometimes the one that appears cheapest is more of a nightmare than the savings are worth, or they’re no savings at all after add-ons.

Boarding Passes – Honestly, we hardly use paper for this process anymore. We never show up to the airport with anything but the information on my phone, and the reservation agents are all used to it. We only ever have paper if they hand it to us. So don’t worry about printing out your tickets or boarding passes. We’ll give you some tips for different ways to sort this info on your phone.

Official Identification – If you’re traveling domestically, don’t forget your ID or they won’t let you into the airport.

Booking and Reservation Numbers – Your airline ticket, car rental and hotel reservation all come with special confirmation codes. You want to have these at your fingertips. They’re not always necessary, but when they are, you don’t want to have to go hunting for them.

Prescriptions and Medications – First, have plenty of the medications you need and pack it in your carry-on. If you’re going for a longer trip, your insurance company (US) can issue a ‘vacation supply’, usually 3 months’ worth.

Second, keep a list of your medications, brand name and generic, including dosage. If you have anything that might be challenging to acquire where you’re going, get an official prescription from your doctor. SCAN THESE DOCUMENTS and send them to yourself. Make a couple of printouts as well, in case you need to get something at a local pharmacy.

TSA Pre-check and Global Entry – (US only) Essentially, you pay the authorities to do a background check on you so you get special consideration going through airport security. You get to go through the express line and usually don’t have to remove your shoes, or your laptop from its bag. TSA Pre-check is for domestic flights. Global Entry covers both domestic and international travel. If you have any inkling to travel internationally, go for Global Entry right off. It eases your re-entry to the US as well. Both of these are a bit of a hassle because you have to show up in person in addition to the application process, and they can take anywhere from a few weeks to a few months to obtain. However, they do make getting through the airport much easier, so we recommend that you consider them.

Apps to Help Manage Your Travel Documents

TripIt – This immensely popular app does almost everything. It keeps track of flights, car rental, hotel, including those all-important reservation codes. You can input your passport number as well as numerous other vital documents (PIN locked). There’s a space for all of your travel contacts, whether at home or your destination. You can include maps and calendar items, like meetings and tours and there are other functions as well.

What doesn’t it do? There’s no space for listing meds and prescriptions. Nor can you save scans, like those of your passport. It would also be nice if there was a space for in-destination notes, like SIM card numbers, info for people you meet and recommendations from locals.

ScanBee – or similar – This app simply scans documents using your phone’s camera. You can save them to the Notes or other apps on your phone and email them as a .pdf. This is great for those passport scans and any time you want to get around dealing with paper, or if you have to handle business, like sending signed papers, while you’re on your travels. And if you need to keep receipts while you travel, this is a great way to do it and not have to carry around a bunch of little pieces of paper.

The reason I keep emphasizing having a scan of your passport is that there are MANY times you can show the scan instead of having your actual passport. We’ve used it for checking into hotels, exchanging money and using credit cards. It can save you so much hassle. And, if your passport were to be stolen, it would only make replacing it (and being without one in the interim), that much easier.

Notes App – I actually just use the one that comes with the iPhone, but any notetaking app will do. All of the things TripIt does can be done on a Notes app, though it’s harder to keep it tidy. It’s great for taking notes at your destination, as well.

One last note about documents. Even if I have the information in an app, or my email, I often take a screenshot of anything that’s absolutely vital for the days of travel, just in case. Then I delete the photos later. That way, in case an app crashes, or you’re offline, you’ve got back-up. It’s better to be a little over-prepared when it comes to travel documents.

Home Matters

Don’t forget to have someone looking out after your home while you’re gone. Do you need a house-sitter, or to board your pets? Plan ahead. You can have someone pick up your mail, or you can place a vacation hold at the post office (US). Going for a long trip in the winter and live in a cold place? There are things you’re supposed to do to protect your pipes, and such. (You’ll have to research online or ask your neighbors. Tim and I are from Los Angeles and have no idea what these cold weather tactics are. We just know they exist.)

Make sure your home is taken care of so you don’t have to worry about it while you’re away.

Recovering from Your Trip

Feet in Hammock

Try to schedule so you have a few days of rest before you go back to work. Whether you’ve been on an active vacation, or a relaxing one, it takes time to ease back into the reality of everyday life. Don’t head home thinking you’ll be productive, you won’t. Get home, order Chinese food, or pizza or whoever delivers, be lazy. Meet up with friends and family. Relax and wind down before you have to wind back up for work again.

I’ve gone back to work a day after arriving home. Fortunately I had the option of sitting around entertaining people with my travel stories and getting very little actual work done. Only try this if you’ve got a great boss.


Hey, you’re getting ready for a trip and there’s a lot to be excited about!

You can plan as much or as little as you like, but some preparedness will definitely make your travels easier. Breaking it down into steps, like we have here, makes it less intimidating. Hopefully it will help keep you organized as well.

Did we forget anything, or do you have a favorite thing you do that you want to share? Let us know in the comments.

Don’t miss all of our other Travel Tips and Tutorials. There’s good stuff for both new and experienced travelers.

Trina Phillips

I've been traveling to off-the-beaten-path destinations for more than 20 years. Now I'm sharing my continuing adventures in Africa.

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  • This is a really excellent article, especially for the neophyte traveler. I learned things I didn’t know I needed to know, even for the little one week trip I will eventually take to visit with you guys. I miss you both but I am thoroughly enjoying your excursion.

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