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How to Plan Your First Trip of 2016 in an Hour or Less

United States Insider Guides
by Elaina Giolando Jan 4, 2016

I TRAVEL A LOT, SINCE MY (NOW FORMER) JOB sent me to live overseas on rotating 3-6 month assignments in emerging market countries for over two years as their country director. Even when I was living in one place, I was still planning weekend getaways to nearby cities or countries. Favorite last-minute weekend getaways included hopping into Swaziland from Johannesburg, crossing the border from Paraguay into Argentina for last year’s World Cup final, and catching a camel ride in Cairo while posted to Doha. Now I’m 100% freelance and spending the next 4 months hopping across Southeast Asia and India while blogging, coaching, and running my travel planning business.

Over the years, I’ve realized that EVERYONE loves to travel. Most everyone also enjoys the travel planning process… to a certain extent. At first its fun, but after a couple hours of running in circles about where to go and if the season is right and if Rome is better than Florence or if December is a good time for safari in South Africa, it’s acceptable to want to throw in the towel or just book the next hotel that pops up when the page refreshes.

Planning a trip consumes more time, energy, and research skills than most people realize. And sometimes nothing more than raw experience gets you the answers you need. There’s an over-abundance of travel information on the internet, so more than anything, you need the right resources at your fingertips to answer your questions and give you insight on your trip (or trip possibilities) quickly.

Sit back and breathe easy, globe-trotting friends. I’m going to teach you to plan a trip anywhere in the world in just one hour.

1. Pick a place (10 minutes)

That’s right, 10 minutes to select from 193 possible destinations (UN Member States as of January 2015). We’re only able to be quite this efficient because of my favorite feature on a travel website of all time: Kayak Explore. Select where you’re departing from (anywhere from San Francisco to Sao Paulo), when you plan to depart, and your budget. You can even sort by details like maximum flight time and weather at the destination.

If you’re like me, you’d go almost anywhere at anytime, so it really comes down to flight deals. Pick one or two of the cheapest and most appealing options and do a Google image search. Then type in that country or capital city into the search bar in Facebook and scroll down until you see “Photos of your friends in country X” or “People you know or may know who have lived in country X.” You can then stalk their pictures or send a quick message asking if they enjoyed their time in that place. One more trick if you have Instagram, search for #Croatia or #Vietnam or #Phuket and browse the most recent photos travelers are posting from that location. It’s an easy way to see what appeals to you.

Once you’ve found the best destination for the best price, put that flight on hold on another tab while we take care of a few other things that could potentially change your mind.

2. Scope out the visa situation (5 minutes)

Contrary to the order of what you might be used to, you want to pick a tentative country, check the visa requirements, and then book a flight. Once, in the excitement of finding a good travel deal, I almost made the mistake of booking a $200 round-trip flight to Maputo when I was living and working in Johannesburg before I realized that American citizens need a visa for Mozambique, which is not available on arrival. That would have been a crushing realization to only make at the check-in counter for South African Airways. I changed my plans to Swaziland, which issues a visa on arrival for Americans.

For obtaining the most accurate visa information, don’t waste time consulting anything but the official sources. If you simply Google “India visa US citizen,” you will drown in TripAdvisor threads and Lonely Planet links, which are sometimes not up-to-date. Instead, no Google. You want to check only two places for your information: the US State Department’s website for the country you are visiting and the country’s embassy website in the United States. Let’s say you are traveling to India, you would first go to (hint: replace “India” with the country name you’re traveling to and access the page quickly), and click on “entry/exit requirements.” Then, visit the Embassy website and look for the visa services page (ie. also in the case of travel to India).

For a last-minute trip, it’s helpful to select from countries where you aren’t required to have a visa or a visa is available on arrival. If you still have your heart set on a country with a more involved visa-procurement process, like China, India, or Brazil, consider using a service like Travisa that makes the visa process quick, simple, although slightly more expensive than handling it yourself.

3. Check the weather (2 minutes)

Quick! Before you get too excited, check to see what the weather forecast is for that time of year (or this weekend if you’re planning very last minute). There’s nothing worse than getting a great deal on a trip to Burma, only to realize it’s rainy season when you arrive and roads to the village you want to visit are flooded and impassable. Weather is especially important in countries with very specific rainy and dry seasons (East/West Africa and Southeast Asia) or popular countries where peak tourist season might simply be unenjoyable (Florence, Italy in the summer comes to mind). A quick Google search of “best time of year to visit Cape Town” can yield some essential information.

4. Make sure there are a couple of appealing housing options (15 minutes)

More due diligence before you book those flights: housing. You don’t need to reserve the room before you secure flights (flights are way more volatile price-wise), but you want to take a look around and make sure there’s enough availability to either arrive and wing it backpacker-style or validate that there are a few options you’d be happy with. Personally, I usually use and sort by highest rating, scanning the facilities for air-con and lockers and reading the latest reviews. Using the map tab lets you see places in proximity to the city center or another desirable location, which is extremely helpful. If I’m treating myself to a longer stay or a private room, I’ll use AirBnb. Star a few favorite options and you’ll come back to those in a few minutes.

5. Book it all up (15 minutes)

Congratulations, you’ve handled the prerequisites and now you’re officially ready to book your trip. For booking flights, I like If I have a flexible travel schedule, I’ll always use the “plus/minus 3 days” feature to score even better deals if I come back on a Monday instead of Sunday, for instance. Kayak tells me everything. If you’ve been playing around with flights, clear your cookies and restart your browser to make sure you get the lowest fare without the airlines (supposedly, I can’t verify this is 100% true) tracking your searches and increasing fares on routes you consistently show interest in. Skyscanner is also a good tool.

Once the flight is secured, book your housing. For short trips, I don’t like to wing my accommodation, but if I’m backpacking for months in a well-trafficked region, I’ll skip this step. Again, Hostelworld and AirBnb are clutch. If I’m looking for hotels specifically, TripAdvisor has good reviews and an easy interface to book within minutes.

6. Create a thread on the Lonely Planet Thorn Tree Forum (5 minutes)

Once I know where I’m going, I’ll create a thread on Lonely Planet’s online Thorn Tree Forum, which is heavily trafficked with many well-traveled contributors. If you don’t have an account, it takes 2 minutes to create one and you’ll use it all the time to both post and read recent threads of other travelers. To outsource your travel planning, make sure you post in the correct country forum and specify when you’re traveling and for how long. Ask for specific recommendations in your areas of interest and check the “notify me of responses” box, so any replies go straight to your email.

Side note on travel guides: If I’m going an extended trip (4-8 weeks) in one place, I’ll pick up Lonely Planet as a cursory reference guide. Anything less, I’ll either just download the PDF chapters of the cities I’m visiting or stick to Google and personal recommendations from friends. The more years that go by, the less I find myself relying on any kind of guidebook.

7. Facebook status (3 minutes)

I’m infamous for crowd-sourcing my trips. I ALWAYS put up a status like “Headed to Buenos Aires next month…Who’s in town or who know’s friends/friends of friends there? Looking for trip tips and travel buddies.” Inevitably I get a few messages of the “Hey Dan, meet Elaina. She’ll be in town in a few weeks, so you guys should grab coffee” variety. Or a couple replies like, “Don’t miss eating dinner at ABC restaurant” or “Go horseback riding in XYZ village!” Why buy a guidebook when you have friends who travel?

8. A few financial precautions (5 minutes)

Now that everything is booked and travel advice has been automated to your inbox, there’s just a few final details. Make sure you call your bank(s) and tell them where and when you’ll be traveling. It helps prevent fraud protection from immediately triggering and turning off your card when you go to withdraw cash from the ATM at the airport when you land. Just in case, I recommend taking $300 in cash with you for any trip, even if it’s just a weekend expedition (more like $500 for 3+ weeks). If you’re heading to somewhere more off-the-beaten-path, there will be fewer ATMs and if they are out of service or don’t accept your card, you’ll be grateful to have cash to exchange. It’s also useful for paying visas on arrival, so make sure the bills are crisp and not torn or they may be rejected at the border for visa payments or at exchange houses.

And that, my friends, is how you book a trip in 60 minutes or less. Now go enjoy your adventure!

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