December 2019

So you want to travel but don’t know where to start? Solo trip or kick it with friends? Domestic or international? Beach or mountains? How long to go for? How to pay for it? What to bring? So many questions, so many decisions to make and only so much time to plan. It’s easy to spiral before you’ve even begun. 


But not to worry! Once you dive in and get the ball the rolling, it becomes easier than you think. Bypass the daydreaming and jump right to the brainstorming. With the seemingly infinite amount of information on the Internet, taking an international trip has never been easier. Although traveling can be intimidating, the reward far outweighs the effort. And those fears you might be feeling are guaranteed to be squashed once you start your adventure. 


There’s so much world out there to explore and only so much time to do it. If you don’t take this trip you’re planning now, it’ll delay your plans for the next one. If you keep pushing the trip back, it’ll always replace another potential adventure. Take the leap. You’ve got the itch, now it’s time to scratch it. 


It’s been exactly one year since my last backpacking trip through Southeast Asia and, without any warning, the wanderlust struck again. My work schedule got the better of me, but the nomad inside was clawing to be set free. Unlike most of my past trips, I waited until the last minute to plan this one. For the first time since college graduation, my best friend and I both had the same week free. Without much convincing, we decided to jump on the opportunity and finally make the trip happen. But with such late notice we had to get moving and solidify plans quickly. After nearly a decade of international travel, I’ve perfected my trip planning preparations and boiled it down to a science. I planned this trip for us in less than 2 weeks and decided to share with you how I did it. Follow along for my step-by-step planning guide, which can be used for any trip you might be organizing. 





It might seem obvious, but the first step is to settle on a location. I try to venture outside our country whenever possible. Although there are plenty of unique places within the United States, I’d rather enjoy the opportunity to dissect and absorb a culture completely unfamiliar to my own.


We knew we wanted to escape the winter weather and head somewhere warm and tropical. Europe was too cold this time of year for what we wanted. We avoided some Central American countries that currently have safety travel restrictions. There’s always more to see in Southeast Asia, but it’s a bit far for such a short trip. Peru and Argentina were intriguing, but we wanted to stay on a pretty strict budget. We were looking for a place neither of us had been but somewhere that had an exciting pulse and mix of adventure and relaxation. 


I started brainstorming and began to get my creative blood flowing. I opened up a map that tracks the cheapest flights out of New York, searched online for the most affordable and exciting countries to visit, and reached out for advice from other travelers I’ve met along my journeys. The results triggered Jamaica. 


Initially I had reservations; Jamaica is pretty close to the US, it’s quite a popular tourist destination, and I have never been interested in all-inclusives. However, the more research I did, the more fascinated I became with the country. It has a rich history and a great blend of activities. If you get off the tourist trail, there is plenty to explore and culture to absorb. 


I crosschecked some other key information to make sure Jamaica was our ideal destination. 


            • TIME OF YEAR- Nothing worse than booking a trip and realizing you scheduled it for the coldest temperatures, the rainiest season, or busiest time. Lucky for us, warm temperatures and dry weather are typical for January, and, as long we stay away from the resort areas, we can avoid the holiday crowds. 


            • DAILY COSTS- Before you settle on a place, it’s important to make sure the daily costs are also within your budget. Sometimes you find a deal on a flight, but the expenses when you land skyrocket. While Jamaica is more expensive than some countries we were looking at, we'll make up for it with the money we'll save on flights. We'll make sure to find the most affordable accommodations, limit our expensive activities, and find local budget friendly food options. 


           • SAFETY- There was no travel restriction from the US government, and although there were some safety concerns from people online, we decided as long as we keep our wits about us there is no reason for concern. There is violence and crime everywhere. Some of the worst crime is in the United States. It is no reason to avoid traveling internationally altogether. There is always a risk when you’re in unfamiliar territory, but as long as you avoid dangerous situations and make smart decisions, it should not deter you from visiting that country. 




Hi- I'm Evan, the Travel Wingman!

A Wisconsin cheese head transplanted to New York's big apple, I'm here to help inspire people to explore our incredibly diverse world through international travel. Follow along to learn the tools and information to make it all happen. From budgets and sample itineraries to packing guides and tour experiences- it's all here! So enjoy and feel free to reach me via my contact page.






I’ve found it’s best to book travel 65-45 days before your departure date. If you’re looking for approximate pricing, change the dates to this window in your search. That should give you an idea of what you might expect when you’re actually ready to book. Example: If you're brainstorming in November for a trip you'll take in June, enter the departure flight date sometime in January. That'll give you an idea of what the prices will be for when you actually buy the tickets in April. Make sure to set up price trackers for the dates you’re interested in- even better if those dates are flexible. Check the day of the week you’re flying on. (Avoid returning on a Sunday, if possible). Check the day of the week that you’re booking on (Tuesdays are rumored to be the best day to book airfare). Take a look at my favorite sites to book your travel: Kayak, Sky Scanner, Flight Network, Kiwi, and Cheap-O Air. I set up trackers on each of these sites, compare and contrast, and watch for them to dip. If you’re patient and learn the system, you’ll know when it's time to take the deal. It’s just like knowing when to walk away from the table in Vegas.




Like I said before, I avoid all-inclusives like the plague. Although it may be how some people like to travel, it isn’t my preferred method. I think it’s hard to learn about a country’s culture and see its untouched beauty when you’re surrounded by nothing but other tourists and receiving a watered-down experience through hotel staff. It might be relaxing, familiar and easy, but you’re not really "seeing" a country. My method is a little different. I try to surround myself with locals whenever possible. I spend less time in the big cities and more time in the smaller ones. I experience the tourist draws but spend even more time getting off the beaten path to see the lesser-known wonders. I’ve learned to say “YES” whenever I can and follow my instincts. If someone tells me there's a must see activity or a must visit restaurant, I drop my plans and go! This technique definitely requires more planning, more independence, and more courage, but I guarantee you’ll gain a greater appreciation for their culture and walk away with a more unique experience. 


If possible, I prefer to plan itineraries where I fly in and out of different airports. I find I can travel further distances, see more sights, and experience more cities without backtracking back to my original port of landing. If a country or region allows for this, even if the flight might be a little more expensive, I recommend following this advice. You'll be able to see more and get the most out of your time away. 


I try to get an idea of what each city has to offer and where I want to spend my time. I look at the different routes, distances between the cities, and if there are things to stop and see along the way. I do a fair amount of planning ahead of time for the travel days but always leave a proportionate amount of time up to spontaneity within the cities. I begin with big searches, revealing a picture of the country on a whole. I use key phrases like "What do do in Jamaica," “Off the beaten path,” “Seven days in Jamaica,” “Non touristy Jamaica,” etc., and just dive into the infinite abyss that is the world wide web. 


I began organizing our route for Jamaica bearing all of this in mind. I narrowed down a list of the cities we wanted to see and then got an idea of how long we should spend in each city to properly experience it. I budgeted one day and night for Montego Bay, since it is our first city. One night in the crowded tourist capital is enough for me. From there we’ll drive to Ocho Rios, making a few stops along the way. We’ll spend 1 1/2 days there and then continue on to Port Antonio. I decided to budget three days here (including the drive) since we were most excited about the activities here. After that we’ll drive back to Montego Bay, drop my friend at the airport, and I'll continue head south to Treasure Beach by myself. I’ll have two days in this remote oasis and then head up to the Blue Mountains for two days. The itinerary finishes up in the southern region of the island for one final afternoon in Kingston before my flight out the following morning. A total of 12 days, packed to the brim but with plenty of time to relax and enjoy each city. 


As you can see we are interested in seeing a lot of things, most of which are off the tourist trail. With that in mind, we decided to rent a car. Although I’ve never driven on the left side of the road and it’s a little more expensive than taking a coach bus from city to city, I think we are going to love having the freedom to go where we want when we want while we’re there. I got the best deal by breaking it into two rental reservations. The cheapest option for the first week was with Timeless car rental. For the second week I had to find a company that had locations both in Montego Bay and Kingston since I would be renting and returning it in different cities. Island car rental was the most affordable and had the best ratings for this situation. I could have used ISLAND for the whole time, but then I would have had to pay the higher daily rate for the entire time. All of these prices were found on Kayak. Do your research and see if renting a car is an option for you, or if you're able to get by with public transportation. 


Solidifying your itinerary is always the hardest part in the planning process. I always want to see as much as possible but don’t want to rush through cities. I want time to rest and relax but want to avoid getting bored or wasting time. Always remember that you’re never going to get it perfect. Try your best to prepare, but know that you can always think on your feet and change your decisions. 






Once the itinerary is set, I find it’s best to just take a breath and dive into detailed research of the individual cities. My searches become more specific now. I use phrases like “Best things to do in Port Antonio,” “Hidden gems of Treasure Beach,” “Best way to spend 1 day in Kingston.” I avoid big organizations like Trip Advisor when I am researching. From my experience, I’ve seen that it’s hard to get an accurate depiction of an attraction or experience on these major sites. Since it is organized around a public forum concept, the site often becomes littered with comments from people who are not as well traveled, people who have either had a WONDERFUL experience or an absolutely AWFUL experience, or someone who simply has a different travel philosophy. The searches tend to reveal only the most touristy things and don't show the hidden gems. If you do wind up visiting a site like this, I implore you to take everything you read with a grain of salt and supplement with other information. 


Instead, I find that I get the best information from travel blogs. Bloggers, especially the backpacking type, tend to have the same goals and ideals as myself. While it's still important to cross check your information, these blogs will most definitely give you more unique information and expose the lesser known wonders of a country.  


My technique for planning is to start a document for each city. I add all the information that I sift through, without focusing on or retaining too many details. I keep everything organized so I don’t have too much repeated information. If there is a lot of information on a particular event in one city, I will copy and paste the information into my document under the same bullet point. Then I have all the information for this event, but it isn't disorganized all over my document.


Each city breaks down into “ACTIVITIES,” “EAT,” and “STAY.” Make sure to grasp information to satisfy all my CARDINAL CHECKPOINTS- HISTORY, CUISINE, LIFESTYLE, and EXCURSION. You'll want a mixture of all of these to round out your travel experience. Remember to maintain a balance of tourist sites and lesser known points of interest. Once you have enough information to satisfy your curiosity, start on the next city. You will go crazy if you attempt to read all of the information that’s out there. 


I only look at the details I’ve organized once I'm on my way to that city. This makes it less overwhelming and gives me an opportunity to enjoy where I am in the moment. When I’m headed to the next city, I add the points of interest to my Google maps and find the best route to see everything. I determine how I want to fill my days, usually starting with the “must see’s” and then gradually checking off the rest of my list if I have time. I think it is important to leave part of my time in each city up to spontaneity. I keep my ears open for exciting new places that haven’t been blown up by the Internet and always heed the advice of locals. Remember, budgeting rest time can be just as important as the adrenalin pumping excursions. You don't want to go so hard that you burn out. Some of the best experiences are the quiet moments on a rooftop or a relaxing afternoon in a park.

When it comes to organized activities and tours, I only reserve tickets if it is required or recommended.  You don’t want to miss out on an experience or a specific company if they tend to sell out. But if you can reserve your spot without a down payment or the activity doesn’t typically sell out, I try to hold off on paying for anything in advance. You never know when your plans are going to change or if there’s a better deal when you arrive.






Next step is to sift through the accommodation recommendations and do some research for yourself. Some people prefer to wait until they show up to a city to find a place to sleep. I personally like to know where I’m staying when I arrive. I find that the unique and most affordable places are swiped up in advance and I prefer not to waste time running from hotel to hotel when I arrive in a new place. 


When I travel, I always stick to a budget. I'd rather spend my money on activities and experiences rather than fancy accommodation. Usually once on each trip I splurge and get a more expensive place. This typically is the city where I’m spending the most time or where I have less activities planned. 


My favorite hotel sites are Agoda,, Airbnb, and VRBO. Once I have set my filters for a reasonable price range and the location I’m interested in, I cross check everything and find a place with nice amenities and a sense of character. I tend to avoid dorm rooms with multiple beds in one room. There was a time in my life for that but I’ve had enough snoring neighbors and sex crazed couples for my lifetime. If that’s your style and you want to save some cash, more power to you. I look for budget options with a private room that has a unique sense of character.


There were loads of housing options in our price range in Jamaica. We discovered our splurge hotel first- a beautiful tree house called Kanopi House in Port Antonio. I decided to continue the tree house theme and book cottages in Treasure Beach and the Blue Mountains, Skylarkin Cottage and Prince Valley Guesthouse, respectively. Montego Bay was the most expensive area on the island. We saved money here and went with a private room in a budget hostel. We settled on The Landings, right beside the local beach and walking distance to town. We also wanted to save in Ocho Rios and weren't looking for anything fancy. We stumbled upon a small hotel with a pool called Sunrise Villa, which fit perfectly in our price range. Finally, the most important thing in Kingston was to find a safe location and somewhere with a lovely courtyard or pool. Hardie Terrace ended up having everything. For my reviews of the hotels, check out my Ultimate Jamaican Itinerary post. 


Keep your eyes on reviews and ratings and always check the fine print regarding cancelation policies. Remember to listen to those travel bloggers; they have the most knowledge and can give you a better idea of somewhere that'll provide a memorable experience. 






So you’ve got your flight, itinerary, activities, and accommodation. The last phase is the final preparations. 


CELLULAR SERVICE- The two options when traveling internationally are usually to get a SIM card upon arrival or use your carrier’s international policy. Compare how many GB of data your carrier’s international plan allows with a prepaid SIM card. If it’s affordable, I prefer using my own carrier. You get to keep your number and don't have to worry about shuffling SIM cards around. Sometimes a local SIM card is a much better deal. When I went to Vietnam I paid $10/week for unlimited data vs. $10/day for my Verizon plan. Research the best mobile stores in the country you’re visiting, save the locations, and make sure you get it from a reliable retailer. Double check that you'll even have service- countries like Cuba don't yet have the infrastructure for mobile phones.


MONEY EXCHANGE- If the country you’re visiting has a different currency, do some research before you travel. I find that it’s best to exchange money when you arrive. Check if it’s better to bring US cash or take money out of the ATM. Remember, not to exchange too much. The exchange rate to exchange back to US Dollars is always worse than the initial transaction. For Jamaica, I brought $600 in cash and slowly exchanged once I got to my first city. 


INTER-CITY TRAVEL- I did my research and found the cheapest, best rated car rental company in Jamaica. Luckily my credit card provides primary car insurance, so that was a cost that we avoided. If you’re not renting a car, it’s important to organize travel between cities, and prearrange train and bus tickets when necessary. In some countries you can arrange on the fly, but some require advance planning. 







Do yourself a favor and get a travel Credit Card. I decided to bite the bullet and pay the exorbitant annual fee for the Chase Sapphire Reserve card. Like I said before, it provides not only primary car insurance but also several travel insurance options without any extra costs. It covers the annual fees for VIP airport lounges, reimburses for global entry/TSA Pre-check, gives you a $300 travel credit each year, and offers a large percentage of cash back for purchases on travel and dining. You get even more money when your points are redeemed on more travel. Even better, if you spend $4,000 in the first three months, you get a $750 signing bonus to redeem on more travel. Basically they are just feeding your travel addiction. Didn’t take much convincing for me. Bank up those points throughout the year and only redeem on your next trip!




That’s all folks. You’ve done plenty of research and prepared as much as you possibly can. Remember to stay flexible and be ready for the universe to throw you curve balls. There are always hiccups, but if you can find a way to enjoy those mishaps, you’re guaranteed to have a trip of a lifetime.