Booking a trip can be stressful, even when you’re super excited for your vacation.  The pressures of where to stay, what to eat, and what to do, have made the travel agent industry worth millions, as folks would rather pay for someone else to do all of guesswork for them.  In all of the years I’ve traveled, I’ve only used a travel agent twice, as I tend to enjoy booking all facets of my trip personally.  Now, I am not about to disparage this industry, as a great agent can make your trip unforgettable, particularly as they may have traveled to your destination and know firsthand of where you should stay, etc.  However, in booking a trip on your own, you’re guaranteed to book everything as only you know you like it, without having to explain yourself to anyone.  You can’t really get more personal than that, LOL.  So, if you have it in your mind to personally book your own trip, here are some of my tips to assist you in your journey:


1)Start with the weather – When I have a city/country in mind, the first thing I type into Google is: “When is the best time to travel to [insert country]”, followed by: “What is the weather like in [insert country], in [insert desired month].  Recently, I began planning a trip to Indonesia. I saw the weather was going to be perfect, so I was really excited. I looked at a map, and thought, well the Philippines aren’t too far away, we’ll go to both. I looked up the Philippines for the same time period – and they will be experiencing torrential rain/monsoon conditions during my vacation time.  Had I just assumed the weather would be the same, I’d be barred from seeing most of the island, which shuts down during parts of monsoon season. Umm…no thanks.  Now, sometimes you may want to travel to a country like Thailand or Costa Rica during shoulder season for those deep discounts, but for other destinations you may want perfect weather depending on the nature of your trip.  Definitely check out the weather first, as it will likely dictate how much you’ll be able to see and do.  One thing I’ve noticed is that many countries have their own guide providing information as to their weather, so literally type in the prompts I wrote above into your google search bar, and you’ll be good to go. Of course, if you want to travel to a place like Munich for Oktoberfest, or Trinidad for Carnival, this first step doesn’t apply, as they won’t hold the festival at a more “convenient” time, LOL.  


2)Ok, you have the month down, now think about what you want to do.  What attracted you to this region in the first place? Maybe there’s a beach you wanted to go to, or an art gallery you had your eyes on.  Perhaps you don’t have any particular event in place, but you’ve always heard a region was pretty.  TripAdvisor, Fodor, U.S. News Travel, and country specific local blogs are all invaluable resources to figure out what you should do.  I play around with the searches a bit, so that I can gain access to really specific blogs.  For example, I found a blog post last year that centered on cenotes (sinkholes) in the Yucatan Peninsula area of Mexico, and it greatly helped me decide where I wanted to go –  I found it by searching for “local finds in Playa del Carmen”.  I find that local blogs offer the best insight into what to do when you land somewhere.  They’ll delve into what rental car companies you should book with, where you should eat, places to avoid (tourist traps), and truly local niches that you may not even know to look up. Here’s another example of a site I heavily leaned on when planning my Costa Rica adventure –  So don’t be afraid to play around with the word searches until you have a solid list of activities you want to do.


3)Next, I comparison shop.  Sure, I know I want to do, say, ziplining in Costa Rica, but where?  Again, the local blogs do a great job of giving me a sense of what to expect with each tour operator. Then I typically look to Trip Advisor to ensure the legitimacy of the company (won’t always work for some of the more truly local finds).  I also check out the locations of everything in Google Maps.  I can have an awesome idea in mind, but if its on the other side of the country and that’s not in my plans, then its not workable.   I don’t always go based on the star rating (though you do have to usually have a 4 start to get my attention).  I go based on what type of experience I want. I have been known to read over 50 posts for something as simple as an atv trip. I want to know what experience I am getting into, so I can manage my expectations accordingly.  This process takes the most time – more than when you were sorting out what to do.  For a 7 day trip, it can take me a good month to figure out all of the different tour operators I want to use.  This is especially true as most countries, especially in Europe enjoy “holiday” more often than we do in the States, so it may take longer to receive a response to your inquiry. Just remember, this is your vacation, so take your time, and have patience – it’ll def be worth it.


4)Also – be careful not to forget about “free tours”. You can find free tours all around Europe.  They are usually conducted by college or graduate school students who are native to, or live in the area, and feel deeply connected to the region. Most of the time, you’ll learn that they are studying tourism, history, art history, architecture, etc., and they offer you a glimpse of their city from their point of view during your time with them. At the end of the tour, you tip them how much you think the tour is worth.  For a 2 hour tour, I often pay $20pp.  I’ve only had great experiences with these service, so I highly recommend looking into this.


5)Another great tour operator –  I swear by this service. We’ve used them all through Europe and Asia, respectively.  You put in your region, then put in more specifically what tour you’re looking to do and how many people there are in your group.  I remember when I took my parents to Rome, I wanted my parents to see the Colosseum, St. Peter’s Basilica, and nosh on some pretty awesome gelato.  I put in my info, and saw a group of tour guides that were providing a private car service to these sites.  Then you can contact them directly and negotiate their pricing as often, their itinerary is based on what they think tourists want to see. I always change it up a bit and add/delete sites based on my desires.  If anything, it shows them that you have taken a keen eye to their city, and they will appreciate this, and most often accommodate you, when possible.  And yes, you tip them, same as you would if you booked via a different website.  And remember – these are private tours, so no traveling with 30 other people. I find the pricing is usually comparable, if not ever so slightly higher (and a few times lower), to what you’d pay a cruise company to head out in a coach bus with 30-50 other camera toting tourists.  Keep this on your radar!!


6)Ok, now you have your activities/tours narrowed down, and you mapped it in Google Maps so you should have your geographic radius down.  Now… I book my hotels.  I know, I do this opposite to what most of my friends do, but for me, the hotel is almost never the focus point of my trip (unless I’m in Tahiti/Bali, etc. and part of the experience centers on the hotel). I’d rather have awesome experiences, meet cool locals, and see everything I want to see, rather than be limited by where my hotel is located.  I have already shared with you in previous posts that I am an SPG snob, so yes, I look at what deals they offer, and now Marriott is part of that game plan, but they’re not everywhere, and I’m not always willing to shell out what they want for a particular property.  Thus, I again turn to Google…first I want to see if the area I’m traveling to is known for anything (ie: over-water bungalows in South East Asia/Pacific, tree houses, snow domes, etc.).  I LOVE unique experiences, so I like to first confirm that nothing is available in this realm.  Don’t be afraid to check out Airbnb too.  I’m about to stay in a really cool, glamping treehouse site in the Monteverde region of Costa Rica, and its through Airbnb.  Hotels don’t always offer the most local feel, so depending on what you want out of your stay, you may wish to branch out a bit, and find your particular perfect fit, within the geographic radius of your activities.  Again, this process can take you several days, so take your time!


7)Now comes my favorite part…eating.  Yes, I usually know what/where I’m going to eat for breakfast and dinner (we tend to skip lunch or snack lightly when traveling). Again, I look at what I want to eat first – usually I want to have the local cuisine if its a short stay or branch out and try multiple cuisines if we’re someplace for 5-7 days.  I pull up my Google Maps and then plug in my hotel and  tours/activities.  I then hit “nearby restaurants”, and see if there are any local finds that received high reviews, and thoroughly check out their menu. If its in another language, I translate it via Google’s translation services, haha…  Then I’ll compare it with a general search for the city, and see what other restaurants/bakeries are available that I want to test out, and see if uber exists in the country, if we can drive ourselves, or if local mass transport can take us.  I remember when we stayed in Germany for 2 weeks, we ate in Germany eateries about 6x, and the remaining days were split between Asian, French, and Italian food.  Again, take your time, and check out your general surroundings. There may not be a need to travel 30 min away for a 4.5 star restaurant, if the one next to your hotel has 4.3 stars and has a menu that you love. Conversely, if the restaurants next to you all have 3.2 stars, do some research and don’t be afraid to venture out and eat well.  I promise you, the food can make/break a trip.  I am still dreaming of the croissants and chocolate I had while in France!


8)Last, but definitely not least – I plug everything into a platform like Google Docs.  I want my full itinerary saved, and easy to access when I have wi-fi while abroad. This way, if I change my mind, I can easily look up my tour operator and make the necessary changes. I also print my itinerary and all of my vouchers/confirmations, and make a couple of copies, as I have had to hand my itinerary to the customs agent when they seek specific information as to my plans in their country (I’m looking at you England).


When you book trips on your own, the downfall is that if you forget something or something goes awry, it’s up to you to address it.  Fortunately, these days, we’re all so interconnected, so it shouldn’t be too difficult to get someone on the phone or via email. Personally, if you account for gaps, and realize that when traveling to some destinations, things may not always go smoothly, you’re in for a much more rewarding, and personal vacation, as you are doing exactly what you want, when you want to do it, and have crafted everything, down to dinner, to your liking. So…what are you waiting for? Book that next trip!! Enjoy!!