This post is going to be a walk through of how I go about planning, buying and organizing everything for a trip.
The honest truth is that I have learned everything as I've gone along. There is no magic trick to getting the best deals. You have to be willing to do the leg work and to remember above all:
Value does not always equate to dollars and cents.
It's about the whole picture. Sure, I'll try to save us money anywhere I can, but if spending €8 on a museum ticket means waiting in line for 4+ hours, when I can pay for it online at €12, you bet your ass I'm not wasting 4 hours of my vacation. My time is more valuable than an extra €4 saved.
So with that in mind, we begin:
Step 1: Do Your Research
Start early and Research. the. fuck. out of your flight options.
I think most people work out a budget first and then decide where they can go within that budget, but I don't quite operate that way.
I choose my destination(s) about 8-10 months in advance and then see what the bottom dollar option for getting there is.
I check 7-8+ websites when I am determining my best flight prices.
These sites include (in no particular order):
The Flight Deal
I check the entire years' flight prices on Google Flights as they have a handy price populated calendar that auto updates as you look through each month. This gives me a relatively good baseline to start from so I'll know what an unusually good deal will look like.
I then check prices in the "off season" (September - April) . I do this because I do not like to travel when everyone else and their mother is traveling. It will almost always be too crowded, too hot and way pricier than just waiting till the fall, winter or early spring. Europe is beautiful all year round. You won't miss anything significant by not going during the summer.
Once I've selected my dates, I then reference the prices found on Google Flights with the other sites I have listed above. I don't just look once and then purchase. I set up email and text push alerts over the course of about a week - month to monitor how the prices are moving. Prices can change drastically and at any moment so it's a good idea to keep an eye on them for a bit to get a good idea of when you want to strike.
I always advocate for keeping your eye out for mistake/super saver fares but they are very rare and unreliable occurrences.
I myself, have only ever managed to snag ONE deal and that is why we are going to Europe this October. I just happened to be awake one night around 3am in February when I got a text push to my phone letting me know that Student Universe had just posted a flight from PDX - Paris, France RT for $830 per person in October. That same route is usually in the $1300-1500 RT per person range. We jumped on them immediately.
If you find a deal you like, do not hesitate. Take it.
If you happen to freak out and have buyers remorse, you have 24 hours by law to get a full refund.
I have found that the best cities to fly internationally from (price wise) are: San Francisco, Los Angeles, New York, Newark, Chicago and Baltimore. I see a lot more deals from these airports than anywhere else.
Once you have your flights booked it's time for the next step.
Step 2: Make An Itinerary
Once I know my dates, I can start planning things like: is it possible to jump to other countries in the time frame, should we stay in one place the entire time, What is there to do? What do we want to see?
This is the time to really think about why you chose your destination and what you want to get out of the trip. Travel is about experiences and ambiance for me. I'd be happy to just walk around in a new place all day, but decide what travel means for you and your family and make your plan. There is no wrong way to travel. It's your trip.
In the image above, you'll see an itinerary I made for our Euro trip this fall in excel. If you don't have Microsoft word, just use it's free cousin Open Office. It's exactly the same.
I highly suggest not micromanaging or over packing your itinerary. You will be jet lagged and tired when you get there, so take into consideration that you'll not be gallivanting off as soon as the plane lands. Give yourself the day to get the lay of the land around your accommodation and just soak it all in. Adjust to the new time/culture change.
I tend to plan one big activity a day and then let it unfold however it will while we're actually there. I find this is a good balance between structure and spontaneity.
Step 3: Figure Out $$$
Once I've made the commitment and purchased the plane tickets and worked out what I want to do with our time, I do the grunt work on finding accommodations and fitting it into a budget.
I book plane tickets so far in advance so I can then, after an initial cash purge, focus on paying for our trip bit by bit until it's all settled.
This might freak some people out, but it has yet to bite me in the ass.
I start with researching and booking accommodation.
I typically check:
What usually ends up happening is I will make a free reservation on booking.com for the dates we need as a back up in the event that I don't find something cheaper in the 8-10 months before our trip. Booking.com allows you to make no down payment reservations on their website and most have free cancellation up until the day before your intended check in date.
Europe can fill up fast even in the off season, so it's nice to have the back up handy.
Once I've made my "back-up" reservations. I spend the next 2-3 (or more) months researching places to stay. My ideal lodging are centrally located, wifi enabled airbnbs or hotels in the $0-50 per night range.
Depending on what city you are traveling to, you won't find deals like this often, but they are out there. Just keep looking. For this last trip, I ended up re-booking all of our booking.com "back up" lodgings to cheaper, better lodgings except for Florence. We are staying in a mix of, 2 Airbnb's, 1 hostel, 1 apartment and 1 hotel on this trip. I started looking in February and solidified all reservations in July.
So I spend some time booking a hotel here, buying a ticket there, and generally paying for everything for the trip before we leave so we won't have to worry about it on arrival.
Then, all you'll have to worry about is spending $$$. I always recommend bringing more money than you need and less stuff. Inevitably you will always wish you had done one or the other.
Also tl;dr: Get Travel Insurance.
Step 4: Do Some Reading
I generally reserve this time for reading up on my destination(s) to try to pass the time and ebb my excitement a little.
What do other travelers recommend? I read travel blogs and browse r/travel on reddit.
Are there any travel guides? (Answer, hell yes and I highly recommend Rick Steve's travel guides.) I usually wander around a travel section and pick anything that catches my eye to thumb through. I also look at the travel section of Pinterest.
Are there any tourist scams I should be on the look out for? YES. Please educate yourself and don't let yourself be a victim.
Above All, Have Fun!
Bonus: Helpful Europe Links
Ryanair (Irish based very low budget intra-Europe carrier)
Norwegian Air (Swedish based low budget carrier)
Aer Lingus (Irish carrier)
Easyjet (British carrier)