Where shall we go this Summer? How to plan a travel itinerary & estimate costs like a pro!

Very recently, I ran a survey on Instagram asking you to vote for the kind of posts you would want to see more on Guilt Free. And with the latest updates of my trip to California bombarding your Instagram walls, most of you, or at least a slim majority of 53% of you, chose travel. That was not in the least bit surprising. I am running a miserable backlog as far as my travelogues are concerned. A backlog of… wait for it… 2 full years: years in which I have taken one 3-week, one 2.5-week, one 11-day and one 7-day trip, apart from the several overnight ones. So you can well imagine the amount of writing, memory recollection and photo compilation I have to catch up on. And with this year bringing in its wake promises of more travel (fingers crossed), that backlog clearing might take another two years!
Before I start going about that task, let me tell you how every trip starts, for me at least. I am a compulsive travel planner. At any given day you’ll find in my Vacation folder at least 10-12 excel sheets containing elaborate itineraries and cost estimates of trips I may or may not take! In this post, I’ll hold you by the hand and tell you exactly what I do (and what you can do too) to come up with an itinerary that makes your journey to the place worthwhile and a budget estimate which is on point. This will help you get more bang for your buck and completely eliminate any last-minute fretting and possibility of missing out on places and experiences because you “had no idea about that”!
Okay, this is a lot of text. So arm yourself with a cup of coffee (or a chilled glass of lemonade if you’re visiting this space from the southern hemisphere) and read on!
1. The travel itself is always the cherry on the cake for me. The fun begins when I sit 6-8 months in advance, meticulously narrowing down upon my destination and giving shape to my itinerary. We normally zero in on a couple of options and then I make a rough itinerary and cost estimate of each. That coupled with flight times and fares, feasibility of squeezing in the maximum within the limited time slot, the weather and our bias determines where we are going to set sail. You might eliminate this step altogether if you have a definite destination in mind. I totally understand and consider you sane for not going through two itineraries when you can get away by making just one. It’s me that needs help!

2. Once you KNOW where you’re going to travel, get a Lonely Planet book asap. Go through that meticulously. Check a few sample itineraries and look for basic guidelines from Rick Steves, Frommers, Fodors, Nomadic Matt etc. At this stage, you have to make a broad list of all the places that are worth visiting.

3. This is my most favourite bit. At this stage, you will read up travelogues and blogs, check Trip Advisor forums and make youtube videos your best friend. Do this for a few days. At home, at work, at leisure, while cooking, while cleaning, while eating dinner, while making powerpoint presentations. Okay, maybe only at leisure. All this was too extreme. At the end of three days you will know which places out of that broad list you definitely want to visit. Jot down that list.

4. Okay, so you have narrowed down on your destination and the places you would like to visit there. Great. Now open Google Map and add all those places (if you have a huge list, do only the cities first) on the map in a single trail of entry. Adjust the order so that you get the shortest distance between two places. This is going to be your travel map. At this point, I go back to Make my Trip, Expedia, Kayak, Skyscanner or wherever I look for air tickets to check fares for each of my possible entry points. Eg, if I’m planning a Spain and Portugal trip, I would check flight fares to Madrid, Barcelona and Lisbon. I also check multi city fares (which almost always helps in my itinerary) and note down the most convenient flights in terms of the price, time taken, time of reaching the place etc. Now I know which point in the map I would start my trip from.

5. Since you now know your map as well as your point of entry and exit, check how you can get from one place to another. Depending on the distance between the places, you have to consider bus, train and air options. Check the time it takes by each mode of transport, the cost it incurs and the time it leaves place 1 and enters place 2. For me, if it’s anywhere close to or more than a 6 hour journey I prefer an overnight travel by train or bus. Eg, if I have to cover an 8 hour journey between say San Sebastion to Lisbon, I’d prefer to take a transport that leaves around midnight and reaches early morning than take one where I’m travelling from 12 noon to 8 in the evening. You have to now check bus/train timings and decide which time would suit you the best. Note down the corresponding price against that ticket (we’d need that later!) and get an idea about how often and how much you’d be travelling but most importantly at what times you’d be entering and leaving a place. This helps a hell lot in deciding your daily itinerary and hotel bookings. (Note: You might have to change your route map a little bit according to the mode of transportations available between different points but the changes are mostly minor and almost never non-negotiable).

At this stage, this is how my broad itinerary normally looks like

6. So far we were laying the foundation stones of the itinerary. Now is the time to elaborate on that. So you know which country/state you’re planning to head to, you know the different cities that you want to visit, you know how and when to get from place 1 to place 2. You will now take each city in your stride and make a list of all the places you want to see in that city, all the experiences you’ll want to indulge in. Your good friends Google and youtube will help you immensely in making your list. Make an estimate of the number of days it will realistically take to cover all these places. You already know what time you are entering and exiting the city, so intelligently use up that time to plan your days. Eg, If I’m boarding an 11pm train/bus, I check out from the hotel by 12 noon, keep my luggage with them, go about my daily business, get back to the hotel around 9, collect my luggage and head to the station/bus stand. See what I did there? I saved a day’s accommodation as well!

You can see that I have listed the places I want cover in Madrid, their entry fees, the times at which they are open and any possible free entries or discount. Also, I’ve marked the distance of each place from the other to help me plan my route

7. Okay, you’re doing good. You now know your travel route and the number of days you’re going to spend in each city. How much does everything add up to? Is it well within your control? Or is it overshooting your allotted number of travel days by and far? If it is the former, adding places to an itinerary is never difficult, right? But if it is the latter, go through the lists you’ve made all this while thoroughly. Is everything indispensable? Can you chuck a couple of spots and thereby reduce a day or two? Can you dispense with an entire city altogether? These are calls you have to take and trust me, it’s never ever easy! In fact, I’m guilty of adding an entire week to one of my itineraries because… you know, right?

8. Think you have your itinerary ready now? Congratulations! Step one: check. Let’s crunch some numbers now, shall we?

9. I presume you know the time of the year you want to travel, if not the exact dates. Well, open your flight/train search engine and look for flights. This step needs to be performed once before undertaking step one and during step 4, because you don’t want to plan an entire Patagonia itinerary from India and then realise that a flight ticket to Santiago, Chile, is coming to $2000! Anyway, you already have an idea of your flight fares from step 4, so jot that down.

10. Next comes accommodation. If you know the exact dates of your travel, great. If you don’t, search accommodations with any random date of that particular month. This will not guarantee you a room in that hotel on that very day and at that very price, but will certainly give you an idea of what to expect and the average range of prices in that season. I do my accommodation search on booking.com, hotels.com and Airbnb and have rarely been disappointed. Make a note of the possible tariffs that you might have to pay in different places that you’ll be staying, multiply them by the number of days in each place, and the bulk of your budget estimate is already under your belt.

11. Now for inter-city travel. I’m guessing you’ve already noted down the prices of trains, buses and jets that will be taking you from one place to another (under step 5). Good. Add that to your budget.

12. This brings us to local transportation. For most places, I try to rely on my legs. Where that is not possible, I look for public transport. I check individual fares between places I’d need to visit as well as for any 24,48, or 72 hour day passes in places where I’ll be staying for that long. Many such passes are completely pre-paid and some need top up, like in London and Barcelona. Some also have free access or reduced rates for museums and amusement parks. But before purchasing any such pass, you need to consider carefully how much you’d be spending doing the same things without a pass. If you’re planning to visit only one museum and take maybe 2 bus rides over 3 days, the pass might not be worth it. If you choose to Uber it, then the cost would completely depend on the distance you cover and a budget estimate might not help you assess that accurately! Maybe you can just set aside a certain sum for Uber/taxis if you’re unsure. This step will give you some idea about how much to spend on local transportation. Add that to your budget.

13. What about the sights and sounds? First things first, check out free things to do and free places to go in each city. But it’s still likely that most places you plan to visit will require an entry fee. Even then, look out for days and times when they might give a discount or free entry. Eg, I managed to enter the Alcazar of Seville for free (regular price 9.5 euros) as I happened to be there at 4.30pm on a Monday (in November 2016, don’t know if that policy is still there). Make a list of the total amount you have to pay as entry fees and suchlike and add it to the budget.

14. Now the million dollar question: Where and what to eat without breaking a bank? Tip no. 1: Try to book a hotel/hostel which has breakfast included. Fill yourself up with bread, cheese, deli meat, yogurt, granola, muffins, and coffee at the start of the day (literally for free) and you’ll feel much less hungry throughout the rest of the day. Your next bet is the supermarket. In places where they do not serve breakfast, do your grocery from the local supermarket and make yourself a breakfast of sandwiches and fruits. In today’s day and age, you always have a Zomato or a Yelp at your disposal. First search for “Best cheap eats in *insert name of place*” or if you feel more fancy, “best restaurants in *insert name of place*”. Once you have a list of your preferred places and what their specialties are, look up their menu if available online and get an idea of the prices. You might have to dine out everyday, but that need not be an expensive affair. Select local cafes, ethnic eateries, delis, and once a while a fancy restaurant to balance out your costs. I’ve noted that typically a budget of 20 euros/25 USD/600 INR per day per person works well if you’re not splurging behind food. Multiply that with the number or days and you have your estimated food cost. (An exception to the breakfast rule would be when you’re travelling within India or most other places in Asia. The puri-sabzi or different other breakfast staples you get in local markets are way cheaper and tastier than usual hotel breakfasts.)

This is how my typical food research doc looks like, and no, I’m not asking you to go through this madness. Just a broad survey of the places to eat and rough prices would be more than enough!

This Portland Food Guide is work in progress for a weekend trip I plan to take soon

14. I’m not going into shopping here. You’ll be the best judge of how much to set aside for that. 😛

15. An important thing to note: If you’re booking your tickets and accommodations right after making the itinerary, this point doesn’t concern you. But if you, like me, make your itinerary way ahead before you do the actual bookings, always leave 15-20% leeway for airfares and hotel prices going up.

16. Last but not the least, if you’re traveling abroad, do not forget about the visa. Research on the visa around the same time as you start planning your trip. How much does it cost? What forms do you need to fill up and what documents do you need to submit? Is there a visa office in your city or do you have to travel elsewhere to apply for the same? Upto how many days before the journey date can you apply and how long does it take to reach you? These are important questions and the answers vary from country to country.

This is how my final itinerary looks like. The entire day by day agenda in place supported by the likely cost to be incurred everyday

So now you have your full travel itinerary under your belt and an almost accurate budget estimate, and hopefully your visa too! So what are you waiting for? Pack your bags and get going! Do let me know where you are headed next. I might just meet you there 🙂