This guide is about how I went about planning my own Sri Lanka trip. My actual itinerary and travelogue will be published in a separate post after I complete the trip. This is supposed to help you provide resources and steps in planning any trip your own, and is based on a series of steps I follow when I need to plan any foreign trip.
When and DurationThe first thing to plan is when you will travel, and for how long. Open-ended search on Skyscanner (e.g. from Chennai) can tell you what's the cheapest airfare you can expect to your desired destination. Now you can compare your own airfare for the proposed period against this to decide if your period of travel and any excess airfare is acceptable for you or not. Based on your vacations, leaves, personal desires, and so on you can choose to pay little (or very) more than the cheapest fare for your proposed period. You can also play around a few other months to check what's suitable costing for you. You can also go to Wikitravel to find if your period will have good enough weather. This decides your when.
New go to few tour operators to find out duration of ready-made packages to your destination. Selecting your holiday destination on (e.g.) MakeMyTrip, TravelTriangle, ThomasCook, and SOTC can give you idea of typical duration (and cost) of trip. For Sri Lanka, this was about 4-7 days. Quick Google search or Tripoto search can confirm your decision. This whole thing shouldn't take more than 15 minute as our focus is just overall duration and not cost and not itinerary. For Sri Lanka, I realized that less than 5 is too short and more than 10 is probably too long. This decides your duration
Flight TicketsFlights being most expensive component, you want to nail this down first. Create permutations for duration based on your decision, say 22-28, or 23-29, or 22-29, etc. to find suitable option based on fare and convenience. I usually look at few websites like paytm.com, easemytrip.com, goibibo.com, airline's own website, and few offers if available on credit cards I hold and book the tickets. This step can take 1-2 hours across days.
You may be tempted to try out many websites and offers, but my lesson is that these days prices are pretty consistent across portals and any offer is mostly teaser and benefit will be lost in transaction fee or convenience fee. Prices tend to go up (Murphy's law) during your search period so you should just book within 1-2 days. Do keep in mind arrival and departure times of flights and travel times too (and not just airfare) since odd timings may add to hotel cost at origin station, or have the inconvenience of night wait at the airport, or cost of an extra meal, or unreasonable cost of airport transfer, and so on. Airfare cost alone isn't everything!
Your ItineraryThis is biggest and most time consuming process. Goal of this is to come up with cities you will stay in, and the number of days within each, and transport between cities. This step may take 4-40 hours of time depending on how much in detail you want to go!
You will have to read a lot! Refer itineraries on tour operators websites, pickyourtrail.com, tripoto.com itineraries, and TripAdvisor forum's to identify potential cities you may be interested in. You can plot these on Google Maps to plan a route which is roughly circular and doesn't require returning back, and minimizes overall travel distance and time. You can also get a broad sense of distance and travel times between places so that you can incorporate travel time between cities in your daily plans. You need to decide if the day of travel can also accommodate some sightseeing or will only be spent on travel due to distance and exhaustion.
Refer to TripAdvisor's Things to Do for those places to decide for yourself what things will interest you — not every tourist spot works for everyone, I like slow paced vacations, and not much interested in historical buildings, for example — and how long you think you need to cover those. Read TripAdvisor reviews of tourist spots and see pictures. Split things into 'Must See' and 'Good to See' and 'Avoid' options based on your preference, cost and reviews. This will broadly inform how many days are needed to cover each city. Do note that many places may have ticket cost which isn't easily available (may have to read few reviews), or free days (may have to check attraction's website), or closed days (e.g. every Tuesday), or limited opening (e.g. morning 10am-2pm) which you need to factor in deciding your local route. Use existing itineraries to double-check you duration at each city. At this stage, you can also drop a city from your plan, or choose between cities if you are in two minds. You will have to decide if you want to shift hotel at each city, or can cover one city with another city as base in day's round-trip.
For each place of stay, plot your sightseeing places on Google Maps to broadly understand the density of activities which will, later on, help guide your hotel location and need for local transport.
Based on previous itineraries, your comfort level, and cost comparison you can also decide if you will drive your car (not an option for Sri Lanka), take public transport (an option if you are adventurous, in Sri Lanka), or have dedicated cab for the full duration. Documents on TripAdvisor's Sri Lanka forum have good information on this. Given that I was travelling with family and prioritized convenience, I chose to go with a dedicated cab.
Once your itineraries and places of interest are finalized, you will have to decide if you need to pre-book anything. For instance, Safari at National Parks in Sri Lanka may be pre-booked (but will cost extra) or booked via hotel or done on the spot. Similarly for Whale Watching tours at beaches.
Local TransportEvery country has different options with different cost, and you need to read a lot to find out what will work for you. Rome2Rio is a good portal to quickly get a list of various available options for local transport. As mentioned above, I decided to go with dedicated cab and hence shot an email to key tour operators Tangerine Tours, Red Dot Tours, Walkers Tour, and few others from google search. I also dropped an inquiry at srilankacaranddriverhire.com which is an informal collective of non-branded operators (link found from TripAdvisor's forum).
After comparing cost, few Q&A based on what is covered and what is not covered, and comparing cost of all day hire, or partial hire I decided to go with one operator. Before finalizing the operator, I read its review on Facebook and TripAdvisor, wherever possible, since not all operator have reviews. Be careful to not just go by star-rating but read reviews. It takes time but there are lots of fake reviews! Reviews which are not accompanied by description, or timed in short duration are suspect. You can even click on reviewers on FB to see their profile and ascertain if they are genuine tourists or not. I found many times operators or drivers or folks based in Sri Lanka themselves were giving 5 star to their page. I also found few operator having multiple FB pages. All these are unreliable in my mind, though of course I cannot claim that for certainty as I didn't avail their services.
You can also search on airport transfer options, based on your flight timings. Most airports will have taxis available 24x7 but public transport may be cheaper. You can go through the airport's website or search the internet to find suitable options. Your hotel may offer too though that's likely to be expensive. Pre-booking may work, or maybe expensive. Uber is omnipresent but every country has it's local taxi network as well.
As everywhere, evaluate options holistically for convenience and freedom and not just on price. You don't want to spoil you 100k vacations for saving 5k. Since vacations are experiences, day to day convenience matters a lot in making those memories happy or unhappy!
HotelsHotels may not be very expensive in overall cost of the trip, but have undue influence in your vacation experience. Different countries have different hotel booking websites which work better. booking.com, agoda.com, and kayak.com are good ones to start wtih. Airbnb can be explored and can come out cheaper for Europe and US, but for Asia, hotel operators have flooded listing on airbnb.com and it's not much different. Your map of tourist spots will come handy here and you can select few hotels based on budget, amenities, views, breakfast, and location on the map. Go through pictures and customer reviews of the hotel on TripAdvisor and Facebook to filter out some, and do remember to keep you 'fake review' detector on.
Do remember to email or call the hotel to confirm the booking, and don't just rely on booking portal's confirmation. Many a times inventory is not be updated or hotel may simply overbook and refuse you. You don't want to stuck searching at last minute in the foreign country. If you are staying longer at one place, or like to cook in, you can search a hotel with a kitchen. Hostels and dormitories are good options if you are single or have a tight budget.
Visa, Forex, and SIM CardThere are multiple guides on this on the web and this is a standard official process so you have to do what you have to do. For Europe, I have heard that some countries are more lenient than others in granting Schengen Visa so your itinerary should keep that in mind as a port of entry. For every other country, your Visa is specific to that country so you follow the official process. Sri Lanka Visa is online approval which took less than 30 min to fill and 5 min for approval.
These days you will be carrying a combination of foreign-currency pre-paid card and foreign-currency cash for your trip. Based on hotel cost, local transport cost, meal cost, attraction fee, and a healthy buffer you can estimate how much to carry. Depending on acceptance of card vs cash you can split your amount. For Sri Lanka, you need to convert into local currency in destination only and carrying USD is recommended, though INR may also be acceptable. TripAdvisor forums had good information on where to exchange money.
Similarly, local SIM card from airport, city, or pre-paid SIM card from your origin country can be taken based on price and convenience. For Sri Lanka, generally advise is to take local SIM from the city. You may search for telecom operator with decent coverage at cities in your itineraries. Google, google and google away!