How do we plan a travel itinerary?

with 9 Comments

Last month, a friend reached out for suggestions on a trip she was taking. As we discussed, she casually asked me: how do you plan your trips once you’ve booked your flights? Thinking aloud, I said: Whoa, this sounds like a blog post. Please write this, she said. This was a reminder of a realization I had sensed for a while. People want to travel, but itinerary planning can be daunting.

Pit stop while roadtripping New Zealand, 2013
Pit stop while road tripping New Zealand, 2013

So how do Bharat and I decide on a travel plan and choose what to do?

Fortunately, there’s no one answer to this question. Which gives us so many ways to plan a much awaited holiday.  For a trip that involves prior planning, we divide the following tasks on hand between ourselves:

• flights • visas • gathering information • planning an itinerary • car rental/domestic transfers • accommodations • sightseeing/tours 

Finding a good flight deal and sorting visa requirements (for foreign travel) are steps that often precede or go hand in hand with planning our trip itinerary. As is finding the right accommodations. Before diving in to look for travel inspiration, we typically ask ourselves:

What’s our PRIORITY for this trip?

As enthusiastic travelers, both Bharat and I tend to have a number of places to see on our wishlist. But a respect for each other’s interests allows us to narrow our choices to the ones that matter most. Moreover, what the destination offers and the time in hand also play huge roles in steering the focus for our trip. From here on, whoever takes lead on planning the itinerary (we take turns) roughly decides the places we definitely want to visit.

Watching a male blue-footed booby spreading its wings to woo his lady love ;)
A male blue-footed booby spreading its wings to woo his lady love, Galapagos, 2016

Where do we FIND initial information?

  • Official Tourism websites of countries. It often helps to email or tweet them directly.
  • Travel sites like Lonely Planet, Afar, National Geographic Traveler, Travel & Leisure, Rick Steves and TripAdvisor. 
  • Personal blogs on the web. We sometimes try “destination name+guide” or “destination name+travel blog” to get started. Try not to click on the first link you see.
  • Through conversations with someone who has traveled to the destination we plan to visit 

From here on, we start listing initial places of interest in a Google Sheet or on Evernote.  

The next puzzle that we attempt to solve is the skeleton or framework for our trip. This refers to a simple plan or route and is essential if we’re on a road trip with multiple destinations. At this step, Google Maps is our best friend. By now, our preliminary research has given us enough knowledge to key in names of places and check distances from point A to B.

We found this cottage through a travel blog, Iceland, 2015
We found this cottage through a travel blog, Iceland, 2015

How do we BUILD our trip?

  • Starting with an arrival destination we logically add other places north, south, east or west ending at our departure destination. It’s like joining the dots on Google Maps 🙂
  • If time is a constraint, we avoid crisscrossing too much unless our transportation is sorted and we’re not self-driving.
  • This is also the right time to decide how much time (days or nights) is worth allocating towards each place we’re visiting.
 Two free days in Lisbon was a great idea, Portugal, 2016
Two free days in Lisbon was a great idea, Portugal, 2016

If you’ve followed along this far..thank you! This last bit of planning is actually my favorite. Booking flights, visas, stay, internal transports can be exhausting enough. But once that’s out of the way, one is free to wander the globe..err the web to answer the most important travel question:

What are we going to SEE+DO in this holiday?

The trick to a fulfilling holiday is to find a balance between the things you choose to see and do. And that doesn’t mean ticking off every possible ‘attraction’ in a city. Here is where I let my imagination go wild.

It is fairly simple to gather information about the main sightseeing spots trough a guidebook or on the web. But how does one choose? I use some of the following tricks, and keep saving or noting anything that excites me:

  • Instagram Search + Bookmarking: Instagram’s location and hashtag search is increasingly turning into a time-saving search method for us. It helps to see the most recent and the most popular photos. Plus, with the bookmarking feature, I can always revisit my discoveries.
  • Twitter hashtag search: As a longtime Tweetdeck user, I swear by columns. Once our travel destination is finalized, I usually search for hashtags with the name of the destination followed by #travel and create a column for easy reference. That way, I can track tweets tagged with either hashtag in real time. I also make Twitter lists to easily categorize accounts related to one topic. The cool part about columns on Tweetdeck is that you can filter them based on a search criteria to narrow your results.
  • Pinterest searches: While I use Pinterest every other day, I find it hard to keep up with. Nonetheless, with some time on hand – I do make it a point to search through Pinterest posts too.
  • Facebook Groups: It’s amazing how well spread out the worldwide travel community is. Facebook’s search function within travel groups sometimes helps find relevant and useful blog posts about travel and countries. 
  • Guidebooks and travel magazines
  • YouTube: Videos are a savior when time is short. An overload of information on the internet can overwhelm anyone. Travel video guides or movies are easier to digest and are informative too. 
We took the tourist trail in Pisa ;) , Italy, 2013
We took the tourist trail in Pisa 😉 , Italy, 2013

Participating in activities adds a unique perspective to our notion about the place we are visiting. It’s a chance to surprise, educate and dare ourselves. From here on we pick up things that we’d like to know more about – say, a walking tour or a cooking class and then create a schedule by organizing these activities day wise. If there are too many ideas on our list, we resort to Google Maps to check the feasibility of getting from one place to another.


Walking tour of Munich, which was….


Free but we gladly tipped the guide :)
free but we gladly tipped the guide 🙂

This isn’t the first instance Bharat and I have been asked about how we plan our trips. Friends have called or messaged us for ideas (some, in absolute panic). Travel is so much easier than before. It’s meant to be exciting, and not necessarily a pain. This is my attempt to help 🙂

Because we are beach bums too, Mexico, 2016
Because we are beach bums too, Mexico, 2016




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As a kid, Supriya had to be brought back to reality from her daydreaming excursions. A digital marketer by profession, she enjoys reading, writing, and photography. Her wanderlust list changes each week, but she's strongly eyeing countries in South America and the Middle East as destinations for her journeys :)

9 Responses

  1. It’s interesting to see the different techniques people take to travel planning (excluding those who rely on travel agents). My approach is a lot less formal. It does rely heavily on talking to friends in the travel community who’ve been to the destination (or, even better, locals when I know any). I’m looking not just for the popular sites that everyone instagrams, but for quirky and offbeat attractions. A lot of times I also get suggestions from hotel staff, or people Facebook me when I’m already at the destination, and I learn about a site I hadn’t heard of but which intrigues me. And when I was in Jerusalem recently, a cab driver took me to an Elvis-themed diner, which wasn’t previously known to me but which my friends back home enjoyed seeing photos of. Yes, the most crowded sites are crowded for a reason, and I’m not going to overlook the must-sees, but I don’t only want to hit up the same landmarks that everyone else does.

    So I don’t script my itinerary day by day (besides, if it rains on a particular day I’ll seek out museums and other indoor attractions on that day, rather than take crappy outdoor photos with a gray sky). Even if I have a pre-booked organized day tour, I’ve been known to reschedule it a day or two in advance if the weather forecast looks bad. And I try to maintain flexibility to add in or substitute an attraction that I didn’t learn about until I was already there. No matter how long you spend somewhere you’re usually not going to have time to see everything that’s worth seeing anyway. Also, I haven’t used dead-tree guidebooks in many years. They’re not as up to date, and they’re dead weight to lug around, and their editorial choices are no more valid than those of the best sites on the internet.

    • Supriya
      | Reply

      You’d be surprised at the quirky places we’ve found via Instagram (some of them here in New England itself). Yes – I’d agree with you about recommendations from hotel staff, they’ve always been interesting for us too. As for guide books – they’ve been researched, written and published for a reason. I wouldn’t prefer to carry one around, but would definitely read one before traveling to a destination. I think it’s about having the right balance when you visit a destination and what your approach to travel is..and a balance between informed and uninformed works for some 🙂

    | Reply

    Totally agree with you and find the tips extremely useful! Although planning is a troublesome thing, it will enable us to have a more fulfilling trip!

    • Supriya
      | Reply

      Thanks for dropping by Chole – it’s troublesome but so worth it sometimes!

  3. Bell | Wanderlust Marriage
    | Reply

    These are some great tips! I really never use instagram for looking for things to do, will have to keep this tip in mind. A lot of our travel is last minute these days, which is interesting because there is a lot of room for being surprised, but there is something to planning a researching and dreaming about the trip I miss.

    • Supriya
      | Reply

      I know the feeling Bell – sometimes lack of information can be troublesome. Other times, you can take it easy. I love how Instagram has given us a new way to discover (even though their feeds are throttled too)!

  4. Bon Voyage Lauren
    | Reply

    I always find it interesting to see how other people plan their trips. I totally agree with you – it’s important to find your priority. Great post, thanks for sharing!

    • Supriya
      | Reply

      Thanks for stopping by Lauren. Would love to know your ways around working on an itinerary?

  5. […] born with silver spoons. But the truth is not quite the same. Recently, Supriya wrote about how we plan our travel itineraries, an idea that stemmed from our readers mentioning that they often find themselves scrambling […]

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