How to Plan for a Long Workcation: A 31-day Road Trip + Workcation


Travel is an activity both my husband Rajesh and I enjoy, and it has also become one of our favourite de-stressing activities over the years. Something we both can enjoy together. Other than that, all we enjoy doing together is weekend house parties and watching video content. 😆

So, as you can imagine, the pandemic and the 18-odd months of house arrest that followed hit us hard. We needed to get out of the house and take a long break.

That’s when, out of the blue, Rajesh suggested that we drive around the country for a month, and work from wherever we are. A working vacation (workcation)?? I was unsure at first, but once we started researching and planning, it felt like a great (and cool!) thing to do.

Also felt true to this meme that was floating around during Lockdown 1. 😜

The Doubting Stage

Initially, travelling for a whole month felt like an impractical idea. Where do you even start planning for such a thing?! I had several reservations too.

  1. How would we find affordable places to stay at?
  2. How could we be sure of having good Wi-Fi at all these places so we could work uninterrupted?
  3. 31 days on the road… is that even feasible? What if we fell sick, what if we met with an accident, what if the car broke down in the middle of nowhere?


We didn’t ignore these questions. We actually sat down and thought of answers for it.

  1. We’ll search high and low., Airbnb, Makemytrip, Goibibo, friends who know friends of friends, whatever it takes.
  2. We’ll only reserve places after we talk to the owner of the places we stay at and confirm Wi-Fi availability and speed.
  3. We’ll make sure we carry enough OTC medicines for regular illnesses like headache and flu, and make note of highway SOS numbers and road assistance services. We’ll make it feasible.

The Planning Stage

Even when it’s a 3-day trip, I plan. I create itineraries. I look for things to do and places to see and foods to eat. I’m the researcher, Rajesh is the executer.

For a person like me, a 31-day trip is a nightmare because that means DAYS of worrying and planning.

So, the first step I had to take is to realise that while we must plan, we must not plan to a T. The plan should be a skeleton, not a fully grown human. Took me a few days to let that sink in.

1. Deciding a “Destination”

The second and most important step was to decide a “final destination”, something we would drive towards and back from. Yes, it is about the journey and not the destination, but on a trip like this, you do need a destination! 😅

It also helps you chart a course. You wouldn’t want to be lost on highways and drive around aimlessly while petrol prices hover around Rs.100 per litre, would you?

Of course, the goal was to enjoy the trip. But if we didn’t know where we should start and stop and turn back, the 31-day trip would turn into a never-ending one with our accounts empty and credit cards maxed out.

Rajesh wanted to go to Ladakh. I rejected that idea, because I thought it would be too long and may take more time and money that we can afford. I suggested Darjeeling instead.

Our trip was to be at the end of February, when Darjeeling would be pleasant and cold. Neither of us had been to the eastern parts of India, which added to the excitement.

 The iconic Peace Pagoda, Darjeeling
The iconic Peace Pagoda, Darjeeling

2. Deciding the Route to Take

I opened Google Maps and entered Home to Darjeeling, West Bengal. 3 routes:

  1. Via the eastern coast: Andhra Pradesh, Odisha, and West Bengal (2,469km)
  2. Through Telangana, Chhattisgarh, Odisha, Jharkhand, Bihar, and West Bengal (2,532km)
  3. Through Andhra Pradesh, Telangana, Maharashtra, Madhya Pradesh, Uttar Pradesh, Bihar, and West Bengal (2,586km).

Rajesh and I pondered on the route. Kilometres-wise, the eastern coast route was the shortest (albeit by just 60km to 120km). It also seemed more straight-forward, since we’d only have to go through 3 states.

The third route was the longest but also quite exciting because of the number of states we’d cover.

After a little deliberation, we decided to travel towards Darjeeling along the eastern coast, and to come back home via the longest route.

How to Plan for a Long Workcation: My Experience of Planning a 31-day Road Trip, Workcation, Vacation from Bangalore.
The three road routes from Bangalore to Darjeeling

3. Deciding the Pitstops

On a long workcation road trip, you are most likely to travel on weekends and work during the weekdays. This means you will stay overnight at some places, but for 4-5 days at some places.

The first step was to decide which places we would be working from and which places would be just overnight pitstops.

I zoomed in on Google Maps and made a list of all bigger cities and tourist attractions in the path. Rajesh said he could drive around 600km each day. We studied the route carefully to note which cities fall within 600-650km from each other.

We decided to finalise the stops on the to-Darjeeling route first.

There were multiple contenders for pitstops, but the places we’d work from became clear almost immediately. One week in Puri, one week in Kolkata, and then a week in Darjeeling. We’ll cover a beach town, a historic city, as well as a hill station.

Technically, Kolkata was out of the way to Darjeeling, but I’d been told by so many of my Bengali friends that I would love Kolkata, that I just had to include it on this trip. In addition, one of our close friends lives there, so we could meet him and stay with his family, plus, my favourite colleague lived there and I could meet her too.

 Victoria Memorial Palace, Kolkata
Victoria Memorial Palace, Kolkata

After further deliberation, we narrowed down the following stops on our journey:

  • Vijayawada (overnight stay, 645km from home)
  • Brahmapur (overnight stay, 600km from Vijayawada)
  • Puri (five-day stay, 175km from Brahmapur)
  • Kolkata (six-day stay, 495km from Puri)
  • Darjeeling (six-day vacation, 645km from Kolkata)

Deciding places to stay at on the return trip was a bit trickier, but we finally pinned the spots down to:

  • Bodh Gaya (overnight stay, 575km from Darjeeling)
  • Varanasi (five-day stay, 255km from Bodh Gaya)
  • Nagpur (overnight stay, 730km from Varanasi)
  • Hyderabad (overnight stay, 500km from Nagpur)
  • Back home (575km from Hyderabad)

We could see the Mahabodhi Temple, another UNESCO World Heritage Site, as well as a Hindu religious centre.

But things were about to change.

Before we get into that story, a quick recap of the most important things to consider when deciding the route for a workcation road trip:

  1. Total distance
  2. Total time Google shows for each distance—this will give you an idea of whether roads on a route are good or bad
  3. The distance you can cover per day
  4. Availability of cities/good places as pitstops at driveable distances
  5. Availability of facilities conducive to working wherever you decide to stop longer
  6. Opportunities for sightseeing or doing “touristy” things—scenery, monuments, new foods, souvenir shopping, etc.

How Workcation Plans Evolve

Once we decided the 4 main stops, I started looking at the different things we could do while in these cities.

Puri has the beach, the famous Jagannath Temple, world’s largest brackish water lagoon Chilika Lake, and the UNESCO World Heritage Site of Sun Temple at Konark was just 35km away.

Kolkata has its historic places and monuments.

Darjeeling will be a work-free vacation. Oh, and Gangtok is just 100km away.

That gave Rajesh an idea.

“Nami, for our vacation week, why don’t we stay in Gangtok for 3 days and Darjeeling for the other 3?”

And just like that, our final destination changed from Darjeeling to Gangtok higher up the mountains. We might actually get to see and feel snow. And isn’t Sikkim a bucket list state?

 Nathu La Pass, East Sikkim
Nathu La Pass, East Sikkim

Our friend said that while the distance from Kolkata to Gangtok is 700km, you cannot cover it in a day because once the mountain terrain starts, the drive will be slow.

So, a few changes were made to the itinerary.

  • Vijayawada (overnight stay, 645km from home)
  • Brahmapur (overnight stay, 600km from Vijayawada)
  • Puri (five-day stay, 175km from Brahmapur)
  • Kolkata (six-day stay, 495km from Puri)
  • Siliguri (overnight stay, 585km from Kolkata)
  • Gangtok (three-day stay, 115km from Siliguri)
  • Darjeeling (two-day stay, 100km from Gangtok)
  • Bodh Gaya (overnight stay, 575km from Darjeeling)
  • Varanasi (five-day stay, 255km from Bodh Gaya)
  • Nagpur (overnight stay, 730km from Varanasi)
  • Hyderabad (overnight stay, 500km from Nagpur)
  • Back home (575km from Hyderabad)
How to Plan for a Long Workcation: My Experience of Planning a 31-day Road Trip, Workcation, Vacation from Bangalore.
The route we ended up doing on our workcation road trip

4. Deciding the Budget

If it’s a week-long vacation, we could afford to splurge on a resort or fancy hotels. But a month-long trip needs to be affordable.

First, we made a list of all possible costs we were likely to incur. The four major costs you need to budget for on a workcation road trip are:

  1. Stay
  2. Food
  3. Fuel
  4. Shopping

Stay would consume around 40% of the total budget and food, around 30%. The dent made by fuel would depend on its cost at the time. We had to fill our tank at least once in every state, so while it’s good to know which state has the cheapest fuel cost, you may or may not be able to take advantage of it.

Shopping and other miscellaneous expenses are up to each individual.

Deciding what you’re willing to spend on different segments has to be done first in order to start searching for and booking your stay. We decided to keep our stay budget around Rs.2,000 per day.

This was actually on the higher side and you will get good places at Rs.1,500 as well, but since Wi-Fi and spacious rooms were important to us, we decided not to compromise just because of cost.

Anyway, not every place we stayed at cost us Rs.2,000 per day—most were less than that and only one or two went above the budget.

5. Choosing Rooms/Hotels/Homestays

This will probably take you longer than any other activity in the planning stage. You will need to scour hotel reservation sites for hours to find places that suit your requirements.

We needed the following things from our stay:

  1. Neat and clean rooms
  2. Value for money
  3. Wi-Fi (only for the longer stays)
  4. At least one table and chair to sit and work (only for the longer stays)
  5. Easily accessible (the more remote the place, the less safe it felt!)

Every day I would open dozens of tabs containing hotel information, and each night Rajesh and I would go through them, shortlist some, and then we’d search again.

We discovered that Airbnb was the best place to find rooms for longer stays, and was best to find rooms for shorter stays. Our stays at Puri and Varanasi were booked through Airbnb, and the rest through

The Execution Stage

Once everything was planned and all rooms booked, all we had to do was start driving and enjoying the trip.

When we finally set off, a few changes happened on the way. We skipped Brahmapur altogether and drove directly from Vijayawada to Puri—a whopping 16.5-hour drive across 730km. A personal record for Rajesh.

We also had to change our plans after Nagpur because we had to go to Mangalore to our in-laws’ place instead of Bangalore. So we went from Nagpur to Vijayapura (Bijapur) for an overnight stay and then from Vijayapura to Mangalore.

In the end, we travelled 5,750km through 9 states in 31 days and built memories that would last us a lifetime. Good job, us!

How to Plan for a Long Workcation: My Experience of Planning a 31-day Road Trip, Workcation, Vacation from Bangalore.

Tips to Enjoy Your Workcation Road Trip

Here are some tips to enjoy your workcation road trip without running into trouble:

  1. Research, research, research: Make sure your research includes things to see and do in each city, distance from your place of stay to places of interest, foods to try, etc. If not right away, do your research at least 2 days before you enter a new city. This will help you plan well your day, breakfasts/lunches/dinners, and the driving time, arrivals and departures. You definitely do not want to lose time when exploring a new place!
  2. Book your stays in advance: It’s very difficult to reach a city/town and then look for accommodation. Check out as many booking sites as you can and find the right place for you by looking at affordability, availability of facilities you need, distance from town centre/places of interest to you, and guest reviews. Call up the property and ask for more information/clarification on things that confuse you. Book at least one week in advance, though I would recommend a two-week advance in order to get the rooms you like at a property.
  3. Carry everything you would need for work: Don’t forget things like power banks, chargers for phone and laptop, a good LED torch, your regular OTT medicines/specialty medicines and maybe even a lap desk for emergency. We travelled in a car, so it was possible for us to carry all these things, but if you cannot carry everything, just make sure there isn’t anything you would need to buy anew in a place you know nothing about. Also carry quick foods like Maggi noodles, instant poha, snacks, chocolates, and biscuits, in case you reach your accommodation or get hungry at weird times of the day. We made a huge list of things we would need and ticked off everything while packing.

Most importantly, don’t spend the entire trip worrying about something. Enjoy each day, don’t get flustered and anxious if you meet with an obstacle. Keep calm and travel!

If road trips are not your speed, then you could try a regular vacation. How about a vacation in Bhutan?

About Author

Writer, observer, lover of stories. Expert in short-people problems, armchair travel, and overthinking. I like to think that I’m a wise woman with a pinch of quirk.

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