Ask Me Anything: How Do You Decide on a Place for Vacation?

As part of my Ask Me Anything series, I answer common questions I get from readers. You can read other AMA posts here. In this article, I want to answer the question of how I decide on a place to take my next vacation. If you have wanderlust and want to book a trip, here are some things to think about before that will help you narrow down the destinations.

Readers will sometimes email me overwhelmed with their travel options, because don’t all of us travel-lovers want to go everywhere? It’s all on “our list”. They ask me how I decide where to take my next vacation hoping it will help them decide where to take theirs.

5 Ways to Decide on a Place for Vacation

There are things I consider when I choose my next vacation spot, so I’ll kind of share the thought process I go into when I’m choosing somewhere to visit with the 5 questions you will want to ask yourself.

1. Have I been before?

The first thing I’ll consider is if I am in the mood to go somewhere new or somewhere I have been before and like to return to. I love going back to India, Sri Lanka, London, and so many other places so I try to think if any of them are calling me back.

guide to jodhpur india

I know returning to places isn’t as exciting as going somewhere new – but they typically require way less planning and on repeat visits, you get to experience the place more in-depth. You’ll have already done all the touristy things and now you can do the cool things you missed, try new restaurants and bars, and really chill out like a vacation that doesn’t have a checklist of “things to do and see”.

If you want to go somewhere you haven’t been before, think about where friends have gone. Who has told you about a cool life-changing trip they had recently? You can get travel inspiration from Instagram and blogs.

You can also just spin a globe and see where you land! That is what I did in a way with India in 2012. I chose it 100% on a whim. I wanted to go somewhere I hadn’t been before that would provide a little culture shock. I thought, why not India?

2. What the weather like?

It’s important to think about if you want to go somewhere warm like surfing in Maui or you are interested in a cold vacation like playing with reindeer in Finland. Once you decide that, it will help you narrow things down a little bit. Additionally, you’ll have to think about what the season is at the place you want to go – maybe it’s rainy season and all the activities you have in mind aren’t going to be possible at that time.

3. What do I have the budget for?

Do you have the money for flights all the way across the world or just to a few states over? Do you need to take the train/bus rather than fly? Unfortunately, the budget is going to play a major factor. Yes, you can get to places like the Maldives on a budget – but do you want a budget trip to the Maldives or do you want to save it for a luxury honeymoon one day?

Often I will do a close trip – in India, I can do a two-week trip to another state I haven’t visited and spend a lot less than if I flew to Kuala Lumpur for the weekend. In Mexico, I recently did a getaway to Mexico City on a whim. I considered other places but wanted a “big city” break I could afford and it was the cheapest city nearby.

Try using the Skyscanner “anywhere” or Kiwi “anywhere” options with your airport as the departure and “anywhere” as the destination. It will give the results of the cheapest places you can fly to. See if any of them stand out to you.

What to Wear in Mexico City

4. Is it an adventurous trip or a chilled one?

For my bachelorette party, my bridesmaids were up for anything! We could have done an all-inclusive in Cancun and chilled or gone to Lake Tahoe for a relaxing lake vacation. I had to think not just about the destination but about what I wanted to do there. I didn’t want to SUP. I didn’t want to go clubbing or just lay by the pool. I decided I wanted to go to Universal Studios. There is so much to do all day at the parks, it’s sunny, there are bars and restaurants within the park and it makes for an easy trip.

Sometimes I want something really adventurous and want to experience a place I haven’t been. Recently, I wanted to go somewhere new with a friend. Neither of us had been to Central America, so we started there. Costa Rica seemed over-traveled. Honduras wasn’t safe. We went through each country to kind of see what we wanted to do. We decided on Panama because it has the city, the Pacific, the Carribean, whale watching, trekking, culture, pristine islands that hardly anyone travels to, new food we’d never tried, and beautiful boutique and eco-friendly hotels and B&Bs. It had a lot to offer and we could do a lot in two weeks.

If you want an adventurous tip, ask yourself what you are interested in: skiing, surfing, safaris, rafting? You can figure out what you want to do then google “the best places for ___”.

things to do in panama city

5. How much time do you have?

The last point brought us to this: do you have two weeks to go to Panama? If not, and you have one week, is it worth going all the way to just hit up two cities? Would you prefer instead to go to Costa Rica and do a lot in a smaller area?

Maybe you have just a long weekend and could think about flying to Mexico City for a weekend. You can often get flights there from the USA as cheap or cheaper than flights to Vegas, LA, and NYC. Try to think outside the box and make the most of the short time you have. There are international destinations that work for a long weekend. Alternatively, you can do to places in the USA you haven’t explored like New Orleans, Nashville, or St Augustine.

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About the Author:

Rachel Jones left a career in nursing and lived on the beaches of Goa, India for the five years. Now she lives in Mexico where she gives advice on the 40+ countries she’s visited in the last 10 years. She’s the author of two India travel e-books: Guide to India and Insider’s Guide to Goa. Her blog, Hippie in Heels, like its name, is a contradiction combining off-beat adventurous places with glamorous and bespoke travel. Hippie in Heels has been featured in ELLE, Marie Claire, Grazia, and Cosmopolitan magazines. She’s a writer for Bravo TV.

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