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Simple Step-by-Step Guide To Plan Your Next Holiday

I was at a party over the weekend and some friends were expressing interest in visiting South Africa this December. It’s mid-September and they haven’t started planning and they didn’t realize December in-between Christmas and new year is peak season.

I was tacitly surprised that they wanted to go on such a big trip (San Francisco to Kruger is far and not cheap!) but hadn’t really thought about it. Sometimes the barrier to traveling is simply planning the trip itself! It can be a lot of work and time consuming, depending on how thorough and detailed you are about the itinerary.

Everyone is different. Some people throw caution to the wind, book tickets and figure it out as they go. Others are very detailed and still others are somewhere in-between. Part of holiday fun is planning the trip itself. So don’t stress about it. The planning process in itself should be interesting and leisurely, vs. stressful and painful.

ProTip: Seems obvious, but the more you learn about a destination the better experience you can expect. Once I’ve done research about a destination, I have more specific questions and I turn to TripAdvisor and other forums to get the info I’m seeking. And I find the more prepared I am for the finer details, the more enjoyable my holiday will be.

For example: I only had a couple days in Manuel Antonio, Costa Rica and I was looking for accommodation. Booking Hotel San Bada ended up being a great choice! Because of its proximity to the National Park, every morning there were monkeys hanging out on our balcony. Not a big deal but definitely added to the experience of my trip. I wouldn’t have known that had I not first looked into accommodation near the park.

Americans get pretty limited time off of work compared to other countries. So I prefer to plan things out. I don’t adhere to a super strict itinerary but I do like to have an idea of what activities or sites I want to see, how long each takes, and how to get to each destination. It’s happened before where I didn’t put in the time and research and ended up missing out on things I would’ve really liked to see. Here’s my step-by-step guide to planning your next trip.

This guide assumes you already narrowed your holiday down to a location(s) and you’re at the stage of figuring out an itinerary.

Step 1: Look into flights or other ways to get there mainly concerning yourself with cost and time to get there. This is a good place to start because the cost, in particular, may influence when you go. Most destinations are more or less expensive depending on the time of year. And when you go will influence what to do when you get there as well as length of your stay.

Step 2: Read general info about the destination. How big it is, the most popular areas for tourists to visit, things to do there.

Step 3: Make a list of the things to do at your destination(s). I personally rely on Trip Advisor, Lonely Planet and Frommers. And I usually start by Googling, “things to do in ___________”.

Step 4: Gather info about the activities and sites that interest you:

  • geography of each place
  • time to allot in each place
  • how to get to each place
  • relative distance of each destination to one another
  • are any destinations/activities so similar you can prioritize one?
  • which destinations can you bundle together either because of proximity or time needed to visit?

ProTip: Find out about the booking policies for activities and organized tours. Some companies don’t issue refunds, some activities are weather dependent. I typically book excursions and day trips when I arrive at my destination rather than booking beforehand. I like the flexibility in case of travel delays/changes, weather and other variables I can’t control.

The only time I book activities in advance (before departing) is if there’s something VERY popular that might sell out, such as the ATM Cave in Belize during the December holiday season.

Step 5: Based on the things you want to do/see, allocate days to each place.

Step 6: Start looking at organized tours, or other options to visit the places you want to see and activities you want to do. How much do things cost? What’s included in tours? Pay by cash or credit card? Gear you’ll need and what to wear.

Step 7: Look at options for accommodation (complete this step at any stage in trip planning. Personally I like to look at what there is to do a destination before I look into accommodations).

Step 8: Look up places to eat. For my fellow vegetarians, vegans and anyone else with dietary restrictions, this is particularly important for you, because it can influence where and what can kind of accommodation you’ll stay in. For example, whenever I go to Hawai’i I rent a condo with a full kitchen. When I fly in, I grab my rental car and head straight to a grocery store and stock up for the trip. Hawai’i has vegetarian options at restaurants but most of the places are geared towards non-vegetarian and fish lovers.

After spending the day out on excursions or at the beach, I’m tired and enjoy cooking a nice meal and relaxing in an oceanfront condo.

Bonus: I save A LOT of money this way!

Step 9: look up other important travel info: visa requirements, inoculations, money logistics (cash or credit card?), ATM situation at your destination,

Step 10: Plan the clothing and gear you’ll take with you.

ProTip: If you’re going somewhere during the December holidays, order on Amazon sooner than later. Last year (2017) deliveries, USPS and UPS were backed up! I received a few packages 2-3 later than expected.

ProTip for my fellow petite ladies: Increasingly stores are carrying less and less inventory for us in the store and you have to order online. So make sure you order enough ahead of time to get your bikinis, etc. in time!

ProTips for condos in Hawai’i: for anyone renting a condo in Hawai’i. Save some money by packing spices with you i.e. salt, pepper, garlic and onion powder, cumin etc.  You’ll spend a lot of money if you buy that on the island and unless you bring it back with you, it’s kind of a waste. I do this every time I go and pack them in my carryon with no issues.

I always travel with a carryon to Hawai’i and I accomplish this by ensuring the condo I rent has a washer and dryer.


Planning vacations can definitely be time consuming. But if you follow this simple step-by-step guide you’ll save time and enjoy even more as you’ll be knowledgeable and prepared. It’s worth the effort and like anything the more effort and time you put in, the more you’ll get out of it.

But let’s not lose sight of what we’re talking about – going on holiday. You’re probably going to have an amazing time whether you put in 1 hour or 20 hours into planning your trip. And as you travel, you’ll get better at it each time.

I hope you found this info helpful! I really hope this article helps you prepare for your travels! Let me know what you thought of it! I love hearing from our readers, as well as your fun, funny, interesting, and helpful stories from your travel experiences! You might like to follow us on Facebook and Instagram too, where we share a lot of different content and images.

{About PassportPages}

I created the PassportPages travel blog, to provide nuanced, detailed travel advice, tips, and hacks for traveling all over the world — from a unique and different perspective than the other popular travel blogs. There aren’t as many travel blogs geared towards:

  • nuanced, detailed travel tips and advice
  • vegetarians/vegan travelers
  • ethnic Americans, Canadians, and others
  • petite women

As a non-Caucasian there’s an additional layer to traveling abroad that other popular travel bloggers can’t relate to, like my experience on my most recent trip to Paris.

{About Samta}

When I’m not traveling and/or adventuring (and even when I am), I operate my tech startup, ShaadiShop. ShaadiShop is a marketplace for Indian-friendly wedding venues in California.

During undergrad I decided to study abroad which triggered my travel passion. I lived in Adelaide, Australia for a year and after that, for the next 10 years I spent 1-2 months each year, traveling to various destinations around the globe, on my own while I managed my direct marketing company.

I think traveling solo, prepared me to become an entrepreneur – journeying into new experiences, figuring it out as I went, self-reliance, facing your fears head on, trying new things, and so much more!

Then I decided to get a Masters in Business Administration, and I met my husband. Now we travel around the globe together and often. I love backpacks, vegetarian and vegan cooking and of course planning our next trip. I’m also kinda addicted to blueberries. =p

Check in on the blog or better yet follow PassportPages to get travel info from around the world. And definitely post your questions and comments. I love hearing from our readers! Cheers!

Samta, Founder, PassportPages

Other PassportPages articles you might like:

The Best Time To Go Whale Watching in Monterey Bay

Women’s Guide to Dealing With Beggars and Theft While Traveling

Animal Encounters at Chobe National Park, Botswana

9 Non-Obvious Things To Know Before You Book Day Trips



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