It happens to everyone. You’ve finally decided where you want to go with your hard-earned holiday or vacation but the idea of planning something seems like twice the work! Where do you even start? Here are my “Ten simple steps to planning a holiday or vacation” that is perfect for you!
I’ve made all the mistakes that there are to make (hopefully) and I’m here to teach you what I have learned so that you don’t have to feel the travel pain. Not me, for you. Because, when you are on holiday, shouldn’t it always be all about you?
In this guide I take you through a 10-step countdown from 6 months to the day before you depart to make sure you cover off all the steps and considerations in making sure that you have the time of your life! A long-haul destination or multiple week trip will take at least 6 months to plan but gives you loads of time between tasks, so you aren’t overwhelmed. A short-haul or weekend break may only need 3 months of planning. Again, the goal is to start early so you have plenty of time to research and not feel stressed. We all have plenty of stress anyway, right? This is meant to be fun and exciting as you get closer and closer to your vacation! So, let’s get started…
6- 3 months before you go:
Step 1: Trip Length
Get a sense for how long you think you’ll need to stay at your destination. Is this a weekend jolly or week(s)? I will do some initial research using a “Top things to do in…” list from TripAdvisor, Lonely Planet, or Conde Nast Traveler just to get a sense of what there is to do in my destination and surrounding area. If you are going on a “bucket list” trip to do a specific activity then jump to Step 4, Part 1 to read my advice on planning an itinerary. Once I know how many days I’d like to visit then I move to…
Step 2: Investigate travel requirements
Do you need a visa to travel to this destination? While many places are open for leisure travel for up to a month without a visa, you don’t want to be the visitor that has to pay 3 times to price to buy a visa in the airport at midnight because you didn’t plan. Also, some places are strict, and you will be required to have an approved visa before you invest in flights.
Step 3: Book Flights
Personally, I am a fan of loyalty programs when booking flights. Whether you use a miles-earning credit card or points, the farther out you book then the better your options- especially if it’s a long-haul flight. Kayak has a feature that suggests if, according to market factors, whether to buy now or later. 
In general, Tuesday evenings are rumored to be the best time to book flights. But don’t take my word, here is a fabulous article from Skyscanner that totally agrees with me!
This is also often the most expensive part of a trip so it’s good to get this expense out of the way. Think of it as a personal installment plan 🙂 Plus once your flights are booked then you are going on holiday! Yay!!!!
3 -2 months:
Step 4: Accommodation – Where to stay?
Part 1: Choosing your location
Choosing which part of town you’d like to stay has everything to do with what you’d like to do and how much you’d like to spend. Going for a stag do or bachelorette party? Old town tourist district! Cheap drinks and 6 people smashed in a room! Whhooooooooo!!!!!!
OR
Maybe a neighborhood that is slightly more residential that sits adjacent and it’s a 15-minute walk to key sights and activities is more on the money? Neighborhoods close to the tourist district are often cleaner and much cheaper than staying in the touristy areas. If you would like to be close to the action but still get a good night’s rest, stay 2-3 streets away from the streets touted as having a good “nightlife” on TripAdvisor (read: drunk tourists). Either way, walking is your friend when exploring a new destination so keep close, but not too close, to whatever you are planning on the trip.
Part 2: Type of accommodation
We live in fantastic times where there are a whole host (ha! Get it?) of accommodation options. Do you stay in a hotel or Airbnb? My recommendation is to consider if a) you want to be waited on or left alone and b) how close is the culture in your destination versus your own?
If you are traveling in your own country or region, Airbnb it up! If you are traveling to the countryside in your own country or region then I’m a fan of a holiday rental like you might find on Homeaway.com or Airbnb. But, as much as I am an adventurous traveler, I’m not ashamed to admit that, the more foreign the destination to me, the more I rely on the familiarity of a hotel to ground me when I am done exploring at the end of the day – plus, it’s nice to have access to reliable WIFI and a helpful front desk when you are planning to go properly exploring during the day. And sometimes, you just want to relax, drink margaritas, and not change your own bedding. There are special hotels for you, my friend, called “all-inclusive”. Check your free will when you check your bags!
Finally, no matter your accommodation type, make sure to do a Google street view 360 view of your choices and their street. A lot can be determined from the non-website exterior views of your location and accommodation – especially if you are considering a rental or local hotel.
2 Months:
Step 5: Start researching activities
Part 1: Do you need to book early tickets or reservations?
If you are interested in booking something special like a Michelin star restaurant, popular theater or concert tickets, a day trip or transport from 1 destination to another, now is the time to investigate. If a special activity is the reason for the trip, do this step first. I say this as someone who is 2 days away from her “bucket list” trip to the Alhambra only to learn that the Alhambra was sold out even before we booked our flights! DOH!
So, if you are going to Jordan to see the ancient city or Copenhagen to eat at Nopa, book that first and then build to trip around the event. Also, in a less developed country, you may want to investigate city to city transportation before accommodation because trains and buses will often only run on certain days. Also, large events like a concert or convention may cause accommodation to be expensive or sold out so that could also impact your accommodation options.
Part 2: What activities are the “must” do vs. the “you” do?
When visiting certain destinations there are certain things that you simply must do. Its part and parcel of the experience and, frankly no one will believe and, thus, impressed that you were there without the obligatory selfie! Paris without the Eiffel Tower! Sacre Bleu!
Then there are the things that align with your personal interests that you want to experience. I love a good walking food tour. In my experience, it opens so many doors for other trip discoveries. I get access to a local tour guide, meet other travelers, get a feel for the city and its history, and get to eat great food! Whatever your personal interests, here is a general timeframe for when you to pre-book tickets:
| Interest | Timeframe |
| Day Trips outside of city | 3-2 weeks |
| Food Tours | 3-2 weeks |
| Popular sights | 2-1 week |
| Concerts/ Theatre | 2-1 month |
| High-end restaurant | 2 – 1 month |
| The Alhambra, Granada, Spain | 4 – 3 months (DOH!) |
1 Month:
Step 5: How am I getting around?
Now is the time to see if you need train tickets or a rental car. While you are at it, find out what the airport to accommodation situation looks like. It may be an appropriate time to pre-book a shuttle if necessary.
Step 6: Start planning your days!
Again, if there are things that you must do, prioritize them! This is your trip! You can do anything that you like! If you are finding that most of your activities are common attractions, then investigate if there is a tourist or city pass available. A city pass is often an economical way to skip lines and save a few bucks. Some even come with public transportation tickets included!
I also recommend seeking recommendations from trusted sources. As a foodie, culture vulture, I consult my own well-traveled friend network, the Telegraph newspaper travel section, Culture Trip.com, Anthony Bourdain’s recommended restaurants, TripAdvisor for reviews, and scan various creditable blogs that appear in a web search.
I have a simple formula to planning that has proven to work well for me. I start with a day dedicated to the destination’s history. I’ll visit the history museum or a key historical sight to kick things off. I found that understanding the evolution of the destination gives me understanding and context for the rest of the trip. As previously mentioned, I try to book a food tour on that first day also. A food tour generally also helps to guide my culinary choices for the rest of the trip too. No McDonalds for this lady! Well, maybe a Starbucks in the airport on the way home but who’s keeping track, right?
When planning my days, I know that I will start the trip eager and energetic but start to slow down as the trip progresses. I’ll plan a few stops on Day 1, Maybe 2 or 1 on Day 2 and then 1 on the last day leaving loads of time for other activities that I discovered once there. I always recommend ending the trip with the most relaxing activities. Trust me when I say that you want to start with Bangkok and end at the beach (for many, many of reasons).
2-1 Weeks:
Step 7: Anything that you haven’t arranged? Here’s a handy checklist:
- Airport transportation arranged? Have you researched much it will cost?
- Check in times confirmed with accommodation? Have you printed the address in case there is a language barrier with your driver?
- Do you need to have foreign currency upon arrival? Or can you pull money from an ATM in the airport?
- Have you notified your bank that you are going to be using your credit cards abroad?
- Will your phone plan work at the destination? Do you need a special temporary plan?
- Do you know how to turn off data on your mobile phone if you only want to use free WIFI?
- Are their key language phrases that you should practice?
- Did you make travel insurance arrangements?
1 Week:
Step 8: Start packing
Do you have any activities booked that require special gear or supplies? You have one weekend to buy or find all your bits and bobs! No last-minute rushing around for you, well-prepared traveler!
Shameless plug: Stay tuned for my “How to pack for holiday like an expert!” post later this month!
1 Day: Clean
Step 9: There is nothing better than coming home from a relaxing holiday to a clean, organized home. It takes a little bit more effort but post-holiday you will thank you for it. It makes re-entry into daily life just a little bit easier. Enjoy every moment of your holiday. You’ve earned it!
Step 10: