Trip Planning

8 Simple Steps: How To Plan A Trip That’s Perfect

Researching and planning a trip can be overwhelming to think about, but it as actually pretty fun if you have a system.

The first time I went to Europe I did not have a system. I flew solo to Charles de Gaulle Airport in Paris. Once I got my luggage and got through customs I quickly realized I had no plan.  I had my address and that was it. I was there to study abroad for a semester, and had chosen to live in a pension in the City of Paris as opposed to living with a family in the suburbs, so I was on my own!

Dazed from my first ever experience of jet lag, I dragged my semester’s worth of luggage through the airport and walked outside, only to find a fancy car for hire right out the front door.  I decided I was sick of dragging luggage and got in, tired and not really thinking of cost.  As we were pulling away, I turned around and realized that the much more affordable cab stand was about 30 paces away, and had I prepared, even a little bit, I would have been able to figure that out.  That experience in Paris was formative in so many ways, including how I approach travel planning.

Fast Forward to Today

One of the questions I get most often from friends and readers is exactly that:  When researching and planning a trip to a new destination, what is my process?   This post shows a step by step process that shows balances dreaming with the practicalities of travel, and shows it does not need to be overwhelming!

Before you plan your own trip, you may want to check out my post on my 10 favorite travel apps.  Many can help with your research and planning process!

How to Plan a Trip in 8 Simple Steps

1) Start with a General Idea

Have you always wanted to visit China and see the Great Wall?  Do you want to spend two weeks in Tuscany?  Have a beach-y Hawaiian vacation with plenty of relaxation, but peppered with a few adventures?  Do you want to have one home base and take any day trips from that location or are you willing to switch locations so you can cover more ground?

Have your ideal trip in mind before you begin your trip planning. It will make the process easier because you will know what you are looking for.

2) Get to Googling

I start my research and use Evernote to save clippings.   You are looking for information on 1) Things to Do, 2) Fun Activities, 3) Weather at the time you want to go (or best time to get good weather), 4) holidays and festivals to consider, 5) what airport do you fly into, 6) will you need a car and if not, 7) how will you get from the airport to your hotel/lodging?

Research the Following Topics and Take Notes

  • Do some general searches Take some time, but not too much, to get a sense of the place.  Google is your best friend here.  Let’s say you are taking a long weekend to San Miguel de Allende in Mexico.  Search “Top 10 Things to do in San Miguel de Allende”. Several posts come up that reveals a ton of information right there, but it’s not done!  I add searches like:  “Local’s guide to …”, and “Foodie…”, “Insider tips ….” and depending on if it’s a family trip, girls weekend or just Pedro and I, I will also look for “… with teens”, “girls getaway ….” or “romantic ….”
  • Read blog posts – they can be rich with information.  I have often found tours that people took and loved, that I then further research based on their recommendations.
  • Start a wish list – As you skim through this search content, keep a list with things you want to do, places you want to see and stay, and food you want to eat.
  • Note “Day-Specific” activities – oftentimes things like farmers’ markets or street fairs are specific to certain days of the week.  If that is something you want to do, make sure to include that day in your travel window.
  • Note Day-Specific holidays or closures – the flip side of that is finding out what planned closures are happening so you don’t show up at your activity only to find it closed!
  • Note holidays and festivals that you want to attend, or avoid!

3) Research Flights and Lodging


If there is ever a deal-breaker on a trip, researching flights is where it happens for me.  “Wait, the trip to Milan is $2,000+ per ticket?  Hmmm.  Need to rethink”.  Sometimes it is because I just happened to choose the most popular time of year, sometimes it is because it’s just super expensive to get there.  I will either adjust to a different time of year if I can, choose a location that is just less expensive or save up for that splurge.   

  • Note on Travel Time: Consider the destination arrival time as you are making your flights.  When researching San Miguel de Allende, I found that the city is a 90-minute cab ride from the airport, so a flight that arrives at 11:30pm does not really work.  I would much rather leave earlier in the day and arrive in time for dinner. 


Let’s assume we find fares we can live with, and schedule that works so we can move on to lodging.  Draw on your earlier research here, because invariable, people will make lodging recommendations.  Beyond that, I use a combination of Google searches such as “Best places to stay in ….” and TripAdvisor for this.  The Google search gives me a general sense of what types of lodging is available and often, what areas to stay in. The TripAdvisor reviews are super comprehensive and you can really zero in on things that are important to you with the filters. 

Continuing the San Miguel de Allende example, I did this search and landed on Casa 1810 Hotel Boutique as a great place to stay.  I chose it based on all the research, the TripAdvisor reviews, and the fact that it apparently has an amazing breakfast!  I love lazy mornings with coffee and breakfast so finding a hotel that reportedly serves delish food is always a bonus!

4) Book Flight and Hotel

This is where the rubber hits the road.  Not much to explain here other than, double check your availability and book your dates!  And yes, it’s always a good idea to have a back up hotel in the case that the first one is fully booked.

5) Calendar Your Activities, Including Travel Time and Relaxation Time!

This is where we get super tactical.  I’m a visual person, so I like to create a calendar of my trip on one page.

Here is an example of how I calendared this out for San Miguel de Allende:Long Weekend Planner Example | Research | Plan | Travel

The Planner I use, filled out with a trip to San Miguel de Allende Mexico

Want This Planner? Get The Exact Planner That I Use for Trip Planning

If you want the exact planner I use to research and plan my trips, here it is! Just enter your name and email and it’s yours!

    Ok, now you have your calendar, let’s fill it out.   Start by gathering your top level information and research and filling out everything but the activities.

    1. Fill in the day of the week and & dates at the top
    2. Fill in your flight, hotel, and transportation info on the left side
    3. Jot down your list of things you really want to do, along with days they happen if applicable.

    Start by inputting your flights on the days where they take place so that you have an idea of how much time you are working with.  Once you have that in the calendar, input whatever is determined by a specific day (for San Miguel de Allende it was a Saturday Organic Market for example) .  Then, just start slotting in activities where it makes sense and based on when they are available.  Don’t forget downtime!  This trip is just a long weekend with lots of things I want to see and do.  For longer trips we often balance day trips and activities with relaxation days.  Make it work for you!

    6) Purchase Activities with a Long Lead Time and Get Those Coveted Reservations

    Most of your work is done, yay!  The one thing I would recommend here is to find out if any of your activities are likely to sell out, and book those now.  Same goes for reservations at any hard to book restaurants.  Other than that, your planning is done!

    7) Pack a capsule wardrobe appropriate to your destination

    In true She Packs Lite form, one step of your travel planning is figuring out what to bring. We are avid believers in packing a small travel capsule wardrobe, regardless of how long the trip is. The travel capsule wardrobe is a collection of clothing that all share the male color scheme. The idea is to bring separates that mix and match into many different outfits. To find out more on how to pack a travel capsule wardrobe check out this post:

    How to Create the Ultimate Travel Capsule Wardrobe

    8) Finally, Trip-Planning is Important, But Be Flexible Once You Arrive

    This one happens once you are on your trip.  I know this list comes across as super Type A, and it kind of is.  What I have not mentioned is that it it’s just a framework.  With the exception of things that are pre-paid, all these plans are subject to being shuffled, changed or just not happening.  Sometimes I think it’s fun to sit at a cafe and watch the world go by, and that is ok.  I’d rather skip things on purpose than miss something I did not know about.

    So now, many years later, I am not likely to show up at an airport with no plan whatsoever like I did in Paris.  Following this process I feel much more prepared even for trips where the main goal is to sit in a chair at the pool and read a book.  I hope you found this helpful, and if you decide to give this process a shot let me know how it goes!  And of course, if you want to hear more from what we are up to, subscribe below!

    xo Anne

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