Guide to Stress-Free Travel Planning

Planning a vacation is simultaneously one of the most fun and also most stressful parts about traveling, but as with any task, when you break it up into manageable pieces and take it step by step, it becomes less daunting. I was recently asked whether I use inspirational or informational tools when planning a trip, and which resources I use. Quite frankly, it’s a mix of both, starting with inspirational sources to get ideas of where to go, then transitioning to informational resources when it comes to actually charting out the activities I want to do on the trip. Here’s my guide to stress-free travel planning, from start to finish.

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1. Get Inspired

(One year to six months out)

For me, inspiration for places to go comes from so many different sources, and in many forms. It also happens all though the year, sometimes even when I’m ON a trip already. I like to save interesting posts that I come across on my Instagram feed to check out later, and I read travel articles that pop up on my Twitter feed, or peruse the airline magazines when I’m on a flight. Delta Sky Magazine is a pretty good resource. It contains long pieces that cover a specific angle to an interesting destination, but also shorter guides if you only have a weekend in a given location. I particularly love their guides to a city five ways, which offers highlights of things to do and see in a city, morning to night, based on your particular interest (art lover, history buff, nature enthusiast, etc.). It’s a quick and effective way for me to think about visiting a place.

As for accounts that I follow on Twitter and Instagram to get inspiration, it’s the travel giants Conde Nast Traveler, Fodor’s, Lonely Planet, Matador Network, etc., and even other travel bloggers. Looking at the photos and captions might inspire me to think about a place that I hadn’t thought of previously. However, at times if I find my feed inundated with posts from a specific place and with photos that look very much alike (For instance, is anyone else sick of seeing photos of the Blue Lagoon in Reykjavik or yoga retreats in Bali?), I get turned off. That’s why it’s important to follow some unique bloggers and lesser known travel sites that you trust to go beyond what trendy right now. You might come across a hidden gem. I like Luxury Travel Blog, Art of Travel, and Passport Insta.  Conversations with friends who also travel have sparked interest in certain destinations as well. I’m lucky to have so many friends and family who enjoy traveling as much as I do.

Try it now:

2. Look for Deals on Flights and Hotels

(3-4 months out)

Steps 1 and 2 could be interchangeable, and in fact, for our last trip to Cartagena it was. Since we were signed up for email alerts from Scott’s Cheap Flights, we noticed the deal to Cartagena and then looked up the destination to see if there would be enough things to do there.

It used to be that we would think of a destination or time of year we wanted to travel, and then plan our trip around that. However, now, using several flight monitoring websites and apps, I now keep an eye out for deals, like with Scott’s Cheap Flights or Google Flights, which lets you keep track of flight prices on routes in which you are interested.

If you know your destination already, you can use the travel aggregator sites such as Orbitz,, Expedia and Travelocity to look for deals on flights and hotels. I use proximity to my desired location and price as my filters. For each trip my desire for ruggedness or luxury varies.  Most recently this worked out well for me in finding affordable, clean, and comfortable hotels for Key West (a charming bed and breakfast), Cancun (a spacious and elegant suite at the Emporio Hotel), and Miami (half-priced ocean view rooms at the Fontainebleau). Of course more recently for local destinations, we have also had luck with Airbnb.

Keep in mind that some airlines, such as Southwest, may not show up on these travel aggregator sites, so you have to go to their websites to search for flights. They might have some deals advertised on their websites as well. And of course, it’s worth checking out your rewards points and frequent flyer miles to see if it makes more sense to use those. For instance, when fares were just too high to fly to Victoria, BC, we used Delta miles that we had accumulated. I prefer to use these miles on longer journeys because you get more bang for your buck.

Consider the packages available on airline websites as well. Most have the ability to book the flight, hotel and car all together, though I have never tried that feature. Food and language are not a key consideration for me when booking travel because I don’t mind adjusting to a new place and figuring things out.

Try it now:

  • Sign up for email alerts from Scott’s Cheap Flights to get flight deals sent to you. The free version works just fine.
  • Create a Google alert for an upcoming or desired trip
  • Search one of the travel aggregator sites for an upcoming or desired destination and sort by distance or price to find a reasonable deal.

3. Plan for Health, Safety and Weather Precautions

(3-4 months out)

Before purchasing air tickets, if you are going on an international trip, check the visa requirements and that your passport is up to date in case you need to renew your passport or obtain a visa before the trip. If the dates of your flight are sooner rather than later, you’ll want to make sure you have enough time to get those materials in order

Of course, also keep in mind health precautions. Will vaccinations be necessary? Schedule time for those. Are you thinking of going to a country where Zika may be an issue? If you’re pregnant or planning for a family in the near future, you may want to avoid those destinations OR plan to take the necessary precautions, as advised by your doctor and the CDC.

Checking the State Department and CDC websites for travel advisories is a good idea in general, just to know what to expect.

Also, for both domestic and international destinations, I like to do a quick check of the weather. If it’s completely off season and it’s going to be a miserable time to go (as in rain, snow or excruciating heat that would make it difficult to enjoy and see the main sites), then I will try to pick a different time or place, which may take me back to Steps 1 & 2.

Try it now:

  • Check your passport– when does it expire?
  • Go to the state department website and type in an international destination you would like to visit. Look for the health and safety advisories
  • Use or Accuweather to check the expected weather for a desired destination- domestic or international.

4. Plan Your Activities

(2 months out)

Once you’ve decided where to go and booked your flight and hotel, now is the fun part. This is when you get to figure out what you actually want to do in your destination. For this, I use “listicle” guides to destinations that may be posted on travel news sites such as Travel + Leisure, Conde Nast Traveler , Lonely Planet, The Guardian’s travel section, LA Times Travel, New York Times Travel, etc. Normally I just Google “top things to do in XYZ” and clicking through the list of links one after another takes me to these main pages or other blogger sites.

I also use the official visitors’ or tourism board’s website for the destination to get basic information on the key things to see. Do not dismiss this as another government site! There is valuable information here. These sites tell me about the must-see attractions and even logistics of how to get there, fastest routes, etc.

Once I’ve looked through several of these websites, I’ll understand the key things to do in the region and then, I’ll identify those activities I will want to do on my own, or self-guided, versus those activities I want to book through a tour operator. I choose to book through a tour operator when it’s an activity that I cannot access myself or would be cost prohibitive, if it’s an activity I feel could be unsafe and I would want to go with someone who knows the area, or if I want to learn detailed information from an expert while I’m in front of the sites in person.

Based on this information, I search blog posts, Pinterest posts, forums, groups on Facebook and reviews on TripAdvisor to see which attractions are truly worth seeing.  For instance, for our most recent Cartagena trip, I kept hearing the mud volcano was a main attraction, but Pinterest led me to blog posts indicating that this excursion was not worth it.

I also look for specific recommendations on the best ways to view or visit that site or do that activity (spend two days? on foot? by train?). On Trip Advisor, reviews of excursions are usually linked to tour operator websites as well, so you can likely book from here. I will even follow some of the tour operators or local accounts on social media to get ideas of things to do in the months and weeks leading up to the trip.

Try it now:

  • Google top things to do in a particular destination and see what top sites come up. Using those sites, identify three key activities or places to check out at your destination.
  • Join a travel group on Facebook such as Girls Love Travel , or a forum where you can ask questions to other travelers.
  • For that same destination, find the local tourism or visitor website and identify two more places or activities.
  • Use TripAdvisor to search for one of the activities and related reviews.
  • Follow 2-3 tour operator accounts on social media

5. Build Your Itinerary 

(1 month to 2 weeks out)

Start plotting the different places you will be visiting on Google Maps to understand where they are located and which places are close to each other. This includes the restaurants and cafes you want to try as well. Start to jot down how much time you expect to spend at each of these places and begin to formulate a day-by-day itinerary for your trip.

For this, I found the Sygic Travel app to be useful because you can put together daily views of the places you will be visiting, and it populates on visually-appealing map with the walking or driving distances in between each. This new app allows you to easily shift different parts of your itinerary around to a different time or even a different day. I found this to be very useful both before and during our trip so I could work through the places I wanted to see as a checklist. If we ended up not going to a certain place on one day, I could easily shift it to the next and see how it fit with the rest of the plans. The app also allows you to add custom places and notes for your trip, and because it uses satellite to obtain your location, you can use the map offline in your destination even if you don’t have WiFi. This was extremely helpful in the streets of Cartagena’s old city!

Try it now:

  • Using your hometown, find and save a few points of interest on Google Maps. Using the directions feature, see how long it would take to drive or walk between each of these.
  • Download the Sygic Travel app and build a sample day trip to your hometown using these points of interest.

When you break down any process into manageable pieces and over a longer range of time, you’ll find that it’s far less stressful. Space these actions out over the course of several months: first, look for inspiration about six months to one year out, book your air tickets about 3-4 months out, and your hotel about 2-3 months out. Start researching things to do about 2 months out and book any tours about 1 month out. Put the itinerary together a couple weeks before your trip and then one week to a few days before, pack your bags! Bon voyage!

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