Helpful Tips for Planning Your Next Trip

Helpul Tips for Planning Your Next Trip - The Boston Day Book

It will come as no surprise that I love to travel. In 2017, we visited 4 countries (Japan, France, Bermuda, and Mexico) and 5 states (Vermont 2x, Florida, Maine, Texas, and South Carolina). Even though traveling with a toddler has its challenges, it’s still something that we prioritize since we love it so much.

When it comes to planning our trips, I spend countless hours from research to bookings. Although it is quite time intensive, it is one of my favorite parts of travel. I love looking at Google Maps and seeing what kinds of off-beat destinations might appeal to us. I keep a giant dream list of places and hotels that we might hope to visit someday.

Over the years, I have figured out a system that works well when planning travel. Here are a few ways that I research, book, and look for good deals:


My research often starts with inspiration. I love flipping through travel or design magazines (my personal favorite is Travel + Leisure) and jotting notes of places that speak to me. This can be in the form of a hotel, a city, or something more specific like a restaurant. When I’m feeling inspired by a certain destination, I will often search the internet and Pinterest for more inspiration. I have a huge bookmarked folder with all of the blog posts and round-ups that might come in handy someday.

Matt and I have been lucky enough to visit many places, and I like looking at an interactive map (like this one) to see where we haven’t been when plotting future trips. If I am planning a road trip or visiting multiple cities / countries in one trip (which is often the case for us), I like to use to see what flights are available between destinations. This part of the research phase takes a bit of time, as you have to decide whether it is easiest to fly, drive, or take the train between destinations.

Helpul Tips for Planning Your Next Trip - The Boston Day Book


I am very hotel-oriented and have a massive list of places on my radar. Matt and I have always loved small boutique hotels that are focused on customer service. Any place can have cool furniture and beautiful design, but customer service is always the most important (and memorable) aspect of a hotel stay for us.

I love researching places to stay and a few of my favorite sources include:

Travel + Leisure
Mr. and Mrs. Smith
Boutique Homes
Design Hotels
Relais & Chateaux
iescape (they have a kid-friendly section too)
Leading Hotels of the World
Tablet Hotels
Cereal Guides
Trotter Mag
Tiny Atlas
Culture Trip
– Depending on where I am going, I also look at Airbnb and Kid & Coe to see what options are available.

Instagram is a wonderful source of inspiration, too. Once you find an account you like, it’s nice to see what other trips / hotel stays they have planned. Instagram is a great discovery tool!

I also like to keep a running list of hotel groups that I like. If one of their hotels resonates with you, likely others will too! For our upcoming trip to Austria, we are staying at Haus Hirt which is part of the White Line Hotels group. All of their hotels look dreamy especially Sanders in Copenhagen and Kinloch Lodge in Scotland.

Helpul Tips for Planning Your Next Trip - The Boston Day Book


If you are flexible on when you travel, you have so many more options. Since Matt and I both work for ourselves we are lucky that we can usually be open to travel dates. I love using Kayak’s Explore page when I am open to where and when I want to go somewhere. You put in your home airport and then have a number of options to choose from including length of stay, season or month of travel, and price point. Then you move the map to see various deals around the world. It kind of reminds me of when I was young and would spin the globe to see where I’d like to end up. :)

If I know my destination and am semi-flexible on my dates, I also choose +/- 3 days when searching for flights. Sometimes leaving a day before or coming home a day later can make a huge difference. Also, many smaller airlines don’t offer flights every day, so it is best to be open-minded if possible.

If you have a specific destination in mind, I like signing up for notifications from Kayak or Airfarewatchdog. When a good deal surfaces, you will receive an email alert. As I mentioned above, I like using which I use utilize when planning routes. It helps tell you which airlines fly direct between destinations and will often include information about seasonal routes.

In less than two weeks, I am headed to Europe where I’ll be visiting several countries. I’ll be going to Austria (Salzburg and Bad Gastein), Slovenia (Lake Bled and Ljubljana), Hungary (Budapest), France (my grandfather’s farm), and a quick stop in Portugal (Lisbon). Where are you headed to next or dreaming of going? Any helpful tips that you’ve discovered along the way?

Image credit: Natalie Chassaigne Kurtzman (taken from a trip to Cappadocia, Turkey)

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