How I Choose My Travel Destinations (and Loosely Plan My Itineraries)
READING
Before we get into this month's books, a little housekeeping.
My reading has been suffering lately.
Not in a dramatic, "I've fallen out of love with books" sort of way. More in a "it's the end of the school year and my brain is completely fried" kind of way.
If you're a teacher, you get it. The students are done. The teachers are done. Patience is running low, behavior is ramping up, and there are approximately 437 end-of-year tasks that all need to happen before summer break.
I've started and abandoned more books than I'd like to admit, and instead have found myself reaching for podcasts about travel, relationships, and personal growth.
What I have noticed, though, is that the books holding my attention right now all have one thing in common: they make me want to go somewhere.
Have you ever been inspired by a book to visit a place?
I certainly have.
Elin Hilderbrand sent me to Nantucket. Carley Fortune put Prince Edward Island on my list. And as I plan my upcoming trip to Scotland, I'm finding myself drawn to stories that transport me there before I ever board the plane.
If I can't focus on a big literary masterpiece right now, I'll happily settle for a book that takes me someplace beautiful.
BOOKS THAT INSPIRED TRAVEL (FOR ME)
A book that sparked my interest in visiting Prince Edward Island
Nantucket does not disappoint, these books will take you there without leaving the comfort of your reading nook: Hotel Nantucket, 28 Summers, The Five Star Weekend, and The Perfect Couple **These are all available for FREE on Kindle Unlimited!!**
I am listening to Mothers and Strangers, this is exactly the type of book I love and I am struggling to stay focused
Recent ARCS I have been enjoying, along with release dates! (Pre-Order NOW)
Heather (June 9) - Set in the NJ Pine Barrens
It Could Have Been Her (June 23) - Lisa Jewell's latest
Crash into Me (July 7) - If you read The Idea of You, you are highly anticipating this one
The Shampoo Effect (June 30) - I loved Pineapple Street so much, hoping this one is just as good if not better
MUSING
How I Choose My Travel Destinations (and Loosely Plan My Itineraries)
People often ask me how I choose where to travel next. The truth is, I don't have a complicated system. Most trips begin with a tiny spark of curiosity that slowly grows into a full-blown obsession.
Here's exactly how I choose my destinations and plan my itineraries.
Step 1: Build a Travel Bucket List
Every trip starts long before I ever book a flight.
I'm constantly collecting places. A recommendation from a friend. A beautiful photo on Instagram. A travel newsletter. A podcast. A movie. A random article I stumble across on a rainy Sunday morning.
More often than not, though, my travel is inspired by books.
Elin Hilderbrand sold me on Nantucket long before I ever stepped foot on the island. After reading countless novels set there, I finally booked a trip and discovered that it somehow managed to exceed my expectations. The hydrangeas, the beaches, the cobblestone streets, the bookstores, the bike rides. It was every bit as magical as I imagined.
The same thing happened with Prince Edward Island. Before I ever saw it in person, I had already fallen in love with it through Carley Fortune's This Summer Will Be Different.
Books have introduced me to some of my favorite places, and anytime a destination sparks my curiosity, it goes onto my travel bucket list.
Step 2: Figure Out What's Realistically Possible
As much as I'd love to disappear whenever the travel mood strikes, I work full-time as a teacher.
That means my travel windows are limited to summer break, long weekends, and school holidays. Unfortunately, those are also the times everyone else is traveling.
Before I get too attached to a destination, I ask myself a few questions:
How many days do I actually have?
Is this a one-location trip or a road trip?
How much time do I want to spend moving around?
Will I need a rental car?
How many hotel changes am I willing to deal with?
This step helps me narrow my options and determine whether a destination makes sense for the amount of time I actually have available.
Step 3: Research Like It's My Part-Time Job
This is where the fun begins.
Once I've chosen a destination, I go down the rabbit hole.
I read Reddit threads.
I join Facebook groups dedicated to the destination.
I listen to podcasts.
I read blog posts.
I watch YouTube videos.
I save Instagram posts.
I search suggested itineraries and travel guides.
I ask people who have already been there.
Then I create a giant note in my phone and start collecting everything that catches my attention:
Bookstores
Cocktail bars
Walking trails
Cafes
Hotels
Historic sites
Hidden beaches
Small towns
Restaurants
Tours and experiences
At this stage, I'm not planning. I'm gathering possibilities.
Step 4: Build the Route
Once I have my giant list, I start looking at a map and figuring out the logistics.
What route actually makes sense?
Where should I base myself?
How many nights should I spend in each location?
What order should I visit things?
I usually identify a handful of experiences that I absolutely don't want to miss and build the trip around them.
Then I intentionally leave space.
I've learned that trying to see everything is a terrible strategy. Some of my favorite travel memories happened because I had nowhere specific to be.
A wrong turn.
A bookstore I wasn't looking for.
A beach I stumbled upon.
A conversation with a stranger.
A scenic drive that wasn't on the itinerary.
Those moments rarely happen when every minute of the day is scheduled.
Step 5: Book the Essentials and Leave Room for Magic
Once the route is finalized, I book my flights, hotels, rental car, and any experiences that truly require reservations.
I also make a list of restaurants I want to try, especially vegan restaurants.
Then I stop planning.
One of the best parts of solo travel is having the freedom to change your mind.
Want to spend another hour in a bookstore? Go for it.
Want to sit by the water and read all afternoon? Nobody is stopping you.
Want to skip your plans and wander instead? Even better.
In fact, one of my favorite things to do when traveling alone is grab a seat at the bar. I've gotten local recommendations, hidden gems, bookstore suggestions, hiking trails, and some wonderful conversations simply by talking to bartenders and locals.
Every single trip, they point me toward something I never would have discovered on my own.
And those unexpected recommendations often become the highlight of the trip.
The older I get, the less interested I am in checking boxes.
I'm not trying to see everything.
I'm trying to experience a place.
That's why I plan just enough to feel prepared and leave enough room for something magical to happen.
If you need help planning and organizing, reach out to me and we can work together, This is my love and passion after all!
My mom, currently in Italy
RECOMMENDING
My under $40 set from Target
I want this for all my summer adventures
I’ve heard great things about this under $40 set. I picture riding a bike with a picnic basket wearing this ;)
A great shirt to throw on top of the above mentioned set
And if in New England, I must have this
Love the crinkle on this suit, reminds me of Hunza G for a fraction of the price. Just ordered in the fun green
This feels very Nantucket to me
Speaking of Tuckernuck. This just arrived and I am super excited to wear it!
ODDS & ENDS
Book Club
Some great summer trip ideas, not far from us
My next trip, I am booking someplace with a Martini Trolley
Friend clubs - love some of these! Which one(s) sound most appealing to you?
