Mapping Out Travel Memories

My method for planning unforgettable trips.

Thomas here.

So, you've booked your flights and probably your lodging. Now comes the tricky part—filling your itinerary with activities that transform a trip from good to unforgettable. For me, this stage is both a joy and a challenge. I love diving into the details, discovering hidden gems, and crafting experiences that feel personalized. Yet, there's also a deep sense of pressure—it feels endless, and since I'm responsible for 100% of the initial planning before getting final approval from Julia, the stakes feel high. During a particularly long dinner in France, a friend asked if I enjoyed planning trips. My honest reply? "It gives me more pain than joy but it’s worth the investment."

If you've ever felt overwhelmed or unsure where to start, here's my straightforward, stress-reducing approach to itinerary planning.

Step 1: Establish a Blueprint

Every great trip begins with structure. My go-to method is a meticulously organized spreadsheet. Columns typically include:

• Date

• Start Location

• End Location

• Breakfast

• Morning Activity

• Lunch

• Afternoon Activity

• Dinner

• Daily Notes

This spreadsheet forms the foundation, ensuring each day flows logically and balances exciting activities with necessary downtime.

Step 2: Gathering Recommendations

There are no shortages of recommendations for things to do on your travels. Below are a few of my favorites methods for collecting recs.

Trusted Advisors and Friends

• I start by consulting our reliable travel advisor (huge thanks to Louisa!), who deeply understands our tastes and travel habits.

• I also tap into friends who have visited our destination, gleaning insights and candid reviews to guide our choices.

Local Concierge

• A skilled concierge can elevate your trip. I collaborate closely with local concierges from hotels, villas, or specialized agencies. A great tip: craft a detailed "family travel resume" outlining your preferred travel style, likes, dislikes, and activities we typically enjoy or avoid. This ensures recommendations match our unique preferences.

Instagram as a Travel Guide

Coccaro Beach Club was an Instagram find and favorite from Puglia last summer.

• Instagram isn’t just eye candy—it’s a dynamic resource. I love exploring carousel posts that function as mini travel guides, rich in local tips, charming eateries, and tucked-away spots not featured prominently elsewhere. Scrolling through Instagram tags and location markers feels like peeking into personal travel diaries, offering practical, vivid insights that traditional guidebooks miss.

Travel Blogs: Beyond the Obvious

I discovered Spello in Umbria, Italy from multiple blog recommendations

• Travel blogs sourced through Google or Pinterest offer an authentic, narrative-driven approach. Bloggers often capture hidden gems, candid reflections, and nuanced experiences with a depth of storytelling rarely matched by commercial travel sites. These personal accounts resonate more strongly, allowing me to vividly imagine my own family in those scenarios and better tailor our adventures. I find there's a sweet spot in the google search results between 5-15 where the recommendations top those from the top 3 results which are normally websites that are more business and less personal. One of my favorite discoveries during my Paros searching was from a blogpost about restaurants written by a local scooter rental service on the island.

Leveraging Technology

• ChatGPT: The latest GPT models are invaluable—especially when customized with our "family travel resume." A cautionary note: GPT often leans on TripAdvisor, so cross-checking is essential. However, its detailed, tailored itineraries and thoughtful suggestions are impressively useful.

• YouTube: I make treadmill or rowing sessions productive by watching travel vlogs. These videos give a realistic glimpse into destinations, helping set accurate expectations far beyond picture-perfect Instagram or inconsistent Google images. Remember, vloggers travel differently, so I use these insights primarily to discover hidden highlights or avoid pitfalls.

Step 3: Pre-Exploration and Discovery

There are few substitutions for the level of exploration and discovery that can occur once you're on the ground in your final destination (that's why I always try to leave empty space in the itinerary later in our stay). You can however go through a pre-exploration and discovery phase if you want to take your plans to another level.

• Instagram & Maps: While expert recommendations and curated travel guides are invaluable, they often spotlight already popular places. For truly unique finds, I rely heavily on maps—both Instagram’s tagged locations and Google Maps. Virtually exploring through these tools helps uncover breathtaking spots and local favorites that haven't reached mainstream attention. Satellite views and street-level imagery add another layer of clarity, showing the true charm and practicality of potential discoveries. I discovered this beach location two summers ago in Portugal thanks to some Google Maps exploration. It was one of our favorite spots.

I discovered Praia da Aberta Nova in Comporta by exploring Google Maps

Step 4: Organizing

This year, I've adopted ChatGPT’s advanced o3 model to distill my extensive list of recommendations into a practical itinerary aligned with my established blueprint. Over multiple iterations, adjusting preferences such as evening downtime and midday breaks, ChatGPT streamlines the process effectively. After getting the itinerary about 80% of the way there, I make final tweaks manually in my spreadsheet. Once finalized digitally, I present the itinerary to Julia for any tweaks, ensuring it perfectly aligns with our family's pace and preferences.

Step 5: Booking

At the point where the itinerary feels solid, I move into booking mode. By this stage, logistics like transportation and accommodation are already settled. Booking 30 days or more in advance generally ensures availability, especially for sought-after restaurants that typically open reservations exactly one month prior. Our concierge is instrumental at this stage, leveraging their local networks and expertise to secure optimal dining and activities, skillfully navigating local booking nuances.

Color Coding for Clarity

My spreadsheet features a simple yet effective color-coding system:

• Yellow: Needs booking

• Orange: Awaiting confirmation from a third party

• Green: Booked

This visual system makes tracking progress and prioritizing next steps effortless and intuitive.

Final Thoughts

Careful planning significantly reduces travel stress, enhances enjoyment, and creates space for memorable moments. Your itinerary is the key to unlocking a seamless and deeply rewarding travel experience tailored specifically to your family’s unique style.

Happy planning!