This is part two of my travel planning series—designed to help you plan better, travel smarter, and enjoy every trip more.
In part one, I showed you how I choose destinations, find design-forward hotels, and book flights that balance value and comfort. This time, we’re getting practical: budgets, daily itineraries, and the easiest way to plan what to pack.
If you missed part one, catch up here.
We’re in the middle of planning the perfect vacation—and I’m sharing my exact process from start to finish so you can do it too.
In part one, I walked through how instinct, inspiration, and aesthetics shape the early stages of planning: choosing a destination, booking a design-forward hotel, and making sure the whole trip feels aligned before you ever press “confirm.” But a great trip isn’t just about ideas, it’s about execution. That’s where this guide—part two—comes in.
In this post, I’ll show you what happens after the hotel is booked: how I build a realistic (but luxury-aligned) budget, gather recommendations without getting overwhelmed, map out a flexible itinerary, and plan outfits for easy packing. Whether you’re planning your next vacation or just dreaming of one, this is the part that turns inspiration into reality.
Inside, you’ll find:
The exact ChatGPT prompt I use to build luxury-aligned budgets in minutes
How I easily sort through hundreds of recommendations to narrow down what to do and where to go
A tool that maps your itinerary down to the neighborhood, walking time, and vibe
My favorite way to visually plan packing lists without spreadsheets or stress
In partnership with Zeen
If you haven’t figured it out by now, I’m a planner through and through—and yes, that includes what I wear on my trips. I rely on editorial-style moodboards to map out the full vibe of a trip in advance and build mix-and-match outfits with a cohesive throughline. (Being able to mix-and-match helps me pack lighter, smarter, and more stylishly.)
For years, I did this in Photoshop—an hours-long, manual process that required way too much time and effort. Then I found Zeen: a beautifully minimal digital collaging tool that replicates my system, but only takes seconds. It’s clean, intuitive, and actually really fun. Sign up using my link and get 3 months of Zeen Pro for just $0.99 to try it out for yourself.
As much as I love luxury, art, and beauty, I still have to stay grounded in reality, and that means building a clear, robust budget for every trip. Luckily, ChatGPT comes in handy here, too, making this part easy even if you’ve never built a budget before.
When budgeting, I consolidate the major costs—hotels, airfare, and some rough daily spending estimates. It helps me decide where to splurge and where to scale back.
Here’s an example of a ~$5k trip (where part of the hotel costs are expensed):
Chat GPT Prompt: I’m planning a summer trip to Menorca for two people and need help estimating a realistic travel budget. We’re staying 7 nights total — 3 nights at Son Blanc and 4 nights at Torre Vella. Flights are booked with points, so I just need a breakdown of expected spend on hotels, car rental, food and drinks, one boat day excursion, and a small buffer for miscellaneous costs. Assume mid-to-upper-tier pricing. Please format it as a clean table with two columns: “Category” and “Cost.” Show the total trip cost, subtract the Son Blanc stay as a business expense, and display the final out-of-pocket cost.
💡 Pro tip: Ask ChatGPT if you’re forgetting anything in your budget—like trip insurance, international data plans, or tourist taxes/resort fees—as these can vary based on the destination(s) you’re planning to visit.
Using the trusted resources I outlined in part one, I start gathering information on where to eat, what to see, and what to do during the trip. Anything that catches my interest gets saved into a Notion page as one big brain dump. Whether it’s a highly recommended restaurant from Yolo Journal or a must-do activity from a trusted friend, I make sure to note the source of each one.
Once I have a solid pool of options, I’ll copy everything and paste it into ChatGPT. I ask it to tag each recommendation with its original source and organize everything into one clean, categorized list.
ChatGPT Prompt: "I’m going to give you a list of Menorca recommendations pulled from several different sources. Please do the following: Denote the source of each recommendation using a unique icon; Group the recommendations into categories such as 'Where to Eat,' 'What to Do,' 'Where to Stay,' etc.; Keep the formatting clean and organized for easy reference."
I get recs from so many different places that it can get overwhelming to keep track. This helps me organize everything I want to see and do—and prioritize the spots with the most cosigns.
Once I know what I want to do on the trip, I can start building an actual itinerary, which for me means loosely slotting activities into specific days.
I’m not someone who likes to fill every day with plans. I like breathing room—time to enjoy the hotels I’ve so carefully chosen, a slow afternoon at the spa, space to wander, or simply time to rest. Especially on this upcoming trip.
Where my itineraries “live” depends on the kind of trip I’m taking, which I divide into two categories:
For faster-paced (usually city-based) trips, I use Wanderlog to organize everything by neighborhood and category. There’s usually a lot to pack in when visiting cities, so you have to optimize based on proximity. Wanderlog is a one-stop shop that keeps all the info you could ever need organized in one place (without you having to add it), and even tells you the distance between two points on your itinerary (whether you’re walking or taking a taxi or public transport). I used it in Japan and don’t think I could have survived without it.
For slower-paced (usually beach) vacations, I create an “itinerary” in Notion, which is more a list than a strict agenda. There might be some restaurants to try and sights to see, but most of my days will be based on vibes and of-the-moment whims. It’s something to reference, not follow.
For me, planning travel is part instinct, part obsession, but when done right, it transforms my entire trip. You stop moving through your days like a tourist on a sightseeing conveyor belt and more like a version of yourself that’s fully present: you notice more, stress less, and leave so much space for spontaneity—and that’s where the magic always happens.
If you’ve made it through both parts of this guide, you now have the exact tools I use to bring my dream trips to life—from choosing a hotel that sets the tone to planning outfits that match the mood. Hopefully this is proof you don’t need to be a spreadsheet person or a full-time traveler to make your vacations feel more artful and intentional. You just need a system that works for you.
Now I want to hear from you: what are your favorite tools, rituals, or hacks when it comes to planning a trip? What do you always forget? What would you love a guide on next?
Whether you’re in the midst of planning or just mentally packing your suitcase, I hope this gave you helpful tools—and a little inspiration!—to plan your next great escape.
Window Seat covers the intersection of luxury hospitality, aviation innovation, and the culture of modern travel, written by Tori Simokov, a writer and designer based in New York. For partnership opportunities: tori@v1projects.com. You can also connect with her on Instagram, TikTok, or ShopMy.
I so appreciate people sharing their ChatGPT prompts and as someone who similarly denotes sources for their travel “lists” this is brilliant!
Great post as many new to me tips especially how to use ChatGPT! Based on your previous rec, I now subscribe to Wanderlog (used for 3 week Japan trip and am keeping running lists on it for various places. Guess I’ll have to take a look at Notion too and so happy about your zeen rec as I’ve been curious about digital collaging.