I used to be the last-minute kind of traveler. I’d scramble for deals, overstuff my itinerary, and come back more tired than when I left. But after learning how wealthy travelers plan their getaways, I started making a few small changes and it transformed the way I experience travel.
At first, I thought it was all about money. But as I dug deeper, I realized it was more about strategy than spending. Wealthy travelers don’t just throw cash at a trip; they plan thoughtfully, prioritize their energy, and design their vacations around personal joy and peace of mind. And guess what? Many of their habits are totally accessible even if you’re not flying private.
In this post, I’m sharing 10 habits inspired by millionaires that anyone can adopt. Whether you’re planning your dream trip or just want to travel smarter, these tips will help you make the most of your time away.
1. I Started Planning Earlier And It Made Everything Smoother
Rich travelers don’t wing it. They plan 6 months or more in advance and I can see why. I used to wait until the last minute, only to face sky-high flight prices and hotels that were either fully booked or overpriced. Once I started mapping out trips early, I got better deals, more choice, and way less stress.
It’s not just about scoring cheap flights (although that’s a bonus). Early planning gives you time to research the best neighborhoods, restaurants that require reservations, and experiences that book out fast like cooking classes or guided hikes. I now keep a simple spreadsheet with tabs for accommodations, experiences, food spots, and even local etiquette. It sounds intense, but it’s become my favorite part of trip planning.
Tip: If you know your travel dates, book your accommodation early even if flights aren’t released yet. You can often lock in the best boutique stays before they fill up.
2. Experiences First, Not Just the Price Tag
I used to make decisions based on what was cheapest. But millionaires often ask: What kind of experience do I want? Now, I do the same. Whether it’s an oceanfront villa or a guided food tour, I focus on what makes the trip special not just what saves me a few bucks.
This mindset shift changed everything. Instead of choosing the cheapest hotel, I think about where I’ll actually enjoy spending time. Instead of skipping a scenic train ride to save $30, I book it if it adds magic to the journey. One of my favorite memories was a splurge on a sunrise hot air balloon ride in Cappadocia. It wasn’t cheap but I’d do it again in a heartbeat.
Now, I budget for joy. I’ll skip an airport lounge pass or cut one night off a city stay if it means I can book something memorable.
3. Off-Season Isn’t Just Cheaper It’s Blissfully Quiet
One of the best tips I picked up was traveling during shoulder season. I visited Florence in November and had the Uffizi almost to myself. The weather was still mild, and restaurants didn’t need reservations days in advance.
Luxury travelers often favor off-season or shoulder season trips because they prioritize comfort and ease over checking a destination off a list during peak season. That quiet museum visit, that unhurried sunset walk they’re worth more than hitting every tourist landmark.
Now I check weather trends and event calendars before picking my dates. I avoid school holidays, cruise ship ports, and festivals (unless I’m going for the festival itself). The result? More space, more serenity, and way better photos.
Bonus: Flights and hotels are often cheaper too, but that ends up feeling like a perk not the main reason.
4. Wellness Is a Priority, Not a Perk
Luxury travelers often build in downtime: massages, spa time, slow mornings, and walks with no agenda. I started doing this and noticed a huge shift. Instead of needing a vacation from my vacation, I came back feeling actually refreshed.
Wellness doesn’t have to mean a full spa retreat. It can be as simple as scheduling one yoga class during your trip, booking a hotel with a sauna or soaking tub, or leaving a full day without plans to just sleep in, stroll, and see where the day takes you.
One thing I now do on every trip: I leave the morning after arrival completely open. No tours, no commitments. I ease into the destination, get grounded, and usually stumble upon something delightful by accident.
5. Concierge Services Changed the Game
At first, I thought concierges were only for the ultra-wealthy. But even mid-range hotels often have great concierge teams that can help you plan local tours, restaurant reservations, or transportation.
Once, a concierge in Vienna scored me last-minute opera tickets I couldn’t find online. Since then, I always ask you never know what doors they can open. They also helped me book a private cooking class in Chiang Mai, gave me insider tips for avoiding the crowds at Angkor Wat, and found a reliable driver when local apps failed.
Don’t be afraid to ask specific questions: Where can I get fresh seafood by the water? What’s the best time to visit the museum without crowds? Do they know a trusted local massage therapist?
Concierges live in these places. Tap into their knowledge it’s one of the easiest ways to elevate your trip without spending more.
6. Trip Insurance and Backup Plans = Peace of Mind
Wealthy travelers rarely skip trip insurance, and now I know why. After losing a non-refundable hotel booking due to a canceled flight, I started protecting my trips. It’s not glamorous, but having that safety net means I can enjoy my trip without worrying about the worst-case scenario.
It’s not just about weather disruptions or flight cancellations. I’ve had bags lost, tours canceled, and even gotten sick abroad. Travel insurance gave me coverage for medical visits and reimbursements I never would have expected. I now consider it a must-have especially for international trips or anytime I’m traveling during unpredictable seasons.
I also always keep a digital copy of my key documents (passport, IDs, confirmation numbers) in my email and a Google Drive folder. That small habit has saved me multiple times.
7. Rewards & Points Make It Feel Like a Hack, Not a Splurge
I always assumed luxury travel meant shelling out a ton of money. But many seasoned travelers use credit card points and loyalty programs to stay in 5-star hotels for a fraction of the price. I’ve started using a travel rewards card and I’m already planning my next trip using points.
By consolidating most of my spending on one travel rewards card, I earn points faster than I expected. Last year, I booked a business class ticket to Spain entirely on points. It felt surreal. These cards often come with extra perks too: free checked bags, lounge access, travel insurance, and upgrades.
If you’re just starting out, choose a rewards program that matches your travel style. If you like boutique hotels, avoid airline-branded cards. If you mostly fly one airline, consider co-branded options. A little research goes a long way.
8. Custom Itineraries Are Worth It
I used to rely on generic travel blogs and group tours. But now, I spend time customizing my itinerary based on what I actually care about. Whether it’s food, hiking, or photography, tailoring your trip makes every day feel intentional. Sometimes I even splurge on a local guide for half a day it’s always worth it.
9. I Built in “Work Time” So I Could Travel Longer
This one’s not for everyone, but adding a little remote work here and there has let me stretch my trips. A few hours of emails in the morning, and I have the rest of the day to explore.
This tip came from entrepreneurs who blend business with leisure and it’s helped me see the world without taking tons of time off.
10. Slowing Down Made My Trips More Meaningful
Instead of racing through five cities in a week, I now choose one or two and really settle in. I spent a week in Oaxaca instead of trying to do all of Mexico in 10 days, and it changed everything. I found my favorite coffee shop, chatted with locals, and didn’t feel like I was constantly packing.
Sometimes, less really is more.
Final Thoughts
I used to think luxury travel meant flashy hotels and expensive restaurants. But what I’ve learned is that it’s more about how you travel not just where you go or what you spend. By adopting a few habits from travelers who do it well (and yes, wealthier than me), I’ve made my trips feel more relaxing, fulfilling, and unforgettable.
These habits shifted my focus from “What’s the cheapest option?” to “What do I actually want from this experience?” And in doing so, I’ve found that I come home happier, more rested, and with richer stories to tell.
You don’t need a fortune to travel like someone who values their time, comfort, and peace of mind. You just need a mindset shift and a little planning. If even one of these tips changes your next trip for the better, it’s already worth it.
So the next time you’re planning a getaway, try thinking like a millionaire. You might be surprised at how much more enjoyable and intentional your travels become.
