Ten Tips to Travel like a Boss

Gary Gorny
8 min readMar 20, 2023

1. Money buys happiness…if you spend it wisely

Before preparing for any trip, the first thing I do is set aside an annual budget for travel. My go-to is, trips may not exceed 10% of my after-tax income, which for me, is $8K per year. Annually, I’m aiming for 4 trips a year, 2 abroad, and 2 domestically. This means that I may NOT spend more than $2.5K per trip internationally, or $1.5K domestically (unless I spend less on a previous trip, or take less trips, in which case, if needed, I can use the savings to offset/justify higher expenses). To ensure I stay within budget, I literally have a spreadsheet with every cost I’ve booked/incurred. Every flight, hotel, and attraction is documented in my spreadsheet, by trip, and I also add $100 daily for food, entertainment, souvenirs, and unplanned, miscellaneous expenses (which I ensure I stick to!). Wherever possible, I try to travel with friends, to split hotel expenses, to split car rental costs, if applicable, and to identify group discounts.

2. The early booking always gets the savings worm!

So, now that you have seen my budget, you may be asking, “Gary, how do you afford all these exotic vacations? You’ve been to expensive Switzerland, exotic India, and half the world away to Australia, how can you afford all these with your limited budget?” The answer is actually quite simple! Always book your flights over 6 months in advance, for the best deals. I was able to book round-trip flights to Switzerland for less than $500, to Australia for under $1,000, and to Brazil for $800. Same deal with hotels; whenever I booked one at least 2 months in advance, I’ve never had to pay more than $150 per night. Definitely research where hotels are located, too! Once, in Charleston, I naively booked a hotel, which turned out to be a one-way, 30-minute Uber ride from downtown, each way, and that was an expensive lesson! Now, before I book, I always confirm: Are the hotels within walking distance to places? Is parking included? May I add a free breakfast? Once the flights and hotels are taken care of, all that’s left is to figure out how to get around. A month before travelling, I analyze transportation options. Where do the trains go, and when? Are there ticket or rail passes? Are they cheaper than renting a car? If I take public transportation, how much more time will this take than simply renting a car? If I do rent a car, how much of a hassle and cost is parking? What makes logistical AND economical sense? Driving, public transportation, or Rideshares? My go-to lifesavers are Expedia for flights, car rentals and hotels, Booking.com, Airb&B, and VRBO for lodging, and Viator for activities, sites, and excursions.

3. No prep is crap!

Plan out an approximate itinerary to the day. A month before a trip, I always put an Excel spreadsheet together. This includes a daily itinerary, including sites to see, how I’m getting from one attraction to the next (walking? Train or bus? Uber? Car rental?), broken out by day AND by time period (morning, afternoon, evening, night). Any sites, entertainment, etc, I research and book online, at specific times. My spreadsheet includes attractions, sites, transportation time, and time for breakfast (45 minutes), lunch (60 minutes), and dinner (90 minutes). My go-to for planning activities is Viator for activities and excursions. Being prepared minimizes my time figuring things out; I can jump right into activities or excursions. A detailed, tangible plan saves me valuable time, keeps me focused, and allows me to maximize points of interest, rather than wasting time figuring out where I’m going, and how I’m getting there.

4. Be a chameleon, not a target!

Blend into the crowd, but don’t put a target on your back. Dress casually and comfortably. Unless you’re going to a wedding, business meeting, or fashion show, leave the suits. Wear comfortable sneakers, at home, as they just scream “I’m rich, go rob me!” Avoid wearing jewelry, including necklaces, chains, and watches, unless you want to attract the attention of pick-pocketers and thieves. But do and rock those t-shirts and shorts when it’s warm out, the hoodie and sweats for hikes, and jeans and a coat for just walking around the city. Always carry one credit card and some cash, while keeping at least one more credit card (and always carry cards without foreign transaction fees) and more cash in lock box at your hotel.

5. Stock it, lock it, block it!

Lock your passport, but not before making a copy of it, and carry the copy around! Loc a credit card and some emergency cash into that same lockbox. For the credit card and cash you do carry, and your phone, always put these into your front pockets. This way, if thieves try to steal from you, they will need to first touch your dick or vagina, before pickpocketing you, and you will notice that right away! When moving between cities, make sure your wallet and passport are in zippable or lockable, deeper pockets; wear shorts or pants that can zip up or/and button up and have plenty of room to store small items. Always be 100% aware of where all your stuff is, and NEVER leave bags unattended. You can be like my mom, who had her purse stolen at Virginia Beach, while leaving her bag while she took a walk….or you can be like me, who never had any issues in Italy or Spain, countries notorious for pick-pocketers.

6. The social butterfly flies with her wings intact!

When in a less safe neighborhood, or going out at night, travel in groups! If possible, my favorite way to travel is with friends. There is strength in numbers, as thieves and criminals are not ballsy enough to take on large groups. This is even more critical if you are a woman, especially if you plan on going to bars and clubs. Bring a friend…male, female, boyfriend, double date….the more the merrier! The friend(s) need to make know where you are at all times, watch your drinks to prevent spiking, and be a shout away to come to your aid if someone attacks you, or if you’re in trouble. If I do travel solo, I try to meet people! Go online, see who is around the area, and see if they want to do things with you. Go onto viator and book a group tour, find a pub crawl, pop into a hostel, be social! Not only will you make lifelong, awesome friends, but you will keep each other safe and accountable!

7. Friends with Benefits.

Especially when travelling to a city or country I’m not familiar with and alone, I always identify who I know there. When visiting India, my buddies ensured we ate only at specific places, and drank clean, filtered water. They helped me cross the street in insane traffic. They took me shopping, and bargained prices. When I was in London, and Munich, and Sydney, I stayed over with friends or family. Not only are these people experts on where it’s safe to go, how to buy souvenirs, what sites to prioritize, and how to get there (why wouldn’t you want a free, built-int tour guide?), but staying at their houses saves money daily. Right now I’m planning an epic trip to Brazil, and I’m talking to my friends to identify safe hotels, neighborhoods and sites to visit, and when, and how to get around.

8. Plastic, it’s fantastic!

Whenever you’re dealing with a business, always use a credit card, not debit card, nor cash. Several reasons. Say, you buy a souvenir, which breaks by the time you get home. You can easily initiate a dispute, sending in the photo of the broken product. Be sure to review each receipt for accuracy as soon as they’re printed….and keep them until you get home If a restaurant overcharges you, or an entertainment venue adds a charge for something you’ve never done, you have the original receipt to prove it to your credit card company. However, definitely always carry cash, too! You can use it for places that don’t accept credit cards, such as street vendors. But limit the cash to one-time consumable items (food which you eat and then no longer use), or cheap clothes (which shouldn’t spoil easily, but also if they get ruined cost minimal money, so not too big of a loss if you do still get ripped off.

9. Sharing is caring!

Share your flight, hotel, and daily itinerary details with family and best friends! Check in daily, to confirm you’re safe, where you’re going next, and when you’ll next reach out. This will keep your loved ones from worrying about you, and also keep them more comfortable and relaxed when you travel, especially family. Even more importantly, if the worst-case scenarios do happen (you get kidnapped like those Americans in Mexico, or arrested like Amanda Knox in Italy, or mistaken for a gang member or drug dealer), you have a significantly higher chance to survive the ordeal! Your loved ones know where you’ve last been and where you’re going, because you’ve told them. If someone I cared about just disappeared while travelling, I would be immediately on the phone with the police, the embassy, and heck, flying into the last known area myself to search, and I hope you would do the same for me! In many cases, such timely information can help authorities narrow down where to look for you, and hopefully allow them to save your life, if the unthinkable does happen!

10. Always be prepared…for spontaneity and the unexpected!

No matter how organized and prepared you are, something WILL go wrong! Plans will get delayed. Someone will accidentally take your luggage, forcing you to get delayed and get on another flight. Your plane will be first delayed, then cancelled. You miss your bus. There’s traffic. Your tour guide is a no-show. Always keep your phone, with an international plan on you! (T-Mobile and their unlimited international plans are the way to go, work practically everywhere, including Internet and GPS!). You will need to quickly go on Expedia and book another flight…from the airport. You will need GPS, to find the train station, the stop to get off of, and your hotel. Or, you may be walking around, and use GPS to see what to check out nearby, where to eat, where to shop, etc. You will need to look up a last-minute, emergency activity, because your planned one got cancelled. But don’t be too dependent on your phone! As you’re walking, REMEMBER what you passed, and get a general sense of what is around you! I have had my phone die, and then needed to find my own way back to the hotel. Or, locked in a friend’s car, with no friend in site, and needing to walk back to where I’m staying. Use your GPS when you can…but always carry, and know how to read, a paper map, too!