No one likes the penance of travel, but you can make it go faster. Paul Theroux said travel is only glamorous in retrospect.
1/ Never stay in a hotel for more than three days – even if you’re in the same city, you should jump everywhere – variety is the spice.
2/ If something serious happens to you with an airline, accept it. The information counter, long waiting time and online form is a long dark hallway with a dead end.
3/ Double the valet parking fee and ask the driver to leave your car out front, like all service people – introduce yourself, tell them stories, ask them questions about their life and family. Getting the “welcome” and extra service is always worth it.
4/ Amex is worth it, stop telling us about your Chase Sapphire, you’ll never be cool.
5/ Always book on Amex Platinum – the hotels are better, you’ll get a late check-out and won’t get ripped off by the American hotel scam leaving before 11am and arriving at 4pm. I can’t even have 10 p.m.?
6/ Make sure there is an adult pool. Every child pees in the pool, I did.
7/ Don’t be cheap, Clear, TSA pre and Global Entry are all your friends trying to save you from getting another sinus infection, oh and one more note – stop touching your face.
8/ If you find a good trick or a secret, don’t tell anyone – that’s how it disappears. I told everyone about the secret valet behind the restaurant – now I can’t park my car and have to walk through the front door with everyone. Nothing you tell another person is a secret.
9/ Summer in the Mediterranean every year, there is more culture than America, put your phone on airplane mode, your customers will forgive you later.
10/ Carry only five days of clothes maximum, and always carry with you. The cost of laundry in luxury hotels all year round is worth not getting things stolen by the TSA behind the wall or losing luggage – The first time this happens to you, you won’t will never do it again.
11/ The Admiral’s Club needs a coat of paint, reach the airport later.
12/ Know in which cities to get a car service versus renting a car. Get a Vespa in Italy, get car service in New York. If you are in a town where you don’t know anyone, just take the jeep, if you will be seen, don’t be cheap, rent a luxury car.
13/ Verbally shaming the guy next to you for his emotional support animal.
14/ Always remove this carpet at the foot of the bed immediately and burn it, it has not been washed since the opening of the hotel.
15/ Keep a bag in the two main cities where you are traveling with a week’s worth of clothes and a suit. Stay at a nice enough hotel that won’t charge you to store it. Come back often. Your freedom to fly to London with a laptop and sweatpants will inspire you to fly there more often.
Uber at the airport, but always get a driver to take you home
16/ Save money and Uber at the airport, but always have a driver take you home, don’t be cheap – airports like LAX will make you feel like a peasant if you try to find an Uber.
17/50/50 rule, every trip should be a mix of your mainstays and new locations, and always have someone you see every time you go to a town.
18/ Leave your Louis Vuitton steamer trunk at home – if you travel enough in Europe, you’ll learn that everyone has lux branded luggage. The real ones know it doesn’t matter. Avoid the mark – you need something solid, aluminum and most importantly that fits into the ceiling. Luggage is not a Rolex.
19/ Nashville was better before the bachelorette party, think Austin.
20/ Stop talking about your air miles. An upgrade has not taken place this side of the day from Saint Swithins and the flights are full. Own a business or reach Partner level in order to delist Business Class.
21/ Airlines don’t care about your points or your dedication – if you want loyalty, buy a dog. Also, if you care about points, you’re probably eating the continental breakfast.
22/ In a pinch don’t be too good for the bulkhead aisle seat, we all have red blood, and we all have to go to the DMV.
23/ Buy a Rolex GMT to travel to London – you won’t need to reset your watch to the time zone, follow the third hand.
24/ Call on the concierge service and use it well in advance for reservations. You can’t jump into anything last minute anymore, and they have a relationship for a reason.
25/ Flying during the week is for people who are not focused.
26/ Ask your hotel to ship things to your house – the cost is offset by the convenience.
27/ Find the best cocktail bar in every city, whether it’s upscale or dirty – sit at the bar, meet the bartender and many times you can come back.
28/ If you turn on the air, you can guarantee you’ll miss the company retreat next week.
29/ Never mind the new AMEX lounges, it’s another version of the Mayflower. Don’t get excited – everyone has an Amex now.
30/ JSX isn’t exciting anymore – your kid’s school teachers are driving it now.
31/ Do not take a domestic flight in the evening, you can lose the last ounce of happiness in your life because half of them are delayed or rescheduled.
32/ Don’t take reservations before 7pm or after 9pm unless you’re in a late town – that means they don’t care about you.
33/ Cruises are for the poor, period.
34/ Traveling for work during the week, and staying the weekend for pleasure. You should see every major city in the world once and do the basics. At the beginning of my career, I spent my time checking the sound, in tourist buses and in hotels and I never saw anything.
35/ Do not travel with a razor or a toothbrush, order them each time at reception.
36/ For short flights like LA to Vegas and such, avoid ads and consider doing a quote with friends.
37/ You do not need insurance for your rental, again take an Amex license plate.
38/ Don’t be too good for Southwest only if you go to Nashville – it’s the commuter commute, and the rich fly in too.
39/ Don’t be too good at a connection if you’re traveling to smaller corners of the world – just keep it and never check a bag. Also, most of America is obese, walking is your friend.
40/ Look twice, book once. Also don’t be too cheap for travel insurance, if I learned anything in life things change.
41/ When traveling – wake up early and stay up late, take Whole Foods Counter Attack all the time. You will soon be home, you will live and you will certainly not get sick.
42/ If you need a seat belt extender, consider being courteous and buying the middle seat in white.
43/ Find yourself a sacred place and go there once a year. Turn off your phone. Mine is Iceland.
44/ Determine the high season for tourism in a destination, and the high season for those who know. The locals will tell you and you will know when to go.
45/ Book Aman, Montage or Rosewood when you can, but don’t be too good for a Hilton when you’re in a small town.
46/ Don’t do Airbnbs, rent a villa from a good private company. Plus, you want to leave the black light at home. Support mom and pops!
47/ Support local art in any way you can on your travels and bring something back for your home. You don’t need to leverage your real estate portfolio for a Caravaggio, a lithograph will do just fine. Take it easy, there is a difference between a collector and a collector. Even if you are uneducated, your friends will believe it.
48/ Nothing that interests you during your trip is free or cheap, this applies to flights, experiences, hotels, restaurants and more. Benjamin Franklin said it best – the bitterness of low quality remains long after the sweetness of low price is forgotten.
49/ Don’t book hotels on Expedia or Priceline or other travel sites – the savings will get you a view of the 150 square foot luxury parking lot.
50/ Your family is not worth a double connection, propose a Zoom meeting instead.
Lucas Keller is Chairman and Founder of Milk & Honey Music + Sports + Ventures, a global entertainment management company with offices in Los Angeles, New York, Nashville, Dallas, London and Sydney. On the music side, the company’s roster has collectively sold more than a billion records across all genres, and on the sports side, the company operates a traditional agency and marketing arm that represents 20 NFL athletes. Keller has sold over $150 million in publishing catalog assets since the pandemic and continues to be a thought leader in the music rights space.