Nobody loves the penance of traveling, 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 around — variety is the spice.
2/ If something bad happens to you with an airline – accept it. The information counter, the long hold time and the online form are a long dark hallway with a dead end.
3/ Double the valet fee and ask the driver to leave your car out front, as with all service people – introduce yourself, tell them stories, ask them about their lives and families. Getting the “welcome back” 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 not get ripped off by the scam that is American hotels check out by 11am and check in at 4pm. I can’t even have 22 hours?
6/ Make sure there’s an adult pool. Every kid pees in the pool, I did.
7/ Don’t be cheap, Clear, TSA pre and Global Entry are all your friends trying to prevent you from another sinus infection, oh and another note – stop touching your face.
8/ If you find a good tip or secret, don’t tell anyone – that’s how it goes away. I told everyone about the secret valet behind the restaurant – now I can’t get my car parked, and have to walk in the front door with everyone else. Nothing you tell one other person is a secret.
9/ Summer on the Mediterranean every year, there’s more culture than America, put your phone on airplane mode – your clients will forgive you later.
10/ Pack only five days of clothes maximum, and always carry on. The cost of laundry at luxury hotels throughout the year is worth not getting things stolen by TSA behind the wall, or losing luggage – The first time it happens to you, you’ll never do it again.
11/ The Admiral’s Club needs a coat of paint, just get to the airport later.
12/ Know what cities to get a car service versus rent a car. Get a Vespa in Italy, get a car service in New York. If you’re in a city where you don’t know anyone just get the jeep, if you will be seen don’t be cheap, rent a lux car.
13/ Verbally shame the guy next to you for his emotional support animal.
14/ Always take that runner at the foot of the bed off right away and burn it – it hasn’t been washed since they opened the hotel.
15/ Keep a duffel in the two main cities you travel to with a week of clothing, and a suit. Stay at a nice enough hotel that won’t charge you to store it. Go back often. Your freedom to get on a plane to London with a laptop and sweatpants will make you go more often.
Uber to the airport, but always have a driver take you home
16/ Save money and Uber to 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’re trying to find an Uber.
17 / 50/50 rule, Every trip should be a mix of your mainstays and new places, and always have one person that you see every time you go to a city.
18/ Leave your Louis Vuitton steamer trunk at home – if you travel Europe enough you’ll learn everyone has lux brand luggage. Real ones know this doesn’t matter. Skip the brand – you need something tough, aluminum, and most of all that fits in the overhead. Luggage is not a Rolex.
19/ Nashville was better before the bachelorette parties, consider Austin.
20/ Stop talking about your flier miles. An upgrade hasn’t happened this side of Saint Swithins day and flights are full. Own a business or reach partner level so you can write off business class.
21/ Airlines don’t care about your points or your devotion – if you want loyalty buy a dog. Besides, 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 for travel to London – you won’t need to reset your watch on the time zone, follow the third hand.
24/ Use the concierge and use them well in advance for reservations. You can’t get into anything last minute anymore, and they have relationships for a reason.
25/ Flying on weekdays is for people who are unfocused.
26/ Ask your hotel to ship things home for you – the cost is outweighed by convenience.
27/ Find the best cocktail bar in every city be it high end or down and dirty — sit at the bar, meet the bar tender and many times may you return.
28/ If you turn on the overhead air, you can guarantee you’ll miss the company retreat next week.
29/ Who cares about the new AMEX lounges, it’s another version of the Mayflower. Don’t get excited – everyone has an Amex now.
30/ JSX is not exciting anymore – your kid’s school teachers are flying it now.
31/ Don’t fly domestic in the evening, you can lose any last shred of happiness in your life as half of them get delayed or rescheduled.
32/ Don’t take a pre-7pm or post 9pm reservation, unless you’re in a late town – it means they don’t care about you.
33/ Cruises are for poor people, full stop.
34/ Travel for work during the week, and stay the weekend for pleasure. You should see every major city in the world once and do the essentials. Early in my career I spent my time at sound checks, on tour buses and at hotels and never got to see anything.
35/ Don’t travel with a razor or tooth brush – order it from the front desk every time.
36/ For short flights like L.A. to Vegas and the like, skip commercial and consider going in on a citation with friends.
37/ You don’t need insurance for your rental, again get an Amex plat.
38/ Don’t be too good for Southwest only if you’re going to Nashville – it’s the commuter shuttle, and rich people fly it too.
39/ Don’t be too good for a connection if you’re flying into smaller corners of the world – just keep it tight and never check a bag. Besides, 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’ve learned anything in life – things change.
41/ When traveling – wake up early, and stay up late, take Whole Foods Counter Attack the whole time. You’ll be home soon, you’ll live, and you definitely won’t get sick.
42/ If you require a seatbelt extension, consider being courteous and buying the middle seat out as a blank.
43/ Find a sacred place for yourself, and go there once a year. Turn off your phone. Mine is Iceland.
44/ Figure out the high season for a destination’s tourism, and the high season for those that know. The locals will tell you, and you’ll learn 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. Besides, you want to leave the black light at home. Support mom and pops!
47/ Support local art in any way you can while traveling, 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. Go easy on yourself, there’s a difference between a hoarder and a collector. Even if you’re not cultured – your friends will believe you are.
48/ Nothing you care about while traveling is free or cheap, this applies to flights, experiences, hotels, restaurants and more. Benjamin Franklin said it best — the bitterness of poor 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 deluxe 150 sq ft parking lot view.
50/ Your family isn’t worth a double connect, offer a Zoom meeting instead.
Lucas Keller is the president 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 over a billion records across every genre, and on the sports side the firm runs a traditional agency and marketing arm that represents 20 athletes in the NFL. 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.