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For the average person, traveling is not a pleasant experience. Long lines at airport security, uncomfortable seats, bad food, jet lag and language barriers are just some of the complaints I hear all the time.
But you are not the average person. You don’t accept the status quo and you would be right. Over the years, I have learned how to travel like a boss, even when I wasn’t one. Here are 16 insider tips on how you can travel comfortably and in style, on your next trip.
1. Cruise Through Security and Border Control
If you are a frequent traveler, joining TSA Pre-Check is a no-brainer. For too many times, I have breathed a sigh of relief after realizing I could bypass the long snake line of travelers waiting impatiently to go through airport security.
Just being a TSA Pre-Check member (meaning you have been pre-vetted as a trusted traveler) means you could cruise through U.S. airport security in a dedicated lane AND not have to remove your shoes, belt, laptop and a light jacket. Talk about traveling like a boss!
A five-year membership to TSA Pre-Check costs a very reasonable $85. TSA Pre-Check, at last count, is offered at over 53 U.S. airports in partnership with over 200 airlines.
Better yet, if you intend to even travel out of country once, just apply for Global Entry (costs $100) instead, for expedited customs processing whenever you return to the U.S. You will truly feel like a boss when you cruise through border control and not have to wait in line like everyone else. All Global Entry members even get TSA Pre-Check included with no extra fees.
Tip! Many credit cards now pay for your Global Entry membership or allow you to redeem loyalty points to pay for it.
Bonus Tip for Canadians! Canadian travelers with NEXUS membership are eligible to use TSA Pre-Check for flights departing from U.S. airports.
No matter which membership you have, just include your Known Traveler Number (your membership number from TSA Pre-Check, Global Entry, or NEXUS) in the appropriate field in your airline reservation. If approved, you will spot the TSA Pre-Check symbol on your boarding pass; simply cruise through security like a boss!
2. Global Airport Lounge Access
If you are already traveling in Business or First Class, then you must appreciate the privacy and comfort of airport lounges, before departure. And if not, then a membership to Priority Pass is a must for frequent and world travelers.
Priority Pass is the largest network of airport lounges, dining and spa experiences in the world with over 1,200+ locations in 500 cities across 140 countries. Because of the sheer number of locations on offer, a Priority Pass membership is incredibly versatile.
Tip! A Priority Pass membership is a benefit that is offered by many Travel credit cards in the U.S. and Canada. It can also be purchased directly from Priority Pass.
3. Fly in Premium Cabin by Travel Hacking
There’s nothing quite like jet-setting in the comfort and luxury of Business Class or First Class around the world. Airlines around the world have designed their premium product to suit the needs of business and luxury travelers.
There are many benefits, of course, including:
- Getting work done: comfortable seat with large table
- Sleeping better and longer so you could hit the ground running: flat bed seats anyone?
- Eating better: multiple courses of chef-designed cuisine and fine wines
- Eating when it suits you: so you could sleep or work as you please
- Extra comfort and convenience: ground services including airport lounge and limousine transportation
I have had the pleasure of flying in Business and First Class on long-haul flights aboard Cathay Pacific, American, Turkish, and Scandinavian. Believe me, having a flat bed seat that you could work and sleep in is something that never gets old.
I have managed to travel this way by leveraging the power of miles and points, commonly known as Travel Hacking. If you are interested, I highly recommend this course by author Chris Guillebeau where he teaches his students on how to make their dream trip a reality, by leveraging the power of loyalty miles and points.
4. Beat Jet Lag, Every Time
When flying to destinations more than three time zones away, the struggle can be real when it comes to jet lag. Fortunately, since you’re a boss, you understand that it is all about managing your sleep before, during and after the flight.
Here are three quick tips on how to avoid and to beat jet lag:
- As soon as you step on the plane, set your watch and devices to the local time of your destination and observe the meal and sleep times at your destination as closely as possible.
- During your flight, avoid screen time at least one hour before you intend to sleep. The blue light emitted by electronic devices can delay your falling asleep and affect the quality of your sleep.
- Plan to arrive at your destination in the early evening or late afternoon, which will ease your transition into the local time. After you arrive, check in at your hotel and focus on getting a good meal and a good night’s sleep.
Related: For more helpful tips, read 16 Tips on How to Beat Jet Lag When You Get Home from Asia.
5. Cocoon Yourself with Noise Cancellation
Whether you are in the air or on the ground, finding peaceful solitude could be easily arranged by donning a pair of noise cancellation headphones. For frequent travelers, they are a must.
When you want to focus and get some work done or enjoy an in-flight movie, a pair of over-the-ear Bose QC 35 or Sony WH1000XM2 wireless noise cancellation headphones will more than do the trick. They are comfortable, stylish and extremely effective.
6. Book Last Minute at Higher End Hotels
Are you the spontaneous type? Booking last minute can mean huge savings at higher-end properties. It makes sense since hotel operators would rather give you a discount than have the room go unoccupied. I recommend using the HotelTonight app to land some pretty significant discounts at amazing properties.
Here’s how it works. With HotelTonight, you get some pretty incredible prices on unsold rooms. Every property may be booked as far as 100 nights in advance for 14 nights but of course, the best prices are displayed for last minute bookings. You can book properties in over thousands of cities in 35 countries in the U.S., Central and South America, Europe, Middle East, Africa and Australia.
I have used the HotelTonight app many times, especially when feeling spontaneous or when my travel plans are loose. My last HotelTonight stay was at a beautiful riad in the middle of bustling Marrakech. I booked it literally a few hours before I arrived and found myself in the middle of the action, just minutes away from the bustling Jemaa el-Fnaa square.
7. Stay Fit While Traveling
Make no excuses when it comes to staying fit and feeling in charge, even when traveling. Book properties that come with a fitness facility so you don’t have to go far to enjoy a workout. Hotel brands like Westin has even partnered with New Balance to provide guests with workout clothing and sneakers on loan, so there really is no excuse! (you get to keep the socks)
Even better is Westin’s 250+ running leaders (called runWestin Concierges) who lead frequent group runs at their properties around the world. Not only do you get to meet your fellow guests, but you also see the city from a local’s perspective AND stay fit at the same time.
8. Upgrade Your Hotel Room
Want to feel like a boss when you arrive at your hotel? It pays to be loyal. Joining at least one hotel loyalty program and giving them your business over time will ensure that you are treated like one, often with complimentary room upgrades and other perks.
Bypass the Stay Requirements: Certain credit cards such as the American Express Platinum Card in the U.S. and Canada offer complimentary Gold elite status to the likes of Starwood Preferred Guest (Marriott) and Hilton Honors programs, simply for being a cardholder.
Tip! Another trick is to simply slip a $20 note with your ID and credit card at check-in to the reception and politely ask whether complimentary upgrades are available. 8 out of ten times this technique has worked in my favor and I bet it would work for you too.
9. Live Like A Local With Vacation Rentals
If I plan to be in a city for more than a few days, I usually look into staying at an Airbnb apartment in a desirable neighborhood, right in the middle of the action. I look for close proximity to cultural hotspots, museums, cafes, galleries, bars and even city parks or waterfront for a nice place to jog.
Having your own space means a comfortable place for your travel companions and/or guests to hang out, especially late into the evening for an after party.
If you are new to Airbnb, discover how to search for amazing properties and local experiences and save up to 50% at the same time.
10. Always Stay Connected
One of the pains of international travel is staying connected, data wise. You could pay the outrageous international roaming charges OR you could stand in line for a temporary, tourist SIM card and data plan when you arrive. It is a bit of a pain though when you travel often but only stay for a short time at each destination.
Here’s another option. Enter Google’s Project Fi. Data just costs $10/GB up to $60 max per month for an individual (even cheaper for multiple users on a shared plan) for while you’re at home in the U.S. AND in 170+ countries. Yes, same price. For talk and text, it’s a simple $20/mo for unlimited domestic talk and text, unlimited international texts, Wi-Fi tethering to use your phone as a hotspot, for all your business and personal needs.
Want to order an Uber car as soon as you arrive? Jump on a video Skype call? Navigate your way using Google Map? Now you can do it at any time, at the same (reasonable) price as you would pay at home.
Arriving at a new destination where you don’t speak the local language is tricky. It’s even trickier when you’re trying to communicate where your hotel is to a driver who doesn’t speak English. In some countries, you may even meet taxi drivers who conveniently turn off their meters, resulting in a shocking fare at the end of the ride.
To avoid all that, I’d like to install the ride share apps on my smartphone before I even land. That way I can roll out of the terminal and jump into an Uber (or the equivalent) right away, like a boss.
Of course, Uber is not the only player in the ride share game. Depending on where you are in the world, there are a number of alternatives to consider.
|Ride Share / Taxi Apps||Markets Served|
|Careem||Middle East, North Africa, Pakistan and Turkey|
|Gett||U.K., Russia and Israel|
|Lyft||U.S. and Toronto, Canada|
|mytaxi||Germany, UK, Ireland, Italy, Greece, Poland, Spain, Austria, Portugal, Sweden, Romania, Peru and Chile|
12. Look Good, Feel Good
When you look good, you feel good. Now, you don’t need to put on a suit to prove this point, but there are a few brands out there that make stylish, travel-friendly clothing using sustainable materials and processes, including Nau, Prana, Duer and Frank and Oak.
For travel purposes, look for materials with a bit of stretch for ease of movement and neutral-colored designs that are easy to mix-and-match and are versatile enough to help you transition from day-to-night and work-to-play.
13. Carry Your Own Travel Amenity Kit
Traveling like a boss means staying fresh and hitting the ground running when you land. One sure way is by carrying your own amenity kit. Pull it out at your discretion while in the air. I recommend packing an eye mask, earplugs, toothbrush, and travel aromatherapy roll-ons, all packed in a handsome dopp kit.
14. Pre-book Dinner Reservations
Got some idle time in the lounge before departure? Just open up the OpenTable app and make a dinner reservation at your destination shortly after you arrive. Save yourself the hassle of searching for a restaurant on the ground, especially in an unfamiliar city. Use OpenTable to make a reservation in advance. Search and filter by neighborhood, cuisine, price, rating and seating options.
When I looked into making dinner reservations outside the U.S., I was pleasantly surprised to see that OpenTable also operates in Canada, Canada, Mexico, Japan, Hong Kong, Singapore, Thailand, Australia, U.K., Ireland, Germany, Spain, Netherlands, Italy, and the U.A.E. Consider your first meal in a foreign city taken care of!
15. Earn USD, Spend Pesos
If you earn U.S. dollars, you are in luck. There are plenty of destinations where the U.S. dollar has increased in value against the local currency in recent months.
I just did a quick check and in the last six months, the U.S. dollar has increased in value against the Colombian peso, New Zealand dollar, Argentine peso, Norwegian krone, Azerbaijani manat, Indonesian rupiah, and Mexican peso, making their namesake countries very attractive destinations. So go ahead and splurge a little.
16. Work Anywhere Using Coworking Spaces
Coworking spaces in recent years have become somewhat of a global phenomenon. When traveling, I love checking out new coworking spaces, especially if I know I’m going to stay in a new city for a while.
When I choose to work on the road, no question, I prefer taking calls and getting work done in coworking spaces over cafes. You can’t beat their fast, dedicated Wifi, flexible day rates, ergonomic workspaces and conference rooms.
It is also a fantastic way to tap into the local tech and startup scene. Many coworking spaces I have visited organize regular events, encouraging networking, idea sharing and collaboration. You might even get some new business ideas.
I recommend using coworker.com, which is a global directory of coworking spaces. If having a dedicated workspace is important to me in an unfamiliar city, I would browse their directory for some excellent options, sometimes even before booking a hotel. Tip! Most spaces even offer a free day pass, just for checking them out.
Traveling can be done in style and in comfort so you can focus on exploration and productivity. How do you travel like a boss?
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