Your Questions Answered: ALL My Best Travel Tips! Airlines, Hotels, Upgrades, Points And More!

Most of being an expert is knowing about best practices. No two reservations on earth are the same because no two people will ever respond to them in the same way. We all have different financial outlooks, needs, cares and wants. Knowing that there are options, knowing how to see and find value and honestly just endless hours of research are what makes for seamless travel. Here's my best attempt to answer many common questions.

When And Where Should I Buy My Airline Ticket?

There is no crystal ball for buying airline tickets. Only best practices. In general early is good, too early is bad and last minute is rarely ever good. Many studies show that somewhere in the 60 day range is often successful but there are plenty of caveats. The best thing to do is know a deal when you see one. Know what the standard cost for the ticket you want is and if you find a price lower than expected, book it. Like business class round trip to London yesterday from the US for as low as $454 and 30,000 miles. You would've been a fool to pass that up. From the USA you always have 24 hours to cancel risk free with the exception of American Airlines. 

Shopping around is very important. It's great to use the ITA Matrix to see all the possibilities of an entire month and if there's any benefit to staying a little longer or less in your destination. As for actually booking and pressing pay now, It's always going to be easiest to change or deal with reservations if you book them directly with the airline. if you can't find the same good deal directly with the airline that's when you'll want to book through a site like Expedia, Orbitz, etc. 

Favorite Flying Perk?

Lounges! No doubt. I, like anyone on earth generally prefer to fly up front when a reasonable situation on a long flight presents itself but mostly I want a great experience at the place people hate the most: the airport. People are surprised to learn that whether you're flying economy, premium economy, business or first there is almost always a lounge you can gain access to, either by paying for one time use or having a card or lounge membership which gets you in. It's surprisingly cheap. Plus, after a few glasses of wine in a lounge my knees are numb enough to forget they are getting squashed on the plane anyway. 

Should I Book My Hotel Directly Or Use A Third Party Site (Expedia, Orbitz, etc)?

Sometimes booking direct is the cheapest, sometimes credit card companies offer third or fourth night's free when booked through them and sometimes discounters and online travel agencies like or TripAdvisor get shockingly great rates. If you care about elite status or hotel points you'll almost always do best booking direct with the hotel. If you care about earning airline miles for your hotel stay and can find a competitive rate, can be great. Price shop. And of course, use my tips to never pick the wrong hotel again

I Have X Number Of Miles, What Should I do With Them?

My general tip is to look at potential for cents per mile and expense. Cents per mile essentially is the miles required for a "free ticket" divided by the estimated actual cost using dollars. If I spend 100,000 miles for a free ticket that would cost $10,000 using cash I am getting ten cents per mile. If I use 25,000 miles for a ticket that costs $125 I am getting half a cent per mile. Hopefully you know the better value. Everyone has unique circumstances but since miles are fairly easy to come by, I prefer to use mine towards tickets I would never buy (or afford) without miles and pay for the things I can. After all, paying for flights earns more points and helps you get towards elite status with an airline. My mom hit elite status with British Airways this year after one round trip flight from an awesome business deal to my wedding and a one way flight in America. Three total flights! For your miles, long haul business or first class generally seems to work best for extracting value. Alternately sometimes short economy flight price horrifyingly high and using miles can be a fantastic value. Especially when a flight from New York to Montreal or London to Prague only requires 4,500 miles! It's finding the space using these tips that is the trick....

What Was Your Best Flight Ever? 

It was in economy! It takes me back to a time before national security issues. I was on my way to Australia for a tennis tournament and a kind cabin crew member invited me to the upper deck of the Boeing 747, past all the sleeping passengers in first class to meet the captain mid flight. I got to spend about 15 minutes in the cockpit observing the goings on and asking questions. Hands down the best experience ever. Knowing it's strictly forbidden now no matter who you are makes it even more special. 

Any Upgrade Tips?

This is a harmless intelligent question but nonetheless, one that makes me laugh slightly. Upgrades are more a function of well thought out work, planning and time spent traveling than sheer luck. Most standard upgrades involve elite status or having the sufficient miles needed to make the bump. I of course do have a post with a few other upgrade tips and ideas to help you make the most of your travels regardless how infrequent or planned. The best practice for upgrading is to book a flight with upgrade space in a fare class that allows you to upgrade using miles. I recently found cheap "K" medium level economy fares on Delta that allowed me to immediately upgrade for 12,500 miles for flat bed business. I like to call and ask which flights have upgrade space before I book. 

What's The Best Credit Card For Travel?

The wisest words spoken on credit cards follow the logic that there are cards you get for the sign up bonus, cards you get for continued benefits and the third ideal situation is the card you get for both reasons. I love putting my spending on cards which I can collect transferrable points (those which I can move to different airlines or hotels) such as American Express Membership Rewards Cards, Chase Ultimate Rewards Cards, Citi ThankYou Preferred Cards, Starwood Preferred Guest Cards and so on. These cards allow me to turn every day purchases into miles with over 30 different airlines. When it comes time to book an airline ticket I find out which one has the best value for my points and move them over. Figure out which airline or hotel you'd like to collect points with and see what cards allow you to earn points with them and others for every single purchase. I personally think you should treat a credit card like a debit card and wrote this post about clever ways to meet spending bonuses.

Any Vacation Tips For This Or That City?

I am a huge fan of privately guided day tours. I do my best to pick fantastic hotels and don't want my vacation to turn into a job of staring at maps. I always look to book a top guide based on TripAdvisor reviews or trusting a good hotel recommendation so that I can condense the best sights of the city in as little time as possible. In most cities we've been in we've lucked out and picked guides who were able to help us skip lines and listen to the things we wanted to see. In Rio for example we were very interested in seeing the Vista Chinesa, Christ the Redeemer, Sugarloaf Mountain and our guide Ederson expertly crafted an itinerary that helped us zip from place to place avoiding all the rush times for each. Genius. Other than that? Do research! It's half the fun. Figure out where the things you want to see are and walk around. Assuming you're in a relatively safe city it's ALWAYS the best way to see it. Open your eyes. 

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How Do I find Dates And Availability To Use My Miles:  

Pretty complicated and pretty simple actually. It's complicated because it's not always easy to find two seats you want on the same flight for any days of the year. It's easy because If there are some seats available they will be found on a couple great tools. The best tools available are AwardNexus and ExpertFlyer which allow you to see availability seven days or more at a time across many different airline points and miles. Once you find availability on one of these sites, you can go to your airline's site to finish the job. These tools save tons of time.... 

The Airline, Hotel Or Car Rental Screwed Me And Messed Up My Reservation, What Should I Do?

When things go wrong; compensation, compensation. The main question you must ask yourself is how much of your time and money is the issue worth. If your inflight TV is not working, perhaps a simple email to customer service and their offer of a few miles in return for lackluster service will suffice. If you are stranded for hours or days and end up losing out on reservations, money or lost business you should fight for your right to fairness. I recommend first using publicly available portals like twitter, telephone, facebook and the dreaded complaint portal on airline/hotel websites. If after a week your issue has not been rectified, try to escalate by speaking to supervisors on the phone, looking up executive email and mail addresses and writing a concise intelligent complaint. I once wrote eight emails to every airline executive address I could find, sent mailed copies of the emails to the corporate headquarters, emailed the Attorney General of New York and finally the Department Of Transportation. This was over a major issue and after being told flat out "no", "not possible" by all the front line reps, who were down right useless in this situation, the issue was rectified and we received exactly what we asked for and were entitled to. It's all about what it's worth to you and how severe the issue is.

Do You Work For An Airline?

Nope. I hold a regular day job which has nothing to do with travel and this is my passion. Knowledge should be free and I am happy to provide insights for fellow travelers. The blog is not as financially rewarding as it is personally rewarding. I get emails ever so often from someone expressing their unbelievable success in taking the flight of their dreams for a honeymoon, family vacation or just a fun getaway. I get pictures from lounges from people saying I never knew I could get into one of these toasting a nice glass of champagne. It's an unbelievable feeling bringing "elevated" travel to good people. 

What Are Your Favorite Places On Earth?

I seek a couple of things. I love incredible geography generally including rolling hills, cityscapes, mountains and pristine beaches. I love places on every continent but some of my favorites are certainly Rio De Janeiro, Cape Town, Sydney, New York and London.

Hopefully you can find a few pointers here to keep making your travel as great as humanly possible. There are so many resources and opportunities it would be a shame not to make the most of them. I genuinely appreciate every one of you that reads and comments on these posts. My best advice is to to take a look at anyone that even remotely seems of use. You never know when circumstances will change or when you might need that little trick that seemed like too much of a grind to read at the time. Give it a go, it's a free education.

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