How to Win at Travel Quotes

“As I walked out of the terminal that day, smiling through my tears, I realized that becoming a real traveler isn’t about how many countries you’ve been to or how much value you can extract from your frequent flyer miles. The best journeys are not the ones we plan, but the ones that life plans for us. Opening yourself up to experience them—now that’s winning at travel.”
― Brian Kelly, How to Win at Travel

“Here’s how I get a sense of whether I’m getting good value for my airline miles. I take the cash price of the ticket I’m redeeming for and subtract the taxes and fees I’m paying on my award flight. For example, I want to fly from New York to London round trip in business class. The cash price of the ticket is $3,566 and to redeem it would cost 189,500 AA miles and $326 in taxes and fees. I first subtract the taxes and fees from the cash price: $3,566 – 326 = $3,240. Then, I divide the updated cash price by the number of miles: $3,240/189,500, which gets me a value of 1.7 cents per point. This would be a decent redemption for AA miles. I can get higher when I redeem for their partners, like Qatar Airways and Cathay Pacific long-haul business-class awards, but I wouldn’t feel bad about getting 1.7 cents. US airlines give around 1 to 1.4 cents per mile with their dynamic redemptions, though sometimes more (and sometimes less). Here’s a cheat sheet to see if you’re getting a good value on your redemption. In most airline programs: Less than 1 cent per mile = bad redemption 1–1.4 cents per mile = average 1.5–1.9 cents per mile = good 2–3 cents per mile = great 3–4 cents per mile = excellent 5+ cents per mile = quit your job and become a points blogger”
― Brian Kelly, How to Win at Travel

“AwardHacker.com is a free tool that I often use to start my search, entering the route I want to fly to see what the cheapest options are. It doesn’t search for availability but tells you the best loyalty programs for that route.”
― Brian Kelly, How to Win at Travel

“Points Path is a free Google Flights plug-in that shows you how many miles the airlines are charging for flights on the airlines in the search results.”
― Brian Kelly, How to Win at Travel

“The safest way to track your balances and perks is by creating a spreadsheet with multiple tabs: one for your current balances, one tab for credit cards, one tab with notes for any special spending requirements or perks you need to use and by which dates, and a final tab for all redemptions so you can keep track over time and remember how much value you got from each redemption.”
― Brian Kelly, How to Win at Travel

“Tips for Buying Points and Miles 1. Buy miles and points when you know you’ll be able to redeem them for more than what you paid for them. 2. Wait for promotions to get a discount—avoid buying them when asked while checking in or at a kiosk. 3. Understand the expiration rules of the miles and make sure you know how to keep them active. While many loyalty programs have done away with expiration policies, some have tricky expiration rules that require flight activity to keep miles from expiring.”
― Brian Kelly, How to Win at Travel

“American Express even offers Platinum cardholders a $200 statement credit toward prepaid stays of two nights or more.”
― Brian Kelly, How to Win at Travel

“I think it’s worth the money to consider the free cancellation, as you never know what could happen. Plus, hotels sometimes do get cheaper as your stay approaches, so it’s nice to have the ability to cancel and rebook for a lower price”
― Brian Kelly, How to Win at Travel

“The Points Guy’s yearly top airline roundup, which takes fees, bumps, timeliness, affordability, baggage, and more into consideration. Delta was the top winner for the sixth year in a row in 2024, followed by Alaska and United.”
― Brian Kelly, How to Win at Travel

“Statistically, the earliest flights are less likely to face delays, and after 3 p.m. your flight is 50% more likely to be delayed or canceled.”
― Brian Kelly, How to Win at Travel

“It can make sense to buy a cheap flight to get you to a major city to buy affordable airfare from there, which is called positioning (or repositioning) flights. One example: You buy a $100 ticket on Southwest from Oklahoma City to Los Angeles, and then you book Los Angeles to Tokyo for $800 round trip, instead of $1,800 if you booked Oklahoma City to Los Angeles to Tokyo (Southwest doesn’t partner with other airlines, so you’re paying a premium to book other airlines).”
― Brian Kelly, How to Win at Travel

“For domestic travel, book about six to eight weeks before departure, and for international three to six months in advance, on average (though more if you’re traveling on peak periods, for special events, or on holidays”
― Brian Kelly, How to Win at Travel

“It’s a myth that booking travel on Tuesdays and Wednesdays can save you money. The day of the week you book doesn’t have much to do with it, but the day you fly does. Airfare is largely based on demand between city pairs, so traveling on days when there are fewer business and leisure travelers (such as Tuesday, Wednesday, and Saturday) or on actual holidays versus days prior and after can help you save.”
― Brian Kelly, How to Win at Travel

“If you want to use credit card points to book your ticket (and not transfer them to a partner loyalty program), you’ll have to book through the credit card portal (Chase Travel, Amex Travel, Capital One Travel, etc.), which is basically an OTA and at times even powered by the big OTAs. The difference is there’s another layer of customer service if things go wrong, and credit card customer service is often more helpful than a regular OTA. They’re trying to retain you as a valued customer, and they often have travel concierges that have better training than the average OTA phone rep. Plus, many of these platforms give extra miles or points for booking through them, even though they work using general OTAs. For example, I book most of my airfare directly on airline websites or via Amex Travel using my Amex Platinum, which earns me 5X points per dollar spent.”
― Brian Kelly, How to Win at Travel

“Culture and Food 1. Japan: Tokyo, Kyoto, Osaka (bonus winter add-on: skiing in Niseko) Edition Ginza, Park Hyatt Kyoto, St. Regis Osaka 2. Thailand: Bangkok and Koh Samui JW Marriott Bangkok, Conrad Koh Samui 3. Argentina: Buenos Aires and Mendoza for wine Palacio Duhau - Park Hyatt Buenos Aires and Park Hyatt Mendoza 4. Paris, France: Park Hyatt Paris-Vendôme, Prince de Galles, a Luxury Collection Hotel, The Westin Paris-Vendôme, or the Kimpton St Honoré Relaxation 1. The Maldives: The Ritz-Carlton Maldives, Fari Islands, the St. Regis Maldives Vommuli Resort, and the Waldorf Astoria Maldives Ithaafushi 2. Hawaii: Kauai or Maui Grand Hyatt Kauai Resort or the Andaz Maui at Wailea Resort - A Concept by Hyatt 3. Cabo San Lucas: Waldorf Astoria Los Cabos Pedregal or The Cape, A Thompson Hotel, by Hyatt Adventure 1. Dubai: Park Hyatt Dubai or Conrad Dubai plus a desert safari with a stay at Al Maha, a Luxury Collection Desert Resort & Spa 2. South Africa: Cape Town and safari at Kruger or wine country (Stellenbosch or Franschhoek) Westin Cape Town and Hyatt Regency Cape Town (there aren’t any luxury traditional points hotels in the bush but splurge on any Singita; I love Sabi Sand). Or, tack on a safari at Cheetah Plains or at the JW Marriott Masai Mara Lodge in Kenya 3. Iceland: Edition Reykjavik, Hotel Ranga (Hilton)”
― Brian Kelly, How to Win at Travel

“finding the local emergency phone number in the country you’re visiting takes a minute and having it on hand will be useful if you need to call it quickly.”
― Brian Kelly, How to Win at Travel

“Always leave your passport and extra credit cards/cash in your hotel room safe when possible. (However, this isn’t 100% secure as hotel safes can be breeched by employees and thieves.) 7. Never hire random cars—always use a ride service app or arrange through a hotel.”
― Brian Kelly, How to Win at Travel

“She also suggests using intuition as a key way to figure out if something is wrong, which has occasionally happened to her. “If something doesn’t feel right, trust that energy and get out,” she advises.”
― Brian Kelly, How to Win at Travel

“Nabongo often uses Google as a resource to find local, on-the-ground tour guides for countries, especially those with reputations for being “dangerous.” “At the end of the day, the people living in those countries are the experts. That person will know more about their country than anyone else.”
― Brian Kelly, How to Win at Travel

“However, don’t buy travel protections through airlines, hotels, and credit card companies. You’re almost always better off buying a policy with a reputable provider through an insurance marketplace, such as InsureMyTrip.com, where you can compare and contrast policies and read the fine print. Take the time and read the policies as the most expensive policies often don’t have the best coverage.”
― Brian Kelly, How to Win at Travel

“You can take out foreign currency at your bank before you leave, but you’ll usually get the best exchange rate when using your debit card abroad at an ATM.”
― Brian Kelly, How to Win at Travel

“When in a foreign country always choose to have a purchase processed in the local currency and not in USD.”
― Brian Kelly, How to Win at Travel

“according to a Cornell University study, people get greater satisfaction from buying experiences than they do from material objects.”
― Brian Kelly, How to Win at Travel

“being sweet to phone agents was the key to getting what you wanted. That’s still true today.”
― Brian Kelly, How to Win at Travel

“of photos to prove it. A great gift for your young children is to create a journal from all of your travels and include pictures and key memories”
― Brian Kelly, How to Win at Travel

“For domestic travel, book about six to eight weeks before departure, and for international three to six months in advance, on average (though more if you’re traveling on peak periods, for special events, or on holidays).”
― Brian Kelly, How to Win at Travel