The Busy Person's Guide to Travel Hacking

Travel doesn’t have to be expensive.

For the trip that led to Tortuga, my roundtrip plane ticket from San Francisco to Frankfurt cost $520. Now I pay for international flights with points and miles. I sleep for free in Airbnb apartments. I never take taxis. Life is good.

Here’s how you can do the same.

Accommodations

Airbnb

Rent a room in someone’s apartment or the whole place. Airbnb is cheaper than a hotel but with more amenities. My favorite part is that you can stay in any neighborhood you like, not just downtown where all of the hotels are located.

Get $40 off your first stay by signing up at this link.

Hotel Tonight

Book last-minute (within the week) hotel rooms at a discount. Hotel Tonight is perfect for business trips and impromptu getaways. Instead of having hundreds of mediocre options, you’ll choose from a short list of quality hotels and one or two budget options.

Get $25 off your first stay with the discount code FPERROTTA.

SPG

When I stay in hotels, I stick to Starwood because Starwood Preferred Guest (SPG) is the best hotel rewards program, especially since they've merged with Marriott. You can exchange points between each chain even though they aren't fully integrated yet.

You can get 25,000 Starpoints as a signup bonus with the SPG card. The American Express Platinum card will give you automatic Gold status with Starwood, which Marriott will match. Gold status will get you early checkin, late checkout, bonus points, and other perks.

Flights

Flight Search

Flight booking is an inexact science. Start with Hipmunk, which does the best job of displaying search results. With a sense of the airline, timing, layover, and price options, cross-reference Skyscanner and the airlines’ websites to see if you can beat Hipmunk’s best results.

Within the US, check Southwest or Virgin America (soon to be Alaskan) if they offer the route you want. Both airlines offer a better experience than the larger domestic carriers.

For complex and international itineraries, I don’t have the knowledge or time to decipher airline point redemption systems. They’re intentionally obtuse so that you don’t redeem your points. In these cases, buy your flights with credit card points, like Chase's, or outsource the work to the experts at Flightfox. Pay $75, tell them the points and programs that you use (tracked via AwardWallet below), and they’ll give you the best options for booking.

Lounges

The Chase Sapphire Reserve and American Express Platinum card will both give you access to Priority Pass Select, a subset or airport lounges around the world. Alternatively, you can buy one-off passes from the Lounge Buddy app.

Lounges are handy on long layovers or just for better food (free), seating, and amenities than the main terminals.

Transportation

Uber

San Francisco (where I lived for years) has always been short on taxis. To avoid waiting and paying in cash, I use Uber to get around. UberX is affordable, the cars are clean, the drivers are friendly, and you know that the car is coming and when it will get there, even if you’re somewhere remote. Thankfully, Uber is now available in most major cities in dozens of countries. In some locations, you can “carpool” with Uberpool to save even more money.

Get your first ride free (up to $10) by signing up through the link above or using the code 99fm4.

Lyft

If Uber's business practices appall you, try Lyft instead.

Save $10 on your first ride with code FRED303.

Credit Cards

Read my guide to the best personal and business travel credit cards. Choose the card that's right for you and offers the best rewards.

Logistics

Global Entry and TSA PreCheck

Get through airport security and customs faster. If you travel more than once/year, sign up for Global Entry with TSA PreCheck. You can sign up for both programs with one application process. The combined programs cost $100 for five years. If you have the Chase or AmEx cards recommended above, you get access to both programs for free.

Global Entry lets you skip the customs line upon re-entry to the US. Instead of standing in line, scan your passport at the kiosk and go home. After a fourteen hour flight home, I would pay anything for Global Entry. The self-satisfied feeling you get the first time you walk past everyone else on your flight is worth the $100. Several of my favorite travel credit cards will reimburse you for this purchase.

TSA PreCheck gives you access to the expedited security line at select US airports. In the PreCheck line, you can leave your electronics and toiletries in your bag and don't have to take off your shoes or jacket. PreCheck essentially rolls back security to pre-9/11 levels. Empty your pockets and walk through the metal detector.

TripIt

Keep all of your travel details in one place with TripIt. Track your flight details and confirmation number, your hotel reservation, and your car rental information. TripIt also provides up-to-the-minute flight alerts in case your gate or departure time changes.

Award Wallet

Always know how many points and miles you have with AwardWallet. If, like me, you aren’t loyal to any one airline or card, you’ll appreciate having all of the information in one place.


Disclosure: Some of the links on this page are affiliate links. If you sign up or buy something through an affiliate link, I make a small commission at no additional cost to you. I use these products and highly recommend them. If you think my recommendations can help you, use them. If not, don’t.