For the trip that led to my co-founding my business, 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.
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.
Book last-minute (within the week) hotel rooms at a discount. HotelTonight is perfect for business trips and impromptu getaways. I use it for weekend roadtrips from the Bay Area.
Instead of having hundreds of mediocre options, you’ll choose from a short list of quality hotels with one or two budget options.
Get $25 off your first stay with the discount code FPERROTTA.
When I stay in hotels, I use Marriott, which acquired by previous choice, Starwood. The Starwood Preferred Guest program was the best option for years. Now that title is up for debate. So far, I'm using the new, combined program called Marriott Bonvoy.
Read my credit card guide to learn which cards to get to maximize your sign up bonus, points earned, and automatic status upgrades.
I've also had success booking Marriott hotels through HotelTonight at reduced rates, getting the Gold perks at check in (see the credit card guide for how), then requesting Bonvoy points for the stay after I've checked out. While this system is a bit more work, you'll save money, get your perks, and get your points. I haven't been told no yet.
Flight booking is an inexact science.
I start by opening up a few tabs.
- Travel portals for each credit card program that I use. For me, that's Chase Ultimate Rewards and American Express Membership Rewards.
- Award Hacker for searching across credit card points and airline frequent flyer programs. Award Hacker will show the cost (in points) of flights by airline. You'll also see if you need to transfer points from a program you use to the airline for redemption.
- Skyscanner for general search.
Across those tabs, you'll see your options for booking with points via your credit card's portal, transferring those points to an airline for direct booking, or buying a flight in cash.
Lounge access is helpful when traveling internationally or with long layovers. Find some respite from the masses in a lounge with free food, comfortable seating, and sometimes even showers and nap pods.
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. You won't have access to every lounge, but you'll have at least one option at most larger airports. Your AmEx card will also provide access to Centurion Lounges.
Alternatively, you can buy one-off passes from Lounge Buddy starting at $25.
Uber and Lyft
San Francisco (where I lived for years) has always been short on taxis. Uber completely changed transportation in SF. Once Uber went mainstream, I never had to stand around waiting for cabs during busy times. Suddenly, I could get to or from anywhere in the city at any time.
To avoid waiting and paying in cash, I use Uber or Lyft to get around. The rides are affordable, the cars are clean, and the drivers are nicer than cabbies. You know that the car is coming and when it will get there, even if you’re somewhere remote.
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. Lyft is still US-only but often a better option.
Get your first Uber ride free (up to $10) by signing up through the link above or using the code 99fm4.
Save $10 on your first Lyft ride with code FRED303.
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. As mentioned in this guide, the right card can get you status with a hotel, free lounge access, and reimbursements from TSA's travel programs.
Global Entry and TSA PreCheck
Get through airport security and customs lines faster. If you travel more than once per 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 from China, I would pay anything for Global Entry. The self-satisfied feeling you get the first time you walk past everyone else on your flight who is still waiting in line is worth the $100. All of the best 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 for select passengers. Empty your pockets and walk through the metal detector. That's it.
Even with PreCheck, I'm still keeping an eye on Clear, a private company that provides expedited screening and identity verification.
Keep all of your travel details in one place with TripIt. Track your flight details, 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.
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.