How to Plan Travel

Please watch Part 3 of our Travel Planning Series on YouTube for all the details and a visual of the tools I used, but here’s a quick outline of the process to help you remember what we covered. All of the free travel planning tools I use are listed at the bottom of this page.

This video is a bit long but packed full of ways you can save money on your travels. We’ll show you HOW TO BECOME A MAX VALUE TRAVELER—not just by saving but getting the most for your dollar.

1. This is for you whether you use credit card points or not.

• Not just about points—getting free stays by strategic credit card usage is just one of many strategies

• We are unbiased. We are not putting up referral links for credit cards or affiliate links for booking sites, etc. If you’d like one from a card we have, let us know. But this is about YOU saving money and the truth of how we do it. We don’t make anything from our YouTube channel either. As a life-long travel enthusiast, and currently full-time nomads, we just want to share what we’ve learned to help you.

2. First, the basics—these save you money by not losing/wasting money on bad bookings

• Read the Fine Print

• Do You Need the Insurance? Is a Travel Policy better than buying separately? See our info on buying insurance here.

• Be aware that many hotels and airlines give reward points if booked directly with them.

3. Why are the prices always changing?

• Dynamic Pricing and Patience

• Comparing Sites

• Strategy: Book, Watch, Rebook, Cancel

• How to Find Deals: news, ads, subscribe to travel deal newsletters and facebook groups (see below); NEW flight routes, ships, etc.; offer pages/emails for your hotel/airline/booking loyalty programs.

4. Does it matter HOW I pay for my bookings?

• Working on points for a new card sign-up bonus, or on a card you are focusing on.

• Using a card that gives you free baggage (i.e. your American Airlines card if booking on American) or insurance (i.e Chase Sapphire cards, IHG, American Express—check your card benefits), or extra points on a branded card for the brand you’re using.

• Paying with gift cards you bought at a discount (i.e. for cruises, booking sites, Airbnb etc using percentage-off cards from AARP Rewards or giftcards.com which you got a discount on through a coupon site etc—see video and stacking).

5. BILT card

• If you don’t have a solid travel card on which to book travel, we recommend BILT by Wells Fargo because it has no annual fee, it accumulates points you can transfer to multiple partners, if you rent you can earn points on that also comes with a modest degree of travel insurance (read the fine print) and no foreign transaction fee. If you want to accumulate points for free travel with no hassle and fees, this is the simplest way but do read all the conditions.

6. Where to Learn More About Free Travel Using Points

• There’s no end to the sources on this topic and some of the big ones listed here even have tutorials and guides. Don’t pay to learn—there’s plenty out there for free on YouTube and the internet. Here are some of the big players you can google, most of which have websites, facebook groups, newsletters and YouTube channels: Loyalty Lobby (has my favorite email alers), The Points Guy (TPG Lounge on FB), Frequent Miler, Daily Drop, NerdWallet, Award Wallet, Finance Buzz (FBZ Elite FB group). The most basic place to get started is with Travel Freely, a free app you can put on your phone to track your cards and deadlines and benefits while playing the points game and they also have a great free tutorial on the app (you don’t give them credit card numbers or personal info).

7. Transportation

• Use sites like Rome2Rio and seat61.com to look at your various transportation options while you are also using Google Flights.

• Rental cars: Costco, AARP, rentalcars.com etc have good discounts and look at coupon sites too. Then keep checking back to see if you need to rebook and cancel for something cheaper. In Europe you may also want to consider leasing a car instead if for a longer period of time.

• Getting around: Some cards earn better points on transportation. Some have partnerships with Uber or Lyft to save you money. Google what rideshare companies there are in the destination you’re going to: for example, in SE Asia Grab and Gojek have been cheap.

8. Saving Money on Flights

• Credit Card Points (booking through that card’s portal is not always cheapest—unbranded cards have transfer partners—you can learn a lot more about this through the sites listed in #6 above)

  • Maximize value by using on the best flights: beware of high taxes and fees, or low redemption value that may be better to pay cash.

  • Book early for best selection.

• Companion Passes like Southwest and Alaska (including multi-stop)

• Flying midweek and at less-crowded times of day.

• Adding a long stopover for a bonus destination.

• Compare whether one-way or round-trip is cheaper and consider the looping strategy (be sure to manually have connecting flights joined if booked separately)

• We recommend booking directly with the airline.

9. Researching Flights for the Best Deal

• Check surrounding cities/alternate airports

• Check Google Flights (or other) calendar view and grid view to find cheapest days/combos to fly.

• Set up price alerts.

• Monitor cheap flight sites/emails like Daily Drop, Dollar Flight Club, The Flight Deal etc (some have membership charges—watch for sales or free trials).

• Be sure to factor in baggage inclusions or costs (if you need more, prepay online to save). Consider the value of using an airline with which you have a credit card with free baggage benefit.

• If cost is too high, follow the video instructions on working your way backwards using Google Flights “Explore” and using alternative transportation or local airlines for end flights to/from major hubs.

• Use a VPN to disguise the country you are “shopping” from. See video and read this article by Cybernews for more information on how and why. Their recent study shows these are the cheapest countries to use a VPN to pretend you’re in when buying flight tickets but do your own comparison (the origin or destination country is also good to check): Mexico, Thailand, Malaysia, Singapore, India, Sri Lanka, New Zealand and Hong Kong.

10. Saving Money on Accommodations

• Use any “free night certificate” you’ve earned through a hotel credit card—many give you one each year.

• Maximize your point stays by length—IHG (includes MANY common chains from Holiday Inn to InterContinental) gives you the 4th night free; Hilton & Marriott give you the 5th night free on point stays. Also, with many brands you save on point stays by paying no tax and/or resort fees.

• Stay at places with free breakfast, free happy hour, etc. if it makes sense.

• All brands are not equal in value when it comes to points—see on video how a Hyatt stay with extra food included cost 1/4 the points of a comparable Marriott nearby with no food included. If you are transferrring points from Chase, Amex or others, choose wisely to maximize where those points get you the most value.

• Some branded credit cards also have annual credits on charges at their hotels—check on yours.

• Develop loyalty or discounts on booking sites, like Genius levels on Booking.com, or the OneKeyCash loyalty program of hotels.com, expedia and VRBO group. Hotels.com also gives you a free night after 10 paid nights. AARP often has good deals on stays through their own Expedia portal.

• Try to get free cancellation as close to the stay as possible so you can watch prices and change your plans—watch, rebook, cancel—if it will save you money.

• Check hotel and cruiseline special offer pages to sign up for offers of discounts or extra points before you book.

• Always go through Rakuten and RetailMeNot first to see if they have a cash back offer and/or promo code for your booking site or brand. And see if they have (or AARP) has a discount on a gift card for that booking site which will save you even more if you purchase a gift card to pay with (refunds will usually be to credit or to the gift card so be sure to save it!). You can also get discounted AirBnB gift cards sometimes especially through AARP, or buy them with points at Staples using a card that earns high points for office supply stores.

• On a long stay, look for a discount, especially if staying a month or so. If no discount appears on your booking site (even if one does), contact the property or host directly to ask for a bigger discount. Sometimes it’s cheaper to book direct instead of through another site. You can also look at booking through a local rental agency (in the video we recommend researching how to do this at A Suitcase and a Smile and watching this YouTube video by Nomad Life: Eat.Walk.Learn, who also has videos on housesitting as a way to get free accommodation.

• Utilize nearby resort amenities to up your value while paying less at an accommodation nearby. Watch our video on how to do this as we did in Gili Meno, Indonesia.

• Book the best value you can afford. Staying outside the main city is usually cheaper but be sure you have affordable transportation available to see the sites you are interested in. Is it cost effective?

11. Other Ways to Save

• If you have a refrigerator, you can save money on food but purchasing milk and cereal at the store for your breakfasts. Grab some sandwich fixings for lunches. If you have a kettle or microwave you can make ramen noodles, etc. If you have more kitchen tools, you can cook bigger meals. Food is an area you can really save some money by eating in, even if just a meal a day. Same for alcohol—buy at the grocery store to drink in your room or on your balcony. See the video for some tricks.11

12. General Savings Tips

• Travel midweek

• Travel on shoulder season (in between the cheapest and most expensive time of year for that location when you have lower prices but usually still decent weather), or even off-season.

• Check on the costs of tickets for tourist sites before you leave your home country (sometimes you can get a pass cheaper); also compare ticketing sites like GetYourGuide, Klook and Viator for tickets and even for airport transportation and more. If you’re cruising, look at alternative excursion sites to save money and be in a smaller group, over official cruiseline excursions. See our cruise page.

• Be aware of hotel taxes. Sometimes it costs even more than usual to eat at a hotel if you are subject to a higher tax there (we have had that happen). Also check your bills for service charges to see if a tip has been included already. Use the TripIt app premium or just google to know the tipping (or non-tipping) practices of the countries you visit.

13. Stacking to Get Maximum Value

• See the video for examples, but stacking is a way of getting the most discounts possible by layering them. You can also google travel reward stacking strategies for lots of examples and ideas. But the simplest type is finding a good deal on a booking site, getting additional promo codes and hopefully also a cash back deal from a coupon site like Rakuten or RetailMeNot, while using another promo code/cash back to buy a gift card for the booking site to use for payment and using a good points-earning credit card to purchase that gift card. Another example might be finding an extra points earning offer at your favorite hotel brand, and activating it for a stay that you are purchasing with another great deal on points at that brand, getting points/discounts/credits through your credit card’s special offers, shopping portals or partnerships, etc.

• There are many, many ways to stack on travel purchases, and they constantly change based on current offers and availability. I gave you an example that can commonly be found (but not always). If you read lots of newsletters like Loyalty Lobby and are in FB groups, you’ll get ideas based on current promotions and explore ways to maximize them. Always read the fine print on whether you can use multiple offers.

• You can stack as much or as little as you want based on the time you have and how much you need to save to make you dream trip a reality, or subsidize your nomad lifestyle.

14. The Easiest Way: If all this seems too difficult and time consuming and you want an easy vacation booking, try looking at Apple Vactions and Travel Zoo. Groupon also may have good deals. Be careful to research deals you come across on social media ads, etc, to be sure they are legit and aren’t essentially time share presentations where you spend much of your vacation getting the hard sell instead of relaxing.