Beginners Guide to Free Travel

When I started my site about a year ago I set out to make free travel easy and digestible for the masses. I feel like there are many travel blogs out there that put heavy emphasis on luxury travel. I am not saying that there is not a demand for luxury travel tips and advice for elite status, clearly there is, but I want to help beginners get their feet wet. Many of the people I talk to can’t remember their last vacation and they definitely aren’t worried about what fare class their flight is booked in. If that sounds like you, this post is for you!


The most important thing to keep in mind is that flexibility is the key to scoring a good deal, whether you are using points or cash. You have to balance these three factors if you are going to get the most value on your next trip:
• Best Price
• Destination
• Date


You need to pick two of these three factors, if you happen to get all three then you should buy a lotto ticket. If you have already picked out your date and destination don’t count on being able to get the best deal possible. If you already know where you want to go but you are flexible on the date, you should be able to find a good price. If you have set dates but are flexible on any Caribbean island, you should be able to a great price. If you are looking for all three factors to align, you are going to be looking for a long time.


The Travel Triangle
The Travel Triangle



Let’s start with points, all points and miles are not created equal. In fact, some points are worth up to 6 times more than the low value points. Hilton points, for example, are only worth about .5 cents which is very low. That means that 100,000 Hilton points are worth about $500. On the flip side, Starwood SPG point are worth over 2 cents a piece. That means that 100,000 Starwood points are worth well over $2,000, whoa! A free night at a category 3 Hilton property will require 20,000 points where a category 3 Starwood property will only require 7,000 points per night.


Oh yea, if you stay 4 nights with Starwood the 5th night is free (for cat. 3,4,5,6,7). That means you will only need 28,000 points for 5 nights at a category 3 property like this one in Phuket, Thailand.


The Westin Siray Bay - Courtesy of Starwood Hotels
The Westin Siray Bay – Category 3 Starwood property



Before you begin collecting points you will need to figure out where you want to go and how you plan on getting there. You now understand that 1 point with company A may not be equal to 1 point with company B. Southwest Airlines and Alaska Airlines are, in my opinion, the most flexible and valuable airline miles. Southwest award flights (‘award’ which means you booked with points rather than cash) can be cancelled with no penalty all the way up to your departure. If you change your mind or your plans change an hour before your Southwest flight, just cancel and receive all your points back immediately.


With Alaska Airlines you are able to cancel your award flight up to 60 days before departure with no penalty ($125 fee it if is within 60 days of departure). Delta and United charge $150 and $200, respectively, to cancel your award flight at anytime and have your points deposited back into your account. American is a little more flexible since they do allow you to change your award flight date and connections, you just can’t change your start and end point. ($75 fee if done within 21 days of departure)


Once you know your preferred airline, you will need to figure out how you want to start earning points. The quickest way is to sign up for a travel credit card (or 3 at a time). If you have a credit score of at least 670 you should be able to sign up for a travel credit card. If you aren’t able to or don’t want to sign up for a credit card, you can still earn points using these methods. If you are choosing to not sign up for a credit card because you think it may hurt your credit score, read this article.


How many miles do I need for a free flight?
Standard rates for a one-way flight (some rates are lower for short-haul flights or intra-state flights):
American Airlines – 12,500 one-way in lower 48
United Airlines – 12,500 one-way in US & Canada (excluding Hawaii)
Delta Airlines – 12,500 one-way in US & Canada (excluding Hawaii)
Alaska Airlines – 12,500 one-way in US & Canada (excluding Hawaii) Great option if you want to fly somewhere remote in Alaska
Southwest Airlines – A $100 flight will cost around 6,000 points. One Southwest point covers about 1.6 cents in airfare. A $50 flight would require roughly 3,000 points
JetBlue Airlines – A $100 flight would cost you about 7,100 points. The point structure is similar to Southwest, except points are worth only 1.4 cents a piece. JetBlue and Southwest are great options since you can start using points before hitting 12,500.


Alaska has one of the highest rated award programs
Alaska has one of the highest rated award programs


A big misconception with hotels is that you must stay in a  conventional hotel/resort when you are on vacation. Most people don’t even bother exploring additional options with AirBNB or VRBO. Hotels are very expensive, especially if you are travelling at peak travel times (which is usually when you have time off). AirBNB is a great option for renting a room or an entire house. You can even share a room or rent a couch if you want to stay for dirt-cheap.


VRBO will show you awesome vacation home options all over the world. If you want to get a home for your family of six near the beach, VRBO is your go-to. If you stayed a conventional hotel near the beach you are going to need at least two rooms, you will likely pay a daily resort fee for each room, parking, wifi, and you won’t have a kitchen thus increasing your food cost. If you are paying cash, you should really do yourself a favor and check out hotel options outside the conventional norm.


If you have points to use, check out awardmapper to see all your hotel point options. Like I mentioned earlier, Starwood points are the most powerful and valuable, followed closely by Hyatt. If you are starting from scratch, I would highly recommend accruing points in one of these two programs.


Remember, your 1.5% cashback card may not be your best option. My Starwood card may only earn 1 point per dollar spent but Starwood points are worth 2.5 cents a piece. The effective “cashback” rate is then 2.5% assuming you don’t mind spending that return on hotels or airfare. And yes, you can transfer Starwood points to over 150 airlines. If you transfer 20k Starwood points they will add a 5k bonus netting you 25k points transferred to your airline of choice.


As always, if you have questions be sure to reach out on Facebook

Leave a Reply

Fill in your details below or click an icon to log in: Logo

You are commenting using your account. Log Out /  Change )

Google photo

You are commenting using your Google account. Log Out /  Change )

Twitter picture

You are commenting using your Twitter account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s