Travel Planning Routine

Here is my complete travel planning routine. Everything from what booking sites I check, to how I put it in my calendar.

This is the nitty gritty details. I realize I have the same simple routine, and it’s been working for me for years.

Google Calendar

I know this sounds too basic, and I’ve mentioned it before, but it’s the only system that works for me, and why you should use Google calendar (especially if you use Gmail or have an android… who doesn’t use gmail?!).

Because I’m not a tedious planner, I just try to book it and put it out of mind… I live on my calendar. And thus, I really can’t screw up flight times and whatever… because I often don’t double check.

Summary:

• Edit for details and alerts
• Sometimes Gmail autoposts things received in my inbox to my calendar
• I have calendar card on my phone, so I can see where I’m supposed to go, or click and instantly get my confirmation number
• Tip: careful of time zones

 

Basic in title.

For hotels I always just put the name of the hotel and in parenthesis I put whose name the reservation is in. It helps, trust me.

If it’s a flight I say “AA: JFK-AUS @2:40pmEST”. It auto translates to “AA: JFK-AUS” and has the time put into the details.

Edit for details! Destination, alerts, conf #, etc…

For a hotel I often put the hotel in the address box, and hopefully it autocompletes and puts the entire address. The reason is that on the ground I can now click it and it will pull up Google Maps to that hotel without first searching for the right Marriott, or whatever.

I sometimes make an email alert for cancelation time.

If the hotel was not booked via the big chain hotels, and booked on Orbitz or something… In the details box I include which site I booked on, confirmation #, and the email I used.

Dates – Minor detail, but for hotels I never put the check out date as a date, I only do nights. In other words, if I’m still missing a hotel that night, the date should be blank.

Gmail syncs with Google Calendar

I’ve noticed with more and more confirmation bookings Google automatically puts the travels in my calendar… which I think most people would like. It’s simpler than using an entirely different site to keep track of travel dates, imo.

However, I’m pretty particular about how my things are set up.

Why have a Calendar card on your phone!

When I land I can swipe to the right and see my calendar and it will have which car rental counter I’m supposed to go to, or when my next flight is.

But the best parts are that the details are one click away. Again, I can click and have it pull up directions on Google Maps (I’ll explain how to do it offline too). Or, I can click and get my confirmation number, in case of an incompetent agent.

Big Tip: Careful with Time Zones

I said for flights I type in 2:40pmEST and it auto fills in the date… well, if I don’t do the time zone it gets confused.

For instance if I put just 2:40pm into my calendar while I’m in Austin, then in NYC it will show up on my calendar as a 1:40pm flight. Which… is way better than doing the reverse, it showing 3:40pm and making me miss my flight!

 

Booking Hotels

Summary:

• My “Complete Maps” for general ideas with a specific brand
• Hotel Hustle for specific idea with any brand
  • And alerts
• FlyerTalk OTA deals
• FrequentFlyerBonuses.com
• Complete Guide to Best Rate Guarantees
• Airbnb (currently giving $85 in credits – click here!)

 

Finding Hotels

If I’m getting ideas for where to go I use my Complete Maps.

If I’m planning for a specific city, I use Hotel-Hustle. If one isn’t available, you can set an alert – which is how I got so many free nights in an Overwater Bungalow in Bora Bora.

Many times when planning for a specific city, I know exactly what hotel I want and it’s a matter of going to the chain and booking it.

Note: I always book cancelable rooms! You never know when a better deal might pop up.

When I’m not redeeming points…

I’m either earning them or trying to get a good deal elsewhere.

Earning:

Often either there are no points hotels, or the redemptions are terrible. Like we had a short layover in NYC and there were IHG hotels for $85+, and yet the points rates for the same hotels were 40,000 points or more! But we got a $100 room at the Hotel Indigo, got upgraded to a suite, and it will likely count towards our IHG Accelerate promo.

Check Frequentflyerbonuses.com for promotions by hotel chain.

Or if I don’t want to spend cash, I check for Best Rate Guarantees. (Finding a lower rate on competing sites gives a bonus – like with IHG this means a free night, with Hilton it’s a $50 discount).

Non points hotels

I check for OTA deals and referal bonuses.

It’s hard to find these things and it’s completely about having lucky timing.

Multiple times now I’ve seen promotions to book on Orbitz and get a $100 discount when using Visa Checkout. This was an extreme case, as we booked slightly over $100 hotels night by night, and got them for nearly free.

But checking for discounts on random sites is about the best option when you don’t have points hotels or airbnb credits.

I pay attention to FrequentMiler’s Quick Deals, and I check the FlyerTalk thread for OTA coupons. Every once in a while there’s a good coupon.

I’ve also been into regularly checking RoomerTravel.com (for rooms people can’t use and want to resell). Unfortunately, because they are specific bookings – specific hotels with specific dates – I’ve never found a deal I can use! It begins to feel like watching the stock market.

Airbnb Deal:

Also, there is a deal currently with airbnb where you can get $85 in airbnb credits.

Basically, a referral link can get you $35 towards your first airbnb (click here to use my link and get $35).

Then if you register for a business account (click here for my business account referral), and mark your trip business (instead of personal), you’ll get emailed a $50 credit.

 

Booking Flights

Summary:

• Use whatever is left in my AwardWallet
• Compare Award Charts
• Check FlyerMiler.com
• Check SkyScanner
• Check Avios Map
• Last minute bookings – put tickets on hold, or use 24 hour cancelations and hope for something better.

Long Routes → Use Whatever Miles I have

Generally I look at my AwardWallet account, and the options are usually limited – “Do I want to use AA miles, United miles, or Alaska Miles?”.

It’s pretty easy to do a search for my route on all 3 of my options. Just go to the website → put in my dates and route → check “award travel” → “search” for saver awards.

For my routes I know the economy prices off the top of my head, but for an obscure route I might compare the List of Award Charts, or check FlyerMiler.com.

This way I may find a transfer partner I don’t have miles in that has a half priced route. This is likely the case when going from North Africa to Europe, for example, where not only do I not know the price, but they vary greatly.

Short Routes

I always check SkyScanner.com. Read “A guide to finding super cheap flights” to get an idea of its features. But mostly it’s good at checking discount airlines, and with flexible routes.

I still check and use British Airways Avios for short routes since it’s a transfer partner to nearly everyone, and direct OneWorld flights begin at 7,500 Avios. Check out the Avios Map for ideas.

Or again, I compare Award Charts, and check FlyerMiler.

Last Minute Bookings

I have a really bad habit of procrastinating when booking a flight. If there isn’t the deal I want I tend to wait. Which usually turns out okay, but involves a lot of stress in the days leading to a trip.

Our current trip was like that. We booked a $220 mistake fare out of New York, but I waited ’til two days before the flight to get the ticket to NYC.

Basically I keep checking flights, and when something close turns up I put it on hold, or for airlines that don’t do holds they usually allow cancelations within 24 hours.

For this last trip, I ended up canceling an Alaska ticket to put an AA ticket on hold. But the AA ticket left at 5 am, so I still kept checking. Then I ended up booking a direct flight that left at 9am and got us into NYC sooner.

So it turned out fine, but I also end up wasting time this way.

Also, you should be following our travels as we’re live vlogging the trip using Instagram Stories. Follow TravelisFree, and use the app to see stories.

 

Planning to be on the Ground

Summary

• T-Mobile
• Or use Google Maps to download route for offline
• Rome2Rio.com
• We just wing it…

Local Transit

If you have an international phone plan like T-Mobile (or Project Fi), you have google maps all the time.  (Or at least, in T-Mobile’s case a large list of countries.)

If you don’t have international data, you can open Google Maps, search a foreign route and be given the option to download it offline.

For me, I got the option when searching a route:

Or when searching a place (country or city), and then after clicking on the place I get the option to download.

And you can click the menu button, and then “Offline areas”

 

Public Transit

For local transit I check Rome2Rio.com – it searches bus routes, taxi prices, and about everything you need to know locally.

It’s not always complete, as it may not show a bus from the airport, even though there always is one. But 9 times out of 10, it shows you the bus number and everything.

Actually it’s probably much higher considering that most travel is done in big cities that have subways and buses that it can easily catalog. For most places, it’s fantastic.

Personally, we end up winging it a lot, or if it’s a place we’ve been to before (Bangkok, Hong Kong, etc…) I assume I can figure it out easily when I’m there, because they have good public transit.

Often I ask the information desk to get to my hotel. This works 9 times of 10. It’s only lesser traveled destinaions that don’t have desks, or where the people don’t speak english.

What to do?

Honestly, I’m not a good person to ask because I don’t plan ahead. I’m getting better about sometimes looking for special events or holidays… but mostly I don’t plan ahead.

For a country I try to look at pictures to figure out where I want to go, but that’s a basic process.

For example, recently I shared that I just used Google Sphere photos to plan my next trip. Totally true for our current trip.

I generally ask locals.

But the big tip is to never ask the concierge. Especially for advice about food. You’ll never meet a group with worse suggestions.

At the Radisson Blu Ankara, Turkey the concierge clearly got commission –when I asked what was open at that late hour, they made the reservation and then practically stuffed us into a taxi with another pair of guests and sent us across town (we had no idea it was so far away). They assured us it was the only place open at that hour. Our second night we learned about tons of local places a block away. I’m still annoyed.

That was worst case scenario. Best case scenario is that they honestly give you a bad recommendation because they’re used to getting American tourists who hate spicy food, and hate actual local food, as they’re used to the sweet version back home.

So they pick the safest, whitest restaurant in town knowing that it gets the least complaints. Although, that probably describes most people, so maybe you’ll appreciate asking the concierge. I don’t know.

 

Conclusion

While I do very little planning ahead, it’s almost systematized I check the same websites every trip, I use the same mileage programs (for the most part), and I focus on the same deals.

And while this post is long, it’s not that complicated. The post is long because it’s complete.

In short, I try to get the best credit card signup bonuses… then I just use whatever miles I have, it’s not that complicated.

If somewhere I want to go has an amazing deal, I reverse engineer it.

For example, if I see on my Complete Maps that Transylvania (which I still want to go to) has 10,000 point Hilton hotels, then I’ll purposely start getting the Hilton cards again.

Or I check out the cheapest miles to page, and see a deal, I’ll focus on getting that card.

For non-points related stuff, checkout the following posts:

• How to get amazing hotel deals
• How to get amazing flight deals