My Travel Planning Essentials

Although I have been an international traveler since I was eight months old (when I got my first passport) after a very extended lull, the last several years have been very much ramping up for me. You know, despite the general awfulness that is the state of airline travel in the modern world. Ah, remember Pan Am? TWA? Continental how I never knew I’d miss you so! And we thought it was bad back then! At least there’s no more smoking on flights.

When it comes to finding flights, hotels, train routes, and general travel planning, I, am a crazy person. For whatever reason it helps me focus, and doesn’t stress me out like it does most people. I’ve been asked how I go about it all, so I thought I’d give a list of sites, apps, and products that I use. You might have other suggestions (please do comment!) but this is just what I have been using and what works for me when planning a trip.

Skiplagged: The first thing I check is this app, and not because I actually purchase anything. Skiplagged will tell me about airlines that get suppressed by other websites, such as regional Canadian airlines like Porter. Did you know that Albania has an airline that flies out of Boston to various European cities? Well, now you do.

Scott’s Cheap Flights: I’m pretty sure friends are sick of me forwarding them these emails. I signed up for the Premium subscription, but for ages I had the free newsletter; it was how I was able to go to Marrakech for so cheap ($420!) They even featured my trip on their subscriber list. Scott’s is a good jumping off point which will then lead you to…

Google: This is the most basic way to go, and make sure you do it incognito in your browser. The matrix for Google Flights is better than a lot of sites and you can view pricing by the day. Once I see or get an idea of flights — and especially multi-city flights I am doing — my next stop is to…

Airline website: Really, you are never going to get much of a better deal than from the airline themselves. A lot of pricing you see on Google or Kayak does not include bag fees, seat selections, taxes and all of that nonsense. You might as well sign-up for the rewards program and get down to searching the days you had viewed on Google. I have a stupid amount of memberships and I try to transfer points to partner airlines when I can. It is really annoying when points expire but sometimes that can’t be helped. Delta Sky Miles don’t expire which is nice.

Two Things I Love

TripAdvisor: I have been a contributor for over a decade with everything from a roadside motel in New York state to a luxury riad in Morocco. TripAdvisor also is good for picking excursions if you like doing those. The key is to be able to tell what bad reviews are from a crazy weirdo with ridiculous expectations, which are legit from seemingly normal people, and what good ones are fake. I can usually tell and I’m so glad to see traveler photos of a room versus the hotel photos. Sometimes hotel reviews are so bad they will literally change their business name (I’ve had 2 of my only 3 worst reviews ever deleted due to this). Reading between the lines sometimes takes a bit of work and research, but part of me is more concerned with location than anything and I like being able to see what other hotels might be on the same block or just a mile down the road. I won’t go into AirBnb because I had a bad experience in Lisbon, and won’t be doing it ever again after that. If you are a member of any hotel/motel reward program, be sure to book via their portal to get a better room or an upgrade. As a rule, going through any hotel website directly is going to get you a better room and price. For some of the smaller hotels or B&Bs, I’ve actually had little notes left on a dresser or desk thanking me for booking direct! I’m a Choice, Starwood, and Hilton Honors member, and my favorite budget chain when I can find them is Ibis. I also operate with the thinking that the fanciest room in a cheap hotel is better than the cheapest room at a fancy hotel. So far, so good!

Chase Sapphire Reserve: What can I say? I love this card! 50,000 miles as a sign-up bonus and the annual fee pays for itself in other ways. You get a $300 travel credit, your TSA pre-check fee gets waived, and you get up to 3 guests for Priority Pass Lounges around the world! I love me some lounges! In fact I will try to avoid airports that don’t have them if I can. Those long layovers or having a delayed flight are not nearly as painful if you are in a lounge. I’ve never booked a hotel via the Chase partner website, but I am planning on doing it in the future as it features benefits like food/beverage credits, free transfers to airports, and a room upgrade to the next level. You also don’t have to buy extra travel insurance, because it is always built-in when you book with the card. 

Finding What To Do

Eating and Drinking: When putting together an itinerary, I will choose Afar, Hedonist’s Guide, and occasionally the New York Times, The Telegraph, or The Independent. CNT isn’t too shaby, either. 

Instagram: It’s crazy how this app has changed travel, and even crazier that I have to deal with “Influencers” and their sad photographer boyfriends in tow. I nearly shoved one out of my way at the YSL house because she was blocking the walkways doing the same pose over and over, and it has gotten so bad in Notting Hill that homeowners have roped off their stoops so girls can’t post in front of their doors. I hear Palm Springs is pretty overrun with signs in front yards that say “no photography”, too! Despite the annoying part of Instagram and what it has spawned, you can find cool little spots for coffee and whatnot if you do a location search and scroll around until something strikes you. 

What do you dig? A way that I find out about the nightclubs or concerts I might want to go to is just by looking up bands I know have toured in recent years and seeing where it was they have played. Chances are they played a venue that will have other cool random bands you might not have known about otherwise. I do this with art galleries, too, and look up where an artist showed recently or is about to. Obviously asking friends helps, but if it is a city where you don’t know anyone this is how I find all the goth/alternative/indie nights that I want to go to.

The local Alt Weekly: There’s usually one in every city, try to seek it out if you can in print or online.


City Mapper: I love this app because it will tell me how long a trip in a car versus public transit will take, and where all of the stops are. Sometimes an Uber is faster than the tube! 

Google My Maps: If you are a crazy person, like me, and have your cafes, restaurants, bus stops, goth clubs, and museums you know you want to hit, this will help you map it out and you won’t need to be on wifi (yay screen captures too). I’ve never had a SIM card and this was helpful even in a city like a maze. By the way, I get unlimited data from Virgin Mobile for $30/month and I love it. I think I have been with them for 7 years, and I get a strong signal everywhere I have been. Even in the depths of Mississippi!

Yahoo Weather: This app has been a go-to for a long time as it is more accurate than most. It shows a radar with weather patterns. Sometimes there are misfires, but I always check the outlook the day I am packing.

FlightAware: I don’t like having each airline app on my phone, so instead I keep up with any delays on this app if I am traveling in winter. I don’t do layovers or change planes anymore as a rule, so sometimes it won’t matter because you do get an email from the airline. But, it’s also handy maybe if you are picking someone up from the airport. How nice of you!

TripIt: Yes, I do write everything down in my Filofax, but sometimes I just need it on my phone. TripIt will import all email itineraries you get sent by an airline and it auto-populates for you. It is also great for adding in confirmation numbers for trains, hotel reservations, dinner reservations, or excursion reservations. It is essentially a timeline; you can share it with others you are traveling with or to anyone involved in your logistics. 

All the Train Apps:
I download every train app possible for wherever I’m going, whether that is San Diego, Belfast, Glasgow, or Florence. Sometimes you still need a paper ticket depending, but I also like getting deal alerts and purchasing ahead of time for a discount. This is especially true if you are doing something like a train direct to an airport.  

While on the Plane or Train

  • Air mask for travel in cool patterns. Because yes I am that person on the plane, and yes it helps make a difference in jetlag, too.
  • Silk eye mask
  • Back-up charger
  • Sanitation wipes for the tray table and all the buttons — especially the air dial above.
  • CBD oil so I don’t want to murder people if I have no leg room.
  • Use an app like SideStep or take these precautions when in an airport or train station etc. 

If you want to know more about how I go about packing, you can read and watch the video I did with my husband and cats over here. Also, I’m finding I do laundry a lot on trips, and if you love Rick Steves as much as I do, get yourself one of these.

I hope you found this helpful, and if you have any other apps or tips please comment.

6 thoughts on “My Travel Planning Essentials”

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