Drive      Fly      Stay      Login    Signup

San Francisco

General Travel

What are some of your biggest frustrations when it comes to trip planning?

I enjoy planning for my future trips but I find the current process to be way too time consuming and often frustrating. A lot of it has to do with the ridiculous amount of information available for any popular destination. Unfortunately, most of that information is repetitive and poorly written. 

What are some of your frustrations when it comes to travel planning? And what have you done to make that process easier? 

I'd love to learn some travel planning hacks that you guys are using to make things easier and faster. 


13 Answers

top answer by
Sarah from Milwaukee

I do love trip planning (part of my job) - what I don't love is when traveling with others for fun and trying to plan ahead but held back by lack of information on preferences. 

When planning trips with friends, I plan out what I would do if I was by myself, how easy it would be for them to come along if they decide last minute, and then I can move forward knowing I've covered the bases. 

In terms of going through the slog of information... I skim as much as possible & tend to trust what caught my eye initially. 

5 thankscomments (3)

answered by
Regan from Brooklyn

I'm sort of a planning nerd, so I get obsessed with all the info and kind of love it.  But I also love traveling like a local, so a couple sources I rely upon are Trip Advisor and--this takes some digging, but worth it--travel articles in the NYTimes that have comments.  Tucked away in the comments are other travelers' tips and suggestions and are frequently from locals.

As for flights, I LOVE Yapta.  I find the flights that are desirable and put them in "My Trips" and Yapta emails me every time the price changes.  And I love AirBnB and for accommodations.

5 thankscomments (1)

answered by
Billy from Chicago

One frustration I have is fighting off that 'kid in a candy shop' mentality when planning out the trip. If you try to see too much you end up a lot of the insides of trains, planes, and buses. To some extent, that can be fun and adventurous but there's a sweet spot and I think it's probably different for everyone. I lean much more toward staying in one spot for longer and getting a full experience and having less of traveling checklist.

There's also a great book called 'Vagabonding' I read while traveling through South America this year. Wish I would have read it years ago. Author's name is Rolf Potts and he JUST did a podcast on Tim Ferriss's podcast. 

4 thankscomments (3)

answered by
Ross from Fort Collins

I hate finding flights, it's always a hassle. I don't book hotels so that's one less thing to worry about.

I have great answers to this question check it out on my blog!      

4 thankscomments (3)

answered by
Polly from Washington, DC

I love travel planning, so the fact that it can be time-consuming doesn't bother me at all. There are so many amazing sites out there to help, but I haven't found one that covers everything just yet - actually, my biggest frustration might be that I don't have the tech skills to start my own travel planning web site!

Since my dream website doesn't exist, I generally start with Google maps. I pin my must-see spots on a map and check any applicable hours so that I can group things by neighborhood and save time and money. Once I've figured out my itinerary, I write everything down in a table to chart my location, activities, dining, lodging, transportation, and the total cost for each day.

I've found wikitravel to be a huge asset in regards to details about public transportation, museums, and famous sites, and tripadvisor helps with tour, hotel, and restaurant ratings. I search for flights through Kayak, but generally book on the airline's website once I found the lowest price. I also follow suggestions or advice from some of my favorite travel bloggers.

3 thankscomments (2)

answered by
Jack from Cambridge (Massachusetts)

2 things frustrate me most about planning a trip. 

First, the information overload involved in booking flights. I have found it personally very hard to click 'buy' on a flight because of all the different options and the idea that a cheaper/shorter/better flight is out there somewhere. It is a part of my decision making process that I have been working on, and now focus on finding a flight that is good enough and just going for it. 

Secondly, working in the travel/social media space, its hard to see a place with fresh eyes. I find that my itineraries are effected by the photos I've seen from other travelers, and that it leaves less room for the discovery I enjoy so much. 

3 thankscomments (1)

answered first by
Justin from Phoenix

My big complaint is that most of my search results turn up the "usual suspects" of travel writing ... it's hard to find good, independent blogs that go beyond Top 10 lists, bucket lists and hideously overwritten and over-flattering prose to get to the real stuff. I'd love to know what mistakes people made, what disappointed them, what surprised them.

3 thankscomments (2)

answered by
varun from India

The biggest frustration is the unnecessary and rubbish information available on the net. We are hungry to absorb every information available on the net and the worse part about it is everyone is selling the same stuff in different packing still we read it because it is available for free of cost. 

The best available solution is to zero in on a single website which you feel is the best among the best and follow it with your eye closed. Secondly, take the first hand information from someone you know who has been there . Thirdly, explore your contact as much as possible.

2 thanks

answered by
Cherie from Bay Area

Definitely planning flights – I feel like I can't really get excited about the trip until the flights are booked, but I always wonder, "Is this is the best deal I can find, or if another one will pop up closer to the date? Or will it just get more expensive?". 

Secondly, when it comes to multiple destinations, outbound flights, and time differences, as hard as I try to keep everything super organized in spreadsheets, I will often second guess myself thinking, "Did I choose all the right transfers or checkout dates for the hotel/airbnb?". I have my lists and check them often for peace of mind.  ^_^  

2 thankscomments (1)

answered by
Courtney from Los Angeles

This is something that really doesn't have a solution but I'd say I'm most frustrated when two or more things I want to see/visit occur just far enough apart that I have to choose one or the other. Or I just miss seeing something by days. For instance, this year I'm going to New York for Christmas and Rufus Wainwright (my favorite musician) had a concert there last week. That kind of thing drives me crazy. :(

1 thanks

answered by
Ashley from Calgary

Wanting to see it all and knowing you have time and/or money limitations. I feel like I missed out majorly when I learn of something neat in a place I visited but I never got to see it. 

1 thanks

answered by
Felcity from Tucson

Some of my frustrations when it comes to planning a vacation, is when sometimes you thought something was a price then they change it overtime, and when your flight cancels on you.

1 thankscomments (1)

answered by
Izabel from Lisbon

Andy I got a couple of suggestions for you: hire a local travel agency that can give your important tips about the destination youre going to, they can also hire for you a guide to accompany you some days of your trip, you could also buy personalized tours made for you, most agencies do that, after getting to know what are your interests and needs. Or like my 2 sons do when they go anywhere, the bare minimum research on google about the place and just plan anything they will do when they are in place and already got to know some locals, or some people that are already there for a couple of days (they do this because they know, that's how you get the trully hidden gems of any destination).

If you have any other question you would like to ask, or maybe take a look in other tours and experiences Lisbon has to offer, please take a look at my website: ( is google translation friendly)

Or you can send me a e-mail:


1 thankscomments (1)

© 2019   ·   View: Full | Mobile

Follow us:        
Questions   ·   Destinations   ·   Drive   ·   Fly   ·   Airports   ·   Stay   ·   Search

Login   ·   FAQ   ·   About   ·   Feedback   ·   Privacy   ·   Terms