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Friday Fun: What's your best vacation planning hack?

Let's face it, work can be challenging but fulfilling, especially when you enjoy the challenges thrown at you.  However for me, nothing compares to going on vacation (or holiday as some of you may call it) and temporary leaving it all behind.  There's nothing better than relaxing on the beach listening to the waves.  

BUT in order to take a vacation, you have to plan ahead and actually book it.  Here's where I need help.  There are too many options!  Places to go, ways to book, and factors to consider.  


What vacation planning hacks do you use to make it easy and painless? 




My vacation planning hack is to go talk to a travel agent. Many times they earn a commission from the company you're buying through, and you don't pay for the service - but you get all the benefits, discounts, and don't have to work out all the nitty gritty details.

Major time-saver for me since planning a vacation for my family usually takes as at least twice as much time to plan as I'd actually just be on vacation. 

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I've definitely thought about doing this.   Any suggestions on travel agent company to use?  I have AAA so thought about using them but open to other suggestions. 

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My best friend owns this travel agency. The website is a bit janky but he planned the most amazing trip to Costa Rica last summer! He doesn't charge anything. Highly recommend him. (And also Costa Rica, OMG.)

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Same as Mo, I've got friends who do it as their side hustle. Surprisingly you can get travel planning through Costco even. I would say find someone local to you that you can sit down with and talk to.

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Kat Marketplace Partner May 16, 2019

Trello of course!

I searched the public boards for something similar then copied that as the starting point for my trip planning. 

  • I love being able to add ideas while I am on-the-go from my mobile, work computer, home computer...
  • I add copies of important information like insurance and flight details so these can be accessed easily if needed.
  • It is easy to share the board with someone before travelling in case there is an emergency.
  • Checklists make packing very easy especially if you are trying to travel with carry-on only.

Below is a screenshot of my Summit planning and I have anther come for an upcoming 6 week trip.

Screen Shot 2019-05-17 at 8.39.31 AM.png

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Wow and I thought I was organized with my single recurring packing list!  Very nice thanks for sharing 

Kat Marketplace Partner May 16, 2019

I find it to be an antidote to anxiety. I never need to worry about 'what ifs' before my trip as I just note them down. There are a bunch of archived tickets for things like notifying my credit card company (so they don't think my cards been misused) and notifying the government Safe Travel website etc.


The activity ideas can be helpful when internet access is limited overseas as well.

Ive never thought of using Trello, that's a really good idea!

Depends on what type of vacationer you are... I’m the independent, doityourself guy & love preparing for vacation. For flights, try google by just entering the airport codes (eg. LAX LHR), try to be flexible on departure & return date. Set a email notification for price changes. Book well in advance (4 months), if you can. When the flight is set, I’ll go for Airbnb. I love digging around the offers, finding cozy little places to stay. When going with the family, you’ve to make a compromise: Beach or mountains, nature or cities, hotel or camper? Make your family write down their wishes & find a common base. Kids have other expectation then adults.

Places to go are mostly depending of what you like. As a European, I suggest the Canary island Tenerife: Beaches, party, nature, a volcano, good food & wine. Had a lot of fun last fall. Northern Italy is also very nice in spring & fall. Visiting London is a thing I could do every year...

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Great advice, thank you!  Luckily, we don't have kids right now so that makes it a little easier ;) 

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Mike Rathwell Community Leader May 16, 2019

I'm a little different than any of the above... The Boss and I have two different varieties of vacation:

  1. A cruise. Stellar when you really want to relax but still see stuff. Check into a really nice hotel (we prefer Celebrity) once and then let the hotel take you places. Pick from the stuff to do at each spot and maybe do a bit of research to see when/where you might organize something on your own instead of taking the cruise line offerings
  2. Go somewhere. Do stuff. In this variety, we book a flight into somewhere and a flight out of somewhere. Do what seems interesting in between those dates. We might do a bit of looking to see what we would LIKE to go see but not heartburnt if we don't get there because something else turned up more interesting. That was how we ended up going to Angkor Wat; we had two weeks in Vietnam and ended up at the final point (Hanoi) with days left so... got on an airplane to Siem Reap, grabbed the first hotel shuttle we saw that said he had rooms. Flew back to Hanoi after we were done. More work but often far more rewarding
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Rachel Wright Community Leader May 17, 2019

I love cruises when I need to get away but don't want to plan the details.  This way, my only responsibility is not to miss the boat!

Has anyone tried solo cruises?  I've done 2 or 3.  Some cruise lines offer solo cabins with special pricing.  Works perfectly when I want to travel and "The Boss", as you called it @Mike Rathwell, wants to stay behind.  :)

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Bridget Community Manager May 16, 2019

The Skyscanner Power-Up for Trello is such a good hack! 

It lets you access Skyscanner’s flight searches, their database of knowledge on flight price trends, information on the best time to book, etc.

For instance, when using Trello to help research travel destinations in Europe, I can create separate tickets for all my favorite spots :) This way, I can see the average cost of flights to each destination, side-by-side.

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Erica Moss Community Manager May 21, 2019

@Bridget SO cool!

Rachel Wright Community Leader May 24, 2019

AWESOME!  I had no idea you could do this!  Thanks for the great tip @Bridget Sauer 

Well, I am obsessed with planning with all its goods and bads :) I'm not a typical traveler, because I don't like group organized trips or museums or schedules or "we have to go there and there and there.", but I love when my journey is going smooth and simple. My top vacation planning hacks:

  • Book in advance, 2-3-4 months earlier. You get better prices, better locations, and more benefits.
  • Go to vacation in dates that most people don't like :) Good example here is our sea vacation this year (we are going to Thassos) - we'll travel June when it is not so crowded, the weather is perfect, nature is fresh and green, and the best part: everybody thinks that time for that type of vacation is n August (!?).
  • Expect nothing! I don't read anything about the place that I plan to visit, and thanks to that I see so many more beautiful things :)
  • Most important for me is to check all the restaurants and food options near the hotel. I'm sure that you all have experienced the moment with "Let's have dinner in 6." "Sure, where?" "I have no idea...". And 2 hours later we are still browsing Maps and TripAdvisor.
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Wow. I never want to find out after a trip that I missed something great, so I can't go anywhere without research. Deep research. I generally don't care about the big, touristy things. I like to find the stuff that locals do.

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Mike Rathwell Community Leader May 17, 2019

@Karen O'Keefe you nailed a big one there. Find the stuff the locals do. If we do the "unplanned" type of vacation (aside from a short list of "must" and "like" to see) it's almost always not where the tourists go.

There is, for example, an adage regarding Venice: "When the crowd goes right... go left". Served us well there. It's also part of how I ended up piloting a 10m sampan through the floating market in Can Tho, Vietnam... 

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+1 on the Venice tip. I stayed there several times: Visit the market EARLY, use a traghetto STANDING crossing the Canale Grande, take an ombré (glass of white wine @ 10 am together with judges & attorneys from the court) & NEVER sit down when you‘re having an espresso at a bar. And for visiting the St. Marks basilica: Just visit a service. Free entry & enough time to see everything... 😜

carolyn french Community Leader May 19, 2019

@Mike Rathwell Need more of this story about how you ended up piloting a sampan through the floating market!

Mike Rathwell Community Leader May 20, 2019

@carolyn french , that one was a bit of luck and a bit of serendipity. The Boss is Vietnamese and she speaks Vietnamese (duh). What is unexpected is that the big ugly Caucasian can speak it as well. There is always bit of trouble being understood at first (for me) but it seems like they look at me and start listening in English... then they realize it's actually Vietnamese.

Anyway, we were down in Can Tho to see that market. It's rather different from the floating markets in Thailand which are mostly tourist presentations. There it is actually a real thing where the farmers and other wholesalers will come in with rather large boats with their produce and the smaller sellers in the area come and buy from them.

We struck up a conversation with a boat operator there who asked if we wanted to go out. We ended up in the middle of it with no "tour" money being asked for. I was asked if I'd ever run a boat and, on confirming, offered me the wheel. We were rather outside of the market when I started but after watching like a hawk, he let me float on through the market. Was a bit nerve wracking as a long skinny 30 ft sampan handles a LOT differently from my Boston Whaler but I wouldn't have traded that for anything.

That kind of thing and others like it throughout SE Asia have it being one of our favorite places to go.

carolyn french Community Leader May 24, 2019

That is great story! And I share your love of SE Asia and the friendliness of people here.

I can sympathize with not getting understood in Vietnamese (since I'm living here now), but my pronunciation of the tones is passable at best, and a complete mangling at worst. 

I do a combination of planning and not planning. I like to nail down flights and places to stay as early as possible. Do a lot of research, and then make three sets of plans: must-dos, which I schedule; would like to dos; and contingency plans (for bad weather days or for when other plans fall through).

For example, my son and I went to the Eastern shore of Maryland several years in a row, I made plans for every other day and then made plans for a contingency. The non-activity days were beach days. The contingency plan was usually a pretty elaborate trip somewhere like Baltimore or Washington DC in case of bad weather at the coast.

That timing was perfect. We ended up exploring a lot of the eastern shore over the years and we had several memorable trips on bad weather days. Plus we had a lot of relaxation time at the beach.

Cruise Advice: pack lightly. Check to see if they have laundry rooms or laundry service. Book a couple of activities through the cruise line, but save time and space for exploration.

I also use Trello to plan and organize my vacations. I have a recurring packing list, that I can modify and tailor to the weather. I even have a 40 item list for my Dog when he travels with us :) With these reusable lists I don't have to worry about forgetting anything, or waste time to recreate the list from scratch every time I travel. Here is my dream trip list I created for the Trello contest, my husband and I hope to go to Hawaii this upcoming winter so I am one step ahead with our Trello dream trip board.

hawaii board.jpg

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Rachel Wright Community Leader May 17, 2019

Surprise travel:

I read a great article on surprise travel the other day.  You answer some questions, an agency plans everything, and you find out where you're going and what you're doing on the day you leave!  Sounds super fun and easy if you're overwhelmed by planning.  I'd love to do this someday!  See:


I firmly believe there are only two types of luggage:  carry on and lost!  Challenge yourself to travel with just one backpack.  It will change your life!

Planning and itinerary:

I track all my RV trip planning details in Confluence and have just started to try out Trello as alternative.

But when there are flights involved, I track those trips in Tripit Pro.  (  I like this service because it monitors flights, alerts me when gates change, turns confirmation emails into travel entries, has both a web and mobile version, and keeps me organized.  On my return flight from Summit Vegas, I used the app to see how long it would take to walk from my gate to the nearest Xpress spa in another terminal.  It was too far.  :(  The app tells you in minutes and maps the route.  It has lots of great features.

Tripit has a free version too, and of course, there are other trip planning apps out there.  I periodically try the others out but after 46 trips, haven't found one I like better.

TSA Pre-check and Global Entry:

If you're a US citizen that travels often, it's worth the time, hassle, and money to join this program.  But rather than talk about the benefits of the program, here are some tips I've learned along the way, while using it:

  • Pre-check is not supported at every US airport.  Pack your bag like you'll have to go through the regular line, just in case.
  • Pre-check is not always open really early in the morning.  (I'm calling you out, Dulles Airport.  Grrr.)
  • The rules and benefits are not consistently applied between different airports.
  • Once you have it, don't let it expire or you have to start the application process all over again.  Renewal is required every 5 years.
  • Sometimes renewal doesn't require an in person interview.  I was able to do my first renewal online with no hassle.
  • Regarding the little card that comes with your membership:  "You need to carry your membership card only if you'll be traveling by land between the United States and Canada or Mexico. You do not need the Global Entry card for travel by air."
  • (Separate from these programs) US Customs now has their own app.  I haven't used it but heard it's the next best thing to Global Entry.  (Get through the line faster.)

Happy planning @Chris Nicosia ! And let us know what vacation you choose!

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About TSA pre-check, a quick addition to this comprehensive list... The TSA card won't be accepted at the airport (like mentioned above, its for land only) - TSA # must be added to each airline/ticket when you buy your ticket, or add to your airline account, and then it will be printed on the boarding pass. If not, there will be no benefits (at least not in Newark airport, NJ). I found out the hard way (well, not really, but it was still annoying). 

Like Rachel Wright likes this

@Rachel Wright I think I need to upgrade my TripIt to TripIt Pro.


I so want to do this!

Rachel Wright Community Leader May 24, 2019

Hi @Inna Gordin _Appfire_ - That happened to me once.  I booked a flight through a third party (Google, Expedia, etc) on an airline I hadn't traveled with before.  No pre-check privileges were present on my boarding pass.  Solutions:

1. I gave my TSA number to the rep at the airline's ticket counter at the airport.  They reprinted the boarding pass for me with the pre-check credential showing.

2. I make sure to create a quick account with any airline I'm going to use BEFORE buying a ticket from a third party site.  This way, my TSA details are entered with the airline and I can add my airline account number to the booking.

Problem solved!  Hopefully this helps someone else regain their pre-check privileges if you're ever in our situation.

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I agree with a couple of others who have recommended packing lightly. I've started using a large backpack-style bag that qualifies as a carry-on, and I can pack a good deal in that thing. No checking hassle/cost/possibility of theft/loss, and so much easier to get around with it on my back rather than trying to roll a suitcase. I use it and carry-all bag with an across-the-body strap. I can carry the two simultaneously, carry them both on (it's my "personal" item), and I use it for day outings (parka, water bottle, camera, etc.)

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Mike Rathwell Community Leader May 20, 2019

My choice for this is either the Osprey Porter 46 (can squish to the "official" sizers) and has lots of toggles to hang extra crap on OR the one I have, the Osprey Farpoint 40 which is explicitly the international carry on size. I went that way and cannot imagine a generic wheeled bag anymore. Even getting through the airports is easier not to mention getting around some of the more... adventurous... places one finds themselves in. Oh, and Venice was much easier to deal with as well.

Hi @Chris Nicosia This was indeed a fun read! I struggle myself with vacation planning, but here is a hack I use all the time if you travel from the US to Europe:

Buy flights from the European website counterparts (if you are able to see local currency, instead of US$ if searching from the US). For example, don't buy through (nice, cheap airline by the way); buy from (thanks to Google translate) - price will be quoted in Euros. It is always cheaper once converted to the US$, like, 10% cheaper. Probably even worth it if your CC charges conversion fees. 


Also, when looking for flights, I search for both, Google flights and - I find that the "buy/wait" advice in Kayak is fairly accurate. 

And if you arrival is delayed by, I think, 3 hours, to or from EU, then you get up to $600 reimbursement (have to fill out paperwork online). 

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Oh, and have a great trip, whenever you settle on it!

Rachel Wright Community Leader May 24, 2019

Thanks @Inna Gordin _Appfire_ ! I'm trying your Kayak and translated website tip out right now.  :)

carolyn french Community Leader May 19, 2019

If you are traveling with extreme time zone change, I can totally recommend getting a jet lag plan. Basically, it helps you start resetting to your destination time zone before and during the flight by telling you when to get bright light and when to eat, exercise, sleep, etc. It does take lots of will power and doesn't feel great. However, when you arrive, you can maximize the time you have in your destination by already feeling adjusted. 

The website looks spammy, but I've ordered it and it helped a bunch (and am not being paid anything to say it!).

For random other airplane travel hacks, this one might be unpopular, but I generally only try to drink water to stay hydrated in the plane (and give myself an excuse to get up and walk around- prevent those DVTs). Caffeine, sugary soft drinks and juices, and alcohol may be fine on short flights, but for long flights, they just end up making me feel worse for the wear.

Like Inna Gordin _Appfire_ likes this

Huge advice for the plane drinks! I'm also drinking only water in the long flights; all other types of drinks are killing me.

About the jet lag - a intriguing case from the Summit this year: I was traveling only for a week from Bulgaria to the US and back (2 x 22-hour flights in 7 days). My grand reveal was - fitness! Me and one of my colleagues were hitting the gym every morning for 15 to 20 minutes, and this helped a lot! So a little daily activity can save you from the sleepless hours :)

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Mike Rathwell Community Leader May 20, 2019

For me, it's always been a combo of what @carolyn french  noted plus (and this is the gritting teeth part) living in the TZ you're in when you land. I find if you succumb to the nap after you get there one is tired for days.

Another element that helps me on really long haul flights is Tylenol PM. Eases the aches of being in the chair and gets you to sleep. Sleep LOTS on the airplane. It helps.

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Rachel Wright Community Leader May 24, 2019

Thanks @carolyn french .  I'm trying out on my next trip.  I'll report back if I like its advice.  :)

carolyn french Community Leader May 24, 2019

Awesome, @Rachel Wright - let me know what you think (I haven't tried that one).

Such golden nuggets shared here, bookmarking this thread to plan my next vacation :)


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