Planning a Travel Itinerary (An Organizational Guide)

I have quite a few friends and family members that always seem to be astounded at the destinations that Ken and I pick for vacation. It’s not that these friends don’t go on vacation. It’s just that they usually choose one or two of the same destinations for their vacation every year.  In this area it’s typically Myrtle Beach, the Outer Banks, or Ocean City. Rinse and repeat.  (Don’t get me wrong, I loved the Outer Banks!  But every year? No thanks. Too expensive!)

They start questioning the details. “Wow, did you get a travel agent to set that up?”  Nope.  “Did you like book a tour package?” Nope (although sometimes we might book day tours when we’re in a particular destination).

“So how did you figure out all those details?”


At this point I usually launch into a rambling explanation that begins with, “Well, it depends if it’s a road trip from our home, a road trip from a destination we have to fly to first, a cruise, or just a normal mixed-transportation trip that includes flights, rental cars, and an occasional taxi or train or subway.”  Then some additional ramblings about spreadsheets, Google Maps, ExpertFlyer, ITA Matrix, TripAdvisor, Yelp, and TripIt.

By this point, friends’ and family members’ faces have long glazed over and they’re just nodding their heads in polite confirmation that they’re still somewhat paying attention.

In case you’re interested (and in an attempt to organize my explanation for how I actually DO plan a vacation) I’ve listed out some steps below.


1.  Consult my “Trips to Take” spreadsheet.  I’ve maintained this spreadsheet for many years. It plans out the bigger trips we plan to take each year (usually one on the spring and one in the fall).  It also serves as a master list of current bucket list trips and festivals (using that term loosely – more like “events”) that I want to see eventually.  Don’t be fooled by how precise this looks.  I don’t think there has ever been a single year that the spreadsheet hasn’t changed, so it’s always in flux. But it does help me stay organized about what some of my bigger bucket list trips are. Funny how things always get added and moved around though!  I change the font to green when we actually complete a trip.

Trips to Take Organization Spreadsheet

Itinerary Planning

2. Figure out the destinations for a trip. Sometimes I take all these steps, sometimes just one step. It varies depending on the trip! So, let’s say a destination on my “Trips to Take” spreadsheet was the “Albuquerque Hot Air Balloon Fiesta.”

2a.  Google Maps Destinations.  I think this section is best described using a few examples.  For years, I had been wanting to go to the Albuquerque Hot Air Balloon Fiesta. It takes place every October, and I was just so amazed by the photographs of the event.  Back in early 2012, I decided that that was the year to go to the Fiesta. But then I started thinking more about it.  DC to Albuquerque was a nearly five hour flight.  Did I really want to take a five hour flight just to go to Albuquerque for a few days? Nah! Let’s fly to Albuquerque then make a road trip out of it!

I looked at things to do in New Mexico, mostly using TripAdvisor. Then I’d open Google Maps and zoom in on Albuquerque.  Then I’d slowly zoom out, taking a look at some interesting-sounding things on the map.  Oh, Santa Fe? I’ve heard that’s beautiful. Oh, Sedona, I’ve heard that’s fantastic too.  Oh, what is this interesting-sounding place up here?  Glen Canyon Recreation Area? Never heard of that, but it sounds promising. Let me Google it.  Oh wow, and the Grand Canyon isn’t far from that. Let’s check up north. Oh, that Glen Canyon area isn’t very far from Monument Valley, I’ve always wanted to go there!

You get the idea. There’s nothing really precise about it. I just kind of search, Google, and develop ideas.  I tend to use Evernote as a personal bookmarking site. I create an Evernote notebook for “Hot Air Balloon and Southwest Trip” and start bookmarking all the locations I’m searching for. At this point, nothing is “off the table.” If it sounds interesting, I bookmark it.

Google Maps Albuquerque

2b.  Consult organized travel websites for other potential stops.  In addition to the Google Maps technique, I also use TripAdvisor quite extensively. For instance, back in 2010, we booked a one week Mediterranean cruise departing from Barcelona. I had never been to Spain, so I definitely wanted to spend some time in Spain before our cruise departed. After all, why make such a long flight for just a week-long trip?  So, I looked up Spain on TripAdvisor, and browsed the cities and what they had to offer.

2c.  Borrow heavily from expert-developed itineraries. Friends, the internet is a beautiful thing. And so are travel books. Seriously.  Sometimes travel books (like real, paper books you can hold in your hand), are very valuable travel tools. I like them because it eliminates a lot of the distractions you might come across when researching destinations online.  Distractions like random one-off reviews of “I hate this place!” Anyway, one of the things I like most about travel books (like Lonely Planet or Fodor’s), is that they always provide sample itineraries, and usually those itineraries are based on how much time you can spend in each destination. A lot of them even post sample itineraries online. For instance, Frommer’s posts sample itineraries for one week in Spain, two weeks in Spain, and Spain for families.  I’ve never once followed these itineraries precisely, but it usually helps give me a good idea of what the highlights are!

3.  Research sites and attractions in each city / locale identified.  Once I have identified potential cities to visit on my trip (using Google Maps, TripAdvisor, and sample itineraries), I check TripAdvisor and Yelp for “Things to Do” (i.e., attractions) in each city.  Sometimes I eliminate cities if the attractions don’t seem to warrant a special stop. Although that is RARELY a problem! I usually find too much stuff to do in cities. But one example I could think of was Key Largo.  Originally I was thinking about spending three or four nights in Key Largo. However, after I found out that many of the attractions in Key Largo are scuba-diving related (which neither one of us do), we decided to minimize our time in Key Largo to just two nights.  Still plenty of time to enjoy ourselves on the beach!

4.  Pare down the itinerary.  Alas, we don’t have unlimited vacation time from work. Nor do we have unlimited funds (although free travel perks from miles-and-points hacking sure do help!). So, we usually have to cut back on the sites and cities identified in my previous steps.  So, using the Southwest USA road trip example from earlier, we opted not to visit Santa Fe and Sedona (although we definitely hope to visit those places in the future!). Using our Spain trip example, we eliminated Valencia from our trip, and we had originally tried to fit in some stops in Portugal as well, but we decided to save that for a future trip.

Whew, this post is getting long!

In the next post, I’ll talk about how we pick hotels, how we optimize and plan our daily itineraries, and given some examples of how we organize all our trip information.


Pre-Departure Countdown Checklist for Travel | Being an Organized Traveler!

I tend to be pretty compulsive about making lists and I get a stupid amount of satisfaction from checking things off said lists!

I have an folder on my computer that is FILLED with travel-related lists. Packing lists for road trips. Packing lists for international trips. Packing lists for visiting family (when I just mooch off their shampoo).  Pre-departure household checklists.  Pre-departure countdown lists.

You get the idea.

So today, I’m sharing with you my pre-departure countdown checklist. I developed this list a few years ago when I started to hate that harried feeling I’d get when trying to prepare for a trip. For example, I’d go to pack my camera, but realize that most of my memory cards were full, so I’d have to take the time to upload all the pictures to my computer. Or want to make sure I have plenty of things to keep me occupied on a long plane ride, and I’d get distracted trying to find podcasts or magazines to download to my iPad, or books for my Kindle.

Oh, and let’s not forget trying to clean up the house. Because who wants to come home to a messy house? Or was my mother the only one who seemed to pass that on to me?

This list was designed to be the solution! It spreads out the pre-departure tasks over several days so that nothing seems overwhelming. And let me tell you, it helps SO much when I follow this list.  I followed it precisely for our Florida Keys trip back in November, but I only kinda followed it for our trip to Las Vegas in February (thanks to a family emergency the days before our trip), and it made a HUGE difference. I was much more relaxed when it was time to leave for our Keys trip compared to the Vegas trip!

Pre Departure Countdown Checklist for Travel | When to charge your electronics, put your mail on hold, etc before traveling so you don't have to do it all at once!


Keep in mind that this is different from my pre-departure household checklist, which includes things like taking out trash, double checking doors are locked, etc. I’ll share that in a separate post!

Not every task is necessary for each trip. For instance, I don’t put mail on hold if we’re only gone for a long weekend. But I keep it on the list, and if it’s not applicable, I just scratch it off!


Weekend Prior to Trip

  • Take backup hard drives to safe deposit box (in case of disaster at our home while on vacation, our most important data will be protected). You can read more about how we backup our data here.
  • Withdraw cash from bank if necessary
  • Make any necessary tweaks to home security system

T-5 Days

  • Download maps to handheld GPS if necessary (Ken carries a handheld GPS on a trip to geotag our photos. We download all the sites we plan to visit onto the handheld GPS!)
  • Schedule mail hold (only necessary for longer trips. It’s easy to do this right on
  • Alert credit card companies about travel
  • Clear old photos from iPhone if necessary and backup to computer
  • Verify that at least one neighbor still has a key and ask them what days they can check on house
  • Put newspaper delivery on hold

T-4 Days

  • Refill all travel size bottles if necessary (shampoo, soap, makeup, etc)
  • Clear external hard drives taking on travel (we make many redundant backups of our photos when we travel.  See more about that in this post!)
  • Download any desired books to Kindle
  • Purchase any desired movies for laptop or iPad
  • Clear all old video camera files and photo files from memory cards
  • Download audio books if desired
  • Download podcasts if desired
  • Download magazines for iPad if desired

T-3 Days

  • Print out all documentation for trip and put in folder (hotel reservations, car rental reservations, etc.)
  • Make sure all laundry is done for trip
  • Plug in all electronics (camera, Kindle, etc) for charging
  • Get a Manicure and Pedicure if desired
  • Clean out purse and coat pockets

T-2 Days

  • Pack for trip

T-1 Day

  • Straighten up/light house cleaning
  • Relax!

Travel Day!

  • Finish packing things that you couldn’t pack until day-of-travel (like makeup items that you don’t have travel size versions for – eyeshadow, blush, etc., and laptop computer)


I’ve been using this list for a long time, and I’ve found that it’s exhaustive for our purposes. Obviously each family is different, so think about some of the things that might apply to your family. Like do you have to drop off your dog at a pet hotel the day before you leave? Or maybe give the neighbor instructions for checking in on your house?

What tasks do you always find yourself having to do before leaving on a vacation? How do you keep things organized and streamlined?

What I Like to Buy when I’m on Vacation

Although Christmas day has already come and gone, our tree is still up, and I love looking at the ornaments on it!.

Trimming our tree every year is always a stroll down memory lane. I buy Christmas ornaments nearly everywhere we travel, near and far. So as we unpack the ornaments from storage every year, it’s nice to reminisce about the travels associated with each ornament. Like these ornaments from our trip to the Hot Air Balloon Fiesta in Albuquerque and the Grand Canyon in 2012.

Christmas tree sentimental ornaments

I thought I’d share with you what else we buy when we go on vacation. But first, a story.


A Lesson Learned in Buying Local

When I first started traveling extensively in my teenage years, my mom always reminded me of the importance of bringing back small gifts for family. I’d bring back things like magnets or ornaments, and when I’d present one to my grandfather, he promptly look at the back of the gift, exclaim, “BLECH!! Made in China! It’s not even from [Whatever place I had just traveled to!]” And then essentially he’d throw it back at me. He’d end up keeping the gift, but you could tell he was still disappointed. (I should point out that my grandfather really was an incredibly kind man, but he was never quite able to shake off the whole “Made in China” thing.)

I used to be kind of sad at my grandfather’s reaction. So on subsequent travels, when I would be traveling and looking for something to buy him, I would hunt high and low for things that were locally made. I guess this habit kind of stuck, because now that is always what I’m on the lookout for.

And while it is still quite difficult to find a Christmas ornament that is actually locally made (and I still buy them anyway, even if they do say “Made in China” or wherever else), I do try to find other locally-made things that I can buy.

Here are a few of my favorite souvenirs that I like to buy.


Favorite Souvenirs

Tapestries. Ah yes, one of my favorites. It all started in India more than 13 years ago. I was at some small mall-type place, and I walked into a store and found this tapestry that I just absolutely loved. It was WAY out of my price range as a broke college student (I think it was around $35-$45 or so, which sounded like a fortune to pay for a “souvenir.”) But a friend of mine convinced me that it was too beautiful to pass up. It currently hangs on the wall above our bed.

Tapestry from India

Shortly after my trip to India, I was in South Africa. I fell in love with another tapestry that I found at a local craft market in Cape Town. This tapestry is enormous, and I still don’t have a good place for it in the house, but one day, I’ll figure something out!

Hand painted tapestry from South Africa

Anyway, my love of tapestries have followed me throughout my travels, including one like this bedouin tentmaker fabric from Egypt. (You may have seen it hanging on the wall in the pictures on our DIY Console Table post)

Bedouin Tentmaker Fabric from Egypt Tapestry from the tentmaker market in Cairo, Egypt


“Fake” Flowers. This all started with a wooden Tulip my sister bought for me when she went to the Netherlands about 10 years ago. I put it in a skinny vase and always had it out on display, even in my early scummy apartments.

Flower souvenir display

Back in 2009, when I went to New Orleans on a work trip (shortly after my first trip ever to New Orleans), I was walking through the French Quarter and found a small shop that sold art from local artists. I fell in love with a glass flower (the largest flower in the photograph), and I guess I just started my collection from there! A little more than a year later, Ken and I were in Florence (as part of a Mediterranean cruise), and I spied a lovely little orange glass flower at a small artist’s shop. And then last year, when we visited Legoland in Florida, I bought a red Lego flower! My “fake” flower collection is only up to four, and they’re not exactly something I actively seek out when I’m traveling, but if I do happen to see one, it’s hard to resist the purchase!

Flower souvenir display


Christmas Ornaments.  Ah yes, how this whole post started. My mom and dad were avid Christmas ornament collectors. They always picked them up when traveling. When I would travel without my parents, I’d always buy one for them as a gift. But strangely enough, the thought of buying ornaments for myself didn’t occur to me until I was in my late 20’s. I think it had something to do with the fact that I never had room for a Christmas tree! Well, I finally realized that that would not always be the case, and eventually I’d have my own Christmas tree to put up and decorate. So, I started buying Christmas ornaments. And for years, they just sat in a bin, unused. But now for the past few years, we’ve had an actual Christmas tree to put ornaments on, and I love it. I love looking at all our ornaments, like the Coca Cola one from our trip to World of Coca Cola in Atlanta, GA, and a cruise in 2010, a trip to Ontario in 2009, and our camping trip just last year.

Coca cola christmas ornament souvenir Christmas ornaments


Any miscellaneous item for display.  Stuffed camels from Egypt. Nesting dolls from Russia. Butterfly from the Butterfly Conservatory in Key West. Tiny Waterford Crystal clock. What do all these things have in common? They’re things that I have purchased on my travels and now sit on our living room display shelves.

Displaying travel memorabilia at home Waterford Crystal Clock

Although the Waterford Crystal clock was something my grandmother had me buy for her when I went to Ireland in 1999. She then gave it back to me a few years ago because she said her house is “too cluttered.” This coming from one of the most fastidious persons I know!)
If it looks cute or unique, it’s a difficult temptation to resist buying it!

What do you buy when you go on vacation?

Using your iPhone when Traveling Abroad (Data and Voice)

Tips and Tricks for using your cell phone abroad

Over Thanksgiving, I was able to see a lot of my family, including a 19-year-old cousin of mine who is going to France over college winter break. She’s traveled before as an exchange student, but this time though, she wanted to be able to use her iPhone using data instead of just relying on WiFi.

I was pretty proud of myself!  Offering technology help to a 19-year-old girl! I thought kids would be much more ahead of the curve than I am.


Tips and Tricks for using your cell phone abroad

Anyway, as I started to explain to her and her mother what some of the options were, and what to do to ensure you don’t use excess data while abroad, I realized I’d have to compile everything into an email, complete with screenshots, for it to really make sense.

I realize that for seasoned travelers, this may be common knowledge, but since it became apparent to me that it’s not clear to everybody, I thought I’d share my tips with you all!


Signing Up for an International Data (and voice) Plan

First, you’ll want to research the international data and voice plans offered by your carrier.**  We use AT&T, and they have different plans available, and pricing usually varies based on your travel destination. For instance, Canada, Mexico, and Western Europe have less expensive data rates, while data rates in Asian countries are more expensive.  Here’s a good overview of the plans through AT&T.

Sign up for the plan that you want right before you leave on your trip.  When we went to Russia in February, I had signed up for the 120MB plan.  Unfortunately I went over that 150MB of data within the first week, so I had to upgrade to the 300MB plan.  No big deal.

When you get to your destination, you MUST enable data roaming for your international data to work.  Simply because you signed up for an international data plan does not mean that your data is going to magically work abroad.  On your iPhone, go to Settings > Cellular.  Then toggle the “Data Roaming” switch so that it is green.  

Enabling Data Roaming on an IPhone to use your phone while abroad
If you ever want to ensure that you don’t transmit ANY data while you’re abroad, you can always turn data roaming back off.  For instance, if I’m hooked up to WiFi (like in the hotel for the night), sometimes I’ll turn off data roaming.  But keep in mind that only iMessage will be able to transmit if you turn off data roaming (meaning no regular text messages if you have friends/family that don’t use iMessage/don’t have iPhones).  


Tips to Avoid Excess Data Usage while Abroad

  • Right before you depart, it will be a good idea to reset your data usage statistics.  That way you can keep track of how much data you have used while on your trip.  For instance, if you signed up for the 300MB data plan, you can see if you’re approaching the 300MB.  To reset your data statistics, again, go to Settings > Cellular.  Then scroll all the way to the bottom, and it will say “Reset Statistics.”  After you reset the statistics and you scroll back up, your “current period” Cellular Data Usage statistics will say 0 bytes.  I usually check these statistics about once a day when traveling, especially to make sure I’m not using data faster than expected.

Reset data usage statistics on iPhone to Track how Much Data you've used

Viewing current data and voice usage on iPhone


  • To make sure that apps don’t start using phantom data (in other words, continuing to use data in the background, even if you aren’t actively using the app), you can disable apps to prevent them from using any data. For instance, I might leave Mail and Facebook enabled, but I certainly don’t need any games enabled that I keep on my phone for my niece and nephew, or the weather app, etc.  You can disable those in Settings>Cellular. Pretty much every app on your phone will be listed on that page.  Any app that is toggled on (with green), just toggle it off, and it won’t use any cellular data. If you have a lot of apps, it’s kind of annoying to turn them all off, but it should go quickly.  And, if you need to use a specific app while you’re abroad, you can always just go back into this screen and re-enable the option for that app to use cellular data.

Disable data for certain apps on iPhone when traveling abroad


  • Make sure that you disable the setting to have app updates update automatically in the background, or any music or podcasts that might download automatically. This way none of your apps will automatically download an update if one is available.  That’s under Settings > iTunes & App Store.  Make sure all the switches are toggled to gray instead of green.

Disable automatic app update downloads on iPhone


  • Finally, review your apps to disable any data hogging elements.  For instance, make sure you disable Facebook’s “auto play” feature for videos. This option is in the Facebook app directly. Click on More > settings > videos and photos > turn auto play to off.  You’ll still be able to watch a video on Facebook if you want, you’ll just have to click on it directly.  Instagram does the same thing.  For that, go to Instagram settings (accessible from your profile page), then scroll down to where it says “Video.”  Change it from “Always” to “Only on WiFi.”

disable facebook auto play for videos - save data when using phone abroad


Disable video preload in Instagram to avoid excessive data charges



There you have it!  All my tips for using your iPhone abroad, and how to ensure that you don’t use excess data.  Hopefully this goes without saying, but if you are trying to keep your data usage very low, limit things like picture uploading until you are back on a WiFi connection.

I have found that if you need to call AT&T from your cell phone for assistance, they have always waived the voice minutes.  Of course, your situation could vary, but we’ve never had a problem.

When you return to the United States, you must call to cancel all your international services.  It’s billed monthly whether you’re using the international data or not, so it’s up to you to cancel everything!


** Some folks will swap out their SIM card with a SIM card from a local cellular company as a less expensive option. I have never tried this because A) I want to be able to use my phone the moment the plane lands.  I don’t want to have to worry about finding a cell phone store, B) I really don’t find my carrier’s data plans to be overly expensive, and C) It’s just really convenient.



Travel Insurance: To Purchase or Not to Purchase?

I’ve only purchased travel insurance once in my relatively well-traveled life. The reason I almost never purchase it is mainly because I rarely book non-refundable hotels, and much of my air travel these days is on award tickets.

Four years ago, Ken and I traveled to Spain for a week, and then took a week-long cruise out of Barcelona. I did book travel insurance on the airfare (since it was a nonrefundable, expensive, paid ticket … back before I learned about points and miles beyond the basics!), but that was it.

Two years ago, we were planning a trip to Belize (which we had to subsequently cancel.  I talked about that briefly here), and since many of those hotels were going to require non-refundable deposits, I was going to purchase travel insurance.  But, we never got that far in the trip planning process.

We’re taking an Alaskan cruise this summer, and I’ve started to think extensively about purchasing travel insurance for it. There have been a few life experiences that have brought this more to the forefront of my mind.  Beyond things like getting refunded for having to unexpectedly cancel your plans, or having your luggage lost, I’m considering travel insurance mainly for the medical emergency aspect.  For instance, thanks to things like Ken’s ankle incident in Spain, my kidney stones last year (and Ken’s kidney stones in 2012), and my emergency gallbladder surgery in 2005, I just am very concerned about experiencing a medical emergency while away from home.  Particularly in the middle of nowhere. Like at sea, on a cruise ship.

Luckily ailments like a sprained ankle, kidney stones and an infected gallbladder (and maybe even appendicitis) are probably easily diagnosed by a ship doctor and manageable until you get to the next port-of-call.  But God forbid we had some sort of truly life threatening emergency while at sea.  Heck, Jeff Bezos had himself med-evac’ed from the Galapagos after he had kidney stones.  Considering kidney stones literally make you feel like you might be dying (especially if you’ve never had them before and don’t know what is wrong), I’m not surprised.

There are other factors contributing to my decision.  My parents were in a car accident in 2012 when they were traveling.  We were unable to transfer my dad to a hospital closer to his home because his normal health insurance wouldn’t cover it.   How would we cover emergency evacuation costs if we had to be transferred from the ship?  My dad’s air evacuation from the scene of his accident to the nearest trauma center was TWENTY THREE THOUSAND DOLLARS.  I can only imagine what it would be to evacuate somebody from a cruise ship to the nearest hospital.

Okay, is that enough paranoia and depressing text for one post?  Probably.

Bottom line, I’m going to get travel insurance for the Alaska cruise, and probably consider purchasing more frequently in the future.  But, I’m not sure where to start.  I can’t seem to find any “brand” name company that seems reputable?  AAA recommends Allianz, and I’ve seen them mentioned on other sites.  Specifically, when I booked some American Airlines tickets the other day, I was offered travel insurance through Allianz. It appears that some travel bloggers have had to use their travel insurance, and even had good experiences with it. But news articles like this make me think twice.


What are your thoughts on travel insurance?  Have you ever purchased it and had to make a claim?  How did it work for you?