Travel Q & A | Part 2

Happy almost-Friday, friends! I feel like I deserve a medal for making it through the first week of ‘life with a kid at college’…or at the very least, a cookie! It’s definitely gotten easier with each day, especially after hearing the excitement in his voice.

I discovered the hard way that staying busy is key for me. Which fortunately isn’t too difficult between Little Miss’s schedule, home renovations, the blog, and working on our next Gibson x Hi Sugarplum Collection! All good stuff, and I’m excited to share it with y’all in the coming months!

Today we’re talking travel…more specifically, your travel questions. I love sharing Trip Reports from each of our adventures (find those here), but I’m often asked more general questions about travel, so today is Round Two of your frequently asked travel questions! (Find the first batch of Q&A here.)


Why are you so fanatic about the eBags?

Ha! I really am kind of fanatical about them! But honestly, eBags revolutionized the way I pack and travel. No more messy suitcase or rumpled clothes, and I can fit so much more in my bag.

I pile the clothes tall, and they zip down to a compact cube that fits perfectly within the dimensions of my suitcase. I’ve tried other brands, but none are as well-made with sturdy zippers as these. And since the clothes aren’t shifting around, there is minimal wrinkling.

My standard method is to separate clothes by category and place in their own bag (tops in one, bottoms and dresses in another, etc). That way once we’re on the trip, I simply open each bag to grab the piece I need, and zip it back up.

I have assorted sizes (we have several since the whole family uses them!), but the most-used is the medium. Small eBags are great for undergarments and swimsuits. Large eBags are perfect for longer trips, and cold weather locales that require bulky clothes and jackets (great for ski clothes!). Once packed, you simply arrange them in your suitcase like Tetris blocks!

eBay is a great resource for finding them for less, or grabbing single sizes.

hi sugarplum mexico packing tips

hi sugarplum mexico packing tips

hi sugarplum mexico packing tips
packing details here

Do you wear your good jewelry when you travel?

The only ‘fancy’ jewelry I own is my wedding ring, and I never take it off. If I ever am in a situation where I feel uncomfortable, I simply spin my ring so the diamonds are facing down. Another option could be to swap your real ring for a CZ version (eBay has some incredible options here!), but if attention is what you’re worrying about, I’d leave it at home.

Everything else I wear is fashion jewelry, and while I’d be sad to lose it, it doesn’t hold any sentimental value to me.

outfit details here


Do you convert cash before you go?

We stick with credit cards whenever possible, for the convenience and safety factor. But always notify the credit card company of your plans before traveling so they don’t flag it as suspicious activity, and therefore limit your use!

If we think local currency is needed for off-the-beaten track restaurants and shopping markets, we’ll exchange a little at our destination airport. The exchange rate isn’t the best there, but the time and expense it saves from finding a local back is worth it to us.

Also, we stick with smaller amounts so it’s not as painful if the cash gets lost, and we try to spend it all instead of converting back to US dollars. We’d rather invest it in the local economy than take another hit converting it back.


Where do you start after choosing a destination?

Oftentimes, we have two or more destinations in mind, and let the flight availability make the final decision.

For instance for our Summer trip, we narrowed it down to Greece and Italy. After checking flights in and out of all major cities, we realized Greece was much more feasible, from a cost and travel time perspective. So Greece it was!

Once the destination is determined, I plot the preferred itinerary on a map…not necessarily the exact order, but the general route of places we want to see. That will give me flight arrival and departure city options, and I start checking flights, keeping cities and dates as flexible as possible.

I then place the flights on hold (many airlines offer a free 24-hour hold), and start the hunt for hotels. Too many times I’ve booked the flights, only to find out preferred hotels aren’t available those dates. So the two go hand-in-hand. Only once the hotel is booked, do I go back and confirm flights.

From there, I write out the itinerary of days, filling in activities, ferries, arranging transfers, etc. It’s definitely a process, but just another aspect of travel I love!

outfit details here


How do you choose hotels? I get bogged down in choices, how do you pick?

Yes! This is the part that takes the most time for me, too. I feel like I have to look at literally every hotel option before making a final decision!! And the type of hotel depends on the trip…how much time will we spend in the hotel, are added amenities important, what’s the purpose of the trip? If we’ll be doing tons of site seeing, then convenient location is more important than luxury. If the trip is all about relaxation, then we want views or special care.

For instance, the view was most important in Santorini, so we splurged for that. Naxos was all about island exploring, so we saved by staying off the beaten path. And some trips, like this one, are just all about the hotel!

I book the majority of our hotels through…I like the reviews, prices, and the rewards program includes all brands, so it’s easy to rack up free nights. So I start my search there, filtering down the choices by highest guest ranking, stars, and location. Once I’ve narrowed it down to my top 3-5 hotels, I check more reviews and photos on Trip Advisor.

My final step is to check the hotel site directly to see if they’re offering better rates or perks. At this point, I usually still have at least two options, so I weigh the amenities and decide which is most important to us for this particular trip…location vs amenities, luxury vs budget, etc.

So I guess you could say I get bogged down, too, but hotels are a huge part of trips for us, so I like to find the great ones!

nomad hotel los angeles
Hotel details here

How do you find the cheapest flight?

We are so committed to earning miles (they’ve covered the majority of our international flights!), that I rarely shop around. All of our credit card and flight travel is under a single airline to ensure maximum mileage accrual and perks.

But I still want the best price possible, so I always search a flexible date range…sometimes even one day can make a huge fare difference. Flight times and connections can impact fares, too. In my experience though, the first fare is usually the best, I almost never get a better price by waiting! The unofficial ‘rule’ is 57 days in advance for domestic flights, 117 for international, but who knows if that’s true!

If you aren’t loyal to a single airline, I like Travelocity and Expedia for searching all options. And Seat Guru is my go-to for choosing which airplane and seat! Oh, and carrying on a bag means no baggage fee!


Is most of your travel comped?

No, the majority of my travel is booked and paid for by us. There are very few exceptions, like my ambassadorship with Princess Cruises, but those are always disclosed in the Trip Reports! (Find all our cruise trips here.) Even though I always give honest opinions on sponsored travel, I just prefer to choose our own hotels and itinerary, and travel with no obligations. I simply share our experiences because I truly love a place and want to pass it along to you!

Although, considering how many of you have visited the Belmond Maroma Resort, I wouldn’t complain if they wanted to throw a few nights my way! Ha!

outfit details here


You mentioned TSA Pre-Check. What is it and how do I get it?

TSA Precheck is essentially an advance security pass, indicating you’re a low-risk traveler. Once you gain clearance, you can use the TSA PreCheck lane at the airport and go through security without removing your shoes, liquids, or electronics from your carry-on luggage.

Acquiring TSA PreCheck clearance requires online paperwork, an in-person interview, and several weeks of waiting, but once approved it’s good for 10 years! Even better, pay an extra $15 for Global Entry and you’ll breeze through customs when returning home!


What’s on your travel bucket list?

Oh wow, where isn’t on my travel bucket list?! I’d love to spend time in the villages of Southern France like Provence, see more Greek islands, and explore all the coastlines of Italy. As for the US, Maine, Nantucket, and Charleston are high on my list. But my dream is to take the Princess Cruises trip around the world!

outfit details here


Okay, I think that’s enough for today!! So many great questions, and so many more to come in my next Travel Q&A installment! Feel free to leave any in the comments, and I’ll add them to the list! What’s on your travel bucket list? I love adding new spots and dreaming about trips I hope to someday take!

If you’ve got a trip coming up, don’t forget to check eBay for amazing deals on travel necessities, like all Samsonite luggage up to 50% off! If you’re looking for some travel inspiration, check the Travel tab on my navigation bar…it’s broken down by International, Domestic, Cruising, Packing Tips, Great Hotels and more!


*This post is created in collaboration with eBay, but all thoughts, opinions, and wanderlust are my own. Thank you for supporting Hi Sugarplum sponsors!*

Leave a Comment


  1. Barb wrote:

    Great info. Ebags really are travel life changing. Tried them on a 3 week self guided Italy tour. Never stopped using them since. Put all my dirty clothes in a couple, the clean in one. Drop it in my laundry room as we walk in r house. GO TO CHARLESTON! Lol. Shem Creek for happy hour. You will end up staying all evening. Rooftop bars in Charleston for the greatest views. My good friend lives there. Been many times. In fact, going in 3 weeks as a side trip. My son and fiancé that live in Colorado are meeting us in Myrtle Beach for a week. This trip is all about comfort and a beachfront house. Just relax time. Thanks for all the information.

    Posted 8.22.19 Reply
  2. Sandy wrote:

    You deserve a gold medal! See? A happy teen tucked away @ college!
    Luv all the helpful hints. Very interesting stuff from an expert, ha,ha!
    Only thing I would say is say is, when using miles for flights, you cannot book too early, those seats are the first to go.
    I find “my airline” usually has the best, competitive fares, but did you know…they know you are on their sight “shopping” and next time you look, they raise fares? Check rental/air fares on the big travel sites first. When Kayak says buy now, buy!
    Do you ever leave your house w/all the research you do????

    Posted 8.22.19 Reply
  3. Julie wrote:

    Thank you for all of the tips!!
    I’m so glad that Charleston is high on your list- it’s where I live and I love our beautiful city!!

    Posted 8.22.19 Reply
  4. Sarah Tucker wrote:

    Dying to go to Nantucket! Also, most travel credit cards waive the fee for TSA Precheck, so there’s really no reason to get it!

    Posted 8.22.19 Reply
  5. Addison wrote:

    So many helpful travel tips, thank you! I am born and raised in Maine and I was ecstatic to see it on your bucket list destinations. It’s truly magical and so beautiful. Hope you make it up here one day!

    Posted 8.22.19 Reply
  6. Taylor wrote:

    You must go to Nantucket! The weather and the views are perfect. That is one place I can see myself visiting every single summer.

    Posted 8.22.19 Reply
  7. Elisha wrote:

    This is SO helpful, especially the parts about your process of deciding on hotels, itineraries, etc. I’ve discovered that travelling as a family is a whole different kettle of fish when you are the parent rather than the kid! Figuring out the best way to get all the ducks in a row has been a challenge for me, so thanks for your advice.

    Posted 8.23.19 Reply
    • Cassie wrote:

      I’m thrilled it was helpful, Elisha! xoxo

      Posted 8.25.19 Reply
  8. Julie wrote:

    LOVE this post!!! Thanks so much for sharing your tips and tricks! I always read your travel posts multiple times and go back to them the most.

    Posted 8.24.19 Reply
    • Cassie wrote:

      Thanks so much, Julie! I’m thrilled they’re helpful! xo

      Posted 8.25.19 Reply
  9. I’ve been following you for a while now, and I learned of ebags through you! They are a GAME CHANGER! New England is one of my favorite destinations with all the little port towns. Another area you might love and that my husband and I recently discovered is Northern Michigan. It is STUNNING and also has cute little port towns. You can fly right into Travers City and it’s an easy 30-45 minute drive from there.

    I love all your travel tips and posts! xo

    Posted 8.26.19 Reply
    • Cassie wrote:

      I’m thrilled you love the eBags too…I don’t think I’ll ever be able to travel again without them! And thanks for the awesome trip recommendations…my list keeps getting longer! 😉 xo. C

      Posted 8.26.19 Reply