I need to make something very clear: I’m WELL AWARE that I’m stupidly spoiled in this current season of life.

I’ve always been pretty spoiled, given that I’ve never been in want of food or a job or a roof or even an iced tall soy chai latte. But these days, things are pretty ridiculous. I no longer need to work a boring 9-5 in order to pay rent, but instead just get to write random thoughts on this blog every day, thanks to my husband’s support and encouragement of my passions. Don’t get me wrong, I work really, really hard in order to write 1-3,000 words a day, but yes, I can travel whenever I want, make my own schedule, and even get to consider watching The Bachelor a priority. “Sorry, guys, can’t hang out on Monday nights! I have to work!”

olivia gif

This year is particularly outrageous on the travel front, because not only did we (husband + me) get to experience a gorgeous wedding and honeymoon at the tail end of 2015, but we went to Ireland this spring, followed by my 28 day road trip to fun places like Philly, Boston, NYC, and Portland.

Up next: Alaska.

Aaron and I don’t sell drugs on the side to pay for these things, I promise. We only sell our plasma.

It’s a joke, calm down, Dad. We don’t sell anything. (YET…stay tuned for a boatload of crap we’ll be selling from my husband’s storage unit later this year, including but not limited to disco balls, obscure kitchen appliances, and a projector + screen that can play movies on the beach, because obviously everyone needs one of those sitting around.)

Actually, I need to give a very grateful and HUGE shout out to my dad and bonus mom for taking the whole fam-bam to Alaska. I’m pretty much dying of excitement, and feel like the luckiest daughter in the world. I’d feel like the luckiest daughter in the world even without Alaska or all the nice wine they pour down my throat on a regular basis, but I’m not, like, mad that they do those things. Love you guys, so proud to be the only favorite daughter. <3

Thanks to my many travels, which started long before this year, I thought I was a pretty decent packer. This travel confidence comes from the fact that I’ve spent significant time (not just the airport or driving through) in Alaska, Arizona, California, Colorado, Connecticut, Delaware, Florida, Georgia, Hawaii, Illinois, Kentucky, Maine, Maryland, Massachusetts, Michigan, Minnesota, New Jersey, New York, North Carolina, Ohio, Pennsylvania, Rhode Island, South Carolina, Tennessee, Texas, Virginia, West Virginia, Wyoming. (My party trick of being able to say all the states in alphabetical order in one breath came in super handy as I just typed that.)

I’ve also visited the Virgin Islands, Puerto Rico, Mexico, the Bahamas, Singapore, India, France, England, Scotland, Ireland, Denmark, Russia, Estonia, Finland, Sweden, Poland, Norway, Turkey, Italy, and Greece.

In a sharp plot twist, I’ve never been to Canada.

Okay, so maybe this spoiled thing isn’t anything new, rather it’s simply more embarrassing evident these days since everyone can see my spoiledness all over the interwebs. Which is why now, as a reasonable adult with a blog, I feel the need to address it. You know, to prove that I’m not an insufferable brat.

appealing person

My parents did (and continue to do) a great job making me well aware of how lucky I am for all of my experiences. I was forced to save up birthday money from my grandparents throughout my whole childhood, which is what I used to pay for my two trips to India in high school. My mom was right— that was way better than buying mountains of candy from canteen at summer camp, though I certainly did not realize that in the moment. Bless her for teaching me the hard lessons. (At times, probably even harder for her than they were for me.)

My parents also never paid me for good grades, which I think is a pretty tell tale sign of whether or not someone is “spoiled” or just “privileged.” I like to think I’m the latter, but in the kind of way where I acknowledge it with gratitude and absolutely no sense of entitlement. And I still got A’s, so THERE. (To the parents out there: Disappointment and anger are way better motivators than a few $20s.)

This introduction has turned into less of an intro, and more of an unnecessary rant of self-defense…similar to the time I felt the need to defend my high school self’s personality…but instead of erasing it all and re-focusing the whole thing in the direction this blog was supposed to go, I’m just going to leave it. Sorry I’m not sorry. I hope you learned something valuable for your future/current parenting skills, or at the very least, are impressed that I can say all the states in alphabetical order in one breath.

THE POINT IS that I think I’m a good packer.

what gif

Yes, that was supposed to be the point of all that. I own up to my occasional flares of ADHD, which is something I definitely don’t have, but it would be a great excuse right now.

I guess I should say that I thought I was a good packer, past tense, because I no longer think that’s the case. And that is because my friend became a flight attendant, so now she completely schools me in the packing realm to the point where I feel like I shouldn’t be allowed to travel past my front yard.

Thank God I married a man in the military, who can fold any item of clothing—including a winter parka—into a 4”x4” cube. That was a good buffer/transition into understanding how horrible I actually am about choosing contents for my suitcase.

I’m sure any of you who read my post How to Overpack for Ireland 101 probably could’ve told me this months ago.

With all of that said, meet Caroline, my co-blogger for the day, current flight attendant, and future Vice President of the United States. She can still count as a co-blogger as long as you pretend that the first 816 words of this post didn’t happen. Everything she writes for this post will be in italics.


Hi! I’m Caroline. Blogging Flight Attendant, former Miss Vermont, and a candidate for the Vermont State House. You know, your average 25-year-old. I”m friends with Shannon because she was Miss New York, and as a result, we share some mutual pageant best friends. I’ve been a fan of her blog for years, and I’m so excited to join her on this post! I’ve been flying professionally for just over a year, but I’ve spent a lot of my life traveling all over the world. I view packing as a personal challenge. Some people run marathons, I pack carryons.

We’ve decided to put together a lovely little post for you all today that will allow Caroline to drop some knowledge that will benefit us all on upcoming trips, but particularly for my Alaskan cruise that starts tomorrow. You’re welcome ahead of time.

The way this is going to work is that I’m going to write basic lists of what I plan on packing for Alaska, and she’s going to tell me all the things I’m doing wrong. This will probably be a close reflection of how conversations go with my husband about finances.

Other important information that will come into play in her advice:

  • I am taking 3 flights to get to the cruise ship
  • I plan on checking a bag
  • Excursions include one canoeing trip, one horseback riding trip, one hike, and one day just exploring town
  • 2-3 full days of just hanging out on the ship, not getting off
  • I have to look decent every night for dinner


I plan on bringing one rainproof athletic-type hot pink jacket for excursions and one beige duffle coat for generally looking cute.

You’re off to a great start here, actually. To save space while still staying warm (you are going to ALASKA, after all) I’d suggest you swap the duffle jacket for a packable insulated jacket like this one:

alaska jacket

Find it HERE.

Best of all, you can pack it up so that it’s teeny tiny and stash it in your carry on in case you get cold on the plane. Airplanes are cold in the summertime, people.

First of all, YES, I’m always freezing on airplanes. I guess it’s better than being hot, but still. I support this idea of squishable jackets that fit in my carry on. Also, I found the jacket in this print (below) and I’m obsessed. Some people might think florals are grannyish, but that’s never stopped me before. This model looks kind of like my #1 girl crush Candice Swanepoel, so that’s probably drawing me in, too.

alaska jacket 2



I plan on bringing an array of long sleeve tees from The Gap, and maybe a few oversized sweaters because, hi, have you met me?

Shannon, you’re going for a week and cruise ship cabins are notoriously tiny. Way too tiny for multiple sweaters. Ain’t nobody got space for that.

Because you’re going to be doing some outdoorsy activities on this adventure, your casual options should center around layers that you can pile on and take off as needed so that you’re comfortable. You’re lucky I’m from Vermont and well-versed in hiking in the snow.

Here’s your checklist for tops

  • 2 long sleeved tees
  • 4 short sleeved tees (I’m not ashamed to admit that I LOVE Old Navy’s Perfect Tees. They really are, as they say, perfect.)

    old navy t

    Find it HERE.

  • 1 pull over, ideally high performance, like this one: 

    pull over

    Find it HERE.

  • 1 vest (also packable!)

    patagonia vest

    Find it HERE.

WAHHHH MOMMM BUT I WANNA BRING ALL MY SWEATERS. But it’s true, your list looks way more Alaska-ish. I could totally see myself tromping around in a puffy vest, feeling like a J Crew catalog model. I’m definitely open to it.



I’ll be bringing a single beanie.

Perfect. Personally, I prefer earmuffs, but that’s just me.

I did it!! See? I knew I was good at this.



I only wear two pairs of pants, both of which are jeans from LOFT. Basically, I’m bringing everything I brought to Ireland. Sorry for the repetition here, folks.

Try one pair of jeans and two pairs of black/neutral *completely opaque* leggings. You can wear the leggings while lounging around and enjoying room service or while you’re hiking in the Alaskan wilderness.

Oh, how did I forget about leggings?? Winter has been over for like, one month, and here I go turning my back on the only thing that got me through January-March.



I will probably bring 3 pairs of nice pants, 1 fancy-ish dress, and 3 semi-nice dresses. Obviously, I’ll need to bring 3 blouses to go with the pants, and probably a few scarves to serve as shawls to keep me warm, because I’m forever convinced that this world is trying to freeze me out.

Rein it in, my friend. Most week long cruises only have formal or semi-formal dinner dress codes for 4-5 of the nights you’ll be on board.

Try this instead:

  • 2 fancy-ish dresses (nothing is worse than getting onboard and realizing that you’re going to be underdressed)
  • 2 semi-nice dresses
  • 1 pair of nice pants that you could also wear casually
  • 2 blouses that could also be casual
  • 1 patterned scarf that you can use as a wrap
  • 1 neutral solid wrap in a warm fabric like cashmere because you are not crazy and formal events are ALWAYS too cold. They generally set the temperature based on the idea that the men will be wearing jackets, button down shirts, ties, and pants. This is why women are constantly freezing. It’s a fact. P.S.- investing in a giant cashmere wrap is one of the best choices I’ve made. So worth it.

Let me start by saying this: That last bullet point made me laugh because you are such a feminist and I love it. In terms of what I should pack, the more I think about it, the more I’m absolutely only bringing one pair of dark wash jeans (just found out you can wear nice jeans to dinner!) with 2 tops. Easy peasy. Just recently purchased a top that looks kind of like this one (mine is from Target, but I can’t find a pic), and I’m in lerveeee:

off the shoulder




I’m going to try keeping the shoe department under control, because that was my downfall in Ireland. For the record, I don’t regret bringing 7 pairs of shoes to Ireland. But this time, I’d have to face direct judgment from my family members, so maybe I won’t bring four different pairs of boots. I plan on packing 2 pairs of ankle boots, and that’s it. Okay, fine, and flip flops and my new white Keds. Oh, and 2-3 pairs of heels. BUT THAT’S IT. Crap.

For any other kind of trip, I’d be advocating for three pairs of shoes total, but I’m giving you a pass because you’ve got to be both dressy and aggressively active on this adventure

  • 1 pair of ankle boots (bonus points if they’re cute AND you can hike/ride a horse in them)
  • 1 pair of sneakers
  • 1 pair of flip flops/sandals. I personally swear by my Rainbows but many many of my friends are in love with their Chacos. You do you.
  • 1 pair of ballet flats or Keds
  • 2 pairs of heels that will go with all of your dresses

Rainbows all the way! But I’ll probably sandals with a little more flair on this adventure.



I have one bag for things like my toothbrush, toothpaste, shampoo, conditioner, face wipes, etc. Then I have all my makeup brushes wrapped in this special little pouch thing. Then I have my makeup in a cute little green and white polkadotted bag that is now mostly brown and a vague color of turquoise. Then I throw my glasses and contact case in the glasses case, and just tuck that into whatever corner of the suitcase that has room, usually near the socks. I do the same thing with my large bottle of hairspray and equally large bottle of contact solution.

Oh my God, I really am bad at this.

Actually, your toiletry organization system is basically awesome. I’d recommend investing in as many solid products as possible for travel (Lush makes AMAZING solid shampoos), but if you can’t go solid, get a set of reusable travel containers like these: 

travel tubes

Find them HERE.

I also love this toiletry bag for your checked luggage because it packs SO easily and you can hang it anywhere in your bathroom so it doesn’t take up counter space: 


Find it HERE.

If you’re packing any toiletries in your carry on bag, make sure that they are all under 3.3oz and fit into a quart sized baggie. Break down and buy the travel sized saline and hairspray. It’s worth it for the convenience, I promise.

I keep all of my makeup in this bag, and I’m obsessed with it. 


Find it HERE.

FYI, I just had to Google “solid shampoo.” Didn’t know that existed.

I guess I should also mention that I tend to pack like, 80 bras, and wear exactly 1. Help?

How about this:

  • 1 nude bra
  • 1 black bra
  • 1 strapless bra
  • 1 fun bra that you can wear under a tee shirt
  • 3 sports bras

Whoa there, nelly! Looks like I’m not the only one with a bra addiction.

And what about workout clothes? I never, ever work out on vacation, but it’s like a huge internal judgment fest if I don’t at least pretend I’m going to.

Your workouts will be hiking, horseback riding, and walking around on the ship. You’ll get plenty of exercise. Focus on spending time with your family, not on hitting the gym.

God, I love when people make me feel better about my life choices.

Any last words of advice?

Two words: Packing cubes. Buy these now and thank me after your trip- they’re like drawers for your suitcase and they make living out of it SO much easier when you’re on the road. 

packing cubes

Find them HERE.

Wait, you mean I don’t have to search for 45 minutes to find the one t-shirt I want to wear?? GENIUS.

Caroline, I can’t thank you enough for being my own, personal packing guide. Next time, I’ll have you write about the best way to finagle free drinks from your flight attendant. KIDDING! Or am I..?