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Luxury Travel Agent, living on the beautiful Connecticut Shoreline, serving clients everywhere

Meet Jen Terra

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How To Pack For A Beach Vacation In The Winter- My Packing Tips And Travel Essentials

Packing can be a chore and a challenge…but packing for a beach vacation in the winter can be downright demoralizing!  On one hand, I adore all that packing signifies (especially for a tropical trip )-the chance to plan fabulous outfits and feel warm sun on your skin again! On the flip side, my indecisive and sometimes overly analytical nature can be quite the buzzkill. I despise overpacking yet I fear the idea of having too few options.Why do shoes take up so much room? Should I try on my bathing suits first or just throw them in my bag and hope for the best? While I can’t say that I’ve figured it all out yet, over the years I have developed some helpful packing strategies and coping mechanisms to help streamline and de-stress the process.  Even if packing is second nature to you, you may be rusty after a long pandemic inspired travel pause. So read on for my warm weather vacation packing tips, hacks and list of must have carry-on essentials for your beach trip or any destination!


Packing Tips & Tricks

Set yourself up for success

  1. Select your suitcase! Will you be traveling with a carry-on or full sized bag? I always prefer a carry-on but based on the length & nature of your trip it may not be possible to fit everything into the smaller bag. If this is the case, don’t beat yourself up. Own your decision! There is nothing worse than being halfway through a trip and running out of fun outfit ideas or wishing you had brought that additional pair of shoes.
  2. Make a list. This is a no-brainer but many skip this crucial step. I promise there is a 99% chance that you will miss something without a list and I recommend having your basic travel list saved in notes or as a word document so that you can easily access and amend as necessary for the trip at hand.
  3. Get a spray tan. Trying on all of those beachy frocks will come easier with a little color. Unless, you are a pro with self tanners I recommend having this professionally done but someone you trust. Here in southern Connecticut, my go to is Pearl Tan Co.
  4. Do try things on! In many cases, you haven’t worn these clothes for months, or years- so don’t assume they still fit right or you like them. If possible, start this process at least a week or two before you travel so you can pick up or order any items you are in urgent need of.
  5. Enlist the help of an honest friend or professional (and make sure they aren’t an overpacker). Packing is more fun with a friend, you’ll stress less and benefit from someone to help you edit. If you prefer to run solo, snap a pic of your items laid out and ask for opinions. Or, if you simply don’t have the time or courage to diy hire someone to pack for you like Style By Risso- my favorite Connecticut stylist.

Get Packing

  1. Style yourself first and be strategic. Pick your outfits, don’t just throw it in. This is the key to packing the right amount. Pack less bottoms and more tops. Jeans and pants can be worn on repeat with various tops. Figure out which neutral items can be incorporated into multiple outfits.
  2. About the shoes. Don’t fill up all of your cargo space with shoes you won’t wear (this was a tough lesson to learn) At the most, bring a pair of sneakers, travel shoes, flip flops, sandals and one pair of heels =. If you can, wear your heaviest footwear on the plane- assuming it’s not a pair of ugly hiking boots!
  3. Layer, layer, layer. Jeans, heavier items and activewear go on the base and layer delicate items on top. If your suitcase allows, place shoes & bulkier items on one side of suitcase and clothing on the other. Tuck socks and other small items in shoes, hats and other nooks.
  4. Bring the right jacket. When you are traveling from a cold climate, the jacket is an unfortunate necessity. I love a light down compressible jacket in this situation. My current fave is this beauty by Herno.
  5. Pack lots of sunscreen. This is sometimes worth checking a bag for those full size bottles. If you are particular (like I am) about your preferred brands, don’t expect to find them at your new destination. Plus, sunscreen is always 10x more expensive in a gift shop. Your skin will thank you!
  6. Don’t forget your pandemic essentials. Bring a variety of masks for the airport and your actual destination plus your preferred sanitizer and antibacterial wipes for the plane.
  7. If you do opt to check your bag, always bring an emergency outfit! I am forever paranoid about lost luggage and we all know it happens. So plan ahead and bring an extra outfit, underwear and/or bathing suit & flip flops in your carry-on so you don’t miss one moment of lounging poolside in your new destination.
  8. Don’t stress! If you do forget something, you can surely purchase a replacement at your destination. And who doesn’t love vacation shopping?




My Travel Essentials Checklist

Luggage– My go to carry-on sized bag is the Away Bigger Carry-On. It’s super stylish, sturdy and has a built in battery to charge phones & other devices. For longer trips I use the Monos Check-In Medium which I love because it’s very lightweight.

Carry-on tote– I live by my MZ Wallace but when traveling with kids I always carry my State backpack– and possibly both! Both can double as a beach bag.

Belt bag- or for those of you who grew up in the 80s- a fanny pack! These are super handy for any beachy resort vacation and once I accepted how useful they were, I simply had to swallow my pride and embrace function over form. I love this one by Lululemon!

Snacks– Some airports can’t be trusted to have healthy snack options so I always travel with several Raw Rev Glo Protein Bars– peanut butter dark chocolate & sea salt is the best!

Sanitizer & wipes – Most hand sanitizer smells like a bad after party and causes your hands to look like they’ve been dipped in acid. Not the case with EO Products lavender hand sanitizer which has quickly become my go to!  Once I’m seated on the plane, I  like to wipe the seat, arm rests and tray table areas with Sonos medical grade wipes.

Masks & Shields- I always wear KN95 on the plane and in the airport and these are the best. My favorite non-medical mask is made by Happy masks and for a nice lightweight mask I like these by Athleta.

Books/mags– While I do sometimes travel with an iPad for reading, I usually prefer a good old fashioned paperback! Maybe I’m aging myself, but there is something more satisfying about physically turning a page, the smell of a real book and the satisfaction of finishing one. Also, reading an iPad in the sun can be a challenge. My go to mags are always In Style, Travel & Leisure, Afar and US Weekly.

Travel Wrap– I rarely wear a scarf unless I travel- then it’s a definite necessity because I easily chill on the plane. White & Warren makes a dreamy cashmere travel wrap in a multitude of colors and 2 sizes- I prefer the travel wrap mini- it’s still generously sized. Warning- you can’t have just one!

Neck pillow– This is a must have for any flight I intend to sleep on.

Cozy blanket & eye mask– My all time favorite set is from Lou & Grey but they don’t make it anymore. I also like these options by Italic and Barefoot Dreams.

Hats- If you care about your skin, this is your most important accessory! I adore this roll up visor by Hat Attack but I always bring a baseball hat (or two) as well.

Meds/vitamins– There is no circumstance that I will travel without Advil gel tabs (mini preferred), probiotics, melatonin and Bulletproof coconut charcoal. Melatonin is a must have to help your body clock adjust to a different time zone and activated charcoal is super helpful for treating a terrible hangover or a more serious gastrointestinal problem.

Pen/small notebook comboThese are much needed for those creative thoughts that rush in during a long flight and to fill out customs paperwork.

Noise cancelling wireless headphonesBose Quite Comfort Q35s actually work. Plus they include a cord to connect to in-flight screens and come in rose gold!

Cosmetics– I swear by Osea Malibu’s advanced protection moisturizer, anti-aging hand cream and Lanolips 101 ointment to rehydrate airplane parched skin.  I live by this Chantecaille primer with 45 SPF!

Sunscreen– For face I use Supergoop’s unseen sunscreen and for body, Sun Bum is my go to!

I hope that my list of packing strategies and travel essentials is helpful to you. Remember, there are bigger problems in life than not having the perfectly curated suitcase but it never hurts to have a little guidance!


Safe travels friends!!