Packing for Cool Weather Trips

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Have you ever ruled out a destination because you just didn’t want to pack all the bulky clothing for a cooler climate? Or, maybe you have travel plans in place for a trip like this and the thought of packing makes you stressed?

I have an upcoming trip to Ireland in October and figured this is a perfect time to answer the popular question “what are you going to pack for Ireland?” I’m so excited for this trip!  It’s the end of October and the weather will be cool, possibly rainy and hopefully a bit sunny too.  Making the packing task even more daunting.

I recently met with my personal stylist, Carrie Humphreys from Wear the Runway.  Often when I have a special trip coming up, I take the time to upgrade my wardrobe a bit. This is not a travel requirement at all, and perhaps I’m exposing a bit of my inner shopaholic struggle ;-) .   

Carrie is amazing.  I told her where I was going, what the weather will be and the type of clothing I was looking for, and she worked her magic!  Now I have a few key pieces for this trip and I feel ready to start packing!  (Oh, are you thinking…wow, fancy of Emily to have a personal stylist?  Honestly, no extra charge to me.  I’ve come to accept the fact that I’m not a “Jack of all trades” and need fashion specialists to help me out!  Treat yourself too.. why fight the racks at the large department stores when you can have someone do the work for you?) 

My trip to Ireland is a week long guided tour.  I’ll be doing a variety of sightseeing during the day, socializing at night and moving from hotel to hotel-making packing light a necessity.  TIP: A few tips to keep in mind with this type of trip (it applies not just to Ireland.)

  • Wear your heavy shoes on the plane vs letting them take up lots of space in your luggage.
  • Carry your coat on with you. It can double as a blanket for the longer flights!
  • Your daytime attire needs to be a step-up from athletic wear.  Many pubs and restaurants don’t find joggers and sneakers acceptable.  You’ll always want to be comfortable, but presentable.
  • Your nighttime attire doesn’t have to be a complete change from daytime.  Often, it may be changing out your shoes or pants and adding in some jewelry.
  • It’s OK to re-wear items.  Yes, it is OK!  If your travel partner(s) make snarky comments, then you probably can chuckle at them when they’re lugging their many bags thru the airport as you’re strolling thru, sweat free!

This will be a bit long (sorry) but hopefully in the end, helpful.  I’m going to show you my day to day dress plan, based on where I’ll be touring and what I’ll be doing!  TIP:  I always jot down before packing what I’ll wear each day based on my itinerary.

Day 1:  Travel day/Arrival day!  I’ll be on a overnight flight, so I want to be presentable, but comfortable. Once I arrive in Dublin, my vacation begins with a city walking tour! In the evening, we’ll have an authentic dinner at the Merry Ploughboy Pub for a lively show!

TIP:  Pack shoes with a rubber sole, comfortable, and no slip.  Need to be good for many types of terrain – cobblestone, grass, gravel.


Travel Day: My Passport (#1 item), comfy and stylish jogger pants, long-sleeved tee, coat (will also serve as blanket on the plane), necklace, cross body purse and my trusty neck pillow.


Day 1 Evening: Plaid blouse (is it me or doesn’t this look Irish?), black jeans, accent belt aka beast belt (Carrie promised me the beast belt will go with everything & I can honestly say, I love it and feel pretty stylish), comfortable rubber soled flats (I love my Rothy’s)& coat .

Day 2: Jerpoint Farm & Waterford Crystal I LOVE sheepdogs and many of you know, my 4 legged assistant is part border collie, so I’m very excited for this morning of watching the dogs work. Afterwards, we’ll be touring Waterford Crystal and then finishing the day with dinner and a walking tour of the historic town of Waterford. In summary, I need farm clothes, museum attire, dinner dress as well as still remaining comfortable for our post dinner walking tour.


Day 2 items Irish green cord pants (not like the ones from your childhood), floral blouse, accent belt, necklace, & boots. I’ll also need to bring along my coat.

Day 3: Old Midleton & Blarney Castle Well, I think I’ll be saying to myself, “it’s 5’o’clock somewhere” while I’m sampling whiskey first thing in the morning! I guess I’ll need that little jolt to give me some liquid courage for kissing the Blarney Stone afterwards. Dinner will be on my own in the fun town of Killarney, so I’m going to guess I’ll find a fun local pub to enjoy.


Day 3 items for the daytime & night out on the town in a local pub: Black lace blouse, denim jeans, accent belt, necklace, & boots (plus my coat too!)

Day 4: Ring of Kerry, Skellig Experience and fine dinner It’s safe to say, there will be some bus time while touring the southern area of Ireland know as the Ring of Kerry. I’ll be a photographer capturing all the beauty of the region and then a historian learning about the early monks who called the area islands home. The evening will be filled by a fine dinner at our lovely Killarney Plaza hotel.


Day 4 items for the daytime: floral blouse, denim jeans, accent belt, necklace, grey scarf, boots & coat .

Day 4 items pictured below for dinner:


Day 4 Evening: A simple change of pants and shoes!

Day 5: Walking thru the villages of Adare and Ennis, followed by a medieval style banquet served in the Great Hall of the Bunratty Castle. By now, you’re probably catching on – comfy walking / touring attire and then dressing it up for the evening festivities.


Day 5 : I’ll be honest, I’m not sure if I’ll wear this all day or just for the evening. It will be a game day decision. The black blouse is amazingly beautiful and can be trendy during the day and elegant in the evening. I really fell in love with it. Black lace blouse , black jeans, accent belt, necklace and Rothy’s flats!

Day 6: Touring Galway, Cliffs of Moher, St. Tola Farm & dinner Galway is a trendy university town popular with folks of all ages. I can’t wait to see how alive the town is in the morning as it does have a lot to offer for the evenings. Cliffs of Moher – marking a check on my bucket list! Who else has this on their list? I just hope it’s a beautiful day :-) I’m not sure about you, but I love goat cheese and can only imagine how delicious it will be fresh from the St. Tola farm.


Day 6 Plaid blouse , black jeans, accent belt, boots & coat .

Day 7: Tullamore Dew Distillery & Cooking Class in Dublin Drinking & cooking – two of my favorite pastimes! It’s going to be a good day. Starting off with an Irish Whiskey is the way to go. Cooking classes are a favorite excursion of mine. It’s a great way to learn the local culture thru food and honestly, just think all that has been shared thru the years at the dinner table. I’m super excited to hear the old Irish tales while learning to cook as my ancestors did!


Day 7 Cream cotton top, Irish green cord pants , accent belt , Rothy’s flats!

Day 8: Time to go home. It will have been a great trip, full of wonderful experiences and I know I’ll come home with great memories AND will not have broken my back traveling Ireland with a mega suitcase! For the trip home, I’ll pull back out what I traveled across the pond in.

Do you dream of traveling to Ireland? Is Ireland on your bucket list? Are you looking for an “easy” European country to travel to with your family? Emily, Agency Owner/Travel Agent with Relaxing Reservations can help you. Grab some time on Emily’s calendar for your complimentary vacation planning session.

Traveling should be fun, not stressful!

Now that we know what to pack, how should we pack it? I have created a short pos on one of my favorite travel tools – packing cubes. Check it out! Packing with Packing Cubes

Check out Relaxing Reservations’ favorite travel goodies! We love supporting small businesses and hope you do too.

Please know that no products mentioned above were provided to Emily for free.

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