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I’m Packing for an Alaskan Cruise in May

active wear
February 6, 2024

Hello, and welcome to Dressed for My Day. My goal here is always to encourage and inspire women over 50 to get dressed for our unique days in a way that feels authentic, appropriate for the occasion and a little stylish…so we can show up and contribute to the world around us. I know that many of us women over 50 do a lot of traveling, so for the next few months I’ll be sharing updates on how I’m packing for an Alaskan cruise in May.

Packing for An Alaskan Cruise

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I enjoy sharing my travel capsule wardrobes, and I think a lot of my readers enjoy those, too. Last year I shared how I packed for an early summer vacation to Maine HERE and for a late summer week in London, England, HERE, HERE and also HERE. You can check out all of my travel posts through the TRAVEL link under BLOG in the top menu.

In May of this year (2024) we’ll be boarding a Regent Cruise ship for a week along the coast of Alaska. Then we’ll rent a car and explore more of inland Alaska on our own. My husband James and I are so excited. This “trip of a lifetime” is one we have saved towards for a while now, and we’re taking it in celebration of our 60th birthdays.

In a recent subscriber email I asked for readers to share their recommended essentials and tips for my Alaska cruise, and so many responded. It was a wealth of information and I’ve leaned into it heavily as I’ve been making my packing list and beginning to shop. If you’d like, you can see most of those reader responses in the comments section of this recent blog post.

t-shirt // plaid performance shirt // water-repellant hiking pants // similar hiking shoes

But a few of the main pointers I took away from those comments and other reviews I’ve read include:

  • pack & wear lots of layers
  • prepare for every day to be wet and cool to cold (Alaska gets about 250 days of rain each year)
  • pack some waterproof shoes/boots and clothing
  • take a warm hat and sun hat (baseball hat or hiking hat)
  • your top layer coat needs to be waterproof and accommodate multiple layers underneath
  • pack thermals or fleece tights, etc.
  • take gloves

Of course, there’s more. But with those and other pointers in mind I have indeed begun to put together my packing list for an Alaskan cruise and land excursion. While I understand the dress code, so to speak, is very casual, I will still be true to my personal style. That’s very important to me because it helps me to feel confident, be more friendly and outgoing and look my best for the photos we’ll undoubtedly take.

chinos and chambray shirt
chinos // t-shirt // chambray shirt // sneakers // earrings // bracelet 1 // bracelet 2

Today I’m sharing with you just a few of the layers that I’ve already accumulated and will be packing for my Alaskan cruise. Obviously this is not a complete packing list. But I had so many readers who told me they were planning similar trips and that they’d love to hear what I’m putting on my list. So I decided to share a little bit here and there as the trip approaches as a resource.


I will be taking a pair or two of jeans, but I really enjoy wearing other casual pants, too, when I travel. So my updated Talbots chinos will almost certainly go with me. This outfit looks like something I might wear for our day of touring Vancouver, British Columbia, or for a day on the water. It’s comfortable and casual, but a little elevated and polished, too.

Waterproof trench // chinos // t-shirt // chambray shirt // sneakers // earrings // bracelet 1 // bracelet 2

For excursions that involve any hiking or other outdoor activities, I’ll wear my L.L.Bean water-repellant comfort trail pants. (I also ordered these and these and they were way too lightweight and ran small.)

performance shirt and hiking pants
t-shirt // plaid performance shirt // water-repellant hiking pants // similar hiking shoes

These water-repellant hiking pants are not heavy, but they are sturdy and thick enough. And they have so many great hidden features, including interior secret pockets, hidden bungee cords for tightening around the ankles and an adjustable waistband. They fit perfectly true to size. I’m wearing a 10 (which is what I usually wear in hiking pants) very comfortably.

performance shirt and hiking pants

My layers up top include this lightweight slub cotton cropped length tee (I’ve ordered this long sleeve tee in the same color), this L.L.Bean mid-blue pro stretch shirt, a L.L.Bean Katahdin full zip fleece jacket and my Athleta RainOut Sutro long trench. And yes! My beautiful Snowfall Blue jacket is finally on the website and fully stocked in regular, petite and tall sizes.

Rain Trench
performance shirt and hiking pants

For right now I’m planning on taking my Oboz hiking shoes (similar). They are waterproof and I enjoy wearing them. I have good hiking boots with Goretex, but they’re so big. I hesitate to pack those. Let me know if you have any insight to share on that. But I think if I wear my wool hiking socks I’ll be fine with these hiking shoes (similar).

performance shirt and hiking pants

By the way that blue plaid pro stretch shirt is just lovely. It’s soft and silky and stretchy. But it also features at least three hidden zip pockets for storing things like reading glasses, ID, lip balm. I’m so tempted to buy the sunlit coral one, too, but I don’t want to overpack. I’ll hold off for now. And yes, I do plan to take my chambray shirt because it makes a nice, versatile second layer, especially for non-outdoor activity days.

performance shirt and hiking pants
fleece full-zip jacket // t-shirt // plaid performance shirt // water-repellant hiking pants // similar hiking shoes

Obviously I’ll be packing more than this. But I’ll be sharing things as I get them in just in case you’re planning a similar vacation. I’m looking for a simple but elegant black dress to consider for a few dressy evenings at dinner. I think I’ll limit myself to the one dress and just accessorize a little differently. And then I’ll probably take a pair of black pants and a couple of blouses or dressy tops for the other evenings. We have complimentary laundry service on the ship, so I really don’t want to overpack. Oh, and I definitely plan to pack a couple of versatile cotton sweaters and other tees as well.

fleece full-zip jacket // t-shirt // plaid performance shirt // water-repellant hiking pants // similar hiking shoes
waterproof rain trench // fleece full-zip jacket // t-shirt // plaid performance shirt // water-repellant hiking pants // similar hiking shoes

Well, I could go on and on. We’re so excited for this trip. James was born in Alaska, so he’s anxious to go and see a little of his roots. And of course we’re anxious just to see the beauty of God’s creation. Stay with me as I prepare for my trip and I’ll share more. I’ve actually added a few other items to the shopping widget below that I have ordered but that haven’t come in yet.

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Thanks so much for dropping in today. Let me know in the comments if you have a fun trip planned. I’d love to hear about it.

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Blessed for My Day

This week we’re walking through Psalm 19. The beginning of this Psalm of David admires the way nature reflects the glory of God. It serves as a living picture of God’s character. But this next portion of the Psalm notes how the Word or Law of God also tells us about God’s nature, His ways. And here David confesses that God’s law, while seemingly difficult and maybe even cumbersome to some, is exponentially beneficial to those who look to it for direction and wisdom.

Indeed, I’m sure God’s commandments do seem unreasonable and harsh to those who don’t not know the love of God. But when we remember that God gave us His mandates to protect us, to guide us and even to give us great joy, we see them differently. I’ve found that God’s law is perfect and it keeps me safe. His Word brings me wisdom and makes my life more joyful. Be sure to read more of the Bible today. It truly does rejoice the heart.

The law of the Lord is perfect,
    reviving the soul;
the testimony of the Lord is sure,
    making wise the simple;
the precepts of the Lord are right,
    rejoicing the heart;
the commandment of the Lord is pure,
    enlightening the eyes;
the fear of the Lord is clean,
    enduring forever;
the rules of the Lord are true,
    and righteous altogether.
More to be desired are they than gold,
    even much fine gold;
sweeter also than honey
    and drippings of the honeycomb.
Moreover, by them is your servant warned;
    in keeping them there is great reward. ~ Psalm 19:7-11

xoxo, Kay
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32 thoughts on “I’m Packing for an Alaskan Cruise in May

  1. Kay- what a great sounding trip! I like that you’re also taking an inland road excursion too!
    Your wardrobe looks just perfect for this trip! Have the best time!

  2. Your comment about how you look being tied to your being confident, friendly & outgoing really resonates with me. If I don’t feel good about how I look, I have to really push through in order to still be engaging with the people around me and tuned in to them instead of completely focused on the lack of how I look for the day

  3. Our trip to Alaska was my husband’s dream trip and he planned it for three years and for two years it was cancelled because of Covid. Finally made it in 2022. All that time I was collecting pins to my Pinterest board so had hundreds by the time we left. I was especially interested in what people took and what they actually used. Layers, rain gear, rain boots were a frequent theme and I am sure rightly so but I bought rain boots and a rain jacket and never used them, We had a light mist one day of the 14 day trip after we returned from port. My favorite layer was my 32 Degree Heat base wear leggings. Very soft, very warm and thin and light enough to go under regular pants, even under outerwear leggings. I still wear them under my pants in winter now. And they are usually on sale by the time you are buying for a trip in May. My husband had some for base wear too. So close fitting they are really warm under looser pants.

    1. After 2 wonderful Alaskan trips, I’d suggest you reconsider the gortex hiking boots. In Alaska, boots that get wet tend to stay wet.

  4. Kay,
    Do the new Talbots chino pants run true to size? What do you think about the length and color selection? Thank you, Laurie

    1. They do run tts. I’m wearing an 8. I’m 5’8” and the misses fit hits right on the top of my foot. I suppose that’s where they’re supposed to hit, but when spring gets here and I wear different shoes with them I may have them hemmed to more of an ankle length. Just not really sure. I think it’s just taking me a little while to work with this new silhouette but I’m not afraid of the challenge. 😉

  5. Don’t forget gloves. We were in Alaska in September. Everything everyone said about the climate and the changing weather is correct. They also gave great suggestions on clothing and dressing in layers.

  6. You will be so glad that you are doing both the cruise and the land trip. My husband and I went on an Alaskan cruise with a group of friends, and we kept talking about going back for a land tour (my husband also was born in Alaska). It took us 12 years to get around to doing it. We liked the cruise a lot, but we liked the land tour even more. You are definitely on the right track with the raincoat (with hood) that allows room for layers — it got very cold on our cruise in June 2007. When we went sea kayaking, I wore so many layers that I looked like the Pillsbury dough boy, but I was warm enough. Long underwear/base layers are definitely necessary. I am very cold natured, so a light-to-mid-weight puffer layer worked well for me under my raincoat. Our land tour was in August 2019, and the temps weren’t quite as cold, but still much colder than this Southerner is used to. Be sure to book your excursions in advance. I know you’ll love the trip!

  7. Kay, You are definitely on the right track with your layers! I own the same Oboz boots and they should work perfect with wool socks.
    I am really hesitant for you with the jacket you picked from Athleta. Cute BUT I would test it out in a heavy rain storm. The reviews say you get soaked. I would invest in a jacket from Marmot, Patagonia, Lands’ End, L.L. Bean, North face, REI, etc that is designed for true athletic use. If you end up having a rainy week, your raincoat will be your most essential piece of clothing. Just a suggestion.

  8. Sounds like a wonderful trip Kay! Love all the examples of your layered wardrobe! Alaska can certainly be a mixed bag of weather! We were there 11 years ago in May and packed layers for every type of weather imaginable. When we got off the plane in Fairbanks for our land portion, it was a sunny 74 degrees! It remained warm(and sunny) almost the entire trip…our only “cold” times were on the Tundra, Glacier Bay and Denali. We were blessed with the best weather, but have on the same warm weather outfits in most of our pictures. ha! Hope you and James have a great time!!!

  9. Our son lives in Anchorage so we travel to AK several times yearly. My favorite pants to wear on those long flights (we live in SC) are the Endless Pant from Athleta. I wore the lined ones when we flew there in January. I think you have shown a travel pant from Talbots which would also work well. Fairbanks is consistently hotter in the summer and colder in the winter than Anchorage. So glad you are doing the cruise and land visit. You will have a wonderful adventure!

  10. So pleased you are doing this as we will also be doing an Alaskan cruise/overland trip in late August. So I’m creating a folder and dropping this post in. Would also appreciate a quick mention of any excursions you’re considering!

  11. Always love the devotional. I’m very interested in your trip. If all goes well I will be going on an Alaskan cruise in June of 2025.

  12. I just went on a 7-day cruise to the Western Caribbean out of New Orleans and even though I promised myself I wouldn’t, I ended up overpacking a bit. It was hard to limit myself because New Orleans was cool and damp, and Mexico, Belize and Roatan were warm (not really super hot). I did enjoy dressing up for dinner/entertainment in the evening, but I probably didn’t need to bring as many options as I did. I am excited to follow your packing saga because I, too, am going on an Alaskan cruise in a shoulder season (Late September 2025) and will have some similar challenges then. I plan to combine it with a week of touring Washington and Oregon (hiking, wineries, some biking), so will need casual wear and cruise wear. Looking forward to seeing what you keep and what you decide not to bring–and what size bags you are limiting yourself to!

  13. Last June we took a Regent cruise from Seward to Vancouver, much like the one you are taking, but in the opposite direction. We did a ten day road trip from Fairbanks to Anchorage prior to the cruise, and then three days in Vancouver. All I can say is that it was absolutely gorgeous and I’m sure you will both love it. What I can tell you is that we waaaaay overpacked. I ended up wearing the three pairs of jeans I took and almost no other bottoms . Yes, layers are the key. It was too cold for shorts and no one, even in the nicest restaurants wears anything but jeans , cargo type pants, legging, or sweats. It’s very casual. Vancouver was a little dressier but not much. I took boots but never put them on. A good pair of hiking shoes is all I needed, however we didn’t do any serious backcountry hiking. It rained a lot and there was occasionally mud, but we just rinsed off our shoes and we were good to go. For dinner on the Explorer I wore the same pair of black dress pants to dinner every evening, just dressing up a little with the top and jewelry. You cannot wear denim after 6PM in the public areas of Regent ships but there is no other fashion police or rules. We have taken several Regent cruises and this was by far the most casual of any. No dresses, ties, sport coats, etc. are required unless you just want to. Also, be sure to take a good pair of binoculars. They have some in your suite on the ship but I have found them difficult to use. I hope you both have a wonderful tripl

  14. Regent is upscale, so you will want to be dressed appropriately each evening. If they still have formal nights, pack some extra bling

  15. How fun! You will have a great time!!! My daughter-in-law family lives in Anchorage right now 100 plus inches of snow and moose in their front yard most days…lol. But the photos are amazing.

    1. Thanks for your input. I seem to have developed a sensitivity to wool and potentially cashmere. I’m still wearing them, but not directly on my skin. Otherwise I would be taking merino wool base layers.

  16. I’ve done a lot of back country tramping (hiking) over the years in a variety of weathers. Your best friend is wool. It stays warm if you get wet and helps to retain body heat. It is also good if it is warm as it breathes and doesn’t get smelly. I’ve used merino long sleeved under shirts and merino long johns and even in heavy rain I felt warm enough.

    1. Thanks for your input. I seem to have developed a sensitivity to wool and potentially cashmere. I’m still wearing them, but not directly on my skin. Otherwise I would be taking merino wool base layers.

  17. Hi Kay,
    I am no longer receiving the daily blog posts from DFMD. Posts stopped last Thursday. I have signed up again twice using the sign up feature on your blog, but am still not getting any posts.Can you please ask your assistants to check in to this for me? I miss getting your fun and informative blog posts!

    Thank you,

    1. Hi Wendy, I checked my Mailchimp records and you have been sent the daily emails and they were delivered without bouncing. Please check your spam and see if they are in there. If they are, you need to get them out and mark them as “not spam.” Also, I did change the address from which they are sent. They are not sent from So make sure you add that address to your contacts. That may be the answer right there.

  18. Good morning Kay, I’ve read all your comments, and after 7 Alaska cruises, they are correct. But just a few thoughts while you are ON the ship: common areas, dining rooms, your cabin. It is still chilly! I’d plan two small capsule wardrobes around a favorite jacket or sweater. Trust me, that’s all people will see on board. The dining rooms will have you shivering! So plan your evening wear around a wrap or classic jacket. Enjoy!!

  19. Hi Kay,

    I just read some of your blog about going to Alaska and what you are intending to bring. I was in Alaska for 2 weeks, pre-covid in mid-September and was surprised by many sunny and warm days in the mid 60s. Our cruise was an UnCruise, with a lot of activity. I found that having one very light, synthetic layer to wear under most of my clothes was great for the chilly mornings (yoga on the deck at 6:30am anyone?) straight through the day when I could peel off layers as the sun rose in the sky; high rubber boots, Alaskans generally wear these and refer to them as Alaskan sneakers, and warm socks. The other essential was a lightweight, waterproof outer layer. I had goretex rain pants and jacket that rolled up small enough to fit in my smallish backpack/purse so I could don them whenever I needed to. I also had a lightweight puffy jacket. I was warm, dry and comfortable whether bushwacking, getting out on a skiff to see puffins, or climbing on and kayaking near icebergs. I hope you have a wonderful time!! PS…It was my 60th birthday trip (same as Alaska’s)

  20. Alaska is amazingly beautiful! I first went on a cruise there with gf’s in August 1986. We froze. Fast forward and took husband, son, and mom in early June 2016. Highs in the 80s! And we hadn’t packed any cooler clothing. Lesson learned. Layers and t-shirts a MUST. Lol. Highly recommend helicopter ride to a dogsled camp on top of a glacier in Juneau. You even get to drive/mush a team, with trainer in tandem behind. A highlight of our trip, most definitely! Enjoy!!

  21. Your trip sounds great!! I’m going to Alaska for two weeks in July 2024 for a mission trip! We will help host 2 different women’s retreats for local indigenous women. I’m told they have very basic living conditions, most without running water. Our goal is to make them feel loved and special while we share Jesus with them. Please say a prayer that we will be up to the task and that the love of Jesus will be evident to all. Looking forward to hearing more about your trip!

  22. Hi, My husband and I are also going on a Regent Cruise Alaska Cruise for our 60th birthday! I came across this post while looking for things to pack for Alaska Cruise! I can’t tell you how excited we are. Thanks for all the links and how excited we are for our “once in a liftetime” cruise as well!

  23. Your blog was very helpful to aid me in packing. My husband and I are on the same cruise! See you soon 😊

  24. I’m going to Alaska on May 26th, so your post is serendiptious for me and I’ve been following all of your Alaska posts, so thank you for sharing them! I do love the Athleta trench that you picked out and I bought it, too on sale. However, as the other commenter said, I am a little concerned that some of the reviews are saying that it is not waterproof. I also have a black Marmot Goretex jacket, which I may end up taking instead. My packing list is similar to yours; so far, I plan to take two pairs of blue jeans (Democracy blue and black) pair, my thermals (Uniqlo Heat Tech ones), a couple of base layers: one blue Smart Wool long sleeve base layer and one 1/4 zip black one with thumbholes, grey v-neck cashmere sweater, blue-grey Lulelemon leggings for workouts/lounging, and one pair of grey Patagonia hiking pants and a teal Patagonia zip sweater jacket. For the two formal nights, I’m taking one cream and gold long sleeve sparkly cocktail dress with sequins, and one royal blue jumpsuit. I’ll also take my Traveler’s black pants and matching black top and a few nicer tops. My shoes as are: J. Crew gold block sandals, gold jewelry, black Vionic flip flops, and my waterproof hiking shoes. For outerwear, I’ll take my cream Patagonia down sweater, Talbots bright pink down vest, I’m also taking a pink bathing suit, a cover-up, and binoculars. Mine is a ten day round trip from San Francisco on the Crown Princess. I am so excited!