What to Wear on Vacation


Are you planning any vacations this summer? I keep daydreaming about summer trips, and when he can’t sleep, Alex has a funny habit of exploring destinations on Google Street View. (Have you tried it? It really feels like you’re strolling around town.)

So, let’s take a pretend trip. Imagine: You’re heading to Portugal. The big question is, what do you pack? Here are some ideas…


1. Straw hat to keep your pretty face shaded. (Here’s a $40 version, too.)
2. A maxi dress to wear to the beach and out to a romantic dinner.
3. Statement necklace to make even a white T-shirt and cut-offs look beautiful.
4. Beachy perfume with the scent of sand, jasmine, sea spray and mandarin.
5. Caroline swears by this lip butter for getting soft lips with a pop of color.
6. Comfy sandals. This awesome pair has been on my wishlist for three years.
7. Sunglasses to channel an old-school Hollywood starlet.
8. Patterned swimsuit. (I LOVE the back.)
9. Peace towel by the wonderful Lena Corwin.
10. Escape bag for all your adventures.
11. Dark & Stormy because it’s the perfect summer cocktail.

Thoughts? Would you wear these? Are you feeling wanderlust-y?

P.S. A genius tip for packing for your honeymooon, and 9 trends this spring.

(Top by Raúl Deamo. Graphic elements by Miss Moss)

  1. Cátia Oliveira says...

    Hi Joanna! I love your blog…really, for me is pure joy to read everything you and your collegues write. And I just love that you love Portugal…and o mentione so many times here. :D This portuguese girl will be in NYC in Setember for the first time, so excited… Thank you for give us this blog.

    Best Regards,

    • Joanna Goddard says...

      thank you so much for your kind works, cátia! i hope you have the most wonderful trip here!!!

  2. Gabriela says...

    I looove the swimsuit on the image! Where is it from? xoxo

  3. this makes me really want to go on a holiday!! And buy holiday clothes, especially that swimming costume!

  4. love the tips! I am always traveling so this will come in handy!

  5. That travel bag si so chic and roomy, you could fit a huge towel and an extra outfit in it and still have have some space left. You could pair it with almost any dress you want and it would look good.

  6. Prudence says...

    I have been daydreaming about making summer trips to beautiful beaches recently! The featured items will definitely come in handy, especially love the “Escape” bag, such a fun piece!


  7. Lucy says...

    Ah, lovely post :-) Put me in the mood for summer holiday plans! Thanks for the pics :)
    Life inside the Locket

  8. Love your picks! I just got back from South Beach and I swear I’m the worst packer ever. I pack like too many shoes, not enough underwear, and usually forget something logical like a hoodie or pjs. :D
    PS> Yes, the Google street view thing is amazing! I remember one time using it to explore the cliffs of Capetown. I may need to do that today on this rainy morning as I reminisce about the beach.

  9. As a portuguese girl I totally agree with this outfit! This weekend is perfect here in Lisbon. I went for a running with my boyfriend yesterday with just a top and a summer t-shirt. My mom is right now sun bathing in Algarve and by the photos she’s been sending us, it is lovely and super summery. I think you should came to Portugal with Alex and maybe the boys. I think you would like it. And you have to taste our wine. ;)
    PS: You’re new design is beautiful!!

  10. Laura says...

    My husband and I honeymooned in Portugal- I think that it will forever be my favorite place in the world!

  11. I would so wear these items and definitely feeling the call to explore/travel :). Lovely reading your post, thanks for sharing.

  12. Melissa B says...

    For a new take on a towel, check out BeachSpoke blankets – they look great and peg into the sand so never snag or fly away. I absolutely love mine!

  13. A great choice of outfit for a perfect destination.

  14. Yes! Scottsdale with the family soon. And I could totally wear that outfit and items in the desert. Can’t wait! Thanks for sharing

  15. Mariana says...

    Hi Joanna! you’ll be very welcome here!
    If you need any tips, let me know!
    Best regards from Portugal :)

  16. My brother is in Portugal now and his pictures have been really giving me a travel bug to visit. Now I know what to wear when I do!

  17. Caroline says...

    I’m coming to New York from Australia!

  18. Joanna, you should definetly come to Portugal. you’ll be more than welcome! I mean, seriously, have you seen how much portuguese readers you have!!?

    Just commenting on the drinks: in Portugal, go for the sangria and brazilian inspired caipirinhas!!

    (That photo is from Ponta da Piedade, in Lagos (Algarve). You must do the boat ride to see the caves!)

  19. I like this Escape’ bag, it is a good bag for a real get away

  20. yael steren says...

    I completely agree about the maxi dress (in fact I just posted a topic about taking a maxi dress on a trip earlier this week)! I also agree with the hat, the sandals, etc. I would also add to the list a beach cover-up/caftan and one that can be worn when you aren’t at the beach as well (for example if you’re going straight to lunch or dinner). xo yael

  21. Ana Simoes says...

    I love reading all the portuguese ladies commenting :)))
    You have a huge fan-base here!

    I also wear tanks with maxi dresses; or basic zara spaghetti-strap tops.
    As for those sandals… I’m completely in love with them.

    • Totally, Ana! I didn’t knew that so many portuguese ladies read A Cup Of JO. :D Nice to meet you! I’m Tânia!

  22. jbhat says...

    Ah, would that all tourists would heed such a chic packing list. Kudos to those who do!


  23. Patricia says...

    Quick questions to all you lovely people, but what kind of bra do you usually wear with maxi dresses? I usually have hard time trying to find one that is suitable since most maxi reveals the back :-/

    • shay says...

      bralettes, pasties or wear a pretty bra and just let it show :)

    • Caroline says...

      Remember it will be winter!!

  24. Ana says...

    To Portugal visitors, I recommend Arrábida, Sesimbra and Comporta. Perfect beaches near Lisbon.

  25. By far, your blog is still my favorite. I would definitely wear everything you picked. Love the Maxi and the hat.

  26. Ana Bacelar says...

    hello Joanna! you’ll be very welcome here! Best regards from Portugal :)

  27. paula caetano says...

    Hi Joanna
    We hope to see you in Portugal one day :)

  28. I always feel wanderlusty!!! That selection is great (the sandals! The swimsuit!) But I’ll add a jacket. It must be my mum’s voice stuck in my head, but I always think: it’s going to be cold at night, wear a jacket! ;)

  29. Mariana says...

    Good morning!
    What a surprise to open the blog and see a picture of Lagos, where I spend summer vacacion since ever!!
    The outfit choice is great, but you should add a light sweater, as Lagos is a bit windy!
    Love the blog for some years now.
    Kisses from Portugal.

  30. Jenna says...

    What a timely post! I’m going to Portugal (Coimbra) in June to watch my nephews while my brother and sister-in-law are in language school. I’m so excited!

    I’ve been looking for a maxi dress for over a year, but I find that most aren’t designed for someone who’s 5’1″. Any ideas?

    • Emily says...

      Anthropologie has a gorgeous one just for petites in their new petite collection.

  31. The guide is great – love the cocktail! haha xx

  32. I’m *so* glad I’m not the only one who takes “street view” mini vacays! PS love the new logo/look.

  33. Leah says...

    Yes, yes, yes to Street View tours! I do this on tea breaks at work. Also fun is the game GeoGuessr, which plunks you in a random place on the globe (in Street View) and you have to guess where you are.

    • Joanna Goddard says...

      that is so funny, leah!!

    • That’s so addicting! Love it!

  34. Yes am keen on trying the good ol’ once piece again!

  35. Beatrice says...

    Just wanted to order the lip butter on, but it is sold out! The power of A Cup of Jo! :) Will wait for a while to see if they replenish their stock. Otherwise, they have other flavours, would you recommend another flavour, Joanna? Because the colours are a little different…

    • Joanna Goddard says...

      i like the juicy/bright pop of the pomegranate… i’ll switch the link to an available one!

    • Beatrice says...

      Thank you, dear Joanna! You are so sweet :) And thanks a million for the recommendation — I fully trust your taste and therefore will only buy pomegranate :)

    • Beatrice says...

      Just a quick note. I live in Vilnius, Lithuania, and unfortunately not all the sellers linked to provide shipment to Lithuania. But I was determined I wanted the pomegranate lip butter, so I finally ordered it via As I said, I trust your taste, dear Joanna :) Not all products available or popular in the US are available in my country, but I still enjoy your blog very much :) I am a fan of Dior Nail Glow polish, upon your recommendation :) Thank you for your blog!!

    • Emily says...

      I love korres lip butter – one of the few products I’ve stuck with for years! I use it as a cheek stain too (I love quince)

    • Beatrice says...

      Hi Emily,
      Nice to hear that you also love Korres lip butter :) This is the first time that I ordered it, waiting now for my order to arrive in a couple of weeks, and hoping to love it, too :)
      It’s such a nice community of lovely ladies here on A Cup of Jo :)

  36. Hi!

    You’re doing the best to spend your vacations here in Portugal!!
    I live in Algarve, and we have a wonderful weather and the best natural beauty you can expect!!
    If you need something, just let me know!!


    • susana says...

      yes, please! looking for suggestions for 10 days in portugal. a little Lisbon, and then the beach! places, hotels, restaurants, shops?

    • Joanna Goddard says...

      loving all the comments from readers in portugal. would be such a dream to come visit.

  37. Whoa, you are reading my mind right now. Just booked a week in Portugal and CAN. NOT. WAIT. Also, those sunglasses look exactly like ones I just bought (but aren’t the same).

  38. we went to portugal on our honeymoon and hung out on beaches that look just like this photo! maybe we were at this very beach! though, it’s tough to say because there are so many in that beautiful country! i have a work trip in switzerland in a month. my husband is meeting me over there and after my work is done we are heading into the french alps and then up to paris. packing is going to be tough. i prefer to pack light, but i have to pack for three weeks that will include: 1. working at the U.N., 2. gallivanting in the alps, and 3. strolling around paris.

  39. Ha! We are running off to Portugal this summer as a matter of fact! I’ll turn 30 while we’re there, and it just seemed like the right thing to do.
    We’ve been talking about it for a few years, but haven’t left the country since our honeymoon to Scotland 4 years ago. I turned to my husband just a few months ago and said that we should, because life is short.
    29 days and counting!

  40. We’re staying in Newport beach at the end of the month, and I’ve been bent of shape worry about what to wear! Love this, and packing all of it! Thanks Joanna! I’m excited to try that fabulous lip butter.

  41. Hi Joanna,

    Great choice on the destination.

    All the best from Portugal :)

  42. Laura C says...

    Heading to Italy this summer. Thanks a lot for your ideas! I’ll be looking for a low-cost alternatives…

  43. Maria says...

    Hi Joanna!
    Just to tell you that you have here in Portugal a daily reader and a huge fun! Thank you for making me company every day even separated by an ocean. Many kisses!

  44. Evelyn says...

    Now, what do I wear if I were going to Portugal and am breast feeding?! I have a 6 month old and we’re vacationing this summer, but i’m still breastfeeding! All my maxi dresses are in reserve for nights out sans bebe. But for the rest of the days… would love a post on that!

    • Joanna Goddard says...

      good question! are you comfortable breastfeeding in a V-neck tee (or V-neck dress)? i thought those were easy enough to pull down and just go for it. but it depends on your comfort level. i’ll keep thinking!

    • Nadia says...

      Hi Evelyn!

      I’m a Portuguese breastfeeding mamma and let me tell you that you don’t have much to worry about breastfeeding in Portugal. You can quite simply wear a nursing tank top to a normal top or blouse. Anything that you wear usually while you’re breastfeeding is fine. I have breastfed my son in the middle of the grocery store while shopping!

      Enjoy your vacation,

  45. My friends and i have started drinking a version of a dark & stormy we call the “light and breezy” — white wine, ginger beer, ice, and lime. you could drink it poolside all day and never get sick of it…:)

    • Joanna Goddard says...

      OMG YES.

  46. I love this! I’m always daydreaming of new places to travel. I’m currently planning for our week in Morocco in June so lots of loose pants and tops, plus a gorgeous straw hat like you’ve mentioned. Also, sandals that are both sturdy and stylish for all that market wandering!

    p.s. I’ve been to Portugal and you would love it. Hope it becomes a real-life destination for you someday soon : )

  47. ahahaha i love how out of all the world you just picked my own country! whatever you wear and pack to come over, i’m sure you’ll enjoy it!

  48. I’m getting married to the love of my life in Greece in just a few short weeks, and besides the wedding attire this is more or less my entire suitcase (:

    • Joanna Goddard says...


  49. Meghan says...

    Korres lip butter is also awesome for making your lips rosy! Multifunctional items are perfect for traveling!

    • Meghan says...

      I meant making your cheeks rosy!!

    • Joanna Goddard says...

      oh i’ve never tried that! will tomorrow!

  50. Want want want and want! I have a serious case of wanderlust! I’ve been looking for the perfect summer the ones you shared here! My husband also does google street view when he can’t sleep. Such a cool technology!

  51. Loving those sunglasses. I need to get a good pair for this season…and I’m dying for a summery vacation! I’m in pastry school on top of a full-time job straight through September, though, so my eye is on a nice, long vacation upon graduation that will hopefully include visiting good friends in Toulouse and then another friend in Casablanca. :)

  52. Meg says...

    Yes, I have wanderlust! I’m going to Puerto Rico in two weeks and love all of these outfit ideas. One of my typical vacation outfits is to wear a comfy maxi dress on the plane- usually a stretchy black one I have from Gap that feels like I’m wearing pajamas! It keeps my legs covered if the plane is chilly and also saves suitcase space since maxis take up more room than shorts. I usually bring a cardigan in my carry-on to keep my shoulders warm or to ball up as a pillow on the plane.

  53. Christina Trifonov says...

    A true Dark and Stormy contains only Black Seal rum and ginger beer.. just sayin’ :)

  54. Leah says...

    Love this list … and the website redesign. Congrats on that, Jo + team!

  55. Ooohhhh I love these ideas. I’m going on my first(!) cruise to Alaska this summer and love going over what outfits I’ll wear in my head! P.s. Love the new blog design- it’s brilliant.

  56. These are all super stylish and sensible, too! Love the new blog design!

  57. Megan says...

    The numbers in the image do not align with the numbers in the corresponding text

  58. Amy says...

    I have almost the exact same sandals but both straps are black and I can honestly say they look awesome but are so flat and hard that within a few minutes of walking I’m done :( But Jcrew’s collaboration with Birkenstocks would be an awesome choice if you are doing a lot of walking!
    Love all the ideas you posted, the excitement for summer is building!

  59. YAY! A floppy hat! I’ve been searching for an inexpensive floppy hat for a month, and everywhere has been sold out! Now I have one one its way to me – THANK YOU! Now I’ll have some shade on my face as I lounge on the beach in Cape Cod next month. :-)

  60. I’m always worried the straw hats will get damaged on my trip and the last thing I want to do is drag another thing on the plane. But I think you own one that is made of fabric and packable?
    BTW, one of my favourite features of your redesign is that you can directly reply to comments – makes it much easier to follow the conversation. What a great new look you created!

  61. Rachel says...

    Ha I do the Google Streeet View thing too!

  62. Joanna,
    You are my lifestyle compass!
    My husband and I are going to St. Lucia for a belated honeymoon soon (Sugar Beach, as per your recommendation)! And I’ve been stressed about what to bring. This is so helpful, and is making me eagerly ancitipate the trip all the more!
    (Also, I eat the breakfast salad recipe I found on Cup of Jo multiple times a week and our new favorite late night snack is the potatoes your aunt shared her recipe for.) :)
    Thank you for ever-being such a source of inspiration in my life!

    • Joanna Goddard says...

      you’re going to love sugar beach!!! thanks for your sweet note :)

  63. Marissa says...

    Yes, very wanderlusty..
    I’m writing my master’s thesis and it feels like there is no end to this all..

    NEED a vacation!

  64. Catie says...

    You read my mind! I’m about to head to the Mediterranean next week for work, and I’m itching to finish the end of my semester here and head out. I have a bit of a different packing conundrum, in that I’m an archaeologist and gone for a couple of months, so packing is best when it’s light AND versatile. I spend most of my time in fieldwork clothes, which are just fine, but that means that I have to try and figure out what else to pack when I need to dress like a normal person that will give me the most ‘bang for my buck’, space-wise. One effortless dress and one pair of comfortable, versatile sandals are definitely on the list!

    (As a side note, I love that the Greek-style sandals are really in this year (the ones above, and other varieteis). If anyone happens to be heading to Athens, it’s worth stopping to get a pair from the poet sandalmaker! Inexpensive, custom-fitted, and great quality.)

  65. Emily says...

    I’m heading to Greece at the end of June, when I’ll be around 25 weeks pregnant (!)…I’m really looking forward to it, but I’d really appreciate advice on what to wear as it seems crazy to buy a whole new wardrobe just for a week. Do people tend to go for a full swimsuit rather than a bikini?? What sunscreens did/do others use when pregnant? Thanks so much. Emily.

    • Joanna Goddard says...

      good questions!!! (and congratulations!)

      when i was pregnant, i wore a bikini because it more easily accommodated the belly! i also think it’s such a cute look. here’s a (very) old post about that:

      for sunscreens, honest makes a natural spray sunscreen that i really like for both my kids and myself, and also josie maran has a nice natural sunscreen for faces (that’s not as white/peely).


    • Olivia says...

      I use Kimberly Sayer Anti-oxidant SPF 30 moisturiser on my face and it’s so good, no streaky/sticky/yuckiness. I really can’t recommend that moisturiser enough, it’s completely natural and SPF 30 but it’s also a really great product and a great base for make-up/doesn’t make you greasy or leave you white and streaky. (I use Green People sunscreen on everything but my face, also completely natural!)

  66. I really adore the Escape bag! Perfect for Summer travels & the straw hats are a must – especially during the bright sunny days! Thanks for the post. :)

  67. Loles says...

    Dear Jo, dear all, good afternoon, firstly, I would like to introduce myself, my name is Loles and I write from Barcelona, Spain. I’ m sorry, buy my english is not very good. :(…
    I usually read this blog and I love it, Jo…..
    Well, If you want to come to Spain, It s a wonderfull country, you will be wellcome!!!!
    Congratulations for your new look blog ;-),
    King regards.


  68. Sigh, makes me want to go to an island :) We’re still waiting on the whole honeymoon thing, but next year we’re gonna go…to Hawaii!

  69. Jenna says...

    Loft has sandals exactly like that which I purchased recently for only $20

    • Joanna Goddard says...

      Oh my goodness, you aren’t kidding! They look exactly the same:

    • Joanna Goddard says...

      ps just ordered them for $17.70 on sale… THANK YOU!!!

  70. there’s a weeklong vacation to upstate ny this July, i’m thinking layers because even thought it’s mid-summer, there’ll be cool nights: cutoffs, boyfriend chemises over camisoles, or long airy backless maxis with scarf or cardigan. we’re also in the beginning stages of planning an SF jaunt in September. again with the layers! very much looking fwd to some relaxing.

    • Joanna Goddard says...

      totally! or a cute anorak.

  71. Just in time for our Savannah girls’ trip! And I’ll have to try that beach spray–sounds refreshing!

    Kensley from Hot Mess Mamas

  72. Oh my goodness! I totally google street view wander. The first place I “visited” was Copenhagen, and it blew my mind. Hoping to do some real visiting this summer, and top of my list is Amalfi Coast (just picked up some books yesterday to fuel my dreaming)! Any tips for where to stay or eat?

    • Joanna Goddard says...

      that is awesome re: copenhagen. :)

      also, how fun about amalfi coast! we went to positano for our honeymoon and l-o-v-e-d it. we stayed at villa fiorentino (splurgy, was a wedding gift), and there are so many sweet B&Bs and apartment rentals around town, too. also, ravello looks GORGEOUS. i’ve never been, but it’s farther up the cliffs so you get the most incredible views and you can hike and visit a palazzo. (google “hotel caruso” if you really want to daydream!)

    • Thanks Joanna! I’ve been drooling over the pictures of Positano…

  73. Yep, you hit the nail on the head! I’m feeling pretty wanderlusty – pumped up for my trip to Stockholm coming up! There won’t be too many beaches but I think it’ll hit the spot :). I think that ‘escape’ bag would look pretty good there too…..

    • Joanna Goddard says...

      allie, how fun!!!

  74. rebekah says...

    I love maxi dresses, but I’m always so frustrated by the ones sold in stores… I would LOVE to find some pretty maxi dresses that I could actually wear a bra with. I wish I could get away without a bra, but definitely can’t! All these strappy maxis make it impossible to wear a regular bra with support (i.e. not a strapless/backless)

    • Joanna Goddard says...

      that’s a great point. i wore a maxi dress last night and had a hard time with a strapless bra (they always shift around, i find). i’ll keep an eye out for maxi dresses that would look fine with a bra. here are a few in the meantime:

    • Meg says...

      I had trouble with strapless bras for years until I heard this trick, which works great for me: wear a regular strapless bra and then buy a plain bandeau (basically a stretchy loop of fabric, no underwire or anything) and layer the bandeau on top of the strapless bra. It keeps my strapless bra in place without shifting around or sliding down, and adds a bit of extra support. (I found a plain black bandeau at target).

    • i’m probably in the minority, but i don’t mind wearing either a lacy tank or camisole or regular bra under some spaghetti strap maxis. sjp used to do it all the time on sex&thecity and that’s when i realized, who cares? i’ve also seen bikini tops as underthings. granted, this look is very casual, and not for formal or going out to dinner type garb.

    • Joanna Goddard says...

      that’s such a good tip, meg, thank you. and lan, i’m going to try that next time and see how it looks!

    • yael steren says...

      Someone else asked about a bra also! I actually found a great strapless bra, which doesn’t start slipping down your body throughout the day – and that’s even when you’re sweating! I wrote a blog post on it awhile back if you want to check it out! Here is the link! xo yael

  75. I have those sandals on your wishlist! I think i actually bought them after seeing a link to them here – get them! They are amazing, they are my go to sandals all summer :)

    • Joanna Goddard says...

      good to know, shira! i’m actually going to order them right now, with your encouragement:)

  76. I’ve been eyeing this ‘Escape’ bag for awhile… waiting patiently until it goes on sale. I love it as a weekend getaway bag.

    Instagram: @stylishlyinlove
    Twitter: @stylishlyinlove

  77. Anne says...

    I love Dark and Stormys, but I’d drink nothing but port in Portugal! :)

    • Port in the beach doesn’t seem very appropriate. Try Licor Beirao. Or maybe some portuguese beer. You won’t be disappointed.