Romantic Getaway Outfit

On this dreary winter day, imagine: You’re getting on a plane tonight for a week in northern Italy, hiking along the steep cliffs and rocky beaches. You’ll have crisp white wine and fried fish for dinner. Here’s a daydreamy outfit to pack…

1. Red cardigan for a pop of color.
2. Easy linen dress for wearing to the beach and dinner.
3. Buttery soft tote.
4. Large watch for that tomboyish look.
5. Trusty umbrella.
6. Sexy sandals (or this more comfortable pair).
7. Polka-dot bikini.
8. Rolled jean shorts for showing off tanned legs.

What do you pack for vacations? Where would you go, if you could go anywhere today? Winter is getting old!!!

P.S. A genius honeymoon trick, and Parisian wedges.

(Top photo by Max Wanger; graphic design by Rachel for Cup of Jo)

  1. Florence! Italy sounds so much better than the chilly New England weather we’re getting now. Your post makes me look foreword to the blazing heat of summer.I talk about my trip to the Cape on my blog, Classified Q, with my two girlfriends and the icky was definitely noticed. Take a look here The grey day at the beach in the sand isn’t ideal but hanging out with your besties always is.

    Editor & Founder of Classified Q

  2. rk says...

    Mmmmm! I love, Love, LOVE Italy! I’m actually driving to Venice this weekend with my husband and I can’t wait to enjoy the best wine selection on earth again.

  3. Love love love the madewell dress!

  4. Either wishing your family, friends Happy Birthday or for wishing them luck on their recently achieved success gifts are the best complements. Send Gifts to India and connect with the different corners of India along with the online service of gifts provided by

  5. My husband and I are living in Naples, Italy right now and I definitely need all of those things! And thanks for re-posting those Honeymoon packing tips. So genius!

  6. Loving that idea of packing in a single colour scheme (and blue and white is so perfect for a beach holiday!). Might have to do that for my trip to Croatia in the summer!

  7. Hi Joannna!

    I’ve been finding this Italy picture on the web on so many sites! Those houses are so colorful :)
    If I could go anywhere now I would be happy with a sunny and hot place (here it’s raining, thunder and lightning)!

    Have a great weekend,


  8. You look like you’re near where I’m visiting right now. Chiavari in Northern Italy. Right next to Tuscany, and super close to Monaco.

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  12. Oh how lovely! My fiance and I are planning to visit Cinque Terre for (part of) our honeymoon so this gets me dreaming about it…

  13. LT says...

    great post and uncanny timing as my mother and i were watching a televised Andrea Bocelli concert last night (love PBS!) that was set in portofino, italy…we could not get over how beautiful it was!

    i’m not planning any trips at the moment, but it sure is fun to fantasize! the amalfi coast would be very high on the list…

  14. YES! Thank you so much for posting, Joanna. My boyfriend and I are leaving for a romantic road trip through Northern Italy the 1st week of May and I’ve been struggling with deciding what to pack. This is SO perfect (and makes me super excited/giddy about addressing the final details of our trip). Thank you!


  15. yes! sexy sandals for drinking wine under the stars are a must!

  16. Love posts like these! I come back to them over and over again to visualize myself in faraway places. Great and practical packing tips, as always! Thanks, Jo!

  17. I am planning a weeks holiday in northern Italy in June – on my own to see Venice, Florence and Verona then to the south of France for a girls holiday!!!!!!!

    Come on summer

  18. Love the shorts!

  19. ps – just saw your comment message (Nice comments only, please! (That means you, anonymous.))

    very clever!

  20. i’m also curious, what self-tanner do you recommend? i’ve been a little scared to try it again since a bad (orange & blotchy) experience that took a lot of scrubbing to fix.

  21. Love the dress!
    Question: What is your favourite self-tanner, any to recommend?

  22. well Jo, right now in northern Italy is raining and cold. No time for beach and swimming yet :-(
    For this we my dream is to spend two days in the Alps, in a warm spa under the snow

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  24. Winter is getting old so I am planning trips! Warsaw next week (although that’s going to be more wintry but cozy too) and then Southern France and then ITALY! I am so excited and drooling over all the lovely ‘packing’ lists online :)

  25. The dress is perfect. I hope I can find a slightly cheaper version to take on holiday with me this year!


  26. Hello from Italy! The outfit looks great however I rather suggest that you take your coat and wood sweater with you since at present spring is nowhere to be found in Norther Italy! Ciao!

  27. I love this outfit! Love the pop of colour, and the sandals and dress are both gorgeous! x

  28. The Cinque Terre. The air in this little town actually smells like flowers. Thank you for bringing back some good memories to brighten my day.

  29. I could so do a trip there right about now ; So gorgeous!

  30. I assume it’s not March in your daydreams, because Italy is in the Northern hemisphere too.

  31. ss says...

    Is the cinque terra? My husband hiked through there when we were 22. fun memories

  32. jm says...

    Just the post to transport me from my snowy surroundings! Pretty outfit!

  33. Love this dress! Would be cute for my honeymoon! Thanks for sharing! -Liz

  34. Actually…it’s raining in Riomaggiore now.
    So, you certainly need an umbrella ;)

    (I love Orla Kiely)

  35. mmm that sounds perfect! The outfit as well… :) If i wasn’t 6 months pregnant I would totally go!

  36. Love Italy! and that is pretty much exactly how I’d pack! If I could go anywhere right now I’d be in Capri, but in 22 days I’m headed to Cuba, so I can’t really complain!

  37. I always love the outfits that Rachel puts together! She has the best taste in clothes!

  38. AHHHH Cinque Terre! Craving summer and a vacay!

  39. You would freeze this time of year! It is winter in Italy! But that’s a nice ensemble for a summer destination.

  40. Joanna you have to stop posting these awesome travel ideas – it’s making me sad to be stuck in the office!

    Though I really shouldn’t complain – it’s 32 degrees today and next week will be up to 36 degrees (celsius). Summer is never ending in Melbourne this year!

  41. I’m going to Napa Valley this weekend. I am Week 11 with my first baby tho – any advice? No wine I guess? and my clothes are getting tight!

  42. That dress is a dream!

  43. I’d jump right to spring weather and Southern Italy beaches…Sorrento perhaps?

  44. If I could go anywhere right this minute I would go to Vermont. Which would take me from sunny Florida perpetual summer right into that winter everyone else is so tired of. :)

  45. I really want to go to Eden Rock in St Barts or the Viceroy in Anguilla. I’m dying here in Western NY where winter is never going to end!!

  46. Oh you’ve got my wanderlust acting up again! This is beautiful and the perfect wardrobe selection! If only it would all just magically appear in my suitcase!

  47. It’s winter in Italy! You would be cold in that darling ensemble! Egypt would be perfect this time of year!

  48. Ugh, everything about this is gold. I love daydreamy blog posts, especially at the end of the week when I’m daydreaming about the weekend anyway. Thanks for the mental vacation!

  49. Love the outfit but I’m not sure it goes with the description – would you really wear wedges/heels if you’re going on a hike?
    Now I want fried fish and a nice glass of white! :)

  50. Pleased to see Madewell’s Stucco Stripe Dress is back in stock. I remember seeing Caroline and you wear it separately on the blog. And who wouldn’t want to take off for the Cinque Terre right about now?

  51. Wow, I loved this post!! What a wonderful break from this snowy Canadian winter and sitting here in the library writing an essay :) Sigh……

  52. Is this the cinque terre in your photo? I went there last summer and this photo just brought back so many great memories ♥

  53. I need a getaway to Cinque Terre with my husband and a few huge plates of pasta. I’ll skip the hike and take a boat ride! We’re due in July too, congrats on baby #2 and I love A Cup of Jo.

  54. oh my GOD joanna, this TOTALLY got me!!! what a dream!!!! it was almost torture to read, as i will spend my march break marking papers!!

  55. This is just what I needed right now! It’s snowing/raining in Boston again and I am over it!

  56. So exciting. My husband and I are celebrating our one year anniversary in Santa Barbara, California (although Italy sounds super) and this is perfect for getting my packing ideas in order. Thanks!

  57. That dress is perfect. I agree, winter is getting really old! I think I’d go to Northern Italy. I love the way you described it.

    • It’s funny that she mentioned winter getting old because it decided not to pay Dallas a visit this year at all.

  58. Ah! We’re going to Italy on our honeymoon in late May! Thanks for this :)

  59. oh my god joanna! this might be my favorite packing list/collage of yours ever! i’m in love with everything. oh how i wish i could get on a plane right now and go visit italy (i’m half italian, and i’ve never been to the amalfi coast, what a shame) instead of taking my philosophy, my chemistry and my math exams tomorrow and monday….

  60. So funny you posted this because in May my husband and I ARE going to Italy(& Croatia)! We are over the moon excited and this would be a perfect start to my packing!

    • Twinsies! We’re going to Italy in May for our honeymoon! :)

  61. oh yes, jamie, i’ve seen it! good to know. xoxo

    • Joanna you should do a fashion post centered around maternity style :) I’m 17 weeks, just a few behind you.

    • Thank you! :)

  62. I have a similar dress from madewell and LOVE it!! It’s the blue polka dot cotton voile version of the same style. So flattering!

    • And if I could go anywhere today? Greece! Specifically Santorini.

  63. ooooh palm springs would be perfect right about now.

  64. I have started my blog but I can’t find a way to advertise it! Do you have any tips?

  65. That’s all I have been dreaming lately–the Amalfi coast

  66. Palm Springs! Right this minute if I had £2000 spare :)