Goodbye, America—Hello, Italy: Here’s What I’m Purchasing for My 14-Day Journey to Rome, Ponza, and Milan.

      In 10 days, I'll be in Rome, likely enjoying a Campari and exploring a few shops during my two-week journey through Italy. We'll begin in the capital, then head to Ponza for some days of complete relaxation. Once I've achieved the ultimate chill—my skin perfectly tanned and my hair crunchy from the sea—I’ll move on to Monza for the Italian Grand Prix. Finally, I’ll have a day in Milan to indulge in good food, admire beautiful sights, and benefit from VAT tax advantages. It’s quite a lot to prepare for (especially with just a carry-on), so I need the next week and a half to plan my outfits. This also means some pre-trip shopping is necessary. Fortunately, one of my favorite parts of traveling is buying clothes to wear while I’m away. Below is my wish list for my Italian summer vacation (2025 edition), in case anyone reading this is planning an end-of-summer getaway and could use some inspiration. I’ve included walking shoes that can transition to dinner, versatile shorts suitable for both the beach and dining, and my selection for the chicest bikini of summer 2025. You'll find dresses, accessories, eyewear, and more.

      Banana Republic

      Cotton-Silk Crew-Neck Sweater

      I plan to wear this on the plane with my favorite Tibi track pants.

      Reformation

      Fern Satin Short

      While traveling with a carry-on, I need versatile items for various occasions. These shorts can easily transition from the beach to dinner.

      I had these in brown on my last trip to Italy and wore them daily, walking thousands of steps. After they got soaked in one of NYC's storms and I had to discard them, this trip gives me the perfect opportunity to buy a second pair.

      These sunglasses look so high-end for just $13.

      Alfie

      Open Back Cotton Poplin Top

      You’ll have to see the back of this top; it’s such a standout piece.

      Totore Vintage Studio

      Necklace With Gemstone and Tassel

      You don’t need to spend a fortune to indulge in this beautiful jewelry trend—Etsy has plenty of options.

      MANGO

      Balloon-Style Pants With Elasticated Waist

      I ordered these genie pants the moment I found them.

      Havaianas

      Slim Square Flip Flops

      The square toe gives these a more sophisticated appearance than typical flip-flops. They’re super comfy, making them ideal for the beach, lunch outings, and shopping.

      Chan Luu

      Caprice Sterling Silver Crystal Toe Ring

      A great toe ring to elevate my flip-flop outfits.

      This sheer lace dress is perfect for an Italian vacation.

      Camila

      French Twist Stick Hair Fork

      Perfect for styling my sun- and sea-drenched hair.

      gucci

      GG Terrycloth Bikini

      I honestly believe this is the most stylish bikini I’ve ever seen.

      j.crew Collection

      Wrap Skirt in Silk Organza

      This sheer midi skirt is incredibly versatile. Pair it with a tank top and some simple accessories for a fantastic outfit.

      Elaree

      Supple Bucket in White Wood

      This beaded bag is currently trending on fashion Instagram.

      This sarong will be so fun to style during my trip.

      Helsa

      Mini Dress With Lace in Tech Poplin

      Any dress that requires no effort deserves a spot in my suitcase. This is one of those dresses.

      ZHOUMEIWENSP

      French Large Hair Claw Clip

      I’m not one to do my hair every day while on vacation, so I can't leave without a few hair clips.

      H-O-R-S-E

      The Short Short

      If you’re going to buy one pair of athletic shorts this season, make it these.

      tumi

      International Carry-On

      I already own this, but I’d buy it again if needed.

      Tropic of C

      Universo Bralette

      Trying to channel Kendall Jenner with this bikini she wore earlier this summer. Don’t forget to check out the matching Luna Bikini Bottom ($100).

      Polo Ralph Lauren

      Twill Classic Sport Cap

      Perfect for when I get too much sun.

      j.crew

      2025 Rollneck Sweater

      I always include at least one warm item in case it gets chilly on a summer trip. I love this roll-neck sweater since it’s cotton and still breathable.

      I actually have these already for my trip and am trying really hard not to wear them before I go. They’re incredibly flattering and elegant.

      Bottega Veneta

      Marella Thong in Light Butterscotch

      I can’t stop coming back to these stunning thong sandals with an Intrecciato footbed. Bottega’s shoes are the most comfortable, thanks to the rubber grips on the bottom.

      This cuff offers a fun alternative to the metal versions I see all over online.

      Madewell

      Oversized Button-Up Shirt in Poplin

      I just got this striped shirt from Madewell and have already