Panarea is the smallest of the rustic Aeolian Islands off Sicily and is a quiet enclave for worldly vacationers seeking an exclusive (you can only arrive by boat or helicopter) yet understated vibe. It may draw a fashionable crowd, but leave your heels at home. Opt for effortless pieces that can take you from an afternoon spritz to a late dinner overlooking the twinkling harbor.

ULLA JOHNSON Lenore Silk Chiffon Midi-Dress/a> / ALAÏA Laser-Cut Leather Slide Sandals / OLIVER PEOPLES Boudreau L.A. Sunglasses / FENDI Runaway Tote Bag / ANNI LU Baroque Pearl Shell Earrings

Georgia is a rich mix of cultures thanks to its location at the crossroads of the Silk Road. With its mash-up of Old World and contemporary architecture, the capital city Tbilisi has become a burgeoning tourist destination, not to mention fashion center. Dress comfortably for a day of sightseeing that can include a range of activities such as a dip in the Persian sulfur baths, gallery hopping, a vineyard visit, and a can’t-miss visit to the breathtaking Holy Trinity Cathedral of Tbilisi.

ACE & JIG Heights Geometric-Pattern Cotton Jumpsuit / VANS Women’s Style 36 Canvas Sneakers / WANDLER Anna Leather Belt Bag / BARNEYS NEW YORK Logo Baseball Cap / NARS Afterglow Lip Balm

The picturesque French region offers an array of landscapes, villages, and art history offerings. Arles is the perfect place to experience both rural tradition and Roman architecture. After a day of exploration, channel the painterly surroundings by slipping into a breezy floral number like this  from Zimmermann and wander the narrow laneways lined with craft stores, chic wine bars, and inspiring color palettes.

ZIMMERMANN Iris Floral Silk Romper / BARNEYS NEW YORK Leather Platform-Wedge Sandals / CVC STONES Timon Pendant Necklace / BALENCIAGA BA126 Sunglasses / HOUSE OF LAFAYETTE Wild Kate Raffia Hat