Destination: Montauk
The Look
Casual chic with easy, breezy gingham shirts and tortoiseshell accessories. Don't forget a cute (and eco-friendly) bike to get you where you need to go.

Tanning Towelettes, Kate Somerville, $48 for eight; Sephora.com
Swimsuit, $415; MaliaMills.com
Sunglasses, $78; CWonder.com
Shirt, Pip Squeak Chapeau, $215; WendyFoster.com
Bag, $245; MonseratDeLucca.com
Bike, $1,599; MosiBicycles.com

Photo: Richard Majchrzak/Studio D; Towelettes and Bike: Courtesy of companies

Photo: Richard Majchrzak/Studio D

Destination: Panama City, Panama
The Look
Laid-back neutrals get fashion-forward hits of neon and digital prints, fitting for this cosmopolitan Central American city.

Hat, San Diego Hat Company, $34; Zappos.com
Swimsuit, M Missoni, $295; 305-466-3939
Lounge Pants, Charlie by Matthew Zink, $158; CharlieByMZ.com
Bag, $329; ElliotMann.com
Sunblock Powder, $30; BrushOnBlock.com
Sandal, $70; BirkenstockUSA.com

Destination: Baja
The Look
Surf-inspired pieces—pullovers, slip-on sneakers—meet old-school textures like Turkish cotton and raffia. Bright accessories add modern pop.

Surfboard, CB2, $999; CB2.com
Watch, $50; Store.Swatch.com
Swimsuit, Tommy Hilfiger, $149; 212-223-1824
Pullover, $238; FrescoTowels.com
Bag, Mar y Sol, $115; ShopMarySol.com
Slip-On Sneaker, $58; BluKicks.com

Photo: Richard Majchrzak/Studio D; Watch and Surfboard: Courtesy of companies

Photo: Richard Majchrzak/Studio D

Destination: Palm Beach
The Look
Preppy pieces are oh-so-summery in sorbet shades and classic prints. Retro accessories pull everything together.

Bag, $215; Brahmin.com
Hat, $280; Kule.com
Swimsuit, $265; Miguelina.com
Sweater, Wildfox, $198; WildFoxCouture.com
Sunglasses, Fendi, $495; SolsticeSunglasses.com
Espadrille, $250; MaraAndMine.com

Photo: Richard Majchrzak/Studio D

Destination: Goa
The Look
Exotic and opulent, this style is all about intense colors and bejeweled accessories. Glam sunglasses add a Bollywood touch.

Sunglasses, $275; Lumete.com
Bracelets, $105 to $120 each; RosenaSammi.com Swimsuit, Gottex, $178; 800-225-7946
Cover-Up, $375; CalypsoStBarth.com
Sandal, $69; YellowBoxShoes.com
From the June 2014 issue of O, The Oprah Magazine