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;
Swimsuit, $415;
Sunglasses, $78;
Shirt, Pip Squeak Chapeau, $215;
Bag, $245;
Bike, $1,599;

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;
Swimsuit, M Missoni, $295; 305-466-3939
Lounge Pants, Charlie by Matthew Zink, $158;
Bag, $329;
Sunblock Powder, $30;
Sandal, $70;

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;
Watch, $50;
Swimsuit, Tommy Hilfiger, $149; 212-223-1824
Pullover, $238;
Bag, Mar y Sol, $115;
Slip-On Sneaker, $58;

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;
Hat, $280;
Swimsuit, $265;
Sweater, Wildfox, $198;
Sunglasses, Fendi, $495;
Espadrille, $250;

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;
Bracelets, $105 to $120 each; Swimsuit, Gottex, $178; 800-225-7946
Cover-Up, $375;
Sandal, $69;