NEW YORK'S HUDSON VALLEY REGION: This once-sleepy string of small towns is getting some major attention, with world-class galleries and gourmet restaurants joining landmark mansions and mom-and-pop storefronts. Rub elbows with farmers and art-world celebrities at the local tavern.

BOSTON / SOUTHERN MAINE: Think classic seaside charm: lighthouses, harbors, and the spray of the surf meet posh villages and pine forests. Spend the morning on a sandy beach, have lunch at a lobster shack, then spend the afternoon picking blueberries before dinner at a country inn.

WASHINGTON, DC / VIRGINIA WINE COUNTRY: The well-heeled crowd loves this region of rolling hills and country lanes, where accommodations range from an 18th-century manor to an inn with one of the best restaurants in the country. Serious wineries and boutique farms dot the landscape.

PHOENIX / TUCSON: The giant saguaro cactus is the star of the Sonoran Desert, with sacred tribal lands and Spanish missions as the backdrop. Also on hand: snow-covered mountains, a lively culinary scene, and horseback rides into the sunset.

SANTÉ FE / TAOS / SANGRE DE CRISTO MOUNTAINS: Lose the crowds and head to this sprawling stretch of desert, packed with quirky charm and no shortage of superlatives—from the oldest continually inhabited Indian pueblo to a town entirely dedicated to pies.

LAS VEGAS ZION NATIONAL PARK: Welcome to the real American Southwest, where the sky is vast, the cowboy hats big, and the landscape is truly breathtaking. Wade upriver through a slot canyon, discover an authentic ghost town, or get pampered at an adventure-focused spa.

LOS ANGELES / PALM SPRINGS / PALM DESERT: Laze by a saltwater pool, hop in the car for some serious vintage shopping, gape at the icons of Mid-century Modern architecture—and go on a quest for the ultimate date shake. Find out why this part of Southern California is the embodiment of retro chic.

SAN FRANCISCO / NAPA WINE COUNTRY: This is California Wine Country for those in the know—picture-perfect farmstands and family-run tasting rooms with some of the best vintages around. Meander through Sonoma's most sophisticated small town to discover a rural paradise.

SEATTLE / OLYMPIC PENINSULA LOOP: Awe-inspiring rain forest, windswept beaches, wild waterfalls: This trip gets you up close and personal with nature. Round out your journey with a stay at a historic lodge, a feast of Dungeness crab, or a day at a pick-your-own lavender farm.