$106 • Madeira, Portugal
Not so long ago, the name Madeira was associated almost exclusively with the preferred tipple of dainty English matrons. The namesake Portuguese island, some 372 miles off the Atlantic coast of Morocco, however, draws a much younger and more adventurous crowd. They come for the subtropical isle’s bonanza of water-and-wind sports—Madeira is known as the "Hawaii of Europe"—as well as a rum-fueled party scene with nary a bottle of the traditional sweet wine in sight. The Hotel Estalagem da Ponta do Sol (35-129/197-0200; www.pontadosol.com) embodies the new attitude. This grand former farmhouse has been dramatically expanded with a deftly minimalist touch (smooth black slate floors, crisply geometric whitewashed walls, gauzy fabrics, and Modernist furniture) that’s in harmony with the hotel’s backdrop: an endless expanse of azure water and sky stretching to the horizon. The vertiginous cliffside perch over the village of Ponta do Sol (roughly, "Sunset Point") ensures that every inch of the property, from the infinity pool to the restaurant to the 54 guest rooms, has stunning vistas.
While There With an area of just 286 square miles, Madeira is easy to cover by car, which will let you sample the island’s varied delights, from the manicured gardens and urbane nightlife of Funchal, the capital, to the wild shore-breaks at surfers’ paradise Jardim do Mar, in the southwest. Don’t miss the 1,000-foot descent in a glass elevator to the secluded sand-and-pebble beach at Fajã dos Padres, in Quinta Grande. —Andrew Ferren
$177 • San Sebastián, Spain
Though a resort town for over a century—Spanish Queen María Cristina adopted it for her summer holidays in the 1890’s—San Sebastián is more often linked with haute gastronomy than with the picturesque and sparkling white beaches that are her birthright. That classic seaside charm is best experienced from the Hotel Niza (56 Calle Zubieta; 34-943/426-663; www.hotelniza.com), a 1911 Victorian-style hotel in the center of a broad boardwalk in the heart of La Concha Beach. Niza’s 40 rooms, reached by an appealingly démodé elevator, are all designed in clean (if a tad utilitarian) Provençal blues and yellows. At night, locals slip down to the hotel’s restaurants—the Italian La Pasta Gansa and Café Biarritz, a tapas (or pintxos, in Euskera) bar—for their excellent, inexpensive dishes, then head for the bars lining Calle Reyes Católicos. By day, they hit La Concha, surf at Zurriola, or simply loll the way María Cristina once did: on the lawns of her lovely Palacio Miramar above the sea, now open to picnickers.
While There San Sebastián’s restaurants are famed for their pintxos. In the heart of the Old Town—a warren of crooked streets—the bar Gandarias (23 Calle 31 de Agosto; 34/943-426-362; dinner for two $65) displays pintxos like jewels on counters. For simple presentations of fish, head to Aita Mari (21-23 Calle Puerto; 34/943-431-359; dinner for two $78), set at the edge of the old port. —Sarah Wildman