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San Sebastián (La Gomera), Spain

The capital of La Gomera, San Sebastián is not much more than a small town but it sets the tone for what's to come. Here, the pace of life is blissfully slow: lunches at rustic restaurants become long, languid affairs; the sun works its magic on work-weary shoulders; and plans for energetic hikes through the mountainous landscape get shelved in favor of lazing on black-sand beaches. 

Funchal, Portugal

Funchal is a picturesque city on the island of Madeira, Portugal, known for its stunning natural beauty, botanic gardens, charming old town, and lively markets. The sub-tropical paradise was the favored retreat of Sir Winston Churchill - a blissful wonderland of rugged mountains, colorful flowers, and ornate architecture. Once ashore, enjoy browsing through local shops that showcase an array of intricate embroidery, vibrant tapestries, and detailed wickerwork. 

Agadir, Morocco 

Sun, sand, and sea is what Agadir is famous for, yet there's much more to discover in this beach city at the foot of the Atlas Mountains. A devastating earthquake in 1960 reset the townscape but remnants of Morocco's past can be found amid the ruins of the original Kasbah, the bustling maze of streets that is the souk, and the port where fishermen still bring in their catch each day, which you can try fresh from the grill. Take this all in from the Kasbah built in 1990 by Italian architect Coco Polizzi, which doubles as the place for fabulous views of the city and its coast. 

Portimão, Portugal

This southern Portuguese port is the gateway to many historic towns of the Algarve region. The city itself offers a rich heritage of historical monuments and the eternal natural beauty of the Ria de Alvor. Portimão is also known for its extraordinary cuisine, particularly charcoal-grilled sardines and hearty fish stew. To savor the city's spirit, there is nothing better than to sit in the shade of the trees in the gardens of Manuel Bívar, watch the fishing boats sail by, and walk through streets and squares that exude the ambience of an active, hard-working town.