Spend your first day getting your bearings and soaking up the sights of Cascais. It’s a small town so you can quickly learn about its history and culture on a sightseeing tour with a guide who can explain Cascais’ transformation from fishing village to modern day seaside resort. Most tours visit historic landmarks such as the Cascais Palace (Palácio da Cidadela de Cascais) and citadel (Citadela de Caiscais), as well as the town’s lavish mansions. Soak up the scenery of the Portuguese Riviera with a walk along the promenade that connects Cascais to the nearby town of Estoril, which is known for its glitzy casino and as a former haunt of rich Lisboetas.

You’ll likely have worked up an appetite, so indulge in a meal and glass of wine with a view at one of the town’s many waterfront restaurants, and then head for Gelados Santini ice cream parlor for dessert.

Spend your second day on a food- and wine-tasting tour that introduces you to the delicate flavors of coastal Portugal. Typical tours visit the 18th-century Carcavelos Winery to explore its vineyards and cellars while learning about the production of its wines, from grape to glass. These tours typically include tastings of local wines and lunch, offering the chance to enjoy regional cuisine.

For more adventurous thrill-seekers, catch some waves with a surfing lesson on one of the best surfing beaches in the Lisbon area. Whether you are an experienced surfer or trying it for the first time, a guided tour can take you to surf spots at either Praia do Guincho or Praia do Carcavelos. Instructors typically determine which beach to surf depending on your experience level and the day’s surfing conditions.

Cascais’ location makes it easy to explore nearby attractions such as the city of Sintra, a UNESCO World Heritage Site, or the religiously significant town of Fátima. Learn about the history of Sintra on a guided full-day trip while admiring the city’s 19th-century Romantic architecture, including many castles and estates. These tours often also include a stop at Cabo da Roca, the westernmost point of Europe, and the seaside cliffs of Boca do Inferno.

Fátima is famed for the appearance of the Virgin Mary in 1917, and its Sanctuary of Our Lady of Fátima is an important place of Catholic pilgrimage. A full-day tour from Cascais allows you time to visit the Sanctuary and learn more about this significant moment in Fátima’s history. On the way back, some tours visit the fishing village of Nazaré, known for having the biggest surf waves in the world, and the medieval town of Óbidos.