Morning

You’re on a Roll! Once you’ve explored Penha Longa’s exquisite grounds on foot, hop into a Jeep for a tour of the most interesting sites in the surrounding 545-acre Sintra-Cascais Natural Park.

Afternoon

A Towering Achievement. Enjoy the expansive views from the Royal Tower at the Castelo dos Mouros. The parapets and ramparts of this military fort stand as testament to the Muslim Andalusians who controlled the Iberian Peninsula from the eighth century until 1147.

National Treasures. The Palacio Nacional de Pena is a dizzying blend of architecture. One wing is a former monastery built in 1511; the other, added 350 years later, evokes German Romanticist castles. You’ll wander past artwork and artifacts and into chapels and halls. Or take a horseback ride through the gardens and orchards of Pena Park.

Evening

A Taste of Italy. Venture to the Mediterranean with dinner at Il Mercato. The laid-back resort restaurant highlights the most extraordinary dishes found throughout the 20 regions of Italy — never fussy, always fabulous.

Morning

Have a Fling. Try your hand at pétanque on the sports field at Penha Longa. Try to land your boule as close to the target as possible; unlike bocce, players usually toss their ball instead of rolling it, which allows for backspin, and the sport can be played on any appropriate surface — no official court required.

Afternoon

Surf and Turf. The solitary nature of Ursa Beach is why it’s considered among Portugal’s most beautiful — as long as you’re game for the hour long hike back up the cliff when it’s time to leave. Adraga Beach, farther up the Atlantic coast, is popular with surfers because of its crashing waves.

Evening

Wuthering Heights.  Watch the sun drop into the Atlantic from the lighthouse and massive wind-battered cliffs of Cabo da Roca, the westernmost point of continental Europe and, until the late 14th century, believed to be the edge of the world.

Morning

Par Excellence. The world-class golf courses at Penha Longa Resort are ranked among the top 30 in continental Europe and take players on a journey through challenging hills and past picturesque lakes, medieval walls and castle towers.

Afternoon

Scientific Self-Discovery. Test and track your wits and reflexes while discovering tenets of science and technology at the Sintra Live Science Centre. The museum’s interactive exhibits let visitors even measure their own emotions.

Media Blitz. NewsMuseum examines the past, present and future of journalism and media, from radio-fueled revolutions to virtual reality. Browse galleries of famous photos and test your knowledge by answering questions about everything from the Gutenberg press to TV tickers.

Evening

Soak Up Some Local Flavor. The cobblestone streets of Sintra’s town center wend past quaint shops and eateries well worth checking out. The fifth-generation Piriquita bakery, famous for its travesseiros and queijadas, has been in business for 160 years. For traditional Portuguese dinner entrées, duck into Tulhas Restaurante.

Morning

Continental Brehakfast. Power up with espresso, scones and traditional pastries from Saudade, a charming coffee shop that occupies a historic former cheesecake factory (and still sells queijadas today).

The Royal Treatment. Beat the tourist buses and get an early start at the National Palace of Sintra. The palace is the only one in Portugal that has survived virtually intact from its Middle Ages incarnation, so its Moorish features, including dazzling tilework, remain today.

Afternoon

It Will Be Epoch! The Sintra Natural History Museum takes visitors even further back in time — millions of years, to be exact. Thousands of fossils, minerals and other specimens reveal the evolution of life over the geological eras.

Evening

Utopian Ideals. Enjoy a sunset dinner at Villa Tamariz Utopia, the elegant yet laid-back Mediterranean restaurant in a renovated 19th-century villa that overlooks the Atlantic. The impressive menu includes a variety of seafood rice dishes as well as a selection of delicious Portuguese-style tapas and small dishes, divided into two categories: Sea and Land.

Morning

Garden Party. The paths through the elaborate hunting grounds at the Monserrate Palace wind through separate Japanese and Mexican gardens; more than a thousand rosebushes; and Portugal’s first lawn. The building itself is a stunning combination of Arabic, Gothic and Indian architectural styles. 

Afternoon

Robe Warriors Relax and recharge at Penha Longa Spa, which in 2017 was named the best luxury resort spa in Portugal. The 16,000-square-foot, Thai-inspired facility offers signature treatments for adults, featuring products by Spanish luxury brand Natura Bissé, as well as unique options for teens and tweens.

Evening

Freedom of Choice The options are plentiful at B Lounge, where the dinner menu includes more than 100 types of gourmet burgers. The accompanying bar, not to be outdone, offers more than 150 gins.

Morning

Peruse the Past. The Penha Longa Resort, site of what was once a getaway for Portuguese royalty, sits amid the eponymous “long rocks” of a 545-acre national park. Guests can explore the resort’s sights, including a 14th century monastery, with a trainer-led Historical Circuit tour. If the views don’t get your heart racing, the agreed-upon pace of your 60-minute walk will.

Midday

Heighten Your Senses. Relax and recharge at Penha Longa Spa, which in 2017 was named the best luxury resort spa in Portugal. The 16,000-square-foot, Thai-inspired facility offers signature treatments for adults, featuring products by Spanish luxury brand Natura Bissé, as well as unique options for teens and tweens.

Afternoon

Moor to See. Gaze out onto the town of Sintra, the vast plains beyond and even the Atlantic coastline from atop the battlements and walkways of Castelo dos Mouros. The stone-walled testament to the Moorish occupation of the Iberian Peninsula in the eighth century continues to reveal new information about its previous residents; archaeological digs have revealed artifacts dating to 5,000 B.C.

Evening

Sit at the Kitchen Table. Reserve the Chef’s Table Experience at Arola to discover the skills and techniques that go into preparing such an acclaimed menu of modern Portuguese cuisine. You’ll watch chefs create special courses that aim to surprise and delight their guests — including you, of course.

Morning

Fore Play. The world-class golf courses at Penha Longa Resort are ranked among the top 30 in continental Europe and take players on a journey through challenging hills and past picturesque lakes, medieval walls and castle towers.

Midday

Roll With It.  After your game, recover at Penha Longa Spa with a round of Quiro Golf Massage by Natura Bissé. During the hour long, head-to-toe treatment, therapists roll and knead golf balls across muscles to relieve stress, reduce inflammation, improve flexibility and restore energy.

Afternoon

Moor to See. For the most fascinating experience at Quinta da Regaleira, you’ll need to sink to new lows. Subterranean passageways connect the ornate five-story palace with a nearby chapel. Likewise, the path at the bottom of an eight-story deep “initiation well” leads to grottoes, caves and the elaborate 9-acre gardens. (Visitors can always traverse the property aboveground, too.)

Spartan Seclusion. The Convento dos Capuchos offers a stark study in contrasts from the previous stop’s splendor. The only comfort offered in the tiny cells of this convent, carved out of stone and the granite mountainside during the 16th century, was a cork lining, embodying the Franciscan principles of austerity its friars lived by. 

Evening

Coastal Cuisine. Watch the sun sink into the Atlantic as you dine at Villa Tamariz Utopia. The contemporary Mediterranean menu and laid-back coastal glamour of this renovated 19th century villa make it a top spot on the Portuguese Riviera.

Morning

Learn Some Moor. The history of the Palácio Nacional de Sintra begins more than a thousand years ago, when Moorish craftsmen constructed a fortress during the Muslim occupation of the region. Today its twin chimneys are the symbol of Sintra, and its walls are the world’s greatest showcase of azulejos Mudéjar (colored glazed tiles).

Afternoon

Go West. The solitary, unspoiled nature of Ursa Beach is why it’s considered among Portugal’s most beautiful — as long as you’re game for the hour long hike back up the cliff when it’s time to leave. If not, consider Cabo da Roca, the western most point of continental Europe. These massive wind-battered bluffs are home to a lighthouse and unfettered sunset views of the Atlantic.

Evening

Star-Quality Cuisine. Enjoy a true culinary experience at Lab by Sergi Arola, the Michelin Star restaurant that combines an intimate environment with inventive gastronomy. The dining room seats only 22 guests, who can choose from three tasting menus, à la carte options and an impressive 550-bottle wine selection.