Cradled in emerald hills just west of Lisbon, Sintra is Portugal’s celebrated “fairytale” town—an elite retreat for royals and poets, now a UNESCO World Heritage landscape. Picture candy-colored palaces perched over forests, Moorish ramparts snaking along ridgelines, and gardens laced with grottoes and secret tunnels.

Romantics have long swooned here, from Lord Byron to 19th‑century monarchs who built whimsical mansions across the Serra de Sintra. Today, the highlights—Pena Palace, the Moorish Castle, Quinta da Regaleira, and Monserrate—reward early starts, good walking shoes, and a taste for wonder.

Practical note: Sintra’s microclimate means quick shifts from sun to mist—pack a light layer and non-slip shoes. Timed tickets are standard at major sights; public buses (434/435) and taxis help skip steep climbs. Sweet fix: try travesseiros (almond pillows) and queijadas (cheese tarts) between palace calls.

Sintra

Sintra blends legend and landscape: Romanticism in vivid paint, medieval walls with ocean views, and forest trails threading between palaces. It’s compact yet vertical; let buses or tuk-tuks handle climbs, and save your legs for gardens and towers.

• Top sights: Pena Palace and Park, Moorish Castle, Quinta da Regaleira (Initiation Well), National Palace of Sintra, Monserrate Palace and Gardens, Seteais viewpoint.
• Coastal add-ons: Cabo da Roca (continental Europe’s westernmost point), Azenhas do Mar (clifftop village), Adraga Beach.
• Tastes to try: Travesseiros and queijadas at Casa Piriquita, Colares DOC wines, seafood stews, and petiscos (Portuguese small plates).

Where to stay (center and hilltop gems):

• Tivoli Palácio de Seteais (regal oasis with views across the valley). Book: Tivoli Palácio de Seteais
• Sintra Boutique Hotel (polished comfort right in town; great for walkers). Book: Sintra Boutique Hotel
• Moon Hill Hostel (friendly, central, excellent for value-minded travelers). Book: Moon Hill Hostel

Browse more stays: VRBO in Sintra | Hotels.com: Sintra

Getting to Sintra: Fly into Lisbon (LIS), then take the metro to Rossio Station and a suburban train to Sintra (≈40 min, ~€2.5 one way; total LIS→Sintra via metro+train ~€4–6; trains run ~every 20 min). Compare flights and trains here: Omio flights to/from Europe and Omio trains in Portugal. Taxis/Uber from LIS to Sintra take ~35–45 min (~€30–45 traffic‑dependent).

Day 1: Arrival, Old Town Meander, and the Secrets of Regaleira

Morning: Arrive at Lisbon (LIS) and head to Sintra. Drop bags at your hotel, then ease into the day with a late breakfast at Café Saudade—big-window charm, homemade breads, and tostas with mountain honey. If time allows, stroll past the National Palace of Sintra (twin conical chimneys) to get your bearings in the cobbled historic center.

Afternoon: Dive into myth and masonry on a guided visit to Quinta da Regaleira, where underground passages link lakes, towers, and the famous Initiation Well. It’s a short uphill walk or quick tuk-tuk from town; expect 1.5–2 hours inside the estate. For a seamless experience with tickets included, consider this option: Sintra: Quinta da Regaleira Guided Tour with Ticket.

Sweet interlude: swing by Casa Piriquita (since 1862) for warm travesseiros dusted with sugar or classic queijadas. Coffee lovers can duck into Nicolau Sintra for a flat white if you crave something lighter.

Evening: Golden hour at the Seteais Arch frames Pena’s silhouette from below—an easy, romantic viewpoint. For dinner, book Incomum by Luís Santos (creative Portuguese—think octopus with sweet potato and citrus), or try Romaria de Baco for petiscos and a deep Portuguese wine list. Post‑meal, sip a local Colares red at Tulhas, tucked in a stone‑arched lane, or sample craft pours at Villa Craft Beer & Bread near the station.

Day 2: Pena Palace, Moorish Walls, Monserrate Gardens, and Departure

Morning: Book the earliest timed entry to Pena Palace to beat queues. Walk the forested paths of Parque da Pena for fern‑filled valleys and lake viewpoints, then tour the palace’s Romantic interiors and terraces. From here, it’s a 15‑minute downhill walk to the Moorish Castle—climb the crenelated ramparts for sweeping views to the Atlantic. Prefer a guided, ticket‑included experience covering the hills efficiently? Try Sintra Private Hills Tour: Pena Palace & Moorish Castle Tickets.

Lunch: Back in town, graze on petiscos at Tascantiga (codfish cakes, Serra cheese, garlic prawns), or opt for Apeadeiro by the station for hearty grilled fish and daily specials. If you kept it light, add a pastel at Piriquita II—usually a shorter line.

Afternoon: Wander the exotic gardens of Monserrate Palace, an Arabesque‑Gothic jewel with lawns and sub‑tropical plantings; allow ~75–90 minutes. If you’d rather ride than walk, a tuk‑tuk circuit is fun, nimble on steep lanes, and scenic between palaces—bookable here: Private Tuk Tuk Tour around Sintra.

Wine lovers with extra time can detour to the nearby Colares region for a tasting of sandy‑soil Ramisco reds (book ahead), or, on clear days, taxi 25 minutes to Cabo da Roca for a cliff‑edge photo before returning for your train.

Evening: Departure day: aim for the Sintra→Rossio train (~40 min), then the metro to LIS (~35–40 min). If staying a final night, dine at A Raposa (seasonal Portuguese—game, mushrooms, inventive desserts) or head to the coast for sunset seafood at Azenhas do Mar Restaurante (reservations recommended; taxi ~25 min).

How to move around Sintra: Use the 434 bus for Pena/Moorish Castle and the 435 for Regaleira/Monserrate. Day loops cost roughly the price of two single rides; lines can be longest 10:00–14:00, so start early. Taxis and rideshares shorten queues and save time on tight itineraries. Palace entries typically range ~€10–€20; buy timed tickets in advance to avoid sold‑out slots.

Alternative guided day (if you prefer a driver-guide and coast loop): This comprehensive private option covers Sintra highlights plus Cabo da Roca and Cascais with local insight: Sintra & Cascais: Private Tour Pena Park & Regaleira Included.

Dining notes and local favorites: Book dinners for 20:00–21:00 to keep days flexible. For casual bites, try Cantinho Gourmet (soups, sandwiches, quiches), and for an elegant splurge, the garden‑side tables at Incomum. Coffee and pastry breaks are part of the Sintra rhythm—use them to stagger palace entries and dodge peak lines.

Getting back to Lisbon is easy: frequent evening trains return to Rossio. If you’re catching a flight, plan ~90 minutes station‑to‑gate with luggage and security, a bit more at peak times or during summer.

Book your transport and stays: Compare Europe flights and rail on Omio (flights) and Omio (trains). Find the right base via Hotels.com: Sintra or VRBO in Sintra, and consider a palace‑view splurge at Tivoli Palácio de Seteais or central comfort at Sintra Boutique Hotel.

In two days, you’ll trace royal footsteps from Pena’s terraces to Regaleira’s tunnels, taste the Serra in flaky pastries, and watch the Atlantic roar from granite cliffs. Sintra rewards curiosity—wander a garden path, peek through an arch, and let the mountain’s mist reveal the next scene.