Pena, Óbidos’s lanes and Nazaré’s winter coast.
Spend two nights in Sintra, one in Óbidos and one in Nazaré, starting and ending around Lisbon. The first afternoon belongs to Quinta da Regaleira; day two gives Pena Palace and its park room to breathe. On day three, return by train to Lisbon to collect a car, then head north through Ericeira to Óbidos. The airport pickup keeps the Sintra stay car-free and gives a clear return point at the end of the circuit. The final night in Nazaré leaves an afternoon and morning for Sítio and the Praia do Norte headland. October–March is the appropriate season when the main aim is a chance to watch big waves, although a fixed five-day trip cannot guarantee a major swell. There is plenty to see if the sea is quiet: the fort, fishing town, bookshops, palace rooms and gardens give the route its substance. Keep outdoor sightseeing within daylight and use the car for the northern towns.
Regaleira’s wooded estate uses grottoes, a spiral well and revivalist architecture to create a deliberately theatrical landscape. Pena is a royal Romantic palace on a separate hill. Giving them different days avoids treating two distinct places as one crowded uphill excursion.
Ericeira’s coastal breaks earned World Surfing Reserve status in 2011. After a shore-side stop, Óbidos changes the pace to whitewashed lanes, medieval walls and books. It joined UNESCO’s Creative Cities Network for Literature in 2015.
The clifftop Sítio quarter overlooks the main town beach, while Praia do Norte lies on the other side of the headland. The offshore canyon helps concentrate incoming swell there. The fort’s coastal setting makes that geography clear even when no giant wave is breaking.
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StartBooker answer
Stay two nights in Sintra, then one each in Óbidos and Nazaré. Visit Regaleira on the arrival afternoon and Pena the next day. Collect a car in Lisbon on day three, stop at Ericeira and continue to Óbidos. Spend day four and the final morning in Nazaré before returning the car in Lisbon. For big-wave viewing, choose October–March and check the swell forecast near the date; the town and fort remain worthwhile on calmer days.
Explore tours, attractions and local experiences in Sintra, Óbidos, Nazaré along this route through Portugal.
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The four nights are split 2–1–1. Choose walking bases in each town; the northern car days work best with parking arranged at the accommodation or just outside the historic centre.
3 stops · swipe
1
Regaleira’s well, Pena Palace and local pastries
Choose the historic centre for restaurants and the walk towards Regaleira, or the station area for easier arrival and the early train back to Lisbon. Neither puts you at Pena’s entrance: the hilltop visit needs its own bus or walking connection. Keep both Sintra nights in the same room.
Read the Sintra guide →
2
Medieval lanes, bookshops and ginjinha
Sleep within the walls for the quiet evening streets, leaving the car in an agreed space outside, or choose accommodation near the entrance with simpler luggage access. A single night gives you an afternoon and morning, enough to enjoy the town beyond a quick castle photograph.
3
Sítio’s viewpoints and the Praia do Norte headland
Stay near the main beach for the town’s restaurants and the lower funicular station. Sítio is better for the clifftop setting and headland access but requires a separate descent for a waterfront meal. Confirm parking with the property before arriving on a forecast big-wave day.
Arrive in Sintra by late morning or early afternoon on day one. The route ends at Lisbon Airport on day five and contains four hotel nights. A late first-day arrival needs the Regaleira visit moved into day two, with a shorter Pena park visit.
Take a CP Sintra-line train from Lisbon’s Rossio or Oriente station and leave your bags at the accommodation. Walk through the historic centre around the National Palace’s twin chimneys, then continue to Quinta da Regaleira for a reserved afternoon visit. The estate is close to the old town rather than on Pena’s hill. Its principal owner, Carvalho Monteiro, and architect Luigi Manini created a landscape of revivalist buildings, grottoes and symbolic garden features. Follow the paths to the Initiatic Well and its spiral galleries, allowing time for any queue rather than arriving at the last possible entry. In winter, choose an earlier afternoon slot so the outdoor part fits the available daylight. Return to the centre for a café stop: a travesseiro is a puff-pastry sweet with egg and almond filling, a local speciality associated with Piriquita on Rua das Padarias. Have dinner in town and keep the evening free of another monument booking.
Overnight: Sintra
Use the 434 bus from Sintra station or a marked walking route to reach Pena. The approach through the wooded hill is part of the day; a palace reservation does not include getting up from town. Choose the Essential Visit for the New Palace wing, terraces and park, or the Complete Visit if the royal Private Apartments are central to your interests. Inside and outside, look at the contrast between the palace’s coloured volumes, decorative tiles and surrounding trees: it is a major expression of nineteenth-century Romantic taste. After the interior visit, eat at a park café or carry a simple lunch and follow a manageable garden circuit. The Chalet of the Countess of Edla is included in the park but lies farther away; choose it as the afternoon’s walk rather than adding every viewpoint. If you prefer the Moorish Castle, shorten the park and buy that separate admission. Return to Sintra for the second night.
Overnight: Sintra
Leave Sintra early by train for Oriente and take the Metro to Lisbon Airport, where the main rental companies have terminal desks. Collect the pre-booked car and drive towards Ericeira for a short coastal stop and lunch. This is the trip’s longest transfer day once the train, pickup and two drives are included, so do not add a Sintra sight before departure. Ericeira was dedicated as a World Surfing Reserve in 2011 by Save The Waves; its reserve extends beyond the town beach. Enjoy the harbour and shore-side viewpoints without needing a surf lesson or a long detour along every break. Continue to Óbidos, leave the car outside the historic streets and enter through Porta da Vila. Walk along Rua Direita to the squares and bookshops, then explore a section of wall if it is dry and suitable for your group. Save the ginjinha, the local sour-cherry liqueur often served in a chocolate cup, for after the day’s driving.
Overnight: Óbidos
Use the morning for the lanes around Santa Maria and a bookshop visit before driving north on the A8 towards Nazaré. After dropping your bags, take the paid funicular from the town to Sítio. Begin at the Suberco viewpoint over the crescent-shaped main beach, then visit the sanctuary area before walking towards the Fort of São Miguel Arcanjo. Allow roughly half an hour each way between central Sítio and the fort as a walking-planning allowance, longer with stops. The north-facing outlook is towards Praia do Norte, where the canyon and incoming swell can produce exceptionally large waves. Watch from the designated high viewpoints and follow any access restrictions; do not go down onto the beach or beyond barriers to get nearer breaking waves. Finish with dinner in town: grilled fish, seafood or caldeirada connects the visit with Nazaré’s fishing heritage.
Overnight: Nazaré
Keep the morning for a second headland visit if a worthwhile swell is running and access is open. If conditions are calm, enjoy the main town’s seafront and narrow streets, or spend longer around Sítio’s sanctuary and fort exhibits. A quiet sea still lets you see the difference between the sheltered town beach and the exposed north side; it simply changes the day’s emphasis. Begin the return drive on the A8 in time for the rental handover and your onward journey. Allow around one and a half to two hours for the road leg as a planning window, plus separate refuelling, return inspection and airline check-in time. There is no overnight in Nazaré today. For an early flight, return to Lisbon the preceding evening or add an airport-area night; this five-day version assumes a later departure. Return the car to the airport location named in the rental agreement.
Base: Nazaré
Rail gets you into Sintra and back to Lisbon for the car. The two cards show the changes of overnight base; the final A8 drive returns from Nazaré to Lisbon Airport. Road windows are planning allowances, excluding sightseeing, traffic and rental formalities.
2 transfers
Sintra Óbidos
Take the train to Oriente, Metro to the airport and collect the car. Allow about 2–2½ hours of driving for Lisbon Airport–Ericeira–Óbidos, plus pickup and the coastal stop. An early Sintra departure preserves an Óbidos afternoon.
Óbidos Nazaré
Use the A8 north for this short transfer after the Óbidos morning. Park at the agreed accommodation or a signed public car park before exploring. The funicular connects the lower town with Sítio; the fort is a further walk.
For two adults sharing a room, allow €950–1,780 (≈ US$1,064–1,994) for four nights and five days in October–March. This covers Regaleira and Pena Essential admission, a three-day airport car rental, meals, road costs, local transport and Nazaré visits.
Booking tips
The three markers show the overnight bases: Sintra, Óbidos and Nazaré. Ericeira is a day-three stop after the Lisbon car pickup; it is not a fourth hotel base. The map does not display the complete road route.
Sintra
October–March is the usual big-wave season. A major swell depends on Atlantic storms and cannot be promised for your particular overnight. Check local forecasts and webcams shortly before the trip, then use both the day-four afternoon and day-five morning if conditions suit. If witnessing an exceptional swell is the whole purpose of travelling, choose more time in Nazaré or a flexible visit rather than relying on this fixed five-day circuit.
Sintra is straightforward by train, and both Óbidos and Nazaré have coach connections with Lisbon. The challenge is the intervening stops and moving luggage between towns. For an entirely public-transport holiday, use Lisbon-based day trips or allow more days and check the current interurban connections. This version deliberately uses a car after Sintra so Ericeira and the two northern overnight bases fit comfortably.
It covers the New Palace wing and the park, including the Edla chalet. The Complete Visit also includes the Private Apartments and costs more. Choose according to the rooms you want to see, rather than treating the products as interchangeable. Transport up from Sintra and the optional transfer inside the park are separate from the admission ticket.
The wall walk has steep, uneven sections and unprotected drops, so choose only a short section that suits the group and avoid it when wet. The town still works from street level: explore Rua Direita, the squares, church exteriors and bookshops. The castle houses a hotel, so the ordinary visit is not an unrestricted tour of every interior room. Winter daylight is a better time for the walls than the evening.
Keep the two Sintra days flexible enough to place the longer park walk in the better weather, subject to your booked entry slots. Use the actual opening and access notices from Parques de Sintra and Regaleira; if a site closes, follow its operator’s instructions. In ordinary rain, concentrate on the palace interior and town cafés, then shorten the garden circuit. Strong wind can make a woodland visit a different proposition from a rainy city walk.
A second Nazaré night makes six days and five nights overall and adds another chance to see a favourable swell, without guaranteeing one. A third Sintra night instead gives more space for Monserrate or the National Palace. In either case, add the extra room and meals, and extend the rental if you keep the car. A summer Berlengas visit belongs to a longer Peniche-based plan with its own sailing and reserve-access arrangements.
Reviewed by StartBooker
Last reviewed 2026-10-22
Updated
How this itinerary was researched and verified: Monument operators supply the 2026 ticket products, entry rules and winter opening details. UNESCO and Save The Waves establish the literature and surfing designations. National tourism and municipal pages support town history and access; ANA and CP support the rail-to-rental connection. Nazaré Waves supplies forecast-led winter planning. The funicular operator’s current page was unavailable; its dated published tariff establishes paid travel only, while this guide uses a planning allowance rather than claiming a current fare. Complete two-adult costs use approximate ECB conversions.
19 references reviewed
Some photos provided by Pexels.
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