Seven-Day Lisbon and Madeira Itinerary

Morning

Start early at Castelo de São Jorge, ideally arriving around 9:00 when it opens, before the Alfama lanes become busy and the summer heat builds. Allow about two hours for the ramparts, gardens, archaeological areas, and views across the red roofs toward the Tagus. Tickets are roughly €15 per adult; the uphill walk from Baixa takes 20–30 minutes, while Tram 28 or a taxi can get you closer, though vehicles cannot reach the castle entrance itself. Wear shoes with grip—the cobblestones are polished and slippery.

Walk downhill through Alfama to Sé de Lisboa, about 10 minutes away. The cathedral usually opens from mid-morning, though hours can vary with religious services; allow 45 minutes to see the Romanesque interior, cloister, and treasury if open. Continue a few minutes to Miradouro de Santa Luzia, where the tiled panels, bougainvillea, and broad Tagus views make a pleasant early-afternoon pause. Grab a cold drink nearby, but don’t linger too long over lunch here—the best food stop is next.

Lunch and Afternoon

From Santa Luzia, take a taxi or walk downhill toward Cais do Sodré—roughly 25 minutes on foot, or 10 minutes by car depending on traffic—and settle in at Time Out Market Lisboa. It is busiest between noon and 2:00 p.m., so arrive slightly early or expect to circle for a table. Allow 1½ hours and budget about €15–30 per person; try a few small plates rather than committing to one meal, and remember that individual stalls set their own hours. After lunch, walk east along the river for about 15 minutes to Praça do Comércio, passing the waterfront promenade and the Cais das Colunas. End beneath the square’s yellow arcades, with time to admire the monumental Arco da Rua Augusta and watch the light change over the Tagus.

Morning

Take tram 15E or the frequent Cascais-bound train from Cais do Sodré to Belém; allow about 25–35 minutes, and arrive around 9:30–10:00 to beat the tour groups. Begin at Mosteiro dos Jerónimos, one of Lisbon’s great Manueline masterpieces. The church is usually free to enter, while the cloisters require a ticket of roughly €12; check the official schedule because it is commonly closed on Mondays, though your Wednesday visit should be straightforward. Give yourself about 90 minutes, and enter the cloisters first if there is a queue. Afterwards, walk a few minutes to Pastéis de Belém for the still-warm custard tarts—expect €5–12 per person, depending on whether you sit down for coffee and several pastries. The bakery is large, but the takeaway line is generally quicker than the table-service queue.

Afternoon Exploring

Continue west along the river promenade to Padrão dos Descobrimentos, about 15 minutes on foot. The monument’s viewing platform costs roughly €5–6 and offers a fine look back toward the monastery and across the Tagus; allow 45 minutes, including the riverside walk. From there, follow the waterfront path for another 10–15 minutes to Torre de Belém. The tower’s interior access can be restricted by timed entry and narrow stairways, so check availability on the day; even if you only admire it from outside, the riverside setting is one of Lisbon’s best photo stops. In June, bring water and sun protection—there is little shade along this stretch. Later, take tram 15E or a short rideshare to LX Factory in Alcântara, where you can spend a relaxed couple of hours browsing design shops, bookstores, murals, and the industrial courtyards; most shops operate roughly from late morning into the evening, while restaurants stay open later.

Evening

Finish with dinner at O Frade, a small, popular restaurant known for contemporary Alentejo cooking. It is a short taxi or rideshare from LX Factory, or you can return toward Belém by tram 15E and walk from the Belém stop. Reserve ahead, especially for a Wednesday evening, and budget about €30–50 per person before drinks. The menu changes, but expect carefully prepared regional dishes, good bread, and generous flavors rather than formal fine dining; an early seating around 19:00 leaves you time for a quiet riverside stroll afterwards.

Morning

Start at Museu Nacional do Azulejo in Madre de Deus, ideally around 10:00. The former convent is one of Lisbon’s most rewarding museums, with tilework spanning medieval patterns to the enormous panoramic panels depicting the city before the 1755 earthquake. Allow about 90 minutes; the museum is generally closed Mondays, and admission is roughly €8–€10. From central Lisbon, take bus 794 or a short taxi/Bolt ride—walking from the center is possible but not especially pleasant along the main roads.

Continue by taxi/Bolt or bus toward Feira da Ladra in São Vicente, which is held on Tuesdays and Saturdays, typically from morning until late afternoon. Browse slowly through the jumble of old books, ceramics, postcards, furniture, and vintage curiosities, keeping valuables secure in the crowds. Spend around 90 minutes, but remember that prices are negotiable and many stalls accept cash only. Afterward, walk uphill into Graça—about 15 minutes on foot—or take a short ride if the heat is strong.

Afternoon and Evening

Have a relaxed café stop in Graça, choosing a small terrace around Rua da Graça or Largo da Graça rather than rushing into a formal lunch. The neighborhood is best enjoyed as a wander: look for tiled façades, small groceries, and quiet side streets branching away from the main tram route. Continue to Miradouro da Senhora do Monte for the panoramic view over the castle, Baixa, and the Tagus. It is a steep final walk, but the viewpoint is usually calmer than Lisbon’s better-known overlooks; arrive mid-afternoon for softer light and bring water, especially in June.

In the evening, head to A Cevicheria in Príncipe Real for seafood and ceviche beneath its distinctive octopus sculpture. It is popular and does not usually take reservations, so arrive before 19:00 or expect a wait; service often starts around 12:00 and continues into the evening, but confirm hours before going. Plan on approximately €30–€50 per person without extensive drinks. From Graça, a taxi/Bolt is the simplest option, while public transport requires a downhill connection and is slower. After dinner, stroll through Príncipe Real and Rua Dom Pedro V rather than adding another scheduled sight.

Arrival and Afternoon

After landing at Cristiano Ronaldo Madeira International Airport, take your pre-booked hotel transfer or taxi into Funchal; allow about 25–35 minutes, depending on traffic. Leave luggage at your hotel and have a quick snack before heading to Mercado dos Lavradores, where the flower sellers, tropical fruit, spices, and fish market make an easy first introduction to Madeira. It is generally open Monday–Thursday from around 8:00 to 19:00, Friday until later, and Saturday until mid-afternoon; Sunday is usually closed. Browse for about an hour, but treat the famous cut fruit displays as a visual experience rather than a bargain—prices can be surprisingly high. A taxi from the hotel is easiest with luggage, while the market is walkable from most central hotels.

Late Afternoon

From the market, walk roughly 10 minutes east into Zona Velha, following Rua de Santa Maria. The narrow street is lined with painted doors, small galleries, wine bars, and cafés, and it is particularly pleasant in the late afternoon when the stone is no longer at its hottest. Continue uphill toward Sé Catedral do Funchal, about a 10-minute walk away, for a quiet look at its dark cedar ceiling, Manueline details, and Gothic interior. Entry is usually free, though modest donations are welcome; check the posted schedule around Mass, when tourist access may pause. Keep the evening unhurried—Funchal’s old center is compact, and the best discoveries are often in the lanes just off the main street.

Evening

Have dinner at O Giro Restaurant, booking ahead if possible, especially for a Friday or Saturday night. It is a good first-night choice for Madeiran cooking, with dishes such as espetada, black scabbardfish, limpets, and local sides; allow roughly €25–45 per person before drinks. Order a glass of Madeira wine or a local poncha, but go easy on the latter—it is stronger and sweeter than it tastes. After dinner, walk back through Zona Velha toward the waterfront or take a short taxi ride to your hotel; save the more ambitious viewpoints and mountain excursions for the following days.

Morning

Take the Funchal Cable Car from the waterfront up to Monte, ideally around 9:00–9:30. The ride takes roughly 15 minutes and saves you a steep, winding drive; a return ticket is usually about €20–€25, though you only need the uphill journey because you will descend by basket sled. Start with Monte Palace Madeira, allowing about 2½ hours for the koi ponds, oriental gardens, waterfalls, sculptures, and shaded paths. It generally opens around 9:30 and the grounds are hilly, so wear proper shoes and bring water. From the garden entrance, walk a few minutes to Carreiros do Monte for the traditional wicker toboggan ride. Expect a queue, especially in June; the ride itself lasts only about 10 minutes and costs roughly €25–€35 for one or two passengers, with payment normally made in cash or card depending on the operator. It finishes lower down in Livramento, not back at the cable-car station, so arrange a taxi or Bolt rather than walking the entire way.

Afternoon and Evening

A taxi from the toboggan finish to Madeira Botanical Garden takes about 15–20 minutes and is much more practical than relying on several uphill bus connections. Spend around 1½ hours among the formal flower beds, palms, cacti, and vividly patterned planting, with wide views over Funchal; allow roughly €7–€8 for admission and check the current closing time before setting out. Continue by taxi or rental car toward Cabo Girão Skywalk, allowing 30–40 minutes depending on traffic. The glass platform is exposed and can be windy, but the sheer drop to the Atlantic is spectacular; admission is typically around €2, and 45 minutes is enough. From there, drive about 10 minutes down to Câmara de Lobos and linger around the fishing harbor, where the colorful boats and waterfront poncha bars make a good late-afternoon pause. For dinner, book Adega da Quinta in advance and order Madeiran staples such as espetada, bolo do caco, or black scabbardfish; dinner should run about €20–€35 per person. Arrange a taxi back to Funchal after the meal, since buses become less convenient at night and drink-driving rules are strictly enforced.

Early Morning

Leave Funchal around 6:00 AM with your rental car or pre-booked driver, allowing roughly 45–60 minutes up the winding mountain road to Pico do Arieiro. The summit sits above 1,800 metres, so even in June it can be cold, windy, or hidden in cloud—bring a warm layer, water, and sturdy shoes. Parking is limited and fills quickly, while sunrise excursions and tour vans arrive early; check the official trail status before leaving, since access beyond the viewpoint can change with weather or maintenance. Spend about an hour around the summit viewpoints, particularly the balcony overlooking the jagged central massif, but don’t force the hike if visibility is poor.

Morning Hike

From Pico do Arieiro, begin the accessible section of the PR1 Vereda do Areeiro only after confirming current conditions and closures. The route is spectacular but exposed, with steep steps, tunnels, sheer drops, and frequent changes in weather; it is not a casual stroll. A two- to four-hour out-and-back covering the open section is a sensible plan unless you have arranged a pickup and the full route to Pico Ruivo is officially open. There are no reliable cafés or water points on the trail, so carry food, at least 1.5 litres of water per person, sun protection, and a headlamp for the tunnels. If the trail is closed, enjoy the marked viewpoint paths near the summit instead and descend toward Santana—about 45 minutes by car—rather than attempting an unofficial detour.

Afternoon and Evening

Pause in Santana for an easy lunch and a look around the town’s traditional thatched houses; Casa das Queijadas is a convenient stop for local pastries and coffee, while Restaurante Cantinho da Serra offers straightforward Madeiran food if you want something more substantial. Continue to Parque Temático da Madeira, open generally from late morning into the afternoon, where reconstructed village scenes, gardens, crafts, and small exhibits give context to the island’s farming and folklore traditions. Allow around 90 minutes, and confirm the seasonal closing time before setting out, as hours can vary. Finish at Quinta do Furão, a short drive east of town, for dinner on the clifftop terrace overlooking the north coast; reserve ahead for a table with a view and budget about €30–€50 per person. It is worth arriving before sunset, both for the scenery and because the mountain roads become particularly dark and misty after dinner.

Morning

Leave Santana around 7:00–7:30 AM by rental car or pre-booked driver, taking the VE1 toward Funchal; allow 1¼–1½ hours, with extra time for traffic and returning the car. Go straight to Funchal Marina and arrive at least 30 minutes before your whale- and dolphin-watching boat departs. The cruise generally lasts about three hours, and sightings are never guaranteed, so choose an operator that keeps a respectful distance and follows crew guidance around the animals. June can be bright on land but breezy offshore—bring a light jacket, sunscreen, water, and motion-sickness medication if you are prone to seasickness. After returning, have an easy lunch around the marina or Avenida Sá Carneiro rather than rushing into a long meal.

Afternoon

Walk a few minutes along the waterfront to Museu CR7, open roughly 10:00–18:00 in summer, where a one-hour visit covers Cristiano Ronaldo’s trophies, shirts, photographs, and Madeira connections; admission is usually around €5–€6. From there, take a taxi or Bolt uphill to Palheiro Gardens in São Gonçalo—the steep climb and limited pedestrian route make driving much more sensible than walking. Allow about 20 minutes in light traffic and 1½ hours among the camellias, roses, subtropical planting, and old trees. Entry is typically around €16–€18, and the garden café is a pleasant place for coffee before heading back downhill.

Evening

Return to the old town and spend the late afternoon at Forte de São Tiago, the striking mustard-yellow fortress beside the sea in Zona Velha. It usually keeps afternoon hours until around 5:00–6:00 PM, with admission generally only a few euros; allow 45 minutes for the ramparts and art spaces. Afterwards, stroll the nearby painted-door lanes and waterfront before dinner at Armazém do Sal, a polished but welcoming choice in central Funchal. Reserve ahead, especially for June, and expect about €45–€70 per person for refined Madeiran and Portuguese cooking. Try local fish or limpets, and leave room for a Madeira-wine pairing if you would like a fitting final evening.