Itinerary
- Day 1
Lisbon
After you arrive in Lisbon, head to your accommodation and get settled in. Spend the rest of the day at your own pace checking out the city. Walk along the waterfront at Praça do Comércio and look for the Arco da Rua Augusta with its equestrian statue, both solid spots for photos. Later, make your way to Bairro Alto where you'll find street art covering the walls, rooftop bars, and plenty of tapas and drinks for a lively evening.
Optional Activities
- Metro, streetcar or transport to accommodation (payable locally)
- Waterfront promenade walk
- Praça do Comércio exploration
- Bairro Alto district visit with street art, bars and rooftops
Landmarks Praça do Comércio Arco da Rua Augusta Bairro Alto 
- Day 2
Lisbon
Ride the famous yellow Tram 28 through the old town first thing. Head west to the Palácio Nacional in Ajuda and walk through the opulent royal interior with all its gold, velvet, and chandeliers. Travel to Belém to try the local Pastéis de Nata pastries, then visit the Mosteiro dos Jerónimos and Torre de Belém. By evening, head to the water to catch the sunset and wrap up your Lisbon experience.
Optional Activities
- Tram 28 ride through old town
- Palácio Nacional de Ajuda visit
- Pastéis de Nata tasting at original location
- Mosteiro dos Jerónimos visit
- Torre de Belém visit
- Sunset viewing by the water
Landmarks Tram 28 Palácio Nacional de Ajuda Pastéis de Nata Mosteiro dos Jerónimos Torre de Belém 
- Day 3
Lisbon to Sintra
Start with breakfast at a café like Fauna & Flora. Take a train from Rossio station to Sintra and check out the fairytale castles, monasteries, and palaces in the green hills. Visit the Palácio Nacional de Sintra with its distinctive twin chimneys and explore the rooms with royal décor. Then hike up to Palácio da Pena, a colorful fantasy castle on the hilltop that offers great views of the surrounding landscape.
Optional Activities
- Breakfast at Fauna & Flora or similar café
- Train ticket purchase to Sintra from Rossio station
- Palácio Nacional de Sintra visit
- Hike to Palácio da Pena
- Palácio da Pena exploration
Landmarks Rossio Station Palácio Nacional de Sintra Palácio da Pena - Day 4
Porto Moniz
You'll land in Madeira and collect your rental car for the drive to Porto Moniz along the northern coast. After settling into your beachside hotel, head directly to the natural lava pools right at the property. These volcanic pools offer a unique swimming experience you won't find elsewhere, and they're literally steps from where you're staying.
Included Activities
- Swimming in natural lava pools at accommodation
Landmarks Porto Moniz 
- Day 5
Madeira
Put on your hiking boots and drive your rental car to the PR6 hiking trail starting point. Hike through wild laurel forests along ancient stone watercourses called levadas, passing rocky landscapes and gnarled trees. Stop at Risco waterfall where water drops over 100 meters down. End your hike at Levada das 25 Fontes where multiple small waterfalls cascade down a rock face into a turquoise lagoon.
Optional Activities
- PR6 hiking trail to 25 fountains
- Levada trail hiking through laurel forests
- Risco waterfall viewing
- Levada das 25 Fontes lagoon visit
Landmarks PR6 Hiking Trail Risco Waterfall Levada das 25 Fontes 
- Day 6
Madeira
Drive to the village of Achadas da Cruz for an optional cable car ride with a 98% gradient descent. Take the nearly vertical cable car down to Fajã da Quebrada Nova, walk through terraced cultivated areas by the Atlantic Ocean, then take the cable car back up. Head to your hotel to relax and swim in the lava pool while you take in the fresh Atlantic breeze.
Optional Activities
- Cable car ride with 98% gradient at Achadas da Cruz (payable locally)
- Fajã da Quebrada Nova exploration
- Lava pool swimming and relaxation
Landmarks Achadas da Cruz Fajã da Quebrada Nova - Day 7
Porto Moniz to Ponta do Sol
Drive south from Porto Moniz toward Ponta do Sol, making a stop at Cabo Girão to see one of the world's highest cliffs rising 580 meters above the ocean. From there, head to the fishing village of Câmara de Lobos for dinner and try local specialties at one of the waterfront restaurants. Later you'll continue to your accommodation in Ponta do Sol and catch the sunset over the Atlantic from your vantage point.
Optional Activities
- Skywalk viewpoint at Cabo Girão (payable locally)
- Local snacks and dining at Câmara de Lobos fishing village (payable locally)
Landmarks Cabo Girão Câmara de Lobos Ponta do Sol 
- Day 8
Madeira
Start early and drive to Ponta do Sol with your hiking boots ready. Begin the Levada do Moinho trail, hiking along a relaxed irrigation canal through green tunnels past wildflowers and massive trees. Spot a huge waterfall plunging into the depths with refreshing spray. Then continue to Cascata dos Anjos, a waterfall that falls directly over the road so you can drive right through it. Finish with drinks and sunset views at a local bar.
Optional Activities
- Levada do Moinho hiking trail
- Cascata dos Anjos waterfall viewing and drive-through
- Evening bar visit with sea view
Landmarks Levada do Moinho Cascata dos Anjos - Day 9
Ponta do Sol to Funchal
Take one last walk along the beach promenade and photograph the colorful house facades in the morning sun. Say goodbye to your coastal town and drive to Funchal. After checking in, explore the old town alleyways and visit Mercado dos Lavradores, a three-floor market with exotic delicacies, souvenirs, and flowers. Optionally take the cable car up to Monte Palace Tropical Garden, and consider riding traditional wicker sledges from Nossa Senhora church back to the old town.
Optional Activities
- Beach promenade walk and photography
- Mercado dos Lavradores market exploration
- Monte Palace Tropical Garden visit via cable car (payable on site)
- Traditional wicker sledge ride from Nossa Senhora church (payable locally)
Landmarks Mercado dos Lavradores Monte Palace Tropical Garden Nossa Senhora Church - Day 10
Funchal
Join a catamaran adventure out to sea where you'll likely spot whales, dolphins, turtles, and seabirds. Watch from the boat's net as marine life surfaces around you, looking for whales' backs and jumping dolphins. See the steep cliffs of Cabo Girão from the sea to get their full effect. Take a refreshing dip in the Atlantic Ocean before heading back to Funchal with plenty of memories from the day.
Included Activities
- Catamaran boat tour with dolphin and whale watching
Landmarks Cabo Girão - Day 11
Funchal
Start your day walking along Funchal's harbor promenade, checking out the local food stalls and browsing the shops. Stop by Loja do Chá tea house for a break, then tour the 16th-century Fortaleza de São Tiago where you can learn about Funchal's maritime history and take in the coastal views. By evening, head to Praia Formosa, the black sand beach, and watch the sun dip below the horizon.
Included Activities
- Harbor promenade stroll in Funchal
- Visit to Fortaleza de São Tiago (16th-century fortress)
Optional Activities
- Local snacks at harbor stalls (payable locally)
- Tea at Loja do Chá tea house (payable locally)
- Drive to Cabo Girão for cliff views (payable locally)
Landmarks Funchal Harbor Loja do Chá Fortaleza de São Tiago Praia Formosa Cabo Girão - Day 12
Departure
Take one last look at the landscape as you drive to return your rental car. Say goodbye to Portugal and head to the airport for your flight home, carrying memories of Lisbon's charm, Sintra's fairytale castles, and Madeira's natural wonders with you.
