In Funchal, take the cable car up to Monte but skip the touristy wicker toboggan ride down. Instead, wander the Monte Palace gardens, then walk the quiet trails down through the suburbs. You’ll get sea views, local life, and no one charging you €30 to sit in a basket.
Madeira and São Miguel: Guided island trip
Let the colors, scents, and slow rhythms of Portugal draw you in on a Madeira and São Miguel guided island adventures trip designed for curious, discerning travelers. Choose a tailor-made itinerary that blends locally led excursions, hidden viewpoints, and free mornings to linger over coffee or a coastal walk.
Book now to create authentic moments with private guides, handpicked accommodations, and experiences shaped to your tastes. Start telling your story on islands where gentle landscapes and warm hospitality turn trips to Portugal into personal discovery.
Madeira and São Miguel trip highlights
- Tailor-made island itineraries: Design your perfect pace with private guides who personalize every detail for authentic experiences.
- Guided levada and crater hikes: Explore lush levadas and volcanic crater trails with expert guides.
- Authentic local cuisine and culture: Savor regional dishes, wines, and island stories through curated meals and community visits.
- Diverse island landscapes: Witness dramatic coastlines, laurel forests, and crater lakes.
- Stress-free logistics and small groups: Enjoy door-to-door transfers, boutique stays, and thoughtful pacing.
| Day | Location | Activity | Overnight |
|---|---|---|---|
| 1 | Funchal (Madeira) | • Arrival in Funchal • Stroll through Funchal center • Relax at the hotel and enjoy panoramic sea vistas | Funchal |
| 2 | Madeira West Coast | • Swim in the volcanic pools of Porto Moniz • Visit Cabo Girão skywalk and viewpoints • Evening at leisure in Funchal | Funchal |
| 3 | Madeira East Coast | • Full-day exploration of Madeira’s east side • Evening at leisure | Funchal |
| 4 | Funchal | • Free day in Funchal for pool time, gardens or relaxed city wandering | Funchal |
| 5 | Funchal | • Free day to enjoy beaches, spas, cafés or optional mountain hikes | Funchal |
| 6 | São Miguel (Azores) | • Private transfer and flight to São Miguel • Half-day Sete Cidades guided tour | Ponta Delgada |
| 7 | Furnas (São Miguel) | • Full-day trip to Furnas • Taste local cozido or pastries | Ponta Delgada |
| 8 | São Miguel Coast | • Azores sailing day | Ponta Delgada |
| 9 | Ponta Delgada → Airport | • Departure | — |
Day01
Arrival in Madeira
Arrive at Funchal airport and meet your private driver for a smooth transfer to your hotel in Funchal. Begin your Madeira and São Miguel, guided island adventures trip with a warm welcome and personalized travel planning so your Portugal travel feels tailor-made.
If time allows, stroll through the vibrant center of Funchal to discover markets, gardens, and waterfront views, or relax and enjoy your hotel's amenities and panoramic sea vistas.
Day02
Madeira West side
Explore Madeira's dramatic west coast on this tailored day of the Madeira and São Miguel guided island adventures trip. Drive over Encumeada Pass for sweeping north and south views, visit São Vicente and the volcanic pools at Porto Moniz, where you can swim and enjoy lunch in Seixal.
Wondering about the best time to visit Portugal? This route shines year-round, but Madeira’s milder months make these coastal stops especially rewarding. Return to Funchal with stops at miradouros such as Cabo Girão, whose 580m glass skywalk balcony reveals unforgettable panoramas.
Day03
East Madeira discovery
Explore the east side of Madeira on this tailor-made day of your Portugal tour. Visit Ponta de São Lourenço, stroll the north coast at Porto da Cruz, and see a traditional sugarcane factory. In Santana, admire the iconic triangular thatched houses and enjoy local island life.
Take a short, easy Levada walk in Queimadas through the UNESCO Laurissilva forest, then return to Funchal via the lively Santo da Serra market, where you can taste the famous Poncha.
Tips from Luis
Portugal
Travel Expert
Day04
Free day in Funchal
Relax and customize your days in Funchal with authentic, tailor-made experiences. Explore the Old Town, bathe in the oceanic pools, or unwind at your hotel. Ride the cable car to Monte to visit the Tropical Garden and take the thrilling descent in a traditional wicker toboggan.
Visit Funchal Botanical Garden, sample fresh produce at the colorful local market, and join island tours for deeper local insight. If mainland coastal charm is calling next, consider linking this to a coastal Portugal trip for sunlit towns, seafood stops, and Atlantic views.
Day05
Free day in Funchal
A second leisurely day in Funchal gives you options: stroll the colorful farmers' market, ride the cable car to Monte, taste local Madeira wine, join a levada walk, or go whale watching from the harbor.
Spend the day relaxing or let our local guides curate personalized experiences that connect you to culture and landscape on this Madeira trip.
Day06
Sete Cidades lagoon
A private transfer delivers you to Madeira Airport for a short flight to São Miguel. In Ponta Delgada, you will be met and begin a half-day guided tour to the Sete Cidades lagoon.
Sete Cidades is the Azores' most iconic lagoon; hike ridge trails for sweeping viewpoints or enjoy a relaxed scenic drive to savor the panoramas. For a more active island itinerary with hiking, canyoning, and geothermal wonders, explore our full Azores adventure trip.
Day07
Furnas Valley and thermal springs
Drive east on São Miguel to the Furnas Valley, a hotspot of volcanic activity. Walk the Furnas Lagoon shore and visit the mystic Nossa Senhora da Vitória chapel for unforgettable views.
Enjoy authentic, tailor-made travel experiences at Terra Nostra Garden and the Poça da Dona Beija thermal pools. Watch fumaroles, soak in hot waters, and savor the famous cozido das Furnas cooked in geothermal heat. Perfect for travelers seeking local culture and nature.
Day08
Azores sailing
Spend a full day on a sailboat exploring São Miguel's coast. Glide past the volcanic Vila Franca do Campo islet, swim in crystal clear Azorean waters, and soak up ocean views crafted into your tailor-made Portugal trip.
Onboard, enjoy a selection of local products while hoping to spot dolphins and other cetaceans. This authentic experience highlights why the Azores rank among the best places in the world for whale and dolphin watching.
Day09
Departure from Ponta Delgada
Your Portugal tour to Madeira concludes in Ponta Delgada after our Madeira and São Miguel guided island adventures trip. Enjoy a final morning sampling local pastries, strolling historic streets, and capturing last island views. We will pick you up at your hotel and transfer you to Ponta Delgada airport.
Safe travels, and thank you for choosing our tailor-made Portugal trip. Ask us about extensions or private experiences to keep exploring.
PortugalTravel Expert
Travel ExpertStarting from:
3240 USD
per Adult
