2-Week Portugal Tour Packages
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Insider tips: Recommended 2-week Portugal itineraries
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MelissaPortugal travel expert at TourRadar
14 Day The Azores Itinerary, incl. Sao Miguel and Faial
The 14-day Azores adventure visits Sao Miguel, Sao Jorge, Pico and Faial islands. Hiking highlights include Sete Cidades crater (5km), Caldeira de Cima gorge (10km), and UNESCO vineyards (8.5km). Accommodations at centrally-located Neat Hotel Avedina and Azoris Faial Garden, rated 4.2/5.
- Days 1-4
Sao Miguel Island
Begin in Ponta Delgada and explore this historic harbor city. Head to the famous Sete Cidades twin lakes early in the morning before fog sets in. Stop by Europe's oldest tea plantation at Gorreana and try a traditional Cozido lunch cooked in volcanic fumeroles at Furnas. Take time to relax in Terra Nostra's thermal pools but remember to pack dark swimwear since the mineral water can leave stains.
- Days 5-7
Sao Jorge Island
Fly to the long island of Sao Jorge. The best part is walking down through Caldeira de Cima gorge to Faja dos Cubres. Pack good shoes with grip since the trail gets slippery. A visitor noted: "The hydrangea-lined paths and coastal views made this one of the best walks." On clear days you can hike along Pico da Esperanca ridge for some amazing views.
- Days 8-10
Pico Island
Take a ferry to Pico, where Portugal's highest peak stands tall. Walk through the UNESCO-listed vineyards with their unique volcanic stone walls. One traveler suggested: "Book the optional whale watching early in your stay - trips often get cancelled due to weather so you want flexibility to reschedule." Take the Misterios do Sul coastal trail to see interesting lava formations.
- Days 11-14
Faial Island
Finish your trip on beautiful Faial. Walk around the volcanic caldera rim if weather allows and visit the Capelinhos volcano center. Follow the trail through laurel forests down to Praia do Norte beach. Stay in Horta to watch boats come and go from the marina. The Azoris Faial Garden Hotel is a nice place to end your trip with its ocean views and swimming pools.
14 Day Portugal Itinerary, incl. Lisbon and Azores
The 14-day Portuguese adventure covers 8 destinations including Lisbon, Ponta Delgada, and Funchal. Offering 12 hotel nights, 19 meals, featuring Sete Cidades' twin lakes, Furnas Valley's thermal pools, and Cabo Girão's glass skywalk for approx. $260 per day.
- Days 1-4
Lisbon
Begin your Portugal adventure with 3 full days in the capital. Get to Belém Tower early on Day 2 before 9 AM to avoid the crowds. Explore downtown Lisbon's historic areas, where a fellow traveler shared: "The historic trams and steep hills reminded me of San Francisco, but with more character. Wear comfortable shoes with good grip – those cobblestones can be slippery!" Spend Day 3 morning in the Alfama district, Lisbon's oldest neighborhood. Book a food tour on your first full day to find authentic local restaurants since tourist areas near Praça do Comércio often overcharge. End your evening at a fado show in Bairro Alto but reserve in advance because good venues fill up quickly.
- Days 5-8
São Miguel, Azores
Fly to Ponta Delgada in the morning (2.5 hours from Lisbon). Visit the Furnas Valley geothermal area, where they cook food underground using volcanic heat. A recent visitor noted: "The cozido das Furnas was incredible - watching them pull our stew from the ground was such a unique experience. Go early to see the cooking pits steaming in the morning mist." Visit Sete Cidades' twin lakes before 11 AM to catch clear views from Vista do Rei viewpoint before the fog rolls in. You can swim in the natural pools along Ribeira Grande coast, but know the water stays cool at about 70°F (21°C) year-round.
- Days 9-12
Madeira
Fly to Funchal and enjoy Madeira's spring-like weather. Visit Mercado dos Lavradores early to see fish and flower vendors setting up. Take the cable car to Monte's botanical gardens with online tickets to avoid waiting in line. Join locals for poncha in the old town after 6 PM. A visitor suggests: "Don't miss the glass skywalk at Cabo Girão - go early or late to avoid tour buses. And bring a light jacket for the levada walks, even in summer. The mountain weather can change quickly."
- Days 13-14
Lisbon
14 Days in Portugal, incl. Lisbon and Azores
A 14-day Portuguese expedition spans 10 destinations across mainland and islands. Marvel at UNESCO sites like Belem Tower, São Miguel's Furnas Valley and Sete Cidades lakes, and Madeira's Funchal market and Porto Moniz pools, with 12 nights in premium hotels.
- Days 1-4
Lisbon & Sintra
Give yourself 3 full days to explore Lisbon. Head to Belém early (8:30 AM) to avoid the tour groups at the Tower of Belém and Maritime Monument. Take tram 28 through the old town but start at Martim Moniz station to skip the tourist crowds. For a Fado experience in Bairro Alto book dinner for 8:30 PM when most shows begin. Plan your Sintra trip early. Take the 8:15 AM train from Rossio Station (€5 round-trip) to get there before the buses arrive. Start at the National Palace then walk up to Pena Palace. The uphill walk is steep but offers better views than you'll get from the tourist buses.
- Days 5-8
São Miguel, Azores
From Lisbon fly to Ponta Delgada (2.5 hours) and use it as your base for São Miguel island. Visit Terra Nostra Botanical Garden in the morning when the thermal pools are warmest. Bring water shoes since the iron-rich water can stain regular swimwear. Visit the Sete Cidades lakes viewpoint before 11 AM to avoid afternoon fog. Take the northern route through Ribeira Grande and stop at the European tea plantations. Get to Furnas Valley early to watch the cozido (stew) being pulled from the volcanic ground at 12:30 PM.
- Days 9-12
Madeira
Fly to Funchal (2 hours from Azores). The historic center has lots of hills so stay near Avenida do Mar for easy access. Visit Mercado dos Lavradores before 11 AM to see the fish market in action. Take the morning cable car to Monte for the clearest views. Start with the easier Levada do Norte walk before trying the more challenging Pico do Arieiro. A previous visitor noted: "The Levada walks can be slippery - bring proper hiking shoes and don't attempt in flip-flops like we initially did!"
- Days 13-14
Return to Lisbon
What people love about 2-week Portugal tours
- Portugal & Madeira
We had a great experience with Wingbuddy. Great tours, great guide.
- Portugal North to South
Everything went as planned. Our tour guide Gonzalos was excellent and his knowledge was exceptional. He was also fun to be with and he interacted with all of us. The lunch at the winery was also exceptional. We are now looking at using Wingbuddy for next March to Costa Rica. All people on this tour where very friendly I do not hesitate to suggest this package if you are into the history of Portugal.
- Best of Portugal
Was a wonderful tour at a nice easy pace...loved how it covered all areas of Portugal and not just the tourist meccas. Pedro the tour guide was the best ever. His knowledge and passion for Portugal made it an amazing experience.
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