• Overview
  • Trip Outline
  • Trip Includes
  • Booking

Beautiful Lisboa. Its seven hills offering expansive views over the city, the River Tagus, and the city on the south side of the river. Its trams. Who has not heard of the famous Tram 28 which wanders on its daily path from the centre of old Lisboa and up through its hills, its castles and old Moorish districts. Its winding alleys and laneways brimming with shops, bars and restaurants. Bairro Alto and Chiado on the fringe of the centre of the city just above the magnificent Praça do Comércio. The Castelo de São Jorge commanding a presence over the city from its hilltop vantage.

The soulful sounds of the Portuguese national music Fado. Songs about pent up emotions. Passion. Saudade. A word with no English translation. Music and words to be felt, touched and consumed.

The majesty of Belém. From where the great Portuguese navigators set out to discover the unknown world. A world that many thought was flat. A journey of discovery that reached from Brazil in the Atlantic to Japan in the Western Pacific. The Japanese word arigato means thank you and is derived from the Portuguese obrigado. Here in Belém you will see the wonderful Jerónimos Monastery and the Torre de Belém. The Coaches Museum and the Berardo museum. And away from the cultural and to the gastronomic you will find the most famous Portuguese pastry shop. You won’t find it hard to have a pastel de nata anywhere in Portugal but here in Belém at Pastéis de Belém you will find close to the best.

Lisboa has a soul. It is everywhere and no European city can match it. Lisboa will welcome you into its heart and you will never want to leave.

Except for Cascais and Sintra. Portugal’s Riviera at Cascais and Estoril. Its magical fairyland of majestic castles in Sintra. All to be personally brought to you by your guide for your day.

And then to Porto. Portugal’s second biggest city. Quirky we call it. Others call it gritty. That doesn’t do it justice. Full of character. Run down but engaging. Old and beautiful. The Douro River. Famous for its wine and port houses. The Boston Globe says it has a sophisticated new edge. The historic centre is nominated as a UNESCO Heritage.

The city has a pulse. Rawness exudes. But still it has sophistication. Porto is leisure nightlife and fine food. It is shopping. Beaches to play on and to eat at. And a cultural scene which centres around the modernity of Casa da Música and Serralves Museum of Contemporary Art.

To Portugal’s islands. Not forgotten by European and American tourists. Undiscovered by others. But not for long.

Madeira and Porto Santo. In the middle of the Atlantic. A one and a half hour flight. 620 miles from the European coast. Islands of immense natural beauty. An archipelago known as the islands of Eternal Spring. And the Azores. Nine volcanic islands about 1350 miles from Portugal. We take you to São Miguel where you can explore all manner of interests from cheese making to photography and from trekking to cultural tours.

In these two weeks you will see and learn so much about Portugal. You will be seduced and enticed. And you will return. Because there is so much more to see.

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Day 1

  • Arrive Lisbon.
  • Accommodation for the next five nights at the iconic Heritage Hotel in Avenida da Liberade.
  • Breakfast included each morning.
  • The afternoon exploring with a Tuk Tuk tour for two hours familiarising yourself with Lisbon.
  • Head out on your return to the shops of Avenida da Liberade and drop in to Loja das Meias just around the corner in Rua Castilho.
  • Dinner we suggest at zé Varunca and experience the cuisine of the Alentejo. Or if you are weary have dinner in the hotel.

Day 2

  • A day for you to do as you wish.

But some suggestions from us.

  • Wander through Bairro Alto. Have a coffee at Brasileiro café or Padaria Portuguesa. Head down towards Praça do Comércio.
  • Catch Gloria’s lift back to Chiado. Buy some gloves at Luvaria Ulisses in Chiado. Lunch at Aqui a Peixe in Chiado.
  • Return to Bairro Alto. You haven’t seen it all. Visit Cork & Co. You won’t believe what they do with cork. Shoes, chairs and umbrellas.
  • And more. Visit Igreja de Santa Catarina. Back to the hotel to freshen up for drinks at Portas do Sol overlooking the Tagus. And then dinner at Chapitô where you might also see some live theatre.

Day 3

  • Walk down to Cais de Sodré and explore this rejunevated area. Then pick up your Red Buggy with GPS and drive yourself out to Belém.
  • Visit Mosteiros dos Jerónimos, the Centro Cultural de Belém and get your fix of custard tarts at Pastéis de Belém the most famous custard tarts in Portugal. But don’t ruin your lunch at Rosa dos Mares. After lunch do your own thing. For dinner try Brasserie Flo just down the road from the hotel. And don’t forget you have to return the Red Buggy.

Day 4

  • After breakfast head out to Parque das Nações Lisbons Expo 98 site. Now home to apartments, offices, a large shopping centre, and Lisbon’s best railway station. Go for a cable car ride. Visit the Oceanário. Have some lunch and train it back to the city. In the afternoon visit some galleries and museums. We will give you a list of the ones to see before you leave.
  • Have some dinner in Bairro Alto, take in some Fado at café Luso and then wander the night streets. Or dine on some typical Portuguese seafood at Ramiro at Martim Moniz.

Day 5

  • A full day tour of Cascais and Sintra with your lovely guide Catarina Perestrelo.

Day 6

  • All aboard for the train to Porto where you will arrive mid afternoon and book Into the Pestana Porto for the next four nights.
  • Have the rest of the afternoon at leisure and wander around the riverfront in front of your hotel, the Ribeira, and on the other side Gaia.
  • For dinner we suggest you try Barao de Fladgate.

Day 7

  • Today you will be picked up by your personal guide who will show you the sights of Porto and take you on a cruise of the Douro.
  • For dinner we suggest DOP just up the road from the Pestana. Five star dining from Rui Paula one of Portugal’s best known chefs.

Day 8

  • At leisure. May we suggest a visit to the markets Mercado do Bolhão. Do some shopping. By all means do the tourist thing in Rua Santa Catarina. But better still wander the shops in Rua de Cedofeita (Me Allegro), Rua das Carmelitas (Marques Soares & Livraria Lello) and finish with some of the more funky and quirky goods to be found in Rua de Miguel Bombarda and Rua do Rosário.
  • Head down to the beaches for lunch and dine at Praia da Luz. Catch the tram along the river back into Porto. Have a look at the Centro Português de Fotografia.
  • Then relax before dinner. We suggest either Shis on the beach or Cafeína just back from the beach.

Day 9

  • Your guide will pick you up after breakfast for a trip into the Douro Valley.
  • You will visit two wineries and lunch at Régua.

Day 10

  • You will be transported to Porto airport for your flight to Funchal Madeira.
  • For the next three nights you will be accommodated at the lovely Casa Velha hotel.
  • Spend your first day exploring the capital Funchal.Visit the Mercado dos Lavradores.
  • Dine at Gallo d’Ouro.

Day 11

  • Your guide will pick you up for a full day guided tour of the delights of Madeira.
  • Lunch will be included.

Day 12

  • Have a rest day. Travel can be tiring.

Day 13

  • From Funchal you will fly to the Azores.
  • For the next three nights you will be accommodated at Terra Nostra Garden Hotel.
  • Spend the rest of the day at leisure. Have a spa or massage treatment to ready for the next two days.

Day 14

  • Your personal guide will pick you up at the hotel for a day of exploration.
  • We’ll keep your itinerary a surprise. You won’t be disappointed.

Day 15

  • If you thought you had seen it all you haven’t. Another day with your guide who by now is one of your closest friends. And he will surprise you again with the beauty of the Azores.

Day 16

  • Depart for your next CoolPortugal experience.
  • Five nights accommodation with breakfast at Heritage Hotel
  • Two hour Tuk Tuk tour
  • Red Buggy half day tour
  • Guided full day tour of Cascais and Sintra including lunch for two but excluding beverages
  • Train fare to Porto for two
  • Four nights accommodation with breakfast Pestana Porto
  • Full day guided tour for two of Porto
  • Full day guided tour for two of Douro Valley including entrance to wineries and lunch at Régua but excluding beverages
  • Economy airfares Porto/Funchal/Azores/Porto or Lisbon for two
  • Three nights accommodation with breakfast Casa Velha
  • Full day guided tour for two of Madeira including lunch but excluding beverages
  • Three nights accommodation with breakfast Terra Nostra Garden Hotel
  • One spa treatment or massage at Terra Nostra Garden Hotel
  • Two days of guided tours of Azores including lunch
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    Group Size
  • start:
    Group Size: 2 pax
    price: € 5750 /Group