The Madeira Island Experience

5 days

Experience Madeira! Lush green mountains and vibrant tropical gardens form breathtaking backdrops for island walks. Explore Madeira’s charming villages and enjoy fresh seafood in a local taverna. Or head to the bustling capital of Funchal for a cosmopolitan affair.

Trip Highlights

  • Return flights to Madeira

  • Private chauffeured airport transfers

  • Two nights stay in a 5-star country house hotel in the heart of Madeira, with breakfasts included

  • Visit Funchal, and have lunch in the old part of town paired with local wines

  • Two full days private chauffeured travel experiences with an English speaking guide

  • Enjoy lunch at a wine estate with an outstanding view of the sea and mountain

  • Visit five wine estates around the island tasting more than 20 wines

  • Two night stay in a gorgeous 4-star boutique hotel set across 5 historic, classic buildings in the older part of Funchal city

from $1,585 per person

This is a guide price based on 2 people travelling together and sharing a room.

Enquire online now

Trip details

Day 1

On arrival in Madeira relax with private transfers. A 5-star country house hotel, set within the award-winning Palheiro Gardens in the foothills of Funchal. The hotel has been lovingly restored from an 18th century hunting lodge.

Free evening to unwind with dinner at the hotel, the restaurant overlooks the landscaped grounds.

Day 2

Enjoy a full day private wine experience. You will start your day visiting a traditional working Quinta, which has been in the  family for 7 successive generations.

You will then head west where you will stop at Cabo Girão, the highest sea cliff in Europe, from here you will go to the charming and picturesque village of Câmara de Lobos, once
painted by Mr. Winston Churchill during its stay in Madeira, where you will be visiting a famous Madeira Wine Estate, after
the visit you will have the chance to taste a selection of wines. You will then head to Funchal, in the Old part of town to have a relaxing lunch and then visit the Blandy’s Wine Lodge.

Your guide will take you back in the late afternoon to the hotel.

Day 3

Today we will be taking you to the north of the island with breath-taking landscapes of the mountains of Madeira. You will be driven along the south-western coast of Madeira passing through the picturesque village of Serra de Agua. Continuing the route stopping in Boca da Encumeada viewpoint, located at an elevation of 1,007 m, offering a superb landscape over the north and south coasts of the island.

Discover São Vicente village and explore a boutique winery producing Madeiran table wines. Walk through the vineyard while the guide explains you all that you need to know about the project and wines. At the end of the tour you have also the opportunity of tasting some of wine references surrounded by an amazing mountain landscape.

Enjoy the drive from São Vicente to São Jorge with the magnificent landscapes which lies on the northern part of Madeira. The largest vineyard here is Quinta do Bispo, a property belonging to the church, at São Jorge.

After this you will be driven to Santana to have lunch. This is rural Madeira at its best. Surrounded by vineyards with views over the dramatic coast line, the natural reserve of Rocha do Navio and Madeira’s highest mountain.

Tonight you will enjoy  a gorgeous 4-star boutique hotel set across 5 historic, classic buildings in the older part of Funchal city.

Day 4

A day to relax and explore. The city itself is nestled in a great natural amphitheatre, facing the blue Atlantic with a backdrop of dramatic mountains. A chnace to visit the famous market, or Madeiras world famous Botanical Gardens.

Day 5

The morning at leisure, take one last dip in the hotel pool. Enjoy your final lunch at the hotel (not included at this stage) and relax with private transfers to the airport for your flight home.


All of the holidays we create are completely tailor-made to you

This sample itinerary is intended to give you a flavour of what we can do.

Enquire Now +44 (0) 20 8877 4940

Recent Google Reviews

SmoothRed planned a truly fabulous trip from Paris through Brittany to Normandy and back to Paris. Every part of the trip was wonderful and seamlessly executed. It was a trip of a lifetime! Without any hesitation or qualifications, we heartily recommend SmoothRed. They customized an extraordinary family trip.

Dorothy Weinstein

Very well organised trip to Tuscany, getting in 2 wine regions. Lovely hotel with amazing view. The best part was our guide Paula who ensured our wine tasting tours were with smaller wineries which have authenticity and care for the environment. Highly recommend SmoothRed!

Warren De Villiers

To Adam & the SmoothRed Team. Our recent trip to Bordeaux and the Medoc/St Emillion has been a wonderful trip & experience. One I would have no hesitation in saying is top class. I would certainly use SmoothRed & their travel associates in future wine tasting trips. The entire group…

Paul Green

SmoothRed did an outstanding job providing chauffeured driven wine tour through Bourgogne and the Rhone valley (France). The multiple vendors they used were all Courteous, Prompt, and very fluent in English. This 7 day trip went without problems. I would highly recommend SmoothRed.

Dan Lepley

We came to Bordeaux for part of our honeymoon and took the First Growth Bordeaux tour. SmoothRed worked with us to curate a trip based on our desires. The 8 Chateaux we visited, the 3 delicious lunches, and the hotel were wonderful, but what set the trip apart was our…

Tibita Kaneene

“Thanks for taking the time and trouble to call. You really have set the standard by which we compare all other companies!! Thank you so much for organising a fantastic itinerary with such an interesting and varied range of stop-overs. We are already starting to think about next year’s trip to France so would welcome any suggestions.”

Hilary Alder

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