Portugal: the islands edition

9-day Luxury Journey to Madeira & the Azores, Portugal

Pure Drama:
The Portuguese Islands

Madeira remains a well-kept secret in the Atlantic. Its year-round temperate climate makes it feel like it’s spring time all year, with flowers blossoming of different colors at every corner. Madeira is an “anytime” destination, perfect for adventure, relaxation, or both. Hike through the enchanting Laurissilva Forest, a UNESCO World Heritage treasure, or explore dramatic cliffs and scenic coastal trails. Dive into crystal-clear waters, surf Atlantic waves, or sail along the coast. For a more relaxed pace, indulge in garden strolls, wine tasting, or simply soak up breathtaking viewpoints. Food lovers will find a paradise in our cuisine, crafted from fresh local ingredients. From traditional dishes to creative signature menus, every meal is a celebration of flavor and diversity.

São Miguel is the largest of the Azores Islands and it is nothing short of wild and poetic. This is where volcanic peaks meet emerald lagoons and mist drifts over lush green hillsides. Staying at White by Singular, an intimate adults-only hideaway perched on a seaside cliff, offers the most refined base from which to explore this untamed island. Over four days, you’ll uncover São Miguel’s most captivating corners from crater lakes and hot springs to tea plantations and whale-filled waters.

When

Year-Round

Duration

9 days

Price

Starting at $1,200
per person per day

Itinerary Outline

Day 1 - 5 | Funchal, Madeira | Quinta Da Casa Branca (4 nights)

Day 5 - 9 | Sao Miguel, Azores | White by Singular (4 nights)

Day 9 | Departure

Day 1 | Madeira

Arrival & Transfer

Arrive at Funchal Airport in Madeira where you will be greeted by your host and transferred to your hotel, Quinta Da Casa Branca. This stylish and elegant hotel comprises a modern main building as well as a historic annex building surrounded by a stunning botanical garden.

Sidecar Funchal City Tour

Feel the ocean breeze, absorb the stunning views and let yourself be carried away by the island's charms aboard a classic motorbike with sideca. In this 2 hour tour you will explore the rich history and culture of the city of Funchal in style with our sidecar motorcycle tour of the historic area. Let yourself be carried away by the narrow streets, pass by magnificent colonial buildings, and feel the vibrant energy of the local markets. From iconic monuments to hidden secrets, this historic journey provides a captivating insight into the soul of Funchal.

Private Museum Visit

Located in a 16th century palace, the former Paço Episcopal, founded in 1594, the Funchal Sacred Art Museum is one of the oldest museum spaces in the capital of Madeira. The facilities that once served as the residence of the bishops of Funchal, now house an eclectic art collection, with works dating from the period between the 15th and 19th centuries.

Private Madeira Wine (5 Years Old) Tasting at Museum Tower

Arriving at the tower, you will find an 18th century tile panel, allegorically representing the “Faith, Hope and Charity” trilogy with a privileged view of the city of Funchal. Here there will be a private tasting of Madeira wine, paired with local snacks.

Dining Experience

Enjoy a unique dining experience named from “North to South” with different dishes of the island served during a 6-course dinner.

Quinta Da Casa Branca | Suite | Dinner

Day 2 | Madeira

Full Day Jeep Exploration: Northwest Madeira

Depart from the hotel towards Estreito de Câmara de Lobos, where the hillsides are draped in vineyards that paint the landscape in shades of green and gold. The first stop is the Boca dos Namorados viewpoint, perched 1,000 meters above sea level, offering a breathtaking panorama over Curral das Freiras nestled deep in the valley below.

Continue through Jardim da Serra and Quinta Grande, before crossing to the island’s north via one of Madeira’s longest tunnels. Along the way, pass through Rosário and Lameiros, following scenic backroads that wind through the lush Laurissilva forest. After a leisurely lunch, visit the famous natural pools of Porto Moniz, carved from volcanic rock and filled with crystal-clear Atlantic waters, before returning to Funchal.

Lunch at a Private Family Estate

Step into the warmth of a private Madeiran home, where winemaking has been lovingly preserved across three generations. This is no commercial cellar, but a family estate where wines are crafted solely for personal enjoyment — making this encounter both rare and deeply personal.

Savour a guided tasting of Verdelho vintages, beginning with a canteiro wine from 1986 and culminating in an exceptional blend whose youngest component dates back to 1954, a true expression of Madeira’s timeless heritage.

The experience continues with a private lunch prepared from the freshest local ingredients, shaped by the rhythm of the seasons. Menus are tailored to guests’ preferences, ensuring a memorable and intimate celebration of Madeiran hospitality.

Quinta Da Casa Branca | Suite | Breakfast, Dinner

Day 3 | Madeira

Private Yacht Day to Porto Santo

Embark on an unforgettable voyage aboard the Princess V58, a 58-foot luxury yacht offering exceptional comfort and style. Departing from Quinta do Lorde Marina on Madeira’s eastern tip, cruise along the dramatic coastline of Ponta de São Lourenço, where turquoise waters meet striking volcanic cliffs, before crossing the Atlantic toward the golden shores of Porto Santo Island.

Spend the day exploring its pristine beaches and tranquil charm, then enjoy a leisurely return to Madeira as the sun sets over the horizon. The experience includes round-trip transfers from Funchal, a professional crew, and thoughtful onboard amenities: two suites, a cabin, kitchen, air conditioning, and sunbathing areas.

Savour a delicious onboard lunch of freshly prepared local specialties—tuna, shrimp, octopus, and Madeira bread paired with fine wines, fresh juices, and refreshing cocktails. Welcome drinks and light finger foods are also included, ensuring every moment of this private journey feels effortless and indulgent.

Quinta Da Casa Branca | Suite | Breakfast, Lunch

Day 4 | Madeira

Sunrise Above the Clouds

Experience the magic of dawn from above the clouds with a sunrise excursion to Pico do Arieiro, one of Madeira’s highest peaks at 1,800 meters. Arriving in the early morning, you’ll be greeted by crisp mountain air as the horizon slowly ignites in shades of gold and rose, revealing a breathtaking panorama of peaks and drifting clouds. As daylight unfolds, enjoy a freshly prepared homemade breakfast crafted by your guide, featuring local delicacies served against this awe-inspiring backdrop. Hotel pick-up is arranged according to the season, ensuring the perfect timing to witness this unforgettable celestial spectacle.

Hidden Trails of Madeira

The levadas of Madeira are ancient irrigation canals once used to carry water to distant, hard-to-reach plantations. Today, they form a vast network of more than 30 walking routes—over 3,000 kilometers in total, inviting you to explore lush green landscapes, natural rock tunnels, and crystal-clear lagoons. Alongside these water-lined trails are the veredas, equally scenic footpaths that wind through the island’s diverse terrain. Suitable for all ages and fitness levels, these walks offer an intimate connection with nature and the Laurissilva Forest, a UNESCO World Heritage Site. Each step reveals a living tapestry of vibrant flora and fauna, many species found nowhere else on earth.

Enjoy a surprise lunch at an undisclosed, spectacular location. Then, return to your hotel from some relaxing spa treatments and a farewell dinner.

Quinta Da Casa Branca | Suite | Breakfast, Lunch

Day 5 | Azores

Airport Transfer & Flight

Private transfer to the airport for your flight to Sao Miguel, in the Azores.

Spa & Relaxation

In the afternoon, enjoy spa treatments.

White by Singular | Suite | Breakfast

Day 6 | Azores

Slow Morning

Enjoy a slow morning today with a delicious breakfast and time to relax by the floor to ceiling windows. Take in the majestic views of the fjords from your accommodations and enjoy the spa.

Snowshoe Hike

Set off late morning on a private guided snowshoe hike up the mountain-side for spectacular views of the Lyngen Alps. Bring a packed lunch for a scenic rest stop. Later, return to your lodge for an optional wine tasting.

Gourmet Dinner

Enjoy a gourmet dinner prepared by your chef.