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 springtime all year, with flowers blooming 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 the cuisine, crafted from fresh local ingredients. From traditional dishes to creative signature menus, every meal is a celebration of flavor and diversity of the island.
To the northwest, further into the Atlantic Ocean, is São Miguel, the largest of the Azores islands and nothing short of wild and poetic. This is where volcanic peaks meet emerald lagoons and mist drifts over lush green hillsides. Stay at a boutique resort overlooking the great blue horizon, an intimate adults-only hideaway perched on a seaside cliff. 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. From private food tours, to Jeep excursions and lake hikes combined with sailing along the islands, this journey is nothing short of pure drama, in the best way possible.
When
Year-Round
Duration
9 days
Price
Starting at $1,600
per person per day
Itinerary Outline
Day 1 - 5 | Madeira | Quinta Da Casa Branca (4 nights)
Day 5 - 9 | Azores | White by Singular (4 nights)
Day 9 | Departure
Getting There
United Airlines offers seasonal non-stop service between Newark Liberty International Airport (EWR) and Funchal (FNC). It operates three times per week.
Azores Airlines provides direct flights from Boston Logan International Airport (BOS) to Funchal.
Azores Airlines operates year-round non-stop service between Ponta Delgada (PDL) on São Miguel in the Azores and Boston Logan International Airport (BOS) in the U.S.
There is also a non-stop route from Ponta Delgada to John F. Kennedy International Airport (JFK) in New York.
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 sidecar. On this 2-hour tour, explore the rich history and culture of Funchal through narrow streets, passing by magnificent colonial buildings and feel the vibrant energy of the local markets.
Private Museum Visit
Located in a 16th century palace (founded in 1594), the Funchal Sacred Art Museum is one of the oldest museum spaces in the capital of Madeira. You will have exclusive access to the museum. 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 in a private space.
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.
Savor 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, Lunch
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.
If you’re lucky you might catch a glimpse of sperm whales, pilot whales and many types of dolphins on this tour.
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.
Arrival at Sao Miguel in the Azores where you will be greeted at the arrivals terminal and transferred to your hotel, White by Singular.
Chef-Led Food Tour in Ponta Delgada
A chef-led food tour in Ponta Delgada offers a unique culinary experience that combines sightseeing and gastronomy in the picturesque capital city of Ponta Delgada. Led by a knowledgeable chef and culinary expert, this tour takes you on a journey to discover the local food scene, traditional dishes, and hidden culinary gems. As you explore the charming streets of Ponta Delgada together, your chef/guide will lead you to various food establishments, including local markets, traditional eateries, and specialty food shops. At each stop, you'll have the opportunity to taste multiple delicious Azorean dishes and delicacies and get first-hand the welcoming reception of the Azorean people, as everybody on the island knows your chef.
White by Singular | Suite | Breakfast, Dinner
Day 6 | Azores
Sete Cidades Jeep Tour & Hike
Explore the wonders of Sete Cidades, one of the most breathtaking landscapes in the Azores, on an exciting 4x4 jeep tour that combines adventure, culture, and stunning natural scenery. The adventure begins with an off-road 4x4 journey through some of the most remote and dramatic landscapes of Sete Cidades. You will explore rugged secondary trails, crossing lush forests and open fields, reaching breathtaking viewpoints at the top of the crater. Expect thrilling moments as you navigate the unpaved paths along the ridge of the lagoon, offering unparalleled perspectives of the vibrant blue and green waters below.
After the jeep tour, take a break at the lake shore to savor traditional Azorean picnic prepared with fresh ingredients.
Following lunch, the experience continues with an invigorating hike through scenic trails that once served as the only access for local inhabitants. This route, located just outside the main crater of Sete Cidades, will lead you to discover hidden lagoons such as Lagoa das Empadadas and Lagoa Rasa. You’ll also visit Lagoa do Canário and take in the breathtaking panorama from Miradouro da Boca do Inferno, one of the most famous viewpoints in the Azores, offering a spectacular view of the entire Sete Cidades crater.
White by Singular | Suite | Breakfast, Lunch
Day 7 | Azores
Furnas Lake & E-Bike Tour
Your day begins with a hotel pick-up, kicking off an exciting adventure in Furnas. You'll start with an e-bike ride through the lush vegetation of the Furnas area and its charming village, immersing yourself in the unique landscape and tranquil atmosphere.
Next, enjoy a traditional Cozido lunch at a local restaurant—this iconic Azorean dish is slow-cooked underground using the natural heat from the volcanic soil, offering a one-of-a-kind culinary experience.
After lunch, the tour continues to explore some of the region’s most remarkable sights. You’ll visit the Furnas Caldeiras, where geothermal activity brings the earth to life with steaming vents, bubbling hot springs, and mineral-rich mud pools.
The journey then takes you to the stunning Pico do Ferro viewpoint, where you can take in panoramic views over the Furnas valley, its peaceful lake, and the surrounding green hills—an ideal moment for unforgettable photos and reflection. On the return journey, there may be an opportunity to stop at the Gorreana Tea Factory, the oldest tea plantation in Europe still in operation. Here, you'll learn about the traditional methods of tea production, stroll through the scenic tea fields, and enjoy a tasting of the locally grown green and black teas.
White by Singular | Suite | Breakfast, Lunch
Day 8 | Azores
Lagoa do Fogo Hike
This exclusive hike to the banks of Lagoa do Fogo begins on a serene path surrounded by untouched farmlands and pastures, offering an immersive experience in the pure nature of the Azores. As you'll ascend, you'll pass by the ruins of an old factory where fibers were once extracted from the New Zealand flax (Phormium tenax), a plant that has now become part of the island's history.
Continuing the climb, you'll enter an enchanting forest of Japanese Cedars (Cryptomeria japonica), leading you to a levada, where the soothing sound of flowing water accompanies you. To fully enjoy this experience, we recommend wearing proper footwear, as there are some muddy areas along the trail.
At this stage, you are treated to a rare and exclusive glimpse of the endemic flora of the Azores, such as the Azorean Blueberry (Vaccinium cylindraceum), Azorean Heather (Erica azorica), and Laurustinus (Viburnum treleasei), painting the landscape with unique colors and shapes.
Upon reaching the dam, you enter the Ribeira da Praia valley, an open area with majestic slopes on both sides and several water abstraction points. This impressive engineering feat, begun in 1984 and completed in 1998, captures most of the springs filtered through Lagoa do Fogo itself.
When you finally reach the lake’s shore, the tranquility of the place surrounds you. However, caution is advised due to the presence of seagulls, which can be more territorial during the nesting season (April-May).
The return is along the same path, but this time you are rewarded with breathtaking views over the island's south coast and the Vila Franca Islet, making this journey even more memorable and exclusive.
Ponta Delgada Sunset Sailing
Set sail on a breathtaking sunset cruise along the stunning coastline of the Azores, where volcanic cliffs, hidden caves, and the iconic islet of São Roque create a dramatic backdrop. Feel the Atlantic breeze as you glide over crystal-clear waters, with opportunities to swim in the refreshing sea either close to shore or in the open ocean.
As the sun slowly sinks toward the horizon, watch the sky transform into a canvas of fiery oranges, pinks, and golds, offering a truly magical spectacle. The journey concludes with a serene return to Ponta Delgada Marina, where the twinkling city lights welcome you back, rounding off a perfect evening on the water.
Bring your swimsuit and towel to fully enjoy this unforgettable late-afternoon escape in the heart of the Azores!
White by Singular | Suite | Breakfast, Lunch
Day 9 | Departure
Private Transfer
On your last day, private transfer to the Sao Miguel Airport for your flight home.
Flight Home
Azores Airlines operates year-round non-stop service between Ponta Delgada (PDL) on São Miguel in the Azores and Boston Logan International Airport (BOS) in the U.S.
There is also a non-stop route from Ponta Delgada to John F. Kennedy International Airport (JFK) in New York.
Pricing & inclusions
Starting at $15,000 per person
Based on two people in double occupancy and subject to increase depending on itinerary specifics and dates.
Accommodation
Quinta Casa Branca, Madeira
White by Singular Azores
Transport: All private transfers with a personal guide for the entire trip.
Tours & Activities: All tours, exclusive experiences, activities and excursions with an expert English-speaking driver as listed in the itinerary, along with the required entrance fees associated with the tours.
Meals: All meals as indicated in the itinerary
Other: City taxes associated with your accommodations. Restaurant reservations and coordination.
Exclusions
Flights
Travel insurance
Tips
