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Dates and Prices
Why We Love This Deal

This is your chance to immerse yourself in the Azores’ unique and historic wine country! On Pico Island, where the land refused to yield to most crops, vines thrived in the rugged volcanic soil, protected by the iconic currais—a maze of basalt stone walls shielding them from Atlantic winds. This centuries-old winemaking tradition, recognized by UNESCO, produces bold, mineral-rich wines that are truly one of a kind. Then, on São Miguel, you'll experience a different side of Azorean winemaking. With included wine tastings on both islands and a rental car to explore at your own pace, this is the ultimate opportunity to sip, savor, and uncover the secrets of Azorean wine.
Psssst... While in Pico, you can take a short ferry ride to explore two more stunning islands—São Jorge and Faial! (We'll help you plan everything)
Day By Day Itinerary

- Day 1Welcome to Pico Island
It's time for the Azores! Grab your rental car and set off on an unforgettable adventure.
Suggestion for the day: A Relaxing Arrival Day
Welcome to Pico Island, the Azores’ wine country, where majestic Pico Mountain dominates the skyline with breathtaking views! Today's itinerary is designed for a smooth transition into island life, allowing you to unwind after your flights and discover the charming town of Madalena, the main city hub of Pico.
- Settling In: Upon arrival, check into your accommodation and unpack at your own pace. Take some time to relax and refresh after your journey. Step onto your balcony or explore your surroundings, already rewarded with panoramic views of the awe-inspiring Pico Mountain.
- A Touch of History: If you're feeling energized, head into the heart of Madalena. Visit the Santa Maria da Madalena Church, a beautiful 17th-century structure with a distinctive white facade. Step inside to admire the ornate altarpieces and religious artifacts.
- Relaxation in Nature: Head to the Criação Velha Natural Pools, a series of natural pools formed by volcanic rock formations along the island's western coast. Take a refreshing dip in the crystal-clear ocean waters and enjoy the stunning scenery.
- Sunset Sipping with a View: As the sun dips below the horizon, cap off your day with a truly unique experience at Cella Bar. Perched atop a restored volcanic stone barn, Cella Bar boasts a stunning architectural contrast.
- Day 2Pico Wine Tasting (Included)
From11 AM to 11:40 AM: Wine Tasting: One, Two, Terroir (Included)
- Savor a carefully curated tasting experience featuring two vibrant white wines, each bursting with crisp acidity and distinct minerality. Delight in refreshing hints of sea salt and citrus, evoking the essence of the Atlantic breeze. The journey concludes with a light yet expressive red, where luscious red fruit notes intertwine with a subtle touch of vanilla, creating a perfectly balanced finish. A tasting designed to awaken your senses and transport you to the heart of the terroir.
Suggestion for the rest of the day: Next, Hop to Lajes do Pico for Some Whaling Heritage
- Moinho das Lajes: Lajes do Pico boasts its own collection of traditional red windmills. Capture these iconic structures standing tall against the scenic backdrop.
- Maré Natural Swimming Pool: Take a refreshing dip in the natural swimming pool located within Lajes do Pico. These volcanic rock pools offer a chance to cool off while enjoying the tranquil bay and ocean views.
- Whaling Legacy: Immerse yourself in Lajes do Pico's whaling heritage at the Museu dos Baleeiros (Whaler's Museum). Explore exhibits showcasing whaling tools, scrimshaw art, and historical accounts, gaining insights into this significant chapter of the island's past.
- Forte de Santa Catarina: Explore the historic Forte de Santa Catarina (also known as Castelo de Santo António). This 17th-century fort, strategically positioned on a hilltop, boasts breathtaking panoramic views of the coastline. Discover its ramparts, cannons, and exhibits that unveil its role in safeguarding the island.
- Day 3Pico Island
Suggestion for the day: Faial Island Day Trip
The islands of the Azores Triangle are conveniently connected by short ferry rides, making island hopping a breeze. Today's adventure focuses on the captivating southern region of São Jorge (the Azores Triangle = Pico, Faial & São Jorge!)
Board your ferry from Madalena in Pico Island and embark on a refreshing 30-minute journey across the Atlantic Ocean to Horta, the main town on Faial Island.
Not to Miss in Faial Island:
- Peter Cafe Sport - A Legendary Watering Hole: Head to the famed Peter Cafe Sport, a historic establishment known for its lively atmosphere and its connection to sailors from around the world.
- Horta Marina: Immerse yourself in the vibrant atmosphere of Horta Marina. Stroll along the harborfront, admiring the colorful facades of the buildings and the docked yachts and sailboats.
- Capelinhos Volcano: Venture out of Horta and journey to the Capelinhos Volcano and Interpretation Centre. This fascinating site tells the story of the dramatic volcanic eruption that occurred here in 1957-58. Explore the lunar-like landscape, walk along the solidified lava flows, and learn about the impact of the eruption on the island's ecosystem and local communities.
OR São Jorge Day Trip
The islands of the Azores Triangle are conveniently connected by short ferry rides, making island hopping a breeze. Today's adventure focuses on the captivating southern region of São Jorge (the Azores Triangle = Pico, Faial & São Jorge!)
São Jorge may be a small island, but its shape is one of the most iconic of all the islands: São Jorge Island has 53 km of Distance and 8 km of width and its scenery is dramatically beautiful, filled with mountains that tumble into deep ravines, as well as rocky cliffs, crater lakes, and unique fajãs (plains formed by lava flow).
Not to Miss in São Jorge Island:
- Explore Velas, the capital of São Jorge. Visit the town square, Jardim da Praça, and the Church of São Jorge.
- Poça Simão Dias: Walk to the natural swimming pools of Poça Simão Dias near Velas.
- Fajãs: Favorites of both visitors and locals alike are the Fajã dos Cubres, which is accessible by car, and the Fajã do Santo Cristo, which is only reachable by foot or moto. Both destinations are incredibly gorgeous.
- Queijo de São Jorge: Of course, no visit to São Jorge is complete without a stop at the island’s cheese factory, where they produce the famed Queijo São Jorge, a robust, aged cheese characterized by its spicy, tangy flavor.
Additional Tips:
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Consider a Guided Tour: For a hassle-free experience, explore the option of a guided day trip to Faial Island or São Jorge Island. These tours typically include ferry tickets, a guided tour of the island's highlights, and lunch. We can help you book the perfect guided tour for your needs!
- Day 4Flight to São Miguel Island
Welcome to São Miguel Island! Pick up your rental car and get ready for the next chapter of your adventure.
Suggestion for the day: Explore Downtown Ponta Delgada
It’s time to explore Ponta Delgada, the main city, that beckons not only with its charming streets and vibrant atmosphere but also with its status as the economic heart of the archipelago. Ponta Delgada evokes all the charms of Europe with cobbled streets, sidewalk cafes, and a thriving culinary scene.
Don’t Miss:
- Stroll Through Ponta Delgada’s Cobblestone Streets: Start your São Miguel discovery with a stroll along Ponta Delgada's charming city streets. Admire the architecture, from historical buildings to colorful houses. Peek into local shops and soak in the atmosphere.
- Portas da Cidade: Standing proudly at the entrance to Ponta Delgada, the Portas da Cidade (City Gates) serves as a symbolic gateway to the city's rich history and vibrant culture.
- Matriz Church: Visit the impressive Matriz Church, a beautiful example of Azorean religious architecture right in the city center.
- Pineapple Paradise: Embark on a unique adventure to a nearby pineapple plantation. Learn about the island's pineapple production, witness these fascinating plants, and perhaps even enjoy a refreshing pineapple treat.
- Day 5Wine Tasting in São Miguel (Included)
Suggestion for the day: Explore Sete Cidades
São Miguel Island, the largest in the Azores archipelago, is a treasure trove of natural beauty, and Sete Cidades and Lagoa do Fogo are two of its most captivating gems. Today, embark on a journey through volcanic landscapes, serene lakes, and charming villages, and discover the essence of this enchanting island.
- Sete Cidades (A Realm of Twin Lakes): Begin your adventure in Sete Cidades, a village nestled within a vast volcanic crater. As you descend into the caldera, prepare to be awestruck by the sight of Lagoa das Sete Cidades a mesmerizing twin-lake complex. One of the 7 Natural Wonders of Portugal, this show-stopping crater full of lakes has become one of the signature and most famous images of the Azores.
- Mosteiros & Ferraria: Venture to the neighboring village of Mosteiros, a photographer's paradise known for its breathtaking sunsets. As you explore the western region, don't miss the chance to rejuvenate at Ferraria's unique ocean thermal baths. Remember, these thermal pools are best enjoyed during low tide when warm spring water mixes with the ocean for a truly luxurious experience.
From 5 PM to 6 PM: Wine Tasting: Trilogy of the Islands (Included)
- Immerse yourself in the rich wine culture of the Azores with a tasting that showcases the unique flavors of three remarkable islands: São Miguel, Terceira, and Pico. These wines are shaped by the volcanic soil, ocean breezes, and centuries of winemaking tradition, creating a profile unlike any other in the world.
- Pico Island, a UNESCO-listed wine region, is famous for its fortified Verdelho wines, cultivated in lava rock-walled vineyards that protect the vines from harsh Atlantic winds. Terceira’s wines carry a distinct minerality, influenced by its fertile volcanic landscapes, while São Miguel produces elegant and fresh varieties, often with bright acidity and hints of citrus.
- This tasting experience is a true journey through the Azorean terroir, where each sip tells the story of the islands’ resilience, innovation, and deep connection to nature.
- Day 6São Miguel Island
Suggestion for the day: Furnas & Tea Plantations
The thermal hot spot of the Azores! Furnas Valley is the center of São Miguel's unique geothermal activity. Here you can visit two active volcanic sites to see the boiling calderas in action, as well as the gorgeous Terra Nostra Park and so much more.
Don’t Miss:
- Lagoa das Furnas: Visitors can enjoy several hiking trails around the lake, as well as several beautiful parks and the iconic Neo-Gothic Chapel of Nossa Senhora das Vitórias.
- Cozido das Furnas Lunch: A longstanding tradition among the locals, this beloved popular dish is a Portuguese stew (cozido) cooked in holes known as fumaroles that are dug in the hot volcanic soil in Furnas.
- Caldeiras das Furnas: In the center of town, Furnas boasts close to 30 bubbling, steaming calderas and fumaroles of different temperatures and biological compositions, the strong smell of sulfur wafting through the air at every turn.
- Terra Nostra Park: Terra Nostra Park is one of the Azores’ main attractions and with good reason. From its super cool thermal pools to its lavish and rich botanical gardens, Terra Nostra is at the top of every tourist’s itinerary.
- Poça da Dona Beija: Also located in Furnas is the lovely Poça da Dona Beija, which offers visitors an exotic and unique array of six natural thermal pools. Each of Poça da Dona Beija’s pools rests at different temperatures, making it possible for every single person to find their perfect fit.
- Gorreana Tea Plantations: Immerse yourself in history and nature at Gorreana Tea Plantations, Europe's oldest still-operating tea farm (established in 1883). Explore verdant fields, breathe in the fresh scent of tea leaves, and learn the secrets behind Azores' world-renowned tea.
- Day 7São Miguel Island
Suggestion for the day: Unforgettable Hikes
One of the best ways to discover São Miguel Island is through its stunning and well-preserved hiking trails. Here are our top picks:
Sanguinho/Salto do Prego Hike
- Highlights: Discover the hidden gem of Salto do Prego waterfall on this captivating hike and a secluded hidden village. Immerse yourself in lush forests, refreshing waterfalls, and the charming civil parish of Faial da Terra, known locally as "The Nativity Scene of the Island" for its picturesque houses.
- Distance: 4.5 km (2.7 miles)
- Difficulty: Moderate
- Duration: 2 hours
- Trail Type: Circular
Moinho do Félix Hike
- Highlights: Explore the charm of the Moinho do Félix trail. This coastal walk takes you through lush landscapes, past a historic windmill, and several stunning waterfalls. Immerse yourself in nature's beauty and capture unforgettable memories on this beautiful hike.
- Distance: 5.5 km (3.4 miles)
- Difficulty: Moderate
- Duration: 2 hours
- Trail Type: Circular
Serra Devassa
- Highlights: Uncover the enchanting beauty of Serra Devassa, a hiker's paradise in São Miguel. This stunning landscape boasts a collection of pristine lakes, including the iconic Lagoa do Canário. Immerse yourself in nature as you traverse through lush forests and volcanic terrain, and enjoy breathtaking panoramic views from the trail's highest point, Pico da Éguas.
- Distance: 4.9 km (3 miles)
- Difficulty: Moderate
- Duration: 2 hours
- Trail Type: Circular
- Day 8Return Flight Home
One last stop: returning your rental car.
Thank you for choosing us to be your travel companions on this adventure! It's been a pleasure assisting you in creating unforgettable memories. We wish you happy travels and until next time!
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