14 Days Private Portugal Tour: Lisbon + Azores Islands + Guides & Drivers

Founder, American Iberia resident, foodie, family guy & worst soccer player in Spain & Portugal.

USA's Iberia Insiders Since 1998

Itinerary Highlights

✔ Portugal’s UNESCO Highlights + Our Insider Secrets, Just for You, in 14 days.
✔ Savor fine foods & wines, top highlights & insider experiences.
✔ Lovely Lisbon’s heritage + the wine city.
✔ Options to do the rustic Alentejo + amazing Algarve coast
✔ Authentic experiences like a soulful Fado performance.
✔ Opt to see Medieval castles of Templar Knights & modern innovations.
✔ Enjoy our insider restaurant & wine suggestions.
✔ The epic natural beauty + active fun of the Azores islands.

What's Included

A Very Personalized Itinerary, Just For You and Your Schedule

Hand-Picked Ultra-Luxury & Boutique Hotel Options

Insider Experiences + Inspiring Sightseeing + Magical Upgrades

Private Touring with Your Own Personal Expert Guide

Private Airport & Train Station Luxury Transfers

Full Breakfasts + Food & Wine Tasting Options

Your Choice of Activities on “Design Your Days”®

Expert Advice, Restaurant Ideas & Reservations

24/7 Support & Concierge Service from Spain, Portugal & Morocco

Use our itinerary to inspire your expert-tailored dream trip!


Happy Carefree Tourist Woman In White Hat Leading Her Boyfriend And Enjoying Sunny Summer Holiday. Follow Me. Couple On Vacation. Traveling Together. Commerce Square In Lisbon, Portugal.

Day One


Embark on a captivating exploration of Lisbon's cultural treasures. Discover the charm of historic neighborhoods like Alfama and the sophistication of areas like Bairro Alto. Be awestruck by the grandeur of St. George's Castle, the magnificence of Jeronimos Monastery, and the splendor of Belem Tower. Indulge in authentic Portuguese gastronomy and immerse yourself in the artistic richness of local museums. Experience the vibrant energy of Lisbon and let yourself be enchanted by this unforgettable cultural journey.

Petiscos Portugal Private Luxury Travel (1)

Day Two


Embark on a delicious journey through Lisbon's petisco scene, where every bite tells a story of local flavors. Indulge in a tempting selection of gourmet small plates, accompanied by our culinary expert. As the night unfolds, let yourself be carried away by the captivating melodies of fado, evoking the very soul of Portugal. A night filled with delightful experiences and unforgettable emotions awaits you. Get ready to savor the essence of Lisbon.

Isla De Pico

Day Three

Terceira Island

Discover the hidden gem of Terceira Island! Welcome to Angra do Heroísmo, a captivating capital declared a UNESCO World Heritage Site. Immerse yourself in its fascinating history as you stroll through picturesque streets that tell tales of centuries of cultural exchanges. Admire majestic palaces like the Bettencourt Palace and the Capitães Generais Palace. Explore impressive places such as the São Sebastião Fortress and the charming Angra do Heroísmo Marina, while marveling at the beauty of Angra Bay. Complete your day with a refreshing dip in the natural pools of Silveira. A unique experience awaits you in this enchanting destination!

Algar Do Carvao Azores

Day Four

Terceira Island

Ready to experience an exclusive and personalized adventure from your hotel! Hop on our private tour and get ready for a day full of wonders! We'll start at Monte Brasil, passing through charming parishes like Ribeirinha, Serretinha, and Porto Judeu, where you can admire the beauty of Baía da Salga, Salgueiros, and Porto Martins. We'll make a refreshing stop at Cabo da Praia for you to relax. Then, enjoy magnificent views of Praia da Vitória from Serra do Facho and Serra do Cume. Delight in a delicious Portuguese lunch at a specially selected local restaurant. Immerse yourself in the fascinating history of Algar do Carvão, discover the wonders of Furnas do Enxofre, and explore the rich tradition of the Wine Museum. An unforgettable experience awaits you on this exclusive tour that will reveal the hidden treasures of the island!

Pico Montain

Day Five

Terceira Island

Discover the hidden treasures of this amazing destination with a private tour that will leave you amazed. Explore the lush nature, with impressive volcanic landscapes and majestic peaks that will take your breath away. Immerse yourself in the Cultural Landscape of the Vineyard on Pico Island, declared a UNESCO World Heritage Site. Visit the Wine Museum in the old Convent do Carmo to immerse yourself in the local wine culture. Travel along the picturesque coast, enjoying basaltic stone constructions and natural pools in places like Cais do Mourato, Cachorro, Lajido de Santa Luzia, Arcos, and Cabrito. Have lunch at a local restaurant and admire the central plateau of the island with its stunning lagoons. An unforgettable journey through Pico Island awaits you; discover the essence of this unique and special place!

Azores Delfin

Day Six

Terceira Island

Embark on an exciting whale watching tour in the Azores! Before the boat ride, our biologists will give you a talk to explain the different cetacean species that can be observed, onboard safety measures, how we respect the animals, and rules for observing them at sea, along with some historical facts. During this activity, you'll have the opportunity to observe some of the 25+ cetacean species found in the Azores. Get ready for an unforgettable journey into the world of these magnificent creatures!

Natural Pools Faial

Day Seven

Island of Faial

Welcome to the Island of Faial, where an exclusive private tour awaits you, filled with wonders, excitement, and delightful gastronomy! Get ready for an exciting jeep excursion to the volcanic zone of Caldeira, where you'll be mesmerized by breathtaking landscapes and unique energy. Discover the fascinating geological history at the Interpretation Center of Capelinhos Volcano, and then indulge in the delicious cuisine at a carefully selected restaurant just for you. Plus, unwind and relax at the beautiful natural pools of Varadouro, surrounded by the splendor of the Atlantic Ocean. Get ready for an unforgettable and captivating experience on the Island of Faial, delighting all your senses!

Sao Jorge Island

Day Eight

Island of Faial

Enjoy a free day to unwind and immerse yourself in the beauty of the Island of Faial. Whether you choose to relax on the stunning beaches, explore charming villages, or venture into the lush nature, this day is yours to savor. Feel the soothing breeze of the Atlantic Ocean, discover local treasures, and create unforgettable memories in this captivating paradise. Embrace the freedom to follow your heart's desires, making this day truly yours to cherish.

Sao Jorge

Day Nine

São Jorge

Discover the hidden gem of the Azores on a full-day private tour of São Jorge! With an expert guide, marvel at its breathtaking landscapes, from majestic cliffs to lush forests and idyllic beaches. Explore charming coastal villages like Velas and Calheta, immerse yourself in their authentic atmosphere, and savor their delicious cuisine. Also, visit a coffee plantation to delve into the fascinating history and production of this unique beverage. A day full of discoveries, exquisite flavors, and unforgettable experiences awaits you on this enchanting island. Get ready for a one-of-a-kind and delicious adventure on São Jorge!

Sao Miguel Private Luxury Travel

Day Ten

São Miguel

Today, your transfer will be waiting to take you to the airport for your journey to São Miguel, the largest and most captivating island in the Azores! Upon your arrival, we'll be there to greet you and accompany you on a comfortable journey to your hotel. Take this moment to relax and recharge, preparing yourself for the exciting adventures that await you tomorrow. Immerse yourself in the stunning landscapes, rich culture, and unique experiences that São Miguel has to offer. Rest assured that your journey here is just the beginning of an unforgettable escape on this beautiful island!

Lago Do Fogo

Day Eleven

São Miguel

Embark on a full-day tour with an expert guide, exploring the beauty of Lagoa do Fogo and Lagoa das Sete Cidades. Enjoy panoramic viewpoints, scenic trails, and if you wish, the experience of kayaking in serene lagoons. Admire the natural treasures of Portugal, the Green and Blue Lagoons, both considered natural gems. Delight in a delicious lunch in Vila das Sete Cidades and immerse yourself in the lush endemic forest of Lagoa do Fogo. This unforgettable expedition in São Miguel promises an enriching experience guided by experts.

Azores Horse Ride

Day Twelve

São Miguel

Enjoy a private tour with an expert guide and indulge in a 2-hour horseback ride (suitable for both beginners and experienced riders) through breathtaking landscapes near the ocean, mountains, valleys, and lush floral vegetation all year round. After the ride, our driver will take you to the historic Gorreana Tea Plantation. Discover the tea tradition cultivated here since 1883 and taste its varieties of black and green tea. Gorreana is the oldest and only tea plantation in Europe, preserving the Eastern traditions and ancient qualities. An unforgettable experience that blends natural beauty and the authenticity of São Miguel awaits you!

Furnas Azores

Day Thirteen

São Miguel

Embark on a captivating private tour to Furnas Valley and Terra Nostra Gardens, where the wonders of nature come to life. Explore the stunning Furnas Valley, famous for its geothermal activity and breathtaking landscapes. Immerse yourself in the vibrant colors and unique flora of Terra Nostra Gardens, a paradise of botanical treasures. In addition, indulge in the delightful local gastronomy, as this tour also allows you to savor typical dishes cooked in volcanic fumaroles. With personalized attention and expert guidance, this exclusive tour promises an unforgettable journey to the heart of São Miguel's natural beauty and cultural heritage.

Happy Clients Private Luxury Travel

Day Fourteen


It's time to say goodbye to this charming destination! Enjoy a private transfer from the hotel to the airport. Take with you the special memories we've shared on this unforgettable journey. We look forward to seeing you again on future adventures. See you soon!

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Jane Doe

Los Angeles, CA

Our Unforgettable Trips Are Tailored, Just for You!

Hi! We're Dan & Nuria, and as the owners and operators we believe that whatever your interest, you deserve the tailor-made private trip of your dreams.

We guarantee you 7 unique Magical advantages including true expert planning, positive impact travel and 24-7 trip support via our local teams in Spain, Portugal & Morocco.

Get inspired with our sample trips then get in touch about an expert-made custom, curated, luxury itinerary, just for you!

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