Portugal · 14 days · Private and tailor-made
Lisbon and Five Azores Islands
Sail out of Angra do Heroísmo with a whale-watching crew and their marine biologist.
Suggested length
14 days
Price guide
From $13,972 per person, excl. international flights, based on two sharing. Family rates for 2+ children under 21.
Includes hotels, private guiding, experiences and transfers
When
June to September, and spring for whales
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American precision with local expertise · Planned from Europe since 2002 · 17,000+ American travelers · Never cancelled a journey
Fourteen days from Lisbon out to five islands in the mid-Atlantic, unhurried, private and shaped around you.
- Sail out of Angra with a marine biologist to look for whales and dolphins
- Look down on the green and blue crater lakes of Sete Cidades
- Walk inside Gruta do Natal, a cave carved by flowing lava
- Taste wine from vines grown inside black basalt walls on Pico
- Float in the warm thermal pool of the Terra Nostra garden
- Lunch on cozido, a meat and vegetable stew slow-cooked in the volcanic ground at Furnas
“Hi from Europe. After planning luxury travel from Iberia since 2002, we have key relationships across our destinations and the judgment to tailor trips wisely for our discerning clients. Get our experience, relationships and insider savvy on your side. See our reviews and request a custom itinerary.”
Dan O’Beirne, American Founder · Iberia-Based Travel Specialist · Travel Leaders Network member. As featured in USA Today, & Euro Business News · Game of Thrones location consultant.
A Journey Designed Just for You
Our resident experts wrote this itinerary as a starting point, and your planner shapes every day around your interests, pace and travel style.
What do our American travelers say?
The 14-day Lisbon and Azores itinerary at a glance
The route uses four bases and thirteen nights: two in Lisbon, four on Terceira, three on Faial and four on São Miguel. A direct flight of about two hours links Lisbon to Terceira, whose Lajes airport sits about 15 kilometers northeast of Angra do Heroísmo. From Terceira a flight of about 40 minutes reaches Horta on Faial, and from Horta a flight of about 55 minutes reaches Ponta Delgada on São Miguel. Pico and São Jorge need no hotel change. The Atlânticoline ferry crosses from Horta to Madalena on Pico in about 30 minutes, and from Horta to Velas on São Jorge in about two hours.
The route covers the central group of the Azores, then São Miguel in the eastern group. Each island day returns to the same hotel, so you pack only on flight days.
June to September suits the route best. IPMA, Portugal’s weather institute, gives Angra do Heroísmo a mean daily high of 21.1°C (about 70°F) in June, 25.1°C (about 77°F) in August and 24.0°C (about 75°F) in September, on its 1981 to 2010 averages. July is the driest month there, with about 29 millimeters of rain against about 155 in December. Lisbon runs warmer, with a mean daily high of 25.7°C (about 78°F) in June and 26.6°C (about 80°F) in September.
Licensed guides we work with on this route include Luisa and Anabela in Lisbon. Each is a highly educated local expert who cares about the people in their group. We request your guides by name, and your planner confirms who leads each day once your dates are set.
Why the route runs from Lisbon to São Miguel
The route starts in Lisbon because its airport, the main hub of TAP Air Portugal, sits about 7 kilometers from the historic center, and both TAP and Azores Airlines fly direct from Lisbon to Terceira. Two nights in Lisbon give you a full day in the city to settle the time change before the islands. From Terceira the route moves west to Faial, the nearest base for Pico and São Jorge, then flies east to São Miguel for the final four nights.
The angle is five islands from three island bases. Many Azores trips stay on São Miguel alone, and island-hopping trips often change hotel every night or two. Here Terceira and São Miguel each get four nights, and Faial gets three, because Pico and São Jorge sit within ferry range of Horta.
Journey at a glance
Length
14 days
From
$13,972 per person, double occupancy
Family rates for 2+ children under 21
Route
Lisbon, Terceira, Faial, Pico, São Jorge, São Miguel
Your planner adjusts every day to your dates.
Day One
Arrival in Lisbon: Alfama, the Castle and Belém
Your licensed driver meets you at Lisbon airport. In the afternoon, where your dates allow, Luisa, one of our licensed guides in Lisbon and Sintra, leads you up through the Alfama to São Jorge Castle, taken from the Moors in 1147, with red roofs running down to the Tagus. End in Belém at the Jerónimos Monastery and the Belém Tower, both on the UNESCO list since 1983. Our team books a welcome dinner on request.
Day Two
Lisbon's Food and an Evening of Fado
Where your dates allow, Luisa leads a food walk through the old center, so a light breakfast suits the day. In Belém, the bakery beside the monastery has sold pastéis de nata, warm custard tarts dusted with cinnamon, since 1837. On the Largo de São Domingos, try ginjinha, a sour cherry liqueur, or a strong Portuguese coffee. In the evening, opt for a table at a fado house, where a solo voice sings over the twelve-string Portuguese guitar.
Day Three
Fly to Terceira: Angra do Heroísmo
Fly west over the Atlantic to Terceira. For four centuries, fleets sailing between Europe, Africa and the Indies called at Angra do Heroísmo, and its builders angled the streets against the wind. Your licensed driver-guide walks you past the palace of the captains-general and the old Jesuit college, in a town center UNESCO listed in 1983. Late in the day, opt for a swim from the old Silveira wharf below Monte Brasil.
Day Four
Terceira: Monte Brasil and the East Coast
Start on Monte Brasil, the extinct volcano beside Angra, where a fortress begun under Philip II of Spain in 1583 still guards the bay. Your licensed driver-guide then follows the east coast through fishing villages to the bays of Salga and Porto Martins, with time for a swim. From the Serra do Cume, stone walls divide the green interior into a patchwork. Lunch brings alcatra, Terceira's spiced beef, slow-cooked in a clay pot.
Day Five
Terceira: Gruta do Natal, Furnas do Enxofre and Biscoitos
On the north coast at Biscoitos, five generations of the Brum family have made Verdelho from vines in stone-walled plots on the lava, and a tasting is yours if you wish. Inland, a short path leads to Furnas do Enxofre, where the ground steams and the air smells of sulfur. In the afternoon, step inside the island at Gruta do Natal, a lava tube with high ceilings and a loop path, so you never retrace your steps.
Day Six
Terceira: Whales and Dolphins from Angra
Where it suits your party, the morning goes to sea. A whale-watching crew sails from Angra for about three hours, with a skipper, a marine biologist and lookouts on the cliffs who track the animals from shore. Sperm whales and several kinds of dolphin live here all year, and blue and fin whales pass through, most often in spring. The afternoon is yours, with a slice of bolo Dona Amélia, the island's small spiced cake, at a café in the old town.
Day Seven
Fly to Faial: The Caldeira and Capelinhos
Fly to Faial, where yacht crews crossing the Atlantic paint their boats' names on the marina walls of Horta. Your licensed driver-guide heads up to the Caldeira, a deep green crater, by four-wheel drive where it suits you. On the western tip, the Capelinhos volcano rose from the sea in 1957 and 1958. End the day at Peter Café Sport, where Atlantic sailors have collected their mail and swapped stories since 1918.
Day Eight
Pico by Ferry: Vineyards inside Black Basalt Walls
Cross by ferry to Pico, with Portugal's highest mountain rising ahead of you. Since the late 15th century, settlers and friars have planted vines here inside small walls of black basalt, which shield them from wind and sea spray, a landscape UNESCO listed in 2004. In Madalena, the Wine Museum fills an old Carmelite house with dragon trees in its garden. Your licensed driver-guide continues to the vineyard village of Lajido de Santa Luzia, and lunch follows at a local restaurant.
Day Nine
São Jorge by Ferry: Fajãs, Coffee and Cheese
A longer sea day takes you by ferry to São Jorge, a narrow island of high cliffs whose villages sit on fajãs, flat shelves of lava at the foot of the cliffs. At Fajã dos Vimes, the Nunes family grows coffee from seeds an ancestor brought from Brazil in the early 1800s, roasts it at home and serves it in their café. Lunch comes with São Jorge cheese, a raw cow's milk cheese aged for at least three months.
Day Ten
Fly to São Miguel: Ponta Delgada
Fly east to São Miguel, the largest of the nine islands, and settle into Ponta Delgada. The rest of the day is yours, for a walk through the old town to the three arches of the city gate, or a coffee by the harbor. For dinner, our team recommends tables known for lapas, limpets grilled with garlic and butter, and tuna caught off the island.
Day Eleven
São Miguel: Sete Cidades and Lagoa do Fogo
Your licensed driver-guide heads west to the caldera of Sete Cidades, where Lagoa Verde and Lagoa Azul lie side by side, one lake in two colors joined under a small bridge. Legend says the tears of a princess and a shepherd filled them. Opt for a kayak on the water, then lunch in the village. In the afternoon, climb to Lagoa do Fogo, a crater lake in a nature reserve, with only water and native laurel in view from the rim.
Day Twelve
São Miguel: A Morning Ride and Gorreana Tea
Where it suits your party, the morning starts on horseback, with a ride for beginners or experienced riders through pasture and flowering hedges toward the sea. Then head to the north coast and Gorreana, founded in 1883 and the oldest surviving tea plantation in Europe. Rows of tea climb the slopes above the Atlantic, and the tasting covers the estate's own black and green teas.
Day Thirteen
São Miguel: Furnas and Terra Nostra
Furnas lies in a valley of hot springs east of Ponta Delgada. On the shore of the lake, cooks bury pots of cozido, a stew of pork, beef, chicken, sweet potato and cabbage, in the hot ground for almost seven hours, and lunch comes straight from the earth. In the village, the Terra Nostra garden began with an American consul's summer house in 1775. Float in its warm thermal pool under the araucaria trees.
Day Fourteen
Departure from Ponta Delgada
The morning stays free for a last coffee by the harbor in Ponta Delgada. Your licensed driver-guide collects you at a time set around your flight, and our team stays in touch until you board.
Getting around
- Day 1: Lisbon airport to your hotel with a licensed driver, then an afternoon with Luisa.
- Day 2: A full day in Lisbon on foot, no hotel change.
- Day 3: Lisbon to Terceira by direct flight, about 2 hours, met at Lajes airport.
- Day 4: A full-day loop by road from Angra, no hotel change.
- Day 5: Angra to Biscoitos and back through the volcanic interior by road.
- Day 6: A half-day boat trip from Angra with the operator’s crew, about 3 hours.
- Day 7: Terceira to Horta by direct flight, about 40 minutes.
- Day 8: Horta to Madalena by ferry, about 30 minutes each way.
- Day 9: Horta to Velas by ferry, about 2 hours each way.
- Day 10: Horta to Ponta Delgada by direct flight, about 55 minutes.
- Day 11: Ponta Delgada to Sete Cidades and Lagoa do Fogo by road, back by evening.
- Day 12: Ponta Delgada to the riding stables and the north coast by road.
- Day 13: Ponta Delgada to Furnas by road, about 40 minutes each way.
- Day 14: Hotel to Ponta Delgada airport, a short drive.
- In Lisbon, Luisa guides with a licensed driver. On each island, a licensed driver-guide meets you at the airport or pier.
What does a 14-day Lisbon and Azores itinerary look like?
A 14-day Lisbon and Azores itinerary gives Lisbon two nights and the islands eleven, split across three island bases. This one opens with Alfama, the castle and Belém, then a day of Lisbon’s food and fado. Terceira follows for four nights, with Angra, the east coast, the volcanic interior and a morning at sea with whales. Faial gets three nights, with the Caldeira and Capelinhos and ferry day trips to Pico and São Jorge. São Miguel closes the trip with four nights for Sete Cidades, Lagoa do Fogo, the Gorreana tea estate and Furnas. Three flights and two ferries, three island hotels.
Which Azores islands should you visit in two weeks?
In two weeks, Terceira, Faial, Pico, São Jorge and São Miguel give the widest range without long hops. Terceira holds the UNESCO-listed port of Angra and the lava tube of Gruta do Natal. Faial, Pico and São Jorge sit close together in the central group, so one base in Horta reaches all three. São Miguel, the largest island, has the crater lakes, the thermal ground of Furnas and the tea estates. Flores and Corvo, the remote western group, need extra flights and days of their own, and our team adds them on request.
How many days in Lisbon before the Azores?
Two nights in Lisbon suit this route, with one full day in the city between the arrival and the flight to Terceira. The first afternoon covers Alfama, São Jorge Castle and Belém, and the second day goes to Lisbon’s food and a fado evening. American travelers who want Sintra or Cascais as well add a third Lisbon night, and our team shortens an island stay or lengthens the trip to fit.
Lisbon and the Azores, or a mainland Portugal route?
This journey suits travelers who want the Azores as the heart of the trip, with Lisbon as the gateway. A different route serves you better in four cases.
If you want mainland Portugal and one Azores island, the 21-day Grand Tour of Portugal with the Azores runs from Porto and the Douro through Coimbra, the Alentejo, the Algarve and Lisbon, and ends with São Miguel. It covers the whole country but only one island.
If you prefer Madeira to the Azores, the 14-day Portugal tour with Madeira gives the same two weeks to Porto, the Douro, Lisbon, Sintra, the Alentejo, the Algarve and Funchal.
If this is your first trip to Portugal and the mainland comes first, the 10-day Portugal Signature journey covers Porto, the Douro, Lisbon, Évora and the Algarve, and the 10-day Active Portugal journey adds walks, a kayak or e-bike morning and the Algarve clifftop trail.
With one week, the 7-day Portugal private tour keeps to Lisbon, Sintra, Évora, Coimbra, Porto and the Douro. Every Portugal route sits on our Portugal destination page.
Who this journey suits
Returning visitors to Portugal who know Lisbon and Porto and want the islands in depth.
Couples who prefer coastlines, crater lakes and small towns to big-city sightseeing, with a fado evening and a thermal pool as options.
Families with teenage or adult children, since the days mix boats, caves, horses and swimming, and each island base has three or four nights.
Walkers and nature travelers, with crater rims, fumarole fields and coastal paths on four islands.
Food and wine travelers, with alcatra on Terceira, Verdelho on Terceira and Pico, cheese and coffee on São Jorge, tea at Gorreana and cozido at Furnas.
The people behind the route
Luisa, one of our licensed guides in Lisbon and Sintra, leads the two Lisbon days where your dates allow. She works alongside a licensed driver, so the walks through Alfama and up to the castle start where the car drops you, and she shapes the food walk around the season and your tastes. On Terceira, Faial, Pico, São Jorge and São Miguel, a licensed driver-guide on each island meets you at the airport or the pier, drives the touring days and leads the visits.
What the 14-day journey costs and what it includes
This 14-day journey starts from $13,972 per person, double occupancy. The from-price covers thirteen nights in deluxe four-star properties selected for comfort, location and service. Five-star luxury properties are available by request. It also covers a licensed guide and a licensed driver in Lisbon, licensed driver-guides on the islands, private vehicles for every transfer and excursion, and the planning and in-country support of our team.
What moves the price: travel dates and season, hotel category, the size of your party, single rooms, and added private experiences such as the fado evening in Lisbon, the whale-watching trip, the four-wheel-drive trip on Faial, the horseback ride or kayak on São Miguel, or extra nights on Pico or in Lisbon. VIP assistance at the Lisbon airport is available by request, and our note on VIP airport services in Portugal explains how it works. Our team prices each journey to your dates and party.
When five islands and a Lisbon prelude sound like the trip you have in mind, speak with our team about your dates, your party and the pace you want.
Questions about the 14-day Lisbon and Azores itinerary
How many Azores islands fit into two weeks?
Five islands fit comfortably into the eleven island nights of this route, from three hotel bases. Terceira and São Miguel each get four nights, and Faial gets three, because Pico and São Jorge sit within ferry range of Horta and work as day trips. A single-island stay on São Miguel suits a short trip, and two islands suit a week. With two weeks, five islands from three bases keeps the hotel changes to three while covering the history of Angra, the volcanic interior of Terceira, the vineyards of Pico, the fajãs of São Jorge and the crater lakes of São Miguel.
How do you get from Lisbon to the Azores?
A direct flight links Lisbon to Terceira in about two hours, and both TAP Air Portugal and Azores Airlines fly the route. Lajes airport sits about 15 kilometers northeast of Angra do Heroísmo, and a licensed driver-guide meets you on arrival and drives you to your hotel in the old town. TAP and Azores Airlines also fly direct from Lisbon to Ponta Delgada on São Miguel, so the route reverses easily, starting on São Miguel and ending on Terceira. Our team discusses flights with each client while planning the journey, and the schedule we send before you leave lists every flight, ferry and transfer. Travelers adding Porto before the islands will find the two mainland airports compared in our note on flying into Lisbon or Porto.
How do you travel between the Azores islands on this route?
Three short flights and two ferry crossings link the islands. Terceira to Horta on Faial takes about 40 minutes by air, and Horta to Ponta Delgada on São Miguel about 55 minutes, both on SATA Air Açores, the inter-island airline. From Horta, the Atlânticoline ferry crosses to Madalena on Pico in about 30 minutes and to Velas on São Jorge in about two hours. On each island a licensed driver-guide meets you at the airport or the pier, so luggage and timing stay in our team’s hands. Ferry and flight timetables change with the season, and our team sets the order of the Pico and São Jorge days to fit them.
What is the best time of year for Lisbon and the Azores?
June to September suits this route best. IPMA, Portugal’s weather institute, gives Angra do Heroísmo on Terceira a mean daily high of 21.1°C (about 70°F) in June, 25.1°C (about 77°F) in August and 24.0°C (about 75°F) in September, on its 1981 to 2010 averages. July is the driest month in Angra, with about 29 millimeters of rain, against about 155 in December. Spring brings the most sightings of passing blue, fin and sei whales, and sperm whales and several dolphin species stay all year. Summer warms the sea for the natural pools at Silveira and Varadouro. Lisbon runs warmer than the islands, with a mean daily high of 25.7°C (about 78°F) in June.
Why stay on Terceira, Faial and São Miguel rather than Pico?
Each base answers a different need. Angra on Terceira has the UNESCO-listed old town, the harbor and the restaurants, and four nights there cover the island at an easy pace. Horta on Faial sits in the middle of the central group, with the airport, the marina and the ferry pier for both Pico and São Jorge, so three nights there reach three islands. Ponta Delgada on São Miguel puts Sete Cidades, Lagoa do Fogo, Gorreana and Furnas all within a day’s drive. Travelers who want to climb Mount Pico or spend more time among the vineyards add a night or two on Pico, and our team rebuilds the Faial stay to fit.
What does the whale-watching morning on Terceira involve?
The whale-watching morning is an option, and where it suits your party our team books a half-day trip of about three hours from Angra. The crew includes a skipper and a biologist, and lookouts on the coast track the animals from the cliffs. Before boarding, the crew briefs you on the species, the spotting methods and the rules for approaching the animals at sea. More than twenty cetacean species appear in Azores waters. Sperm whales and common, bottlenose and Risso’s dolphins live here all year, and blue, fin and sei whales pass through, most often in spring. Whale-watching boats also sail from Pico and São Miguel, so the trip moves to another island on request.
Who guides and drives us on the 14-day tour?
In Lisbon, where your dates allow, Luisa, one of our licensed guides, leads both touring days and works alongside a licensed driver, two separate people. On Terceira, Faial, Pico, São Jorge and São Miguel, a licensed driver-guide looks after you, one person holding both licenses who drives the car and leads the visits. On boat days the operator’s skipper and crew take over at sea. Every road transfer runs by private vehicle for your own party, from the Lisbon airport pickup to the Ponta Delgada drop-off. Our team plans the whole route, books the site entries and stays in contact through the trip. Our note on driver-guides in Portugal explains how the role works.
How active is the Azores itinerary?
The days mix short walks, viewpoints and optional activities, and you choose how much to add. Gruta do Natal is a walk of about 700 meters on a loop through the lava tube, on a floor that is uneven in places. The Caldeira on Faial and the rim of Lagoa do Fogo have short walks from the car to the viewpoints. The kayak at Sete Cidades, the horseback ride on São Miguel and the four-wheel-drive trip on Faial are all options, and your licensed driver-guide sets the pace to your party. The ferry to São Jorge takes about two hours each way, with time to read on deck. Your guide is glad to advise on suitability before booking.
Is the 14-day route fixed?
The route as written shows one balanced order of islands, and our team shortens, extends or reorders it around your dates, interests and pace. Common changes include running it from São Miguel to Terceira, adding a night on Pico for the vineyards or the mountain, adding Sintra and a third night in Lisbon, or replacing São Jorge with Flores in the western group. Guides, drivers and site entries all move with the change, and you receive a revised day-by-day plan and price before you commit.
Who do we contact if something goes wrong or we want a change?
Your planner designs your journey with you and stays in touch after you land. For the fastest response at any hour, message your private WhatsApp group, where our 24/7 support team works alongside Rachel or Dan. Because we begin no more than five journeys per country each week, peak spring and fall dates fill early, and that limit is what lets us stay this close to every trip.
We keep a list of vetted four- and five-star hotels, well located and enjoyed by our past travelers and by our own team.
Examples for each overnight stop on this route. Choose a deluxe boutique hotel or a five-star stay, and your travel advisor matches each night to your wishes, the season and availability.
Lisbon
Boutique: Memmo Alfama. A design hotel on an Alfama lane, with a pool beside its wine-bar terrace over the Tagus.
Five-star: Four Seasons Hotel Ritz Lisbon. A 1959 landmark beside Eduardo VII Park, filled with mid-century Portuguese art and tapestries.
Terceira, Azores
Boutique: Pousada Forte de Angra do Heroísmo. Inside the 16th-century São Sebastião fort on a cliff above Angra’s bay, in a UNESCO-listed town.
Also consider: Quinta da Nasce Água. A renovated 16th-century mansion 3 km from Angra, with a 19th-century garden lake.
Faial, Azores
Four-star: Azoris Faial Garden, Resort Hotel. A garden resort on the edge of Horta, with an infinity pool and views of Mount Pico.
Also consider: Hotel do Canal. A harborfront hotel with Pico-view rooms, a few steps from Peter Café Sport.
São Miguel, Azores
Boutique: Senhora da Rosa, Tradition & Nature Hotel. An 18th-century farm estate at the edge of Ponta Delgada, with an outdoor pool and spa.
Five-star: Octant Ponta Delgada. A modern seafront hotel near Ponta Delgada’s port, with a seventh-floor pool and bar over the Atlantic.
What's Included
A personalized itinerary, built around you and your schedule
Hand-picked luxury and boutique hotels
Insider experiences, inspiring sightseeing and magical upgrades
Private touring with your own personal expert guide
Private luxury transfers from airports and train stations
Full breakfasts, plus food and wine tasting options
Your choice of activities on “Design Your Days”®
Expert advice, restaurant ideas and reservations
24/7 support and concierge service from Spain, Portugal and Morocco
Magical is an award-winning luxury travel agency
Private journeys with soul & stories
Excellent independent reviews
Your private WhatsApp group with our 24/7 team and Rachel or Dan
Hidden gems, insider fun & vetted hotels
Your private guide, deluxe vehicle & flexible pace
24/7 concierge-style support
Life is short, vacation memorably
American Precision, Local Soul
Our Unforgettable Trips Are Tailored Just For You
Hi from Europe,
Along with our local partners across Portugal, Spain, Morocco and beyond we believe that our clients deserve the truly tailor-made private luxury trips, not generic "one-size-fits-all" plans.
Get inspired with our sample trips then get in touch about an expert-made personalized custom luxury itinerary, just for you.
Kind regards,
Dan O'Beirne & the MPT team
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