Highlights of Portugal in Two Weeks: Lisbon to Porto

You will arrive in Lisbon and be greeted by your private transfer, who will whisk you away to your luxurious accommodation. You can settle in and spend the first evening on a guided sunset stroll around Lisbon while being regaled with interesting stories and fascinating lesser-known facts about Portugal’s capital city. Your expert local guide will then lead you to a delicious meal that will be filled with authentic Portuguese cuisine before you finish the evening be enjoying a traditional Fado performance. This type of Portuguese singing is known for its dramatic flair and is characterized by its melancholic and highly expressive nature. In fact, it will be so gorgeously haunting that the experience will stay with you long after you have headed back to your hotel beneath a balmy Lisbon sky.

Today, you will wake up with the faint memory of the hauntingly beautiful Fado still on your mind. Then, you will begin your morning with an authentic Portuguese brunch. Be sure to try the country’s most famous pastry, pastel de nata, which is a warm and creamy egg custard concoction that has a mouthwateringly flaky crust and is sprinkled with a delicious dash of cinnamon and sugar.

You will then spend the day exploring the unique neighborhoods that make Lisbon such an eclectic and fascinating city. Each tiny burrow is so different from the next, each offering something special. In Chiado, you will stroll down Lisbon’s most famous shopping streets that feature haute couture, high fashion brands, local designers’ masterpieces, historical monuments, and more. You can grab a coffee at one of the chic cafes and people watch as you sip. Alfama offers a more old-world appeal, transporting you back in time with its precious, historical landmarks and immaculately tiled side streets.

After the sun goes down, put on your best dress and your dancing shoes before heading to the Bairro Alto district, which is the trendiest zip code in Lisbon. Here, the hipsters will blend with the elite as live music, upscale bars, and wild partying persists until the early hours of the morning.

Today, you will switch things up as you spend the day seeing even more Lisbon sights from aboard a luxury catamaran. This private tour will take you on a whirlwind offshore tour that will offer you the most unique and unobstructed views of some of Lisbon’s most famous landmarks, including the Tower of Belem, St. Jorges Castle, and Praça do Comercio. While on the luxury catamaran, the wind will be blowing through your hair as your cares and worries disappear. You will avoid the crowds as you cruise amid the sparkling azure waters and enjoy a delicious lunch onboard. From the sunshine to the famous sights and the cool sea breezes, this will make for the perfect stress-free way to spend your third day in Lisbon.

Today, you will enjoy an early morning lift as you literally fly through Lisbon’s skies. In fact, you will fly from Lisbon to nearby Sintra, which is located just 30 minutes away by air. As you peer down at the pastel hues of the fairytale Queluz National Palace and Pena National Palace, you will marvel at the candy-colored turrets, whimsical architectural beauty, and magical manicured gardens that are filled with fountains and statues. This morning helicopter adventure acts as the perfect amuse de bouche, or appetizer, for the next adventure that awaits.

Upon disembarking the helicopter, you will be whisked away to an overnight stay in Sintra, which is the stunning little town that you just flew over and fell in love with. The great news is that it is located just a stone’s throw away from Lisbon. As you arrive and check in to your luxury accommodation, you will have plenty of time to leisurely explore Pena National Palace up-close, as well as the Sintra-Cascais National Park which surrounds it. After soaking up the sheer beauty of this dream-like castle that is complete with gargoyles and a real-life drawbridge, you will return to your hotel and have sweet dreams of magical lands, knights, and kingdoms.

You will spend the morning exploring Sintra's Old Town. You may window shop or purchase as you please amid the shops while sampling local delicacies. You can also just grab a cup of coffee and soak up the old-world charm of a village that will appear to have escaped the modern changes, somehow clinging to its authentic and traditional style. The afternoon will find you whisked away once more by your private driver to explore the splendid seaside resort town of Cascais. Here, you will soak up the sun, go for a swim, or stroll around as you please before heading back to Lisbon along the stunning Estoril Coast.

Day six will begin with a mouthwatering brunch en route to the Lisbon airport where you will escape to the Azores for several days of absolute heaven on earth. After a brief two-hour flight, your driver will be waiting to take you directly to your luxury hotel where you can drop off your luggage and regroup before the afternoon’s adventures. As you will have been traveling, you can take time this afternoon and evening to stroll around Ponta Delgada, which is Sao Miguel’s main city that is filled with gorgeously tiled streets, charming cafes, and endless side streets simply begging to be explored. You can choose among the many wine bars and wind down your first day in the Azores with an authentic meal and a glass of the Islands’ famed pineapple wine.

Today will have you traveling to Furnas where you will first witness the geothermal steam holes that emit their sulfuric smoke amid the beautiful backdrop of Furnas Lake. As you gaze around this natural phenomenon, you will almost feel as if you have landed on the moon it will be such an out of the world experience. You will then spend the rest of the day relaxing in the warm, healing waters of two of Furnas’ natural thermal pools. You will also have the amazing opportunity to visit Poca da Dona Beija and Terre Nostra Park. Optional spa treatments are offered onsite at both thermal pools, making them an ideal addition to your ethereal spa afternoon. You will then return to Ponta Delgada, refreshed, relaxed, and rejuvenated.

Today, you will still be glowing from being absolutely spoiled at the thermal springs, and day eight offers a delicious, enlightening, and educational adventure where you will travel to two very different kinds of working plantations. Your first stop will be at Cha Gorreana Tea Plantation, which is the only tea plantation in all of Europe. While you are here, you will learn the rich history behind the family-owned and operated plantation that dates back to 1883. You will enjoy a tour of the tea factory where you will learn how the tea is harvested and made, taste delicious samples of the actual product, and even have the opportunity to walk through the plantation grounds. There is even a fun maze if the kids, or kids at heart, want to join in on the fun.

The next plantation will be a sweet experience as you journey to a working pineapple plantation. Here, you will traverse the grounds and learn the fascinating facts about how the Azores grow the heavenly fruit. You will even be able to see the greenhouses that help keep the delectable fruit warm enough to thrive. Before you leave, you will be able to stop by the gift shop and onsite cafe where you can sample a plethora of pineapple-themed confections and souvenirs.

You will set out from your hotel today, ready to experience the beauty and majesty that is Sete Cidades. Azores’ legends say that, long ago, a beautiful princess fell in love with a poor shepherd who she had met on a hillside as he was tending his sheep. They would meet at the same hillside daily, but when her father, the king, discovered this, he forbade his daughter to ever see the shepherd again. The legends say that the final time the two lovers met at their same hillside spot, they wept endlessly in despair. It is believed that the two connecting lakes of Sete Cidades, which appear blue and green respectively, were created from the two unrequited lovers’ tears: the princesses’ filling the blue lake while the shepherd’s accounts for the green lake. In this way, they could still close to one another forever. As you journey to this idyllic spot where you will be able to kayak amid these blue and green waters, you can carry with you the sad, sweet memory of Azores lore while making only magical and happy memories of your own. After your full day of being surrounded by the stunning beauty of Sete Cidades, you will return to your hotel and sleep sweetly and soundly.

Although it is already day ten into your grand Portugal adventure, the delight and fun are not about to slow down. Buckle up for an exhilarating Jeep tour around Lagoa do Fogo. Translated as “Fire Lake” in Portuguese, Lagoa do Fogo exists in a huge crater that was formed by a volcanic eruption back in 1563. This thrilling Jeep excursion will take you around the entire base of the volcano, giving you the chance to get the best view of its shimmering majesty from vantage points and perspectives. You will come away from this day well in awe of volcanoes and the wonder that they can muster, in addition to your newfound respect for the raw power of this natural phenomena. The most exciting thing is that your Jeep will allow you to access secret spots within this nature preserve that others will never have the chance to lay their eyes on.

First thing this morning, you will transfer to the airport where you will take a short 2-hour flight to Porto. This is the stunning city where you will spend your last few days exploring. You can settle in at your luxury hotel before attending a private cooking class in the evening where you will learn the fascinating history of the beloved Portuguese pastry, Pastel de Nata, before trying your own hand at baking the mouthwatering desserts, all under the expert guidance of a local master chef. After your cooking class, you will return to your hotel with a belly full of comfort and joy to rest up.

Today, you can take your time getting ready as you indulge in a leisurely breakfast before being swept away on a wine tour of the Douro Valley. Your local guide, an expert sommelier, will lead you on an educational, enlightening, and taste bud awakening excursion that only the elite few can truly appreciate. You will enjoy walking the grounds of a working vineyard while sampling the world-famous Douro white, red, and fortified wines, which will be paired perfectly with the impeccably prepared lunch that you will partake in while on the grounds. As you return to your hotel in Porto, you will be delighted by the jaw-dropping views along the Douro River, which is recognized as one of the most idyllic roadways in the entire world.

You will spend your last full day being surrounded by the rich and wondrous hidden gems of Porto. From fascinating Liberdade Squareto TorreandIgreja dos Clérigos, the marvels of this eclectic city will make you wish you could stay longer to fully absorb their beauty and charm. You will make your way through the maze-like corridors and candy-colored houses in the Ribeira District, which are now officially recognized as a UNESCO World Heritage Site, and you will finish your day with a walk along the famous Dom Luís Bridge while taking in the breathtaking view that is as pretty as a postcard. In fact, pretty much all of Portugal is.

You will spend your last morning in Portugal enjoying an authentic Portuguese breakfast before receiving a personalized Portuguese send-off, which will be a surprise that is specially prepared for you. You will leave Portugal feeling refreshed and renewed, as you will have experienced the best of both worlds, metropolitan Lisbon, Porto, and the idyllic Azores.