Explore Portugal and the Azores through vibrant cities, volcanic islands, boutique wineries, UNESCO vineyards, whale-watching, and immersive regional food and wine.
Learn MoreThis unforgettable 9-day journey begins in Lisbon, where you’ll be welcomed with a traditional Ginginha toast and a panoramic city tour before diving into Portugal’s diverse wine heritage. Explore the Tejo and Lisbon wine regions, visit the historic town of Santarém, and tour boutique wineries showcasing terroir-driven reds and whites. Discover the royal charm of Sintra and the rare fortified wines of Carcavelos before flying to the volcanic wonderland of Pico Island in the Azores.
On Pico, enjoy whale-watching, visit UNESCO-designated vineyards protected by stone walls, and savor seafood by the Atlantic. Island-hop to Faial for a taste of maritime life, then on to Terceira, where you’ll explore the UNESCO city of Angra do Heroísmo and the lava-formed vineyards of Biscoitos. Along the way, enjoy expertly paired meals, curated tastings, and immersive cultural experiences. The journey concludes with a seaside farewell dinner—raising a glass to Portugal’s rich wine legacy.
Arrive in Lisbon, Europe’s sunniest capital. Toast your journey with Ginginha, the city’s signature cherry liqueur, before a panoramic tour and welcome dinner.
Accommodation Boutique hotel in historic Lisbon Included Meals Welcome DinnerExplore Santarém, the heart of the Tejo, for a walking tour and regional lunch. Visit Ode Winery for a terroir-driven tasting of small-production wines.
Accommodation Boutique hotel in historic Lisbon Included Meals Breakfast, LunchHead west to the coastal vineyards of Lisboa for private tastings and lunch. Tour the grand Mafra Palace before returning to Lisbon.
Accommodation Boutique hotel in historic Lisbon Included Meals Breakfast, LunchVisit a secluded monastery and the fairytale town of Sintra. Conclude with a tasting of the rare fortified wines of Carcavelos — a nearly lost tradition reborn.
Accommodation Boutique hotel in historic Lisbon Included Meals BreakfastFly to Pico Island and take in the dramatic volcanic landscape. Evening free to explore the island’s coastal cuisine.
Accommodation Charming hotel on Pico Island Included Meals BreakfastMorning whale-watching adventure, seaside lunch, and visits to UNESCO-listed stone-wall vineyards — a marvel of human adaptation to nature.
Accommodation Charming hotel on Pico Island Included Meals BreakfastFerry to Faial for a walking tour and lunch, then short flight to Terceira. Relax at your seaside hotel in Angra do Heroísmo.
Accommodation Seaside hotel in Angra do Heroísmo, Terceira Included Meals Breakfast, LunchTour the UNESCO city of Angra, visit Biscoitos’ black-lava vineyards, and enjoy a farewell dinner overlooking the Atlantic.
Accommodation Seaside hotel in Angra do Heroísmo, Terceira Included Meals Breakfast, LunchGroup transfer to Terceira Airport for return flights to Lisbon or directly to the U.S.
Included Meals Breakfast
At Crush Wine Experiences, our mission is to introduce you to your favorite craft winery or distillery.
Sam Kimball is not just a sommelier; he’s a storyteller. With years of experience and a passion for wines from Portugal, he’ll introduce you to the art and science of wine tasting. From bold reds in the Tejo to remarkable selections from the Azores islands, you’ll taste a wide range of the region’s wine history and heritage on this tour.
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Read what our satisfied customers have to say about us on Google
Lorraine Romard Fabulous trip, beyond our expectations. The trip was first class all the way. It was great being part of a small group, it made for a more personal experience. Food, wine, location, and accommodations were all fantastic. Our tour guides were friendly and knowledgeable. We really got to experience the local food and culture. This was our first trip with Crush Wine XP, but it will not be our last! Looking forward to our next adventure.
Laurene M. This was my 5th trip with Sam and Crush Wine Experiences. The small group size, knowledgeable tour and local guides; as well as itineraries that immerse you in the food, wine and culture of each destination makes every trip unique. Looking forward to the next adventure!
Larry Harris We have now completed two new tours in 2025--Piemonte and Lake Como, and then Lisbon and Southern Portugal. Both tours were amazingly good. Sam is the ultimate tour host, and finds perfect guides to join us. The food and wine we sampled were world class, and the cultural sites were fascinating.
