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Overview

Portugal & The Azores: A Wine Journey from Mainland to Islands
Lisbon, Portugal
Sep 14 - 22, 2026
Crush Wine Experiences image
Crush Wine Experiences
$5,200
Deposit: $1,560

About your trip

Ancient River Valleys and Volcanic Islands


Overview:

    

This 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. 

What's included

Welcome Dinner

In Lisbon

Lodging

4 nights in Lisbon 4-star hotel

Lodging

2 nights at a charming hotel on Pico Island (Azores Islands)

Lodging

2 nights at a seaside hotel in Angra do Heroísmo, Terceira (Azores Islands)

Ground Transportation

Local transportation via private coach per itinerary

Full-time Guide

Tour Manager for 9 days (fully-escorted tour and 24h assistance while on tour)

Meals

15 meals per daily itinerary, including Welcome Dinner on Day 1 & Farwell Dinner on Day

Local Tours

Walking tours with local guides in Lisbon, the mainland, and the Azores per daily itinerary

Winery tastings

4 tours and tastings

Whale Watch

In the waters surrounding Pico Island, home to over 20 species of cetaceans

Attractions

Ferry to Faial Island and Walking tour of Faial's historic vineyards

Attractions

UNESCO World Heritage vineyards tour on Pico Island

Attractions

Walking tour of Angra do Heroísmo, a UNESCO World Heritage city with pre 16th-century architecture

What's not included

Airfare

Flights to/from Portugal

Local Airfare

Local Airfare Lisbon/Azores/Lisbon (approx $300 pp)

Travel Insurance

Highly recommended

Gratuities

For local guides and coach drivers

Location

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1. Lisbon, Portugal

Lisbon, Portugal

About your organizer

Experience small group, multi-day tours off the beaten path. Our food, wine, and cultural excursions span the world's most interesting regions, and include an American wine host/Sommelier along with charismatic local guides.

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