Portugal & The Azores: A Wine Journey from Mainland to Islands

Lisbon, Portugal

CW
Crush Wine Experiences
  • Email address verified
23 reviews
Sep 14 - 22, 2026
Group size: 6 - 16
Portugal & The Azores: A Wine Journey from Mainland to Islands
Lisbon, Portugal

Crush Wine Experiences
  • Email address verified
23 reviews

Sep 14 - 22, 2026
Group size: 6 - 16

About this trip

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

Available Packages

Double Occupancy
Deposit: $1,560
8 left
$5,200
Deposit: $1,560
Single Occupancy
Deposit: $1,860
Available until August 1, 2026Only 2 left
$6,200
Deposit: $1,860

Available Add-Ons

Pre-Night stay in Lisbon
$250
Available until July 15, 20264 left


Your Organizer


CW
Crush Wine Experiences
23 reviews
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.

Reviews

This was our first trip with Crushwinexp and we were not disappointed! My husband and I loved the small group structure and friendships that developed. The tour guide, David, was fantastic, knowledgeable, on top of all of the small details and went above and beyond for everyone's pleasure and comfort. All the hotels were fabulous and what we enjoyed most was the opportunities we had to truly experience life in Japan through food, beverages and experiences like staying at a Ryokan hotel and enjoying an onsen, natural hot spring, public bath, sleeping on tatami mats, enjoying a traditional tea ceremony and omakase dinner. Sam ensured everyone was taken care of and enjoying the experience which we surely did!! Looking forward to our next adventure and hopefully catching up with our tour friends.
By Mayra S for Enchanting Japan Tour on Nov 13, 2025
This was an epic and unforgettable trip! Being completely immersed in the culture of Japan in four cities with an excellent tour guide, itinerary, and all logistics taken care of, was amazing! I loved that 3/4 of the cities we stayed in were not the typical tourist destinations.(Of course you have to go to Tokyo if you visit Japan), which made the experience even more unique. (The food was great everywhere :) I highly recommend this trip to anyone that's interested in experiencing Japan's unique culture, history, and destinations. Thanks, Sam and the Crush team!
By Jason S for Enchanting Japan Tour on Nov 10, 2025
This was a really fun trip. Especially enjoyed the cooking class and winery tours. Would love to spend a little more time in the small villages we visited.
By Gary S for The South of France on Nov 04, 2025
We just returned from this incredible trip through Piemonte and Lake Como. The itinerary was well-paced, the food and wine were outstanding, and the group experience made it all even better. The truffle hunting and the time on Lake Como were definitely the highlights. A huge thank you to Sam, our overall host, for yet again putting together such a fantastic trip. And to Gabriele, our Tour Manager, who kept everything running smoothly and made sure we were always taken care of — from winery visits to water taxis. We came home with great memories, new friendships, and 4 cases of wine to help us relive it all. This was our 6th tour of Italy with Crush Wines and we have already booked 3 trips for next year. This is really the perfect vacation - great activities, beautiful locations, fantastic food and plenty of free time to explore. Crush Wines knows hot to do it right!
By Michael K for Piemonte & Lake Como on Oct 22, 2025
I previously reviewed our 2023 Tour of Tuscony with Crush Wines Experiences. We have now completed two new tours in 2025--Piemont 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. There is always a licensed professional tour guide who accompanies the tour everywhere we go, making sure that everyone is well taken care of, providing a depth of information, and providing great insight into the local culture. In addition, in specific cities, where appropriate, there will be a local licensed guide for that specific city. The food and wine we sampled were world class, and the cultural sites were fascinating. Sam finds the perfect balance between scheduled activities and time on our own. And, with the small groups involved in the tour, you make friends quickly with your fellow travelers. We are looking forward to trip No 4 with Sam and Crush Wine Experiences.
By Larry H for Piemonte & Lake Como on Oct 18, 2025
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