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Top Lisbon Trips & Tours in May 2026

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Discover Lisbon in May 2026 on one of these 8 tours hand-selected by the travel experts at Adventure Life. Explore the best of during May 2026 as you enjoy Village Visits, Wine Tasting, Archaeological Site Visits, Local Market Visits, and Hiking. Prices for trips in May 2026 range from $5,380 to $18,365 for a vacation of 9 to 14 days. Choose any of the below 8 itineraries in May 2026 and customize it when you contact one of Adventure Life's expert Lisbon trip planners.
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    • Lisbon
Porto with Dom Luis Bridge
from $5,999
EXPLORE

Enticing Douro

11 Day Itinerary aboard MS Amadouro
  • Tour Belem Tower
  • Explore the Castelo da Pena
  • Travel to Lamego
  • Enjoy Sandeman Winery
Starts / Ends
Lisbon / Regua
Activity Level
Variable
Taste wines from historic vineyards on this 11-day Douro River cruise aboard the MS Amadouro. After spending 3 days exploring Lisbon, embark on a 7-night roundtrip cruise from Porto, visiting Salamanca, Vega Terron, Regua, and Pinhao. Stops include Belem Tower, Castelo de Pena, Nossa Senhora dos Remédio, and Sandeman Winery.
Cruise Details
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Visit the historic Belem tower near Lisbon
from $11,850
2for1
EXPLORE

Lisbon & Secrets of the Douro

Lisbon - Porto - 11 Day Itinerary aboard Emerald Radiance
  • Visit Ruins of Lisbon
  • Experience Roman times.
  • Explore Douro Valley
  • Amaze with eclecticmix architecture
Starts / Ends
Lisbon / Porto
Activity Level
Variable
Immerse yourself in authentic Lisbon before heading to the Douro aboard Emerald Radiance. Leaving the metropolis of Porto behind, navigate a path through Portugal’s countryside, where vineyards and landmarks await. Viticulture in Pinhão, UNESCO Heritage sites in Salamanca, and canoeing experiences in Pocinho provide a new perspective on the Douro.
Cruise Details
0
Portuguese city on the river
from $7,079
EXPLORE

Flavors of Portugal & Spain

Lisbon - Madrid - 14 Day Itinerary aboard MS Amavida
  • Explore Lisbon's vibrant charm
  • Discover Belem Tower's rich history
  • Cruise Porto's scenic Douro River
  • Visit Sintra's fairytale palace
Starts / Ends
Lisbon / Madrid
Activities
Land & Sea Exploration, Hiking
Activity Level
Variable
Embark on a 14-day cruise with stays in Lisbon and Madrid aboard the MS Amavida. Discover Portugal's heritage in Lisbon and Porto, then explore Spain's treasures, including Salamanca, Toledo, and Madrid's vibrant culture.
Cruise Details
0
Stop in sunny Salamanca
from $14,065
2for1
EXPLORE

Delightful Douro with Lisbon

Lisbon - Porto - 11 Day Itinerary aboard Scenic Azure
  • Explore Lisbon’s culture
  • Wander Sintra’s hilltop
  • Admire Pinhao’s riverside
  • Visit Salamanca’s cathedrals
Starts / Ends
Lisbon / Porto
Activities
Kayaking
Activity Level
Variable
Set sail on an 11-day cruise from Lisbon to Porto aboard the Scenic Azure, exploring Portugal's rich heritage through the Douro Valley. Enjoy guided tours, regional cuisine, and iconic landmarks, including Lisbon and the historic Sintra National Palace.
Cruise Details
0
Stop in sunny Salamanca
from $18,065
2for1
EXPLORE

Unforgettable Douro with Lisbon

Lisbon - Porto - 14 Day Itinerary aboard Scenic Azure
  • Explore Lisbon’s Moorish hilltop
  • Tour Belem’s grand monastery
  • Discover Sintra’s hilltop palace
  • Admire Porto’s architecture
Starts / Ends
Lisbon / Porto
Activity Level
Variable
Set sail on a 14-day cruise from Lisbon to Porto aboard the Scenic Azure, exploring historic sites, indulging in local cuisine, and enjoying curated excursions. Experience the beauty of the Douro River, visit charming villages, and conclude with a classical concert and evening cruise in Porto.
Cruise Details
0
Porto with Dom Luis Bridge
from $5,499
EXPLORE

Portugal's River of Gold

Lisbon-Porto - 10 Day Itinerary aboard Viking River Cruises
  • Tour the Jerónimos Monastery
  • Visit Vila Real's Mateus Palace
  • Explore Castelo Rodrigo
  • Enjoy Salamanca, Spain
Starts / Ends
Lisbon / Salamanca
Activities
Local Market Visits, Urban Exploration
Activity Level
Variable
Discover Lisbon's rebirth through its newest galleries and cafés on this Portugal cruise from Lisbon to Porto aboard Viking River Cruises. This 10-day tour includes a hotel stay in Lisbon and the added bonus of a visit to Spain. Enjoy stops in stunning ports of Porto, Régua & Pinhão, Douro, and Salamanca.
Cruise Details
0
Visit the historic Belem tower near Lisbon
from $11,850
2for1
EXPLORE

Secrets of the Douro & Lisbon

Porto - Lisbon - 11 Day Itinerary aboard Emerald Radiance
  • Visit Ruins of Lisbon
  • Experience Roman times.
  • Explore Douro Valley
  • Amaze with eclecticmix architecture
Starts / Ends
Pinhão / Lisbon
Activities
Wine Tasting, Archaeological Site Visits
Activity Level
Variable
Aboard the Emerald Radiance to travel to the Douro, and immerse yourself in real Lisbon. Navigate away across Portugal's countryside to reach vineyards and famous sites after leaving Porto's city limits. A fresh viewpoint on the Douro is offered by the viticulture in Pinho, the UNESCO World Heritage monuments in Salamanca, and the paddling adventures in Pocinho.
Cruise Details
0
Hassan II Mosque, Casablanca
from $5,380
$100 Dep.
EXPLORE

Morocco to Portugal Cruise

Casablanca - Lisbon - 9 Day Itinerary aboard SH Diana
  • Visit Casablanca’s bustling medina
  • Visit the Kasbah Museum in Tangier
  • Tour in Doñana National Park
  • Stroll in Lisbon’s historic Alfama
Starts / Ends
Casablanca / Lisbon
Activities
Village Visits, Wildlife Viewing, Small Ship Sailing
Activity Level
Variable
Embark on a 9-day cruise from Morocco to Portugal. Explore the Hassan II Mosque and the bustling medina. Continue to Tangier, a historic gateway to Africa, and Motril, a coastal town known for sugarcane and rum. Enjoy the luxury marina in Puerto Banús and visit the whitewashed villages of Marbella. Experience wildlife in Doñana National Park.
Cruise Details
0
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