01Stop · Start
Boat Rentals·Portugal
Cascais
Elegant coastal town marina near Lisbon with boat rentals and stunning coastline.
⌬Beautiful coastline⌬Boat rentals⌬Water sports⌬Seafood
Slow travel route·🇵🇹 Portugal
Lisbon Coast by Boat – 7-Day Sailing Itinerary
Sailing through Cascais, Setubal and Alentejo
Duration7 days
Stops3 stops
Best timeSpring — Alentejo wildflowers, mild Atlantic and quieter Cascais ahead of summer
CategoriesBoat Rentals · Wine Tasting
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CascaisThe itinerary
The stops.
3 stops03
02Stop · Midway
Boat Rentals·Portugal
Setúbal
Working port city known for sardine fishing, seafood markets, coastal hills.
⌬Hiking
03Stop · End
Wine Tasting·Portugal
Montemor-o-Novo
Historic Alentejo town with wine estates and castle ruins.
⌬Medieval castle ruins⌬Alentejo wine estates⌬Cork production⌬Golden wheat plains
The shape of it
Route map.
3 stops · 2 legs
Why this route
Highlights of this route.
01
Estoril coast marinas and Cascais harbour boats
Sailing boats fill Cascais marina while ferries cross to Belém for custard tarts along the Estoril coast.
02
Sado estuary dolphin watching and Moscatel cellars at Setúbal
Dolphins surface in the Sado estuary near Setúbal's Moscatel cellars and riverside fish markets.
03
Alentejo wine estates and medieval castle ruins at Montemor-o-Novo
Cork-oak plains stretch below Montemor-o-Novo's medieval castle ruins where Alentejo wine estates dot the countryside.
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What's actually available to you.
3 stops
Zoom out
Regions on this route.
3 regions
Portugal14 destinations
Alentejo
Alentejo, the largest region in Portugal, features a rich agricultural landscape dotted with vineyards and olive groves. It is known for its unique wines, particularly the robust reds from the Alentejo DOC. The region is home to Évora, a UNESCO World Heritage site with Roman ruins and medieval architecture, and Monsaraz, a hilltop village offering stunning views of the surrounding plains. Alentejo’s coastline, though less frequented, boasts beautiful beaches like Praia da Amália. Additionally, the region is famous for its traditional festivals, such as the Festa de São João in Évora, where locals celebrate with music and dance. Travelers will find a slower pace of life here, with opportunities to explore local markets and sample regional delicacies like açorda and queijos.
Wine TastingHikingLocal Cuisine
Portugal6 destinations
Setúbal
Setúbal is known for its stunning coastal landscapes and rich cultural heritage. This region features the Arrábida Natural Park, where cliffs meet the Atlantic, offering hiking trails and secluded beaches. Setúbal city is the main hub, famous for its historic fish market and vibrant local cuisine, particularly the fresh seafood and traditional choco frito. Notable nearby towns include Sesimbra, with its picturesque castle and fishing traditions, and Troia, which boasts Roman ruins and beautiful sandy shores. The region is also recognized for its high-quality wines, especially the Muscatel from the local vineyards. Setúbal's local festivals celebrate its maritime culture and gastronomy, providing an authentic glimpse into Portuguese life.
Boat RentalsHikingWine Tasting
Portugal3 destinations
Lisbon
Lisbon, Portugal's capital, is a vibrant city known for its rich maritime history and unique architectural styles, including Manueline and Pombaline. It is situated on the edge of the Atlantic Ocean, making it the only capital city in Western Europe with a coastline. The Alfama district, with its narrow winding streets, offers a glimpse into the city's Moorish past, while the Belém area is home to the iconic Jerónimos Monastery. Off the beaten path, the neighborhood of Graça provides stunning viewpoints and local eateries. The region also hosts local festivals, like Festas de Lisboa, celebrating culture and tradition throughout June. Lisbon's proximity to the Sintra mountains allows for scenic hikes and exploration of palaces, making it a multi-faceted destination for those looking to explore at a leisurely pace.
Wine TastingHikingCamper Van RentalsBoat Rentals