20 days in Portugal Itinerary

20 days in Portugal Itinerary

Created using Inspirock Portugal vacation planner

Make it your trip
1
Lisbon
— 2 nights
Fly
2
Porto
— 4 nights
Fly
3
Obidos
— 2 nights
Drive
4
Sintra
— 2 nights
Drive
5
Lisbon
— 3 nights
Fly
6
Ponta Delgada, Sao Miguel
— 3 nights
Fly
7
Cascais
— 3 nights
Drive

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Lisbon

— 2 nights

City of Seven Hills

Built on seven hills, Lisbon has experienced a renaissance in recent years, making it the cultural star of Portugal.
Start off your visit on the 7th (Tue): take in the views from Ponte 25 de Abril, then snap pictures at Vasco da Gama Bridge, and then pause for some serene contemplation at Capela dos Ossos. Get ready for a full day of sightseeing on the 8th (Wed): browse the different shops at Vasco da Gama Shopping Center, visit Parque das Nacoes, then pause for some photo ops at Arco do Triunfo, and finally admire the natural beauty at Miradouro Sao Pedro de Alcantara.

For other places to visit, reviews, traveler tips, and other tourist information, go to the Lisbon attractions planner.

If you are flying in from Israel, the closest major aiport is Humberto Delgado Airport (Lisbon Portela Airport). In September, daytime highs in Lisbon are 32°C, while nighttime lows are 19°C. You'll have a few hours on the 9th (Thu) to wrap things up before traveling to Porto.

Things to do in Lisbon

Parks · Neighborhoods · Historic Sites · Shopping

Side Trip

Find places to stay Sep 7 — 9:

Porto

— 4 nights

Unvanquished City

Called "Oporto" by many, the city of Porto along the Duoro River lent the country and Port wine their names. Portugal's second-largest metropolis dates back to the 4th century, representing both a rich cultural past and industrial present through its architecture and style.
You'll explore the less-touristy side of things at Parque da Cidade do Porto and Sandeman Cellars. Dedicate the 10th (Fri) to wine at some of the top wineries in the area. And it doesn't end there: cruise the town with Bluedragon Porto City Tours, don't miss a visit to Liberdade Square, do a tasting at Graham's Port Lodge, and go for a stroll along the water at Cais da Ribeira.

For traveler tips, photos, more things to do, and other tourist information, go to the Porto trip planner.

Fly from Lisbon to Porto in 2.5 hours. Alternatively, you can drive; or take a train. Plan for little chillier temperatures traveling from Lisbon in September, with highs in Porto at 27°C and lows at 15°C. Finish your sightseeing early on the 13th (Mon) so you can fly to Obidos.

Things to do in Porto

Tours · Wineries · Outdoors · Parks

Side Trip

Find places to stay Sep 9 — 13:

Obidos

— 2 nights

Wedding Present Town

Striking views of the Estremadura area and a famous medieval castle gave Obidos the name of Wedding Present Town.
You'll discover tucked-away gems like Miradouro do Suberco and Castelo de Óbidos. Explore the numerous day-trip ideas around Obidos: Valinhos Sanctuary (in Fatima), Praia do Norte (in Nazare) and Castelo de Ourém (in Ourem). The adventure continues: hunt for treasures at Grande Mercado Medieval de Obidos and don't miss a visit to Obidos Village.

To see where to stay, reviews, ratings, and more tourist information, you can read our Obidos vacation maker site.

Getting from Porto to Obidos by flight takes about 2.5 hours. Other options: drive; or take a bus. In September, daily temperatures in Obidos can reach 28°C, while at night they dip to 16°C. Cap off your sightseeing on the 15th (Wed) early enough to go by car to Sintra.

Things to do in Obidos

Historic Sites · Outdoors · Parks · Beaches

Side Trips

Find places to stay Sep 13 — 15:

Sintra

— 2 nights
Surrounded by rolling hills and old mansions and castles, Sintra has become known as the first center of the European Romantic style.
Kick off your visit on the 16th (Thu): tour the pleasant surroundings at Praia da ursa and then look for gifts at SintrArt. Get ready for a full day of sightseeing on the next day: contemplate the long history of Chalet da Condessa D’Edla and then step into the grandiose world of Castelo dos Mouros.

For maps, reviews, where to stay, and tourist information, read Sintra vacation planner.

Drive from Obidos to Sintra in 1.5 hours. Alternatively, you can take a bus; or do a combination of bus and train. Expect a daytime high around 32°C in September, and nighttime lows around 19°C. Finish your sightseeing early on the 17th (Fri) to allow enough time to drive to Lisbon.

Things to do in Sintra

Historic Sites · Outdoors · Parks · Beaches
Find places to stay Sep 15 — 17:

Lisbon

— 3 nights

City of Seven Hills

Kick off your visit on the 18th (Sat): gain a rich perspective with HIPPOtrip, then appreciate the history behind Santuario Nacional de Cristo Rei, and then indulge your senses at some of the top wineries in the area. Keep things going the next day: see the interesting displays at Museu Nacional do Azulejo, then get to know the resident critters at Jardim Zoologico, and then make a trip to Rossio Train Station.

Ask Inspirock to suggest an itinerary and make planning a trip to Lisbon fast, fun, and easy.

Lisbon is just a stone's throw from Sintra. Cap off your sightseeing on the 20th (Mon) early enough to catch the flight to Ponta Delgada.

Things to do in Lisbon

Tours · Outdoors · Wineries · Zoos & Aquariums

Side Trip

Find places to stay Sep 17 — 20:

Ponta Delgada, Sao Miguel

— 3 nights
As the busy capital of São Miguel, Ponta Delgada represents the most visited place on the island. Known for its historical buildings, the city offers 17th- and 18th-century convents and churches, as well as cobbled pedestrian streets and hidden squares.
Discover out-of-the-way places like Lagoas Empadadas and Igreja do Santo Cristo. When in Ponta Delgada, make a side trip to see Centro de Monitorizacao e Investigacao das Furnas in Furnas, approximately Furnas away. The adventure continues: tour the pleasant surroundings at Parque Natural da Ribeira dos Caldeiroes, pause for some serene contemplation at Igreja Matriz de Sao Sebastiao, contemplate the waterfront views at Lagoa do Fogo, and take in the spiritual surroundings of Nossa Senhora da Paz.

To find traveler tips, where to stay, other places to visit, and more tourist information, go to the Ponta Delgada trip app.

Traveling by flight from Lisbon to Ponta Delgada takes 3 hours. Traveling from Lisbon to Ponta Delgada, you'll gain 1 hour due to the time zone difference. Expect slightly colder weather when traveling from Lisbon in September: highs in Ponta Delgada hover around 28°C, while lows dip to 20°C. Cap off your sightseeing on the 23rd (Thu) early enough to catch the flight to Cascais.

Things to do in Ponta Delgada

Parks · Nature · Wildlife · Historic Sites

Side Trips

Find places to stay Sep 20 — 23:

Cascais

— 3 nights

Town of Kings and Fishes

A mere 32 km (20 mi) from Lisbon, the coastal town of Cascais has a long history of entertaining royals.
Kick off your visit on the 24th (Fri): walk around Marechal Carmona Park and then tour the pleasant surroundings at Praia de Carcavelos. On the 25th (Sat), you'll have a packed day of sightseeing: enjoy the sand and surf at Praia do Tamariz and then try to win big at Casino Estoril.

To find where to stay, more things to do, other places to visit, and tourist information, you can read our Cascais trip builder site.

You can fly from Ponta Delgada to Cascais in 4 hours. The time zone changes from Azores Standard Time to Western European Standard Time, which is usually a 1 hour difference. In September, daily temperatures in Cascais can reach 32°C, while at night they dip to 19°C. You will leave for home on the 26th (Sun).

Things to do in Cascais

Parks · Outdoors · Beaches · Casinos

Side Trip

Find places to stay Sep 23 — 26:

Portugal travel guide

4.2
Landmarks · Castles · Beaches
Small in size but rich in history, culture, and natural beauty, Portugal features contrasting landscapes that include long beaches, lush vineyards, verdant valleys, and rolling hills dotted with tiny settlements where old traditions still prevail. The country's serene interior, often overlooked by foreigners, remains largely unspoiled by mass tourism and offers visitors a chance to discover this less-trodden part of Europe at their own pace. Ripe for leisurely adventures on foot or by bicycle, Portugal's fertile countryside boasts well-preserved medieval castles and outstanding wineries, producing some of the world's finest ports. The country's cities offer a lively culinary scene known for its many award-winning restaurants, topping the itineraries of foodies from around the globe.