Lisbon and the Alentejo
Who: Couples

7 Days

From $2,115pp

Visiting Seaside Cities, Wine Estates and Beatiful Beaches: A Tranquil Trip to Lisbon and the Alentejo

Harriet is here to help give you the inside track.

Spend a couple of days in the rejuvenated city of Lisbon before indulging in food, wine, country pursuits and beachtime in the varied and under-the-radar region of Alentejo.

Itinerary at a Glance:

  • Learn more about Portugal's age of discovery (and food) in the rejuvenated capital Lisbon
  • Paddle down a blissfully peaceful river in the Alentejo
  • Enjoy a horseback wine tour
  • Hang with the cool kids in trendy Comporta on the coast

Why Book with Original Travel?

Just a few of the extra touches that come as standard on an Original Travel holiday...
Our Local Concierges
100% Carbon Off-Setting
One Point of Contact
Hold Airline Seats
Expert Guides
24 Hour Helpline
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When To Travel













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All of the holidays we create are completely tailor-made to you

This sample itinerary is intended to give you a flavour of what we can do

Day 1: Arrival

Your first day in Lisbon is all about getting your bearings, so after a quick private transfer to your city centre hotel from the airport, why not give our excellent local Concierge a call to arrange a table at one of the best restaurants in town before heading out for a few pre-dinner drinks - your handy destination Dossier is also full of our favourite spots for a sundowner or two.

Day 2: Age of Discovery

Portuguese explorers of old discovered and explored the world over - from Canada to Indonesia - and built an empire from Brazil to the Philippines.

Today, you will meet your expert guide at your hotel for a morning's walking tour of the city. After discussing the Age of Discovery over coffee and a (few) pastis de natas (custard tarts) you will make your way to the seaside district of Belem, from where the great explorers set off to discover the world. Walking around this neighbourhood, visit monuments which commemorate the bravery of the navigators and monasteries that hosted them before they set sail.

This afternoon is yours to while away as you please. We recommend visiting a few spots from your Dossier that you didn't see this morning before enjoying dinner in one of our favourite restaurants.

Day 3: Go To The Alentejo

This morning you will be privately transferred back to the airport (it's much easier to get onto the motorway from here!) to pick up the keys to your hire car.

From here, you will make the two-hour drive south to the heart of the Alentejo region, arriving at your next hotel just in time for lunch. Spend the rest of today settling into your new surroundings and exploring the hotel's wonderful estate.

Day 4: Row Your Boat

Today you will take to the river with a picnic lunch and an expert guide for a day's canoeing.

As you gently float down the blissfully peaceful river which flows through the estate, your guide will point out the interesting flora and fauna unique to the Alentejo. After your picnic lunch it will be time to head back to the estate for a few pre-dinner sundowners.

Day 5: Wine

It would be a crying shame to stay on an estate that produces such wonderful wines and not sample a few.

This morning, you will have a private tour of the vineyards on horseback - the estate breeds the beautiful Lusitano horses that grace dressage fields across the world - learning about the growing and production of wine from the estate's rather dashing horseman. After your ride - and a shower! - you will head into the cool confines of the estate wine cellar for a private tasting with the sommelier.

This evening, we've arranged for you to try the tasting menu in the hotel's wonderful restaurant.

Day 6-7: Comporta

After making the hour and a half drive north to Comporta - just south of Lisbon on the coast - you will have the next couple of days to truly relax and enjoy the sunshine and sea air.

Your lovely hotel has a salubrious spa, so be sure to book yourself in for a treatment or two and spend some time soaking in the various indoor and outdoor pools. There are also bike available for you to borrow and explore on two wheels, alternatively you can simply head to the beach and grab a sun lounger. If you wish, we can also arrange a few activities for you.

Day 8: Home Time

Today you will make the hour and a half drive back to Lisbon airport to drop off your hire car in time for your international flight home.

All of the holidays we create are completely tailor-made to you

This sample itinerary is intended to give you a flavour of what we can do

A Rough Idea of Price

While all of our holidays are completely tailor-made and prices will vary based on things like time of year and level of accommodation, we want to give you as good an idea of how much this itinerary will cost. All of the costs on our sample itineraries exclude international flights, however, ask us if you would like us to arrange your flights at our preferred rates. The below prices are based on two people sharing.

This Itinerary

If you would like to book the exact itinerary mentioned above, during mid-season and staying in our preferred room category at our preferred hotels. Ask us if you would also like us to arrange your international flights.



Bare Necessities

If you would like to pare back the above itinerary by travelling at non-peak times, staying in a standard room and removing some or all of the guided activities.



Bells & Whistles

If you are looking for something extra special and would like to stay in top room categories at some of the most luxurious hotels we work with, and add more activities and guiding.



Harriet is our expert for this itinerary and, as a seasoned traveller, has the inside track on the most memorable adventures.

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