Bay near Lagos town, Algarve region, Portugal

Portugal: Southern Coastal Towns & Madeira

13 Days from $11,890 USD / person

Discover Portugal’s charming coastal towns as you make your way from lively Lisbon to pretty Porto.

Visit landmarks such as Saint George’s Castle and the Sanctuary of Christ the King on a personalized tour of Lisbon. Next, head to Lisbon’s scenic countryside to admire its UNESCO-listed monasteries and quaint villages. Sandy beaches and stunning views await you at the Algarve. Embark on scenic boating tours and hikes to explore the area’s caves and beautiful rock formations.

Get a taste of Portugal’s culture at your next stop – the fabulous Madeira island. Shop for fresh produce at the lively farmer’s market, enjoy a cooking class and sample the region’s renowned wines. While here, you will also get to go on an enthralling excursion to spot dolphins and whales. Round off your Portuguese getaway at Porto, where you can savor more wonderful wines, lovely landscapes and medieval-era architecture.

Luxury Travel. Your Way.

This itinerary will be customized for you. Please reach out and our experts will work with you to create a journey so unique, it could only be yours.

Ideal For

Beaches

Heritage & Culture

Nature & Landscapes

Sample Itinerary

Day

Place

Hotel Opts

1 – 4

Lisbon
Highlights: Alfama & Belem Areas, Tram 28, Saint George’s Castle & Jeronimos Monastery, Street art, Sintra

Heritage Avenida Liberdade Hotel
Four Seasons Hotel Ritz Lisbon

4 – 8

Algarve
Highlights: Lagos, Picturesque Coastline with Grottos & Caves, Ria Formosa Nature Park, Beaches & Relaxation, Hiking

Pestana Alvor South Beach
Pine Cliffs Resort

8 – 8

Lisbon
Highlights: Alfama & Belem Areas, Tram 28, Saint George’s Castle & Jeronimos Monastery, Street art, Sintra

8 – 11

Madeira Island
Highlights: Funchal, The Levadas, Mercado dos Lavradores, Porto Santo, Porto Moniz Natural Pools

Suite Hotel Eden Mar
The Cliff Bay

11 – 13

Porto
Highlights: Cais da Ribeira, Dom Luís Bridge & Church of São Francisco, Port Wine, Douro River

PortoBay Hotel Teatro
PortoBay Flores

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Portugal: Southern Coastal Towns & Madeira

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Sample Itinerary

Day 1 – 4

3 Nights

Lisbon

Explore Lisbon, Portugal’s cosmopolitan capital that graces the Tagus estuary on the Atlantic coast. Covering seven hills and a natural harbor, this intimate city welcomes you with an inclusive culture and a spirit of exploration! Alfama’s steep cobbled paths meander past historic buildings that don pastel shades and street art. St. George Castle and Belem Tower along with several churches stand testament to Lisbon’s rich past. The yellow Remodelado trams and funiculars are a great way to commute. The riverfront Commerce Square is ideal for people-watching, and the century-old Santa Justa elevator offers panoramic vistas of the cityscape. Lisbon’s many themed museums offer glimpses of Portuguese treasures and stories of seafaring heritage. Hip neighborhoods house trendy tascas where soulful melodies of traditional fado entertain over seafood, ports, and ginjinhas, or parties until sunrise!

Included activities

Personalized Tour of Lisbon City

Experience Lisbon’s historical buildings, colorful streets and stunning panoramic views. Head up to the Sanctuary of Christ the King, an iconic monument that overlooks the city. Soak in stunning vistas from the observation deck at the foot of the landmark before going to Edward VII Park. Located in the city center, this vantage point offers panoramic views of downtown, Tagus River and 25th April Bridge. Then, follow your guide through the upscale neighborhood of Principe Real, known for its heritage mansions. Arrive at Miradouro de São Pedro de Alcântara, surrounded by lush gardens adorned with fountains and intricate ironwork. From its elevated position, enjoy splendid views of the ancient Alfama district. Next, visit Saint George’s Castle, superbly sited on a hilltop. Stroll along its ramparts and towers to hidden lookouts. Finally, stop at Miradouro das Portas do Sol for gorgeous views of the National Pantheon and waterfront to conclude your tour. (Duration: half day; Time: 0900/1400 hrs; Private activity & transfers; Meals are not included; Entry fee to Castelo Sao Jorge included; Fitness level: easy)

Personalized Tour of Lisbon Countryside

Discover historic towns, UNESCO-listed monasteries and local cuisine on this leisurely tour of the Lisbon countryside. Head to the Monastery of Alcobaca, a well-preserved ancient Cistercian abbey with its cluster of tombstone monuments. Stop by the 14th century Batalha Monastery, built to commemorate the Portuguese victory over Castile. Travel on to the city of Nazare that has come a long way from its past as a charming fishing village. You could buy yourself lunch at one of the elegant oceanfront eateries specializing in seafood delicacies. Afterward, make your way to the medieval city of Obidos with its traditional residences and quaint shopping streets. Here, you could choose to sample a glass of the local cherry liquer known as ginja before turning back for Lisbon. (Duration: Full Day; Starting Time: 0900 hrs; Ending Time: 1800 hrs; Private Activity & Transfers; Fitness Level: Easy. Please note that this activity involves some walking.)

Hotel options

Heritage Avenida Liberdade Hotel – Opt 1

Room Lisboa Room

Meals Breakfast

Style Boutique

Four Seasons Hotel Ritz Lisbon – Opt 2

Room Superior City Room

Meals Breakfast

Style International

Day 4 – 8

4 Nights

Algarve

The Algarve is a sun-soaked sliver of coastline set at the southernmost end of Portugal. Bordered by the magnificent Atlantic Ocean on two sides and blessed with a warm Mediterranean climate, it makes for an idyllic holiday destination. Sandy beaches and unique geological formations rub shoulders with historic castles and charming hamlets. While the splendid waves are a magnet for surfers seeking thrills, the beautifully designed golf courses are ideal for those who seek a slower pace. Nature lovers can look forward to abundant bird watching opportunities in the many lagoons and islets around. With the easy availability of fresh seafood and colorful produce, mealtimes hold the promise of myriad gastronomic delights. Meanwhile, wine lovers can look forward to leisurely tours of vineyards and tasting sessions at local wineries known for their flavorful whites, reds, and roses.

Included activities

Personalized Benagil Cave Tour by Boat in Algarve

Admire the beauty of the Algarve coastline on a boat tour of Benagil Cave. Set off on a speedboat from Armacao de Pera and take in views of the cliff top villages. Sail through a series of grottos with rock formations, hidden inlets and beaches. The caves are tucked away in the folds of the rugged coastline. Some are dark and submerged, while others have narrow passages. The unique Benagil Cave, formed about 20 million years ago by the pounding Atlantic waves against the coast, has two dome-shaped entry points. This idyllic natural cavern has an ‘indoor’ golden-sand beach with fossils of sea creatures and softly lapping waves. There’s also ‘the eye’, a giant hole in the Miocene limestone roof through which sunlight floods in. Watch the play between azure waters and the light rays that beam into the sea cave and be mesmerized by the ever-changing palette of colors. (Duration: 2 hrs; Time: flexible; Private activity & transfers; Meal included: no)

Group Percurso dos Sete Vales Suspensos Hike with Benagil Cave

Take an exhilarating hike through some of the most spectacular attractions of the Algarve landscape. Your trail begins at the pristine Praia da Marinha beach and then winds through secret coves till you arrive at the Benagil Cave. This seaside cave is also called the Benagil Cathedral, because of its natural arches and dome-like ceiling. Check out the central hole, known as the eye of the Benagil, before you continue with your hike up the cliff. At the top, your exertions are rewarded with breathtaking views of Praia do Vale de Centeanes, where golden sandy beaches present a stunning contrast with the turquoise blue Atlantic waters. If the tide allows, hop on a Zodiac boat for a one hour tour. The boat will stop along the way so that you can jump in the water for a swim, so carry your swimsuit. If you’re up for more, continue to the west where the Algar Seco headland and the charming town of Carvoeiro offer more delightful views. (Duration: Full Day; Shared Activity & Guide; Group size: max 8 ppl; Private Transfers; Time: 0900-1700 hrs; Fitness level: moderate as tour includes 6 km hike; Guests are requested to wear sneakers or hiking boots, bring water & sunscreen, carry swimsuit, sunscreen, and pack their own snacks; Tour can be canceled or rescheduled in case of bad weather).

Personalized Lagos to Praia da Marinha Boat Tour

Discover ethereal seascapes over the course of a boat tour along the Lagos coastline. Stop at the fine golden sands of Praia da Marinha beach for a leisurely spot of beachcombing and sunbathing. Swim in the turquoise blue Atlantic waters or go snorkeling in its crystal clear depths to make your acquaintance with myriad marine flora and fauna. Later, wind your way along the neighboring rocky outcrops to explore secret nooks and hidden coves. The boat tour also includes a scenic cruise along the Lagos coastline. Dotted with natural caves and atmospheric grottos, the coast beckons you to explore these mysterious depths still further. (Duration: 2.5 hrs; Private Activity & Transfer; Time: boat leaves every hour; Tour includes private guide & 1.5 hr boat trip; Guests are requested to bring bathing suit, windbreaker and sneakers as well as water and sunscreen; Fitness level: easy)

Hotel options

Pestana Alvor South Beach – Opt 1

Room Suite

Meals Breakfast

Style International

Pine Cliffs Resort – Opt 2

Room Double Deluxe Atlantic View

Meals Breakfast

Style Beach Resort

Day 8 – 8

Lisbon

Day 8 – 11

3 Nights

Madeira Island

Enjoy Madeira Island, a gorgeous Portuguese getaway located off the African coast in the Atlantic Ocean. Encompassing a mountainous volcanic archipelago, Madeira is a year-round destination with outdoor adventures and vibrant festivities. Popular for its namesake fortified wine, Madeira’s prized producers offer elaborate tastings paired with local specialties. Scenic driving routes weave through the rugged countryside dotted with coastal towns and rustic settlements. From ancient laurisilva and levadas, to lush valleys and dramatic cliffs, Medeira’s wild inland covered in colorful blooms is a haven for nature lovers. Pristine black sand beaches, hidden waterfalls, rivers, and Porto Moniz’s natural pools are ideal for cooling off. Funchal, the capital, charms with its botanical gardens, funiculars, toboggan rides, and vibrant nightlife. At this birthplace of Cristiano Ronaldo, soccer fans can admire his myriad posters scattered across the island. Europe’s highest skywalk at Cabo Girão viewpoint affords fantastic vistas of Madeira’s coastline. The city is also legendary for its spectacular fireworks show every New Year’s Eve!

Included activities

Personalized Market Visit & Cooking Class

Shop at one of Madeira Island’s lively markets and take part in a cooking class! Visit the colorful Mercado Dos Lavradores, a farmer’s market and a foodie paradise which is decorated with traditional Azulejo (panels of tiles) depicting regional themes. Wander through its walkways, lined with stalls selling traditional Madeiran products and fresh local ingredients. Experience the diverse culture of the island as you talk with vendors and browse the items on display with a local guide. Pick up a few souvenirs for your loved ones back home. Afterwards, head to a nearby restaurant and participate in a cooking class, where you will learn how to prepare Madeiran dishes with the help of a professional cook. Finish the tour by sitting down for a delicious meal! (Duration: Half Day; Timings: 10:00 AM to 2:00 PM or 5:00 PM – 9:00 PM; Private Activity & No Transfers; Lunch/Dinner Included; Drinks Not Included; Fitness Level: Easy; Please wear comfortable clothes and shoes.)

Personalized Tour of Porto Moniz With Lava Rock Pools

Discover the outdoor attractions of the Funchal region on this enjoyable tour. Drive out to the fishing village of Camara de Lobos to sample the world famous Madeira wines. Stop by the Henriques and Henriques wine cellars, where you can taste your pick of excellent vino including ones dating back to the 19th century. Travel past the town of Sao Vicente to reach Porto Muniz, that sits by the sea. You could enjoy a traditional lunch with fresh seafood before heading to the natural volcanic pools for a leisurely dip. Afterwards, drive along a picturesque mountain road to reach the plateau of Paul da Serra, situated at an altitude of nearly 5,000 feet above sea level. Capture stunning images of the Madeira mountains and the scenic landscape as your expert guide shares details about the region’s history and geography. (Duration: Full Day; Starting Time: 0900/1000 hrs; Ending Time: 1700/1800 hrs; Private Activity & Transfers; Wine Tastings Included; Fitness Level: Easy. Please note that this activity involves some walking. Do bring along a swimsuit.)

Group Tour of Dolphin & Whale Watching

Spot dolphins and whales in the waters around Madeira Island! More than twenty species of dolphins and whales visit the blue waters surrounding the island throughout the year. Listen to a quick briefing from your local guide before you set out on this enjoyable tour. Get a rare opportunity to observe these gentle creatures in their natural habitats. You can spot pilot whales, sperm whales, humpback whales and orcas if you’re lucky. You can also look out for bottlenose dolphins and Atlantic spotted dolphins. End the tour with a tasting session of the famous Madeira wine. (Duration: Half Day; Timings: 8:00 AM to 12:00 PM; Shared Activity & Private Transfers; Max 8-15 Pax Depending on Boat; Lunch Not Included; Wine Tasting Included; Please wear comfortable clothes, sneakers and a windbreaker; Bring water and sunscreen; Please note that the best time for this activity is from April to October. The tour starts between 8:00-8:30 AM as there is most dolphin and whale activity then; Please note this activity takes place on open water and if you are prone to sea sickness you may want to bring medication..)

Hotel options

Suite Hotel Eden Mar – Opt 1

Room Suite

Meals Breakfast

Style Resort

The Cliff Bay – Opt 2

Room Double Funchal Sea View

Meals Breakfast

Style Resort

Day 11 – 13

2 Nights

Porto

Porto is a delightful city with a laidback vibe, nestled at the mouth of Douro River, which spills into the Atlantic Ocean on Portugal’s western coast. Navigated on foot, tram, and funicular, Porto’s medieval hillside neighborhoods charm with cobbled streets flanked by old merchant houses and fountained squares. Apart from colorful facades adorned with art deco accents, there are Baroque churches, including one with an iconic bell tower, a gothic-style bookstore, and the ornate Stock Exchange Palace to discover. Azulejos and graffiti adorn public spaces, and refreshing contemporary architecture complements Porto’s edgy soul. Being the birthplace of the world-renowned port, and located near a historic port, Porto offers up wonderful gastronomic experiences. With expansive views stretching to Gaia in the distance, the waterfront Ribeira district with its chic rooftop bars and heritage restaurants is worth a visit. Porto’s six bridges, each with unique backstories, and leisurely river cruises afford superb vantages of the picture-postcard cityscape.

Included activities

What to do in Porto at your leisure: our recommendations

Spend a day discovering the lovely coastal city of Porto at your leisure. After a hearty breakfast in your hotel, set off to explore town. You could begin with Porto’s medieval riverside district, strolling down the narrow cobblestone alleys, passing street cafes, old churches and merchant houses. Admire the opulent baroque architecture of São Francisco Church and the lavish Palácio de Bolsa. Stop by the many miradouros or high lookout points around town, taking in the lovely cityscape with its meandering river and medieval stone bridges. Stop at a local tapas bar for a light bite and take a walking tour of the town’s vibrant street art. Enjoy a picturesque tram ride, passing the city landmarks and public gardens to reach the ocean front. Explore the city’s bustling food markets and ancient port cellars and try a wine tasting session. Discover the lively nightlife and dine at a gourmet steakhouse before calling it a day. (Self-explore Activity; Transfers, entrance fees and meals are not included; Choose what best suits your interests and pace from our recommendations; Please note that you may not be able to do all recommended activities)

Personalized Tour of Douro Valley & Private Boat Ride

Discover the breathtaking landscapes and delectable wines of Douro Valley, a UNESCO World Heritage Site! Start off from Porto in the morning with a private guide and drive to one of the most beautiful wine regions in the world. You can stop at viewpoints along the way to take photos of the terraced vineyards and rolling hillsides, and then go for a wine, oil and honey tasting at the Quinta Origem estate. Take a one hour private boat ride along the Douro River and get off at the famous DOC Restaurant, which serves local Portuguese cuisine and wines. Continue on to the Quinta S. Luiz and learn how the famous port wine is made. Indulge in a glass or two or sample some of the dry wines. Head back to Porto through the quiet town of Mesão Frio, another lovely destination filled with wineries, large estates and manor houses. (Duration: Full Day; Timings: 08:30 to 16:30; Private Guide, Boat Tour & Transfers; Lunch and 2 Wine Tastings Included; Fitness Level: Easy; Please wear comfortable clothes and shoes; Don’t forget your camera.)

Hotel options

PortoBay Hotel Teatro – Opt 1

Room Junior Suite

Meals Breakfast

Style Boutique

PortoBay Flores – Opt 2

Room Double Superior

Meals Breakfast

Style Heritage

Price & Inclusions

Option 1

From $11,890 USD / person

Option 2

From $15,190 USD / person

Prices are in USD and exclude international flights. This trip price is based on low season rates for accommodation and other applicable services, and may change depending on availability, currency fluctuations and number of people traveling together. For high season prices, please contact us with your exact travel dates and preferences.

Price Includes

Accommodation and meals, as specified in the itinerary
Activities and excursions, as specified in the itinerary
Transportation services, as specified in the itinerary
Your Trip Coordination Team: Dedicated support throughout your journey, with a primary, personal point of contact. Plus, in case of emergencies while you’re traveling, our trip coordination team are available 24/7 by phone

Not Included

Entrance fees and meals, unless mentioned in the itinerary description
Tips and personal expenses
Visa and tourism fees
Travel, health and cancellation insurance
International airfare

What Our Guests Say

“Enchanting Travels is a wonderful agency that we have now used twice for two long trips, one to Peru and one to Spain and Portugal. Their guidance in planning our trip was outstanding, always with an eye toward accommodating our desires and needs but also with wonderful suggestions made to enhance our experience. All of the staff that we have interacted with at Enchanting Travels have been friendly, professional, and very knowledgeable. During our trips, the transfers have been seamless, the accommodations very much to our liking, and the guides outstanding. The 24/7 support that they provide during our trip takes all the stress out of our travel. We will definitely be using Enchanting Travels again for our next trip abroad.”

October 2025 Rating 5/5

“This was our first start to finish planned tour by an agency like Enchanting Travel. We opted to go with them rather than a Duro Valley boat cruise and are so glad be did. The breadth of experiences in 10 days was simply excellent – we feel we now know so much more about Portugal’s rich history and fantastic tourism offerings.”

September 2025 Rating 5/5

“We recently returned from our 2-week vacation to Portugal and it was amazing! They met with us to hear what we like and dislike when traveling, then they customized an itinerary to fit our preferences and budget. This was our 30th anniversary trip, so we went all out. Michelin restaurants, 5-star hotels, personal drivers and guides. I cannot say enough about how exceptional our trip was and it was all because Enchanting Travels planned everything down to the last detail.”

June 2025 Rating 5/5

“Enchanting Travels can be trusted to offer a well-planned, well-executed trip to any country. They have the expertise and partner with local travel companies who provide the best experiences. Should anything go wrong, Enchanting Travels will ensure a resolution as quickly as possible.”

March 2024 Rating 5/5

“Enchanting truly makes your trip an enchanting experience!! I have used them a few times with the same results. They are all so nice and willing to work with you and make it that very special experience”

September 2023 Rating 5/5

“Everything was perfectly planned and executed! Everyone was putting their best effort to please us!”

November 2023 Rating 5/5

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What our Guests Say

Portugal: Southern Coastal Towns & Madeira

Luxury Travel. Your Way.

Ideal For

Sample Itinerary

Thank You for Inquiring

Sample Itinerary

Day 1 – 4

Day 4 – 8

Day 8 – 8

Day 8 – 11

Day 11 – 13

Lisbon

Algarve

Lisbon

Madeira Island

Porto

Price & Inclusions

Option 1

Option 2

Price Includes

Not Included

What Our Guests Say

Other Itineraries You Might Like

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