Colorful Costal Portugal Medieval Castles, Lisbon and Madeira Island

september 18-27, 2025
10 days / 9 nights

Overall Trip Highlights

• Historic Lisbon Exploration: Visit the Castle of São Jorge and stroll through Lisbon’s vibrant neighborhoods filled with history and charm.
• Fairytale Pena Palace in Sintra: Discover the enchanting Pena Palace, a former royal summer home surrounded by lush gardens.
• Cabo da Roca: Stand at the westernmost point of mainland Europe, taking in dramatic coastal views.
• Porto Walking Tour: Cross the Ponte Dom Luis Bridge and explore Porto’s historic streets, colorful tiles, and riverside views.
• Madeira Wine Tasting at Blandy’s: Enjoy a guided tour and tasting at Blandy’s Winery in Funchal, learning about Madeira’s famous wines.
• Douro Valley Vineyard Visit: Explore the scenic Douro Valley, a UNESCO site, with an organic vineyard tour and wine tasting.
• Funchal Cable Car & Botanical Garden: Ride the cable car up the mountain and visit the lush Botanical Garden with stunning views.
• 4×4 Jeep Adventure in Madeira: Experience an exciting 4×4 jeep tour, driving through Eucalyptus forests and scenic lookouts.
• Old Funchal & Monte: Explore Old Funchal’s markets and head to the picturesque town of Monte for more local charm.
• Farewell Dinner in Madeira: End the trip with a farewell dinner, enjoying delicious food and beautiful island views.

Don’t just tour Portugal, Experience Portugal

Every Beatrice Bradley trip is crafted to maximize the experiences had during the trip.
The itineraries are specially made to allow time for engaging in conversation and having belly laughs with a new friend. We hope that the activities and experiences may allow you to come out of your comfort zone and to try new or unique things.
These trips are made to replicate a ‘friends get-away trip’. 

Day One: Welcome to Lisbon!

Upon your arrival in Lisbon, you’ll be transported from the airport to your hotel, where you can settle in and relax. For those arriving early, we’ll send you information about the hotel and some suggestions for exploring the vibrant downtown area on your own before the group gathers.

Once everyone has arrived, we’ll meet at 6:30 PM in the hotel bar for a warm welcome drink, a perfect opportunity to get to know your fellow travelers. Afterward, we’ll head out for a delightful dinner near the river, where you’ll enjoy authentic Portuguese cuisine and experience the flavors and fun of Lisbon.

Highlights

• Arrival in Lisbon: Transportation from the airport to your hotel.
• Welcome Gathering: Join us at 6:30 PM in the hotel bar for a welcome drink and group introductions.
• Dinner by the River: Enjoy a memorable dinner with delicious Portuguese cuisine in a vibrant riverside setting.

Fun Fact: Lisbon is one of the oldest cities in Europe, predating even Rome by centuries!

Day Two: Exploring Lisbon, Castle of São Jorge, and a Cooking Class

Start the day with a group breakfast at 8 AM before heading out around 9:15 AM for a guided exploration of Lisbon. Our local guide will take us through Lisbon’s historic neighborhoods, where we’ll visit the impressive Castle of São Jorge, a 15th-century fortress offering stunning views over the city. As we stroll through charming districts filled with old shops, cafés, and theaters, you’ll also hear stories of the devastating 1755 earthquake and how Lisbon was rebuilt afterward.

We’ll enjoy lunch together at a local café, followed by some free time to explore downtown Lisbon or shop at your own pace. In the evening, we’ll head to the Lisbon Cooking School for an exciting cooking class. You’ll learn how to prepare traditional Portuguese dishes while sampling wines from various regions of Portugal. The evening will conclude with a shared dinner featuring the delicious dishes you helped create.

Highlights

• Guided Walking Tour: Discover Lisbon’s history and culture, including a visit to the 15th-century Castle of São Jorge.
• Lunch Together: Enjoy a relaxing lunch at a local café after the morning tour.
• Free Time in Downtown Lisbon: Take time to shop or explore Lisbon’s vibrant downtown.
• Cooking Class: Participate in a hands-on cooking experience, preparing Portuguese dishes and tasting regional wines.
• Dinner Together: End the day with a delicious dinner featuring the dishes from your cooking class.

Fun Fact: Lisbon’s Castle of São Jorge offers some of the best views of the city, stretching all the way to the Tagus River!

Day Three: Fairytale Palace and Cabo do Roca

After breakfast together, we’ll depart the hotel at 9 AM for a full day of adventure. Our journey takes us along the scenic coastal route to the enchanting town of Sintra, known for its whimsical architecture and rich history. The highlight of the day is a visit to Pena Palace, a fairytale-like castle that was once the summer residence of the Portuguese monarchy. This unique palace is famous for its vibrant colors, intricate tilework, and beautiful ceramic details.

After touring the palace and its lush gardens, we’ll enjoy a delightful lunch in Sintra, surrounded by the town’s charm. From there, we’ll continue our journey to Cabo do Roca, the westernmost point of mainland Europe, where you can take in the stunning ocean views.

In the afternoon, we’ll head north to Porto, where we’ll check into a lovely hotel along the Douro River. After some time to freshen up, we’ll enjoy a delicious dinner at a local restaurant, followed by an optional evening walk along the river in Porto’s safe and charming atmosphere.

Highlights

• Visit to Pena Palace: Explore the magical summer residence of the Portuguese monarchy in Sintra.
• Lunch in Sintra: Savor a relaxing meal in this charming town before continuing our journey.
• Cabo do Roca: Take in the breathtaking views from the westernmost point of mainland Europe.
• Scenic Drive to Porto: Enjoy the ride to Porto and check into a riverside hotel along the famous Douro River.
• Dinner in Porto: End the day with a wonderful dinner at a local restaurant, followed by an optional evening stroll along the river.

Fun Fact: Cabo do Roca is not only the westernmost point of mainland Europe, but it was also considered by ancient Romans to be the end of the world!

Day Four: Famous Ponte Dom Luis Bridge and a Little Harry Potter Magic

After a delicious breakfast at 9:00 AM, we’ll set off at 10:00 AM for a walking tour of Porto, a city known for its dramatic beauty and rich history. Porto’s hilly streets offer stunning views, so be sure to wear comfortable shoes for exploring. We’ll cross the iconic Ponte Dom Luis Bridge, which spans more than 1,000 feet above the Douro River, providing postcard-perfect views of the city’s colorful rooftops and charming architecture.

As we navigate Porto’s streets, we’ll visit key landmarks with our local guide, including the famous Lello Bookstore, which inspired J.K. Rowling during her time in Porto and influenced her writing of Harry Potter. We’ll also stop by the historic São Bento Railway Station, renowned for its beautiful Portuguese tilework that tells the story of the country’s past.

After a day of exploring, we’ll enjoy another wonderful dinner at a local restaurant, savoring Porto’s rich culinary traditions.

Highlights

• Walking Tour of Porto: Explore the hilly, picturesque streets of Porto, with stunning views from the Ponte Dom Luis Bridge.
• Ponte Dom Luis Bridge: Cross this iconic bridge for breathtaking views of the Douro River and Porto’s skyline.
• Visit to Lello Bookstore: Step into the magical bookstore that inspired J.K. Rowling, filled with literary history.
• São Bento Railway Station: Admire the historic tilework in one of Portugal’s most beautiful train stations.
• Dinner in Porto: End the day with a delightful dinner at a local restaurant, experiencing the best of Porto’s cuisine.

Fun Fact: The Lello Bookstore, one of the world’s most beautiful bookstores, is said to have inspired parts of Hogwarts in the Harry Potter series!

Day Five: Wines and a Foodie Dream in the Douro Valley

Start the day with breakfast at 8 AM before we depart around 9:15 AM for a full-day adventure in the breathtaking Douro Valley, one of Portugal’s most scenic regions. The drive itself offers numerous opportunities for stunning photo stops as we make our way through the valley’s rolling hills and vineyards.

Our first stop is at the charming A&D Organic Winery, where we’ll be welcomed by the owners. You’ll tour the historic farmhouse and admire the beautiful Portuguese tilework that depicts traditional farming scenes. Dalina, the owner, will share her knowledge of organic practices, explaining how they use flowers between the grapevines to naturally manage weeds and pests without chemicals. After learning about their sustainable winemaking process, we’ll enjoy a delightful wine tasting in this serene, picturesque setting.

Next, we’ll head further up the valley for a late lunch at Cozhina do Clara, a cliffside restaurant known for its incredible food and breathtaking views. This will be our main meal of the day, giving us plenty of time to relax and savor the flavors of Portugal in a spectacular setting.

After returning to the hotel, you can unwind in the lovely courtyard with a light snack or a drink to end the day.

Highlights

• Scenic Douro Valley Tour: Enjoy a drive through one of Portugal’s most picturesque landscapes, a UNESCO World Heritage site.
• Visit to A&D Organic Winery: Tour a historic organic vineyard and learn about sustainable winemaking while enjoying a tasting.
• Lunch at Cozhina do Clara: Dine at a cliffside restaurant with fabulous food and stunning views of the valley.
• Evening Relaxation: End the day with a snack or drink in the peaceful courtyard at the hotel.

Fun Fact: The Douro Valley is one of the world’s oldest wine regions, known for its port wine and dramatic terraced vineyards carved into the hillsides!

Day Six: Madeira, Here We Come!

Start the morning with breakfast at 7:30 AM and enjoy some free time to take a last stroll along the River area near the hotel, capturing a few final photos of Porto’s beautiful surroundings. Be ready to depart for the airport at 9:45 AM, as we’ll be flying to the enchanting island of Madeira at 12:30 PM.

Madeira, a Portuguese territory known for its rich history, amazing food, and world-famous wines, is a lush paradise full of scenic mountain views and colorful flowers. After arriving, we’ll head to our stunning hotel, the PortoBay Mare, a true botanical wonderland. You’ll have time to explore the beautiful grounds, relax, or take a swim in the pool before dinner.

In the evening, we’ll enjoy an early dinner at a nearby Italian restaurant, where we’ll dine al fresco and take in the lush surroundings. Afterward, we’ll take a leisurely walk back to the hotel, enjoying the breathtaking views of Madeira.

Highlights

• Morning Stroll by the River: Enjoy a final walk along Porto’s scenic river before departing for the airport.
• Flight to Madeira: Experience the beauty of this lush Portuguese island.
• Check-In at PortoBay Mare: Explore the botanical gardens and relax at the pool of our beautiful hotel.
• Early Dinner: Savor a delicious Italian meal just a short walk from the hotel, enjoying the lush scenery of Madeira.

Fun Fact: Madeira is often called the “Island of Eternal Spring” due to its year-round mild climate and stunning displays of flowers that bloom across the island!

Day Seven: Exploring Funchal and Madeira Wine

Start your day with breakfast at 9 AM, overlooking the ocean and pool area—an idyllic setting to begin your morning. At 10 AM, we’ll meet our guide for a walking tour of Funchal, Madeira’s vibrant capital. You’ll visit the lively fish and produce markets, wander through historic streets, and see the once-thriving embroidery and lace-making factory that was key to Madeira’s economy.

We’ll then stop at Blandy’s, one of Madeira’s most famous wineries, for a short tour and a chance to see how Madeira wine is made, followed by a delightful wine tasting. Afterward, enjoy a delicious lunch in Old Town. Following lunch, take some free time to explore the gardens, shop, or stroll to the port to watch the cruise ships come in.

Later, we’ll regroup at the hotel before heading out for a special dinner with a surprise in the evening.

Day Eight: Cable Car Ride, Monte, and the Botanical Garden

Start your day with some relaxation by the pool or take a morning massage. For those looking to explore, enjoy a walk around the area. Mid-morning, we’ll embark on a cable car ride up the side of the mountain overlooking Funchal, with breathtaking views of the city and ocean.

Our destination is the town of Monte, where you’ll have time to explore its charming streets before we continue to the Botanical Garden, 3,000 feet above sea level. This incredible garden is home to exotic plants from around the world and offers stunning views of Madeira.

We’ll conclude the day with a delicious dinner in Old Funchal, surrounded by the beauty and history of the city.

Highlights

• Walking Tour of Funchal: Explore the markets, historic buildings, and artisanal heritage.
• Madeira Wine Tasting: Visit Blandy’s winery for a tour and tasting of the region’s famous wine.
• Lunch in Old Town: Enjoy a traditional meal in one of Funchal’s charming restaurants.
• Dinner with a Surprise: Savor a delightful evening with a surprise experience.
• Cable Car Ride to Monte: Soar above the city for scenic views before visiting Monte.
• Botanical Garden Visit: Discover exotic plants and breathtaking views at this garden high above Funchal.
• Relaxing Morning: Enjoy time by the pool, take a massage, or stroll the surrounding area.

Fun Fact: The cable car ride to Monte offers some of the most stunning views of Funchal and the Atlantic Ocean, making it one of Madeira’s top attractions!

Day Nine: 4×4 Jeep Adventure and Farewell Dinner

We’ll begin the day with breakfast together at 8:30 AM at the hotel before meeting our guides at 10 AM for an exciting day of exploration in 4×4 jeeps. Our adventure takes us through the stunning landscapes of Madeira, driving through Eucalyptus forests and climbing to a high point where you can enjoy views stretching 25 miles in every direction.

Along the way, we’ll make a few scenic stops, including a visit to a famous hillside café known for its unique, local specialty drink—perfect for savoring Madeira’s distinct flavors. This tour offers incredible photo opportunities as we explore the island from a fresh perspective.

We’ll return to the hotel in the early afternoon, giving you time to relax by the pool, take a stroll by the ocean, or pick up some last-minute souvenirs. In the evening, we’ll gather for a bittersweet farewell dinner, celebrating the unforgettable experiences shared throughout this trip.

Highlights

• 4×4 Jeep Tour: Ride through Eucalyptus forests and ascend to a viewpoint offering 25-mile panoramic views.
• Hillside Café Visit: Stop at a famous café to try a local specialty drink found only in Madeira.
• Scenic Stops: Enjoy stunning photo opportunities throughout the day.
• Free Afternoon: Relax by the pool, explore the hotel’s waterfront, or shop for souvenirs.
• Farewell Dinner: End the day with a fun and memorable dinner, celebrating the amazing journey we’ve had.

Fun Fact: Madeira’s unique Eucalyptus forests not only provide beautiful scenery but also fill the air with a refreshing, aromatic scent that adds to the island’s natural charm!

Day Ten: Departure Day

Our journey comes to an end as we prepare for an early departure. We’ll meet in the hotel lobby at 4 AM for the transfer to the airport, ensuring we catch the first flight back to Lisbon. From there, you’ll transfer to your respective flights and begin your journey back home to the USA.

Highlights

• Early Morning Departure: Meet at 4 AM for the transfer to the airport in Madeira.
• Flight to Lisbon: Catch the earliest flight back to Lisbon before your onward journey home to the USA.

Fun Fact: Lisbon Airport is one of the busiest in Europe, connecting travelers from all over the world to Portugal’s beautiful landscapes and rich culture!

Note: This itinerary serves as a general guide to what we will be doing, seeing, and eating, with the final version provided approximately two weeks prior. The published itinerary is an example and may be adjusted to include accommodations, tours, or restaurants of comparable quality to ensure the best experience.