Lisbon & The South Side Wine Regions Private Luxury Tour

A Guide to the Lisbon & The South Side Wine Regions Private Luxury Tour

Hey there, fellow traveler. If you’re dreaming of a seamless way to explore some of Portugal’s most beautiful landscapes, historic towns, and fabulous wineries without the hassle of planning every detail, then this Lisbon & The South Side Wine Regions Private Luxury Tour might be just what you need. While I haven’t done this particular trip myself, I’ve looked into what it offers and heard from folks who’ve been, and honestly, it sounds like a well-rounded, relaxed way to experience a different side of Portugal—especially if you like your days filled with scenic views, good wine, and history.

What I love about this tour? First, the flexibility to choose between two regions—Setúbal or Alentejo—means you can tailor your experience based on your interests. Second, traveling in a private, luxury vehicle with a knowledgeable guide means you get to relax and enjoy the sights without worrying about navigating or coordinating transport. That makes a big difference when you want to unwind and truly take in the scenery and culture.

One thing to keep in mind is that this is a two-day spread, so it’s not a quick day trip—perfect if you want a leisurely experience, but less ideal if your schedule is tight. Also, note that lunch, entrance fees, and inside visits to monuments aren’t included, so some extra planning or budget is needed if you want to go inside sites or dine at certain stops.

Overall, if you’re someone who values comfort, personalized experiences, and a good mix of cultural, natural, and wine-tasting adventures, this tour could be a fantastic pick. It’s especially suitable for couples, small groups, or friends who want to enjoy Portugal’s south-side treasures without the stress of self-driving or strict schedules.

Key Points

• Flexible regional options allow you to choose between Setúbal or Alentejo.
• Private luxury transportation ensures comfort and ease of movement.
• Two-day itinerary offers a relaxed pace, avoiding rushes.
• Includes wine tastings and scenic stops that highlight natural beauty, history, and gastronomy.
• Not a guided tour inside monuments but plenty of time for exploration and explanation outside.
• Pick-up and drop-off at your Lisbon hotel make it convenient.

What to Expect from This Tour

This experience is designed to give you a broad yet detailed look at some of Portugal’s southern charms. Over two days, you’ll visit iconic landmarks, sample local wines, and enjoy the natural vistas that make this region so special. The tour is private, so you’re not sharing with strangers—your small group (or family) gets the full attention of your guide and driver, which makes every stop more personalized.

The tour begins early, with pickup around 9 am, and the itinerary is flexible—your guide will adapt to traffic and weather, which means fewer disappointments and more quality time at each site.

Day 1: From Lisbon to Setúbal and Arrábida

The Famous Lisbon to the South Side Bridge

Your journey kicks off with a scenic drive across the well-known bridge connecting Lisbon to the south. It’s a classic way to get a panoramic view of the river and cityscape, setting the tone for the scenic drive ahead.

Santuario Nacional de Cristo Rei

Your first stop is the Cristo Rei statue, an impressive monument inspired by Rio’s Christ the Redeemer. Construction began back in 1949, and the views from here are panoramic—perfect for snapping photos. While admission isn’t included, the spot itself is worth seeing for its grandeur and perspective on Lisbon.

Castelo de Palmela

Next, you’ll head to the Palmela castle on one of the highest points in the Serra da Arrábida. It was strategically placed for defense, so you can imagine what it looked like in medieval times. The views over the surrounding countryside are stunning, and the included ticket means you can explore the castle’s walls and perhaps some of the history inside.

Parque Natural da Arrábida

This natural park is a highlight. Located right by the sea between Setúbal and Sesimbra, it’s a photographer’s dream—chalk cliffs, blue waters, lush greenery, and mountain trails. You’ll get about an hour here, which is enough to soak in the scenery or take a quick walk.

Sesimbra

This fishing village is one of Portugal’s oldest, with a charming, laid-back vibe. It’s a perfect spot for a quick stroll through narrow streets or just to enjoy the fresh sea air. It’s free to wander, and many find it’s a peaceful, authentic stop.

Winery Visit at Jose Maria de Fonseca

The day wraps up with a visit to one of Setúbal’s most renowned wineries. The wine tasting session here has garnered praise—“What a fantastic day,” one reviewer said—thanks to their excellent selection and friendly staff. The visit lasts about an hour and a half, giving you time to sample various wines and learn about the region’s viticulture. The winery’s reputation and the quality of tastings make this a real highlight.

Day 2: Exploring Évora and the Alentejo

Évora, a UNESCO World Heritage Site

The second day starts with a trip to Évora, a city packed with history dating back to Roman times. It’s like walking through an open-air museum with well-preserved ruins, medieval streets, and historic structures. You’ll get an hour to explore, so plan your walk to include key sights like the Roman temple and city walls.

Aqueduto da Água de Prata & Muralhas de Évora

The aqueduct, rebuilt in 1537, supplied fresh water to the city and is an impressive sight against the skyline. You’ll also walk along the defensive walls that once protected Évora—and still stand as a testament to its storied past.

Evora Cathedral & Templo Romano de Evora

The cathedral on the city’s highest point offers a view and a chance to appreciate its architecture—though entry fees aren’t included, and some may prefer just to admire from the outside. The Roman temple, known as the Templo de Diana, offers a snapshot of the city’s ancient roots.

Chapel of Bones

A visit to this 17th-century chapel is both haunting and fascinating. Built by Franciscans, the chapel’s interior is lined with skulls and bones—an unmissable stop for those interested in Portugal’s macabre side and reflections on mortality.

Praça do Giraldo & Wine Tasting

You’ll spend some downtime at the city’s lively central square, soaking in the atmosphere. Later, you get to visit a renowned Alentejo winery, choosing one of a selection of top-rated options. This is another highlight, especially if you appreciate a good wine accompanied by local snacks or tapas—“the wine selection is excellent,” noted a reviewer.

What’s Included and What to Keep in Mind

The tour covers private transportation, a knowledgeable guide, and insurance, which all contribute to a stress-free experience. Bottled water is provided, and hotel pickups are available within Lisbon, making planning easier.

However, lunch and entrance fees are not included, so you might want to budget for meals or additional site visits if you want to explore further inside monuments. The tour is fully customizable in terms of the regions you visit, and the itinerary could shift depending on traffic or weather conditions.

It’s a great option if you love a mix of natural beauty, cultural sights, and wine, all wrapped into a relaxed two-day experience. Be sure to wear comfortable shoes, as there’s a fair bit of walking—and some uneven surfaces in historic sites.

Who Would Love This Tour?

This experience is best suited for couples, friends, or small groups who want a private, relaxed way to see Portugal’s south side. It’s particularly appealing if you’re interested in wine, history, and scenic landscapes. People who prefer to leave the logistics to someone else will find this setup ideal, especially with the flexibility to choose regions.

Travelers looking for a structured, yet leisurely, way to explore without the pressure of a packed schedule will appreciate the spread-out nature of this two-day tour. If you’re after insider tips from a knowledgeable guide and a chance to taste some of Portugal’s best wines in beautiful settings, this tour hits the mark.

The Sum Up

All in all, this private luxury tour offers a well-balanced mix of scenic drives, historical sights, and wine tastings, with the convenience of private transport and a flexible itinerary. The ability to choose between two regions, combined with the relaxed pace over two days, makes this a strong option for travelers who want to enjoy Portugal’s south side without rushing.

It’s particularly suited for those who value comfort, personalized attention, and an authentic taste of local culture and landscapes. Whether you’re a wine lover, history buff, or just want a stress-free way to experience some of Portugal’s most beautiful spots, this tour delivers a memorable experience.

Keep in mind that the experience’s value lies in the convenience and customization—if you’re okay with paying extra for entrance fees and some meals, it’s a smart way to explore with a knowledgeable guide.

Frequently Asked Questions

Is this tour suitable for families or children?
While the tour is private and can be tailored, it involves a good amount of walking and visiting historic sites, so it’s more suited for older children or teens who enjoy history and outdoor exploration. No specific family-friendly features are highlighted.

What regions can I choose to visit?
You can select between the Setúbal Wine Region and Arrabida Natural Park, or the Alentejo Wine Region and Évora Medieval City.

How long is each day of the tour?
Each day lasts approximately 8-9 hours, with a relaxed pace and plenty of time at each stop, so expect an early start around 9 am and a full, engaging day.

Are meals included?
No, lunch and other food are not included, but there’s time built into the itinerary for you to enjoy local cuisine at your own expense.

Are entrance tickets included?
Some sites, like the castle or inside monuments, require tickets which are not included. However, the winery visit and city sights outside monuments are included.

Can I customize the itinerary?
Yes, the itinerary can change based on traffic or weather conditions, and the regions you select are flexible.

What is the price for this tour?
The cost is roughly $203 per person, which covers private transport, guide, insurance, bottled water, and the planned stops. Additional expenses for food, entrance fees, or extra activities are on you.

If you’re looking for a well-paced, private way to experience Portugal’s southern wonders with a touch of luxury and flexibility, this tour could very well be your next memorable trip.