Lisbon! Leveraging AI to Plan our First Visit

Charles Jordan
May 14
13 min read

We're planning our first visit to Lisbon! We have been thinking about this for a while and really dragged our feet on the flight purchase. So, we're finally planning everything else.

To be fully transparent, last fall we had been considering a trip to Lisbon and had don a significant amount of manual research. So, we already had some knowledge of Lisbon before we started writing this article. And we'll have lots to share after we visit. We reached out to a friend for a hotel recommendation. The one he gave us was unavailable for all of our dates. So, on April 19, 2025, we went to the Microsoft CoPilot app and asked about hotels in Lisbon. The conversation took us down a rabbit hole, providing lots of information. We thought we'd share this with you as a potential method for planning your own adventures, wherever they might take you.

Our next step will be to verify as much of the information as possible, make a few key reservations, and plot it all on a map so we have a visual and something to use as we plan each day of our adventure. Following is the conversation, edited in spots to redact certain details or amend our sloppy prompts. Enjoy!

Prompt: We're planning a trip to Lisbon... We're looking for a hotel in the same area as the Olissipo saldanha but for no more than half the price. Please provide 5-10 recommendations.

Here are some hotels near the Olissipo Saldanha in Lisbon that are more budget-friendly and could fit your criteria:

Budget-Friendly Hotels

America Diamonds Hotel

Address: R. Tomás Ribeiro 47, Lisbon, 1050-226

Rating: 4/5 (Tripadvisor)

Features: Comfortable rooms, central location, and good value.

Stay Hotel Lisboa Centro Saldanha

Address: R. Gomes Freire 130, Lisbon, 1150-180

Rating: 3/5 (Tripadvisor)

Features: Affordable rates, basic amenities, and proximity to Saldanha.

Exe Saldanha

Address: Avenida dos Defensores de Chaves 5, Lisbon, 1000-109

Rating: 4.5/5 (Tripadvisor)

Features: Clean and modern rooms, excellent service, and convenient location.

Hotel White Lisboa

Address: Avenida da República 9, Lisbon, 1050-185

Rating: 4.5/5 (Tripadvisor)

Features: Stylish design, great service, and close to public transport.

Lumen Hotel & The Lisbon Light Show

Address: Rua Sousa Martins 20, Lisbon, 1050-217

Rating: 4.8/5 (Tripadvisor)

Features: Unique light show experience, modern decor, and central location.

These options should provide a mix of affordability and convenience while keeping you close to the Olissipo Saldanha area. Let me know if you'd like help narrowing down the choices or booking! 🚀

Prompt: Are these hotels in a good location for a first time tourist visitor?

Yes, these hotels are in locations that are convenient for a first-time visitor to Lisbon. They're all near Saldanha, a central district known for excellent public transportation connections, making it easy to explore the city's major attractions. Here's why this area works well:

Proximity to Attractions: You're a short metro ride away from historic sites like the Baixa district, Alfama, Belém, and Chiado.

Ease of Transportation: The Saldanha metro station connects to both the Red Line (direct to Lisbon Airport) and the Yellow Line, which takes you closer to downtown.

Safety and Amenities: Saldanha is quieter than the tourist-heavy districts, but it offers restaurants, shops, and cafés, ideal for unwinding after a day of sightseeing.

If you'd prefer to stay closer to the historic center for walking access to landmarks, you might consider neighborhoods like Baixa or Alfama, though they tend to be pricier. These hotels in Saldanha strike a great balance for cost-conscious travelers who want convenience and comfort. Let me know if you'd like further advice! 🚇✨

Prompt: Is there a metro pass that covers a five day visit? how much does it cost?

Yes, Lisbon offers a Navegante Card, which can be loaded with a monthly pass or prepaid credit for flexible travel. However, for a five-day visit, the most practical option is the 24-hour Carris/Metro pass, which costs €7.00 per day2. This pass provides unlimited travel on the metro, buses, and trams for 24 hours after the first validation.

For a five-day stay, you can purchase five separate 24-hour passes, totaling €35.00. Alternatively, you can use the Zapping option, which deducts fares from prepaid credit at a reduced rate of €1.66 per metro journey3.

Let me know if you'd like help planning your metro routes or exploring Lisbon! 🚇✨

Prompt: What about walking? Tell me what it would be like to walk from Saldanha to Baixa or Saldanha to Alfama or from Saldanha to Baixa to Alfama and back to Saldanha. Are any of these routes hilly? Can I combine walking and trams? I hear there's a famous tram I should take.

Walking in Lisbon is a fantastic way to explore the city, but it’s important to note that Lisbon is famously known as the "City of Seven Hills," so some routes can be quite hilly. Here's a breakdown of your walking options and how you can combine them with trams:

Walking Routes

Saldanha to Baixa:

Distance: About 2.5 km (1.5 miles).

Terrain: Mostly flat with some gentle inclines.

Experience: This route takes you through Avenida da Liberdade, a beautiful tree-lined boulevard with shops and cafes, leading to the heart of Baixa, Lisbon’s downtown area.

Saldanha to Alfama:

Distance: About 3.5 km (2.2 miles).

Terrain: Hilly, especially as you approach Alfama, which is known for its steep, narrow streets.

Experience: Alfama is the oldest district in Lisbon, with cobblestone streets, historic buildings, and stunning views. Be prepared for a workout as you climb towards landmarks like São Jorge Castle.

Saldanha to Baixa to Alfama and Back:

Distance: Approximately 8–9 km (5–6 miles) round trip.

Terrain: A mix of flat and hilly sections, with the steepest parts in Alfama.

Experience: This route offers a comprehensive tour of Lisbon’s highlights, but it’s a long walk, so comfortable shoes are a must.

Combining Walking and Trams

You can absolutely combine walking with Lisbon’s iconic trams to make your journey easier and more enjoyable:

Tram 28: This is the famous yellow tram that winds through Lisbon’s most picturesque neighborhoods, including Baixa, Alfama, and Graça. It’s a must-do for first-time visitors and a great way to navigate the hilly areas.

How to Use It: You can walk from Saldanha to Baixa, then hop on Tram 28 to explore Alfama and return to Baixa or Saldanha.

Amerigo Opinion: We've heard that Tram 28 was crowded and not worth the wait. But if you really want to do it you could get there before it opens and you might not find the lines. Also, apparently there are a few other old trams that follow a similar route.

Tips for Exploring Lisbon

Wear sturdy, comfortable shoes, as the cobblestone streets can be uneven. Carry a reusable water bottle to stay hydrated, especially if you’re walking uphill. Use a 24-hour Carris/Metro pass (€7.00/day) for unlimited tram rides, including Tram 28.

Let me know if you’d like help planning your route or finding specific tram stops! 🚶‍♂️🚋✨

Prompt: What can I expect the weather to be like during the week of may 12, 2025?

During the week of May 12, 2025, Lisbon is expected to have pleasant spring weather. Daytime temperatures will likely range from 57°F to 73°F (14°C to 23°C), with cooler evenings. May is generally a dry month, with only about 3 to 8 rainy days throughout the month, so you can expect mostly sunny or partly cloudy skies.

It’s a great time to explore the city comfortably, but I’d recommend packing a light jacket for the evenings and an umbrella just in case. Let me know if you’d like tips for activities or places to visit while you’re there! 🌞✨

Prompt: Sure! I'd like to know about the must see museums, parks, entertainment events, and even sporting events that will be happening during my visit.

Here’s a curated list of must-see attractions and events in Lisbon during the week of May 12, 2025:

Museums

Calouste Gulbenkian Museum - A world-class collection of art, from ancient Egyptian artifacts to modern masterpieces. Located near the Gulbenkian Garden, perfect for a relaxing stroll after your visit.

Tile Museum (Museu Nacional do Azulejo) - Dedicated to Portugal’s iconic decorative tiles, housed in a stunning 16th-century convent.

MAAT (Museum of Art, Architecture, and Technology) - A contemporary museum with a striking riverside location and rooftop views.

National Museum of Archaeology - Located in the Jerónimos Monastery, showcasing ancient artifacts from Portugal and beyond.

Parks and Gardens

Gulbenkian Garden - A serene oasis with ponds, sculptures, and shaded paths, ideal for a peaceful break.

Estrela Garden - A historic park with a charming gazebo, playgrounds, and lush greenery.

Ajuda Botanical Garden - A beautiful garden with exotic plants and stunning views over the Tagus River.

Entertainment Events

Fado Experience at Casa da Amália - Enjoy an intimate live Fado performance, a quintessential Portuguese music tradition.

Lisbon Boat Party - Dance the night away on a boat cruising along the Tagus River.

Living Van Gogh Exhibit - An immersive art experience showcasing Van Gogh’s works in a dynamic, digital format.

Sporting Events

While there are no major international sporting events listed for this week, you might catch a local football (soccer) match or explore Lisbon’s vibrant sports culture. Check with local stadiums like Estádio da Luz or Estádio José Alvalade for schedules.

Let me know if you’d like help planning your itinerary or booking tickets for any of these activities! 🚀✨

Prompt: What if I just want to witness Fado organically in the streets? Is that possible?

Yes, experiencing Fado organically in the streets is absolutely possible in Lisbon—particularly in the Alfama and Bairro Alto neighborhoods. These areas are known for their intimate connection to the soulful genre, and you might stumble upon spontaneous performances in small courtyards, taverns, or even by local musicians sharing their talent casually.

Tips for Finding Street Fado

Alfama District: Known as the birthplace of Fado, its winding streets often host impromptu performances outside taverns or during evening strolls.

Bairro Alto: Famous for nightlife, you might hear Fado spilling out from traditional bars or even see performers serenading passersby in the early evening.

Events and Festivals: Sometimes, Fado-themed festivals or events pop up in May, where you'll find outdoor concerts or street performers.

For the most authentic experience, embrace the meandering charm of these neighborhoods and follow the music—it's a magical way to connect with Lisbon's spirit. Let me know if you'd like more insight or suggestions! 🎶✨

Prompt: Will this be mostly during certain times of day? what daily time frame should I go to increase my chances of witnessing live Fado?

The best time to experience street Fado performances or spontaneous musical moments in Lisbon is typically in the early evenings and nighttime, as the city comes alive with music and culture after the day's bustle fades. Here's a more detailed breakdown:

Recommended Time Frames

7:00 PM to Midnight: This is prime time for Fado performances, especially in neighborhoods like Alfama and Bairro Alto. Traditional Fado bars and taverns also start hosting live music around this time.

During Festivals or Special Events: If there are Fado-themed events or festivals during your visit, performances might extend into the afternoon or late at night.

Sundown to Early Evening: In Alfama, you might catch informal gatherings or street musicians tuning up as the day winds down.

To increase your chances, start your walk around Alfama or Bairro Alto just before sundown, and let the streets guide you to the music. Let me know if you'd like recommendations for specific spots to start exploring! 🎶✨

Prompt: Yes. Please provide specific spots. Also, let me know if these neighborhoods are generally safe and what precautions I should take.

Specific Spots for Street Fado

Here are some great places to explore for organic Fado performances:

Alfama District:

Largo do Chafariz de Dentro: A small square where you might find street musicians performing Fado.
Rua dos Remédios: Known for its traditional taverns and occasional live music spilling into the streets.
Miradouro de Santa Luzia: A scenic viewpoint where you might encounter musicians playing Fado against the backdrop of stunning views.

Bairro Alto:

Rua da Barroca: A lively street with bars and taverns that often host impromptu Fado performances.
Tasca do Chico: A famous spot for authentic Fado, where you can enjoy music in a casual setting.

Safety in Alfama and Bairro Alto

Both neighborhoods are generally safe for tourists, but here are some precautions to ensure a smooth experience:

Alfama: While it’s safe, the narrow, winding streets can feel isolated late at night. Stick to well-lit areas and avoid wandering alone in secluded spots.

Bairro Alto: Known for its nightlife, it can get crowded and lively. Be mindful of your belongings, as pickpocketing can occur in busy areas.

Precautions:

Stay Alert: Keep an eye on your surroundings, especially in crowded areas.

Avoid Flashing Valuables: Don’t display expensive items like jewelry or electronics.

Use Trusted Transportation: If traveling late at night, opt for licensed taxis or rideshare apps.

Stick to Main Streets: Avoid dark alleys or isolated areas, especially after midnight.

Let me know if you’d like more tips for exploring Lisbon or finding hidden gems! 🎶✨

Prompt: Is Uber available in Lisbon? Is there an app for local licensed taxis?

Yes, Uber is available in Lisbon and operates 24/7. You can use the app to request rides, including options like UberX, UberXL, and Uber Black. It's a convenient and reliable way to get around the city.

For local licensed taxis, the Free Now app (formerly MyTaxi) is a popular choice. It allows you to book regular taxis, schedule rides in advance, and even compare prices. Another option is Bolt, which works similarly to Uber and is widely used in Lisbon.

Let me know if you'd like help navigating these apps or planning your transportation! 🚖✨

Prompt: What are some typical foods I should look for on menus? What about local beverages like beers, wines, liquors/cordials, and cocktails? Please recommend low to moderately priced restaurants and bars where I can sample authentic versions. Since I'll be traveling alone, I'll prefer more casual situations like bars and market stalls?

Typical Foods to Try in Lisbon

Lisbon’s culinary scene is a delightful mix of traditional Portuguese flavors. Here are some must-try dishes:

Pastéis de Nata: Custard tarts with a flaky crust, best enjoyed with a shot of espresso (bica).

Bacalhau à Brás: Salted cod mixed with eggs, onions, and fried potatoes.

Grilled Sardines: A seasonal favorite, often served with boiled potatoes and salad.

Caldo Verde: A comforting kale and potato soup, often paired with chouriço (Portuguese sausage).

Bifana: A simple yet delicious pork sandwich marinated in garlic and spices.

Prego: A steak sandwich, sometimes served with mustard or garlic butter.

Seafood Rice (Arroz de Marisco): A rich and flavorful dish loaded with fresh seafood.

Local Beverages

Beers: Try Sagres or Super Bock, Portugal’s most popular lagers.

Wines: Sample Vinho Verde (a light, slightly fizzy white wine) or Port Wine (a sweet fortified wine).

Liquors/Cordials: Don’t miss Ginjinha, a cherry liqueur often served in small shops or bars.

Cocktails: Look for Caipirão, a Portuguese twist on the Brazilian caipirinha, made with Licor Beirão.

Casual Restaurants and Bars

Here are some low to moderately priced spots where you can enjoy authentic food and drinks in a relaxed setting:

Time Out Market

Location: Mercado da Ribeira, Av. 24 de Julho, Lisbon.

Features: A bustling food hall with stalls offering a variety of Portuguese dishes and drinks.

Rui dos Pregos - Docas

Location: Passeio Doca De Santo Amaro, Lisbon.

Features: Casual dining with Portuguese classics like bifanas and seafood.

Dote República

Location: Av. da República 51C, Lisbon.

Features: Affordable Portuguese dishes, including petiscos (small plates).

DegustAR Lisboa

Location: R. Latino Coelho 63A, Lisbon.

Features: A cozy spot for traditional Portuguese flavors and Alentejana cuisine.

Havana Soul

Location: Doca De Santo Amaro, Lisbon.

Features: A lively bar with Latin and African rhythms, plus cocktails and casual bites.

Don Pablo

Location: R. Silva Carvalho 167, Lisbon.

Features: Creative takes on Portuguese petiscos in a welcoming atmosphere.

Market Stalls

For an even more casual experience, visit Mercado de Campo de Ourique or Mercado da Ribeira. These markets offer fresh, affordable food and drinks, perfect for solo travelers looking to mingle with locals.

Let me know if you’d like help planning your food adventure or finding specific dishes! 🍴✨

Prompt: What are some popular cocktails served in Lisbon with Ginjinha?

Ginjinha, the iconic Portuguese cherry liqueur, is traditionally enjoyed on its own, but it also makes a fantastic base for cocktails. Here are some popular Ginjinha-based cocktails you might find in Lisbon:

Ginja Sour: A twist on the classic whiskey sour, made with Ginjinha, lemon juice, and a touch of sugar syrup, shaken with ice and served in a chilled glass.

Ginja Tonic: A refreshing mix of Ginjinha and tonic water, garnished with a slice of orange or a sprig of mint.

Ginja Royale: A celebratory cocktail combining Ginjinha with sparkling wine or champagne, often served in a flute glass.

Ginja Mule: A Portuguese take on the Moscow Mule, featuring Ginjinha, ginger beer, and lime juice, served over ice in a copper mug.

Chocolate Ginja Martini: A decadent mix of Ginjinha, chocolate liqueur, and cream, shaken and served in a martini glass.

If you're looking to try these, some bars in Lisbon might offer creative Ginjinha cocktails, or you can ask bartenders to craft something unique with Ginjinha as the base. Let me know if you'd like recommendations for bars where you can enjoy these! 🍒🍹✨

Prompt: If I say "Por favor, um Ginja Tonic" are you sure they won't mistakenly give me a Gin Tonic?

That's a great point to clarify! While "Ginja Tonic" is distinct from "Gin Tonic," the similarity in pronunciation could lead to confusion. To ensure there's no mix-up, you can add a bit more detail when ordering. For example:

"Por favor, um Ginja Tonic, com Ginjinha." (Poh fah-VOR, oon ZHEEN-zha TAW-nee-k, kohm ZHEEN-zhee-nyah.) This specifically mentions Ginjinha, the cherry liqueur, making it clear you're not asking for gin.

Bartenders in Lisbon are generally familiar with Ginjinha-based cocktails, especially in bars that specialize in Portuguese drinks. If you're at a more general bar, a little clarification like this will go a long way! Let me know if you'd like further tips. 🍒✨

Prompt: Please list some bars that specialize in Portuguese drinks that are not touristy.

Here are some non-touristy bars in Lisbon where you can enjoy authentic Portuguese drinks:

Augusto Lisboa

Location: Rua de Santa Marinha nº26, Lisbon, 1100-491

Features: A cozy spot with a focus on Portuguese wines and Ginjinha.

Love Lisbon Restaurant and Bar

Location: R. José António Serrano, Lisbon, 1100-143

Features: Offers a variety of Portuguese drinks in a relaxed atmosphere.

Fado & Wine

Location: R. da Assunção 15, Lisbon, 1100-619

Features: Combines Fado music with Portuguese wines and liqueurs.

DaPrata52

Location: Lisbon, 1100-419

Features: Known for its intimate setting and selection of Portuguese beverages.

Time Out Market Lisboa

Location: Avenida 24 de Julho 49, Lisbon, 1200-224

Features: While slightly more popular, it has stalls offering authentic Portuguese drinks, including Ginjinha.

These spots are great for sampling local flavors in a more casual and authentic setting. Let me know if you'd like help planning your visit or finding specific drinks! 🍷✨

Prompt: Can you group all of these restaurants and bars by neighborhood (e.g. Baixa, Alfama, Saldanha)?

Here's a list of the mentioned restaurants and bars, grouped by neighborhood for clarity:

Saldanha