Here’s an easy way to use tools such as ChatGPT to plan a trip around your specific creative or other interests in ways that will amaze you

This post is actually about how to use AI for trip planning. If that’s all you care about, skip this first section and go to “How to use AI to plan your trip” section below.

But for the rest of you, here’s the context for all this.

Enhance your creativity for better trips

I’ve got two new books around creativity and branding for artists, writers, and other creatives coming out in October. More on both soon.

But I tell you all this to call out those of you who think, “Great. More creativity stuff. I just want the goods on travel.” But here’s my belief: Even if you don’t think of yourself as creative, I can promise you that the more you improve your creative abilities, the better trips you’ll have. Promise. Cross my heart and, well, you know the rest.

Why? Because travel itself is a creative act, one of constant problem solving and problem finding. Unless you’re in an all-inclusive resort or on a cruise or trip where every detail is done for you by others, you need to be on creatively to get the most from your trip.

While there are a zillion or so ways creativity can improve your trips, I’ll focus on two here. The first relates to using your creative abilities to solve problems as we just saw. But the second is this: Using your trip to increase the joy of your creative interests. And to illustrate, I’m going to give you an example of how I use AI to do that.

How to use AI to plan your trip

Yep, here’s the section some of you have been waiting for.

Later this year, my wife and I will be traveling to Portugal. So here are some of the prompts I’m using (and the results) to incorporate creative interests/hobbies into our planning. I’ll focus only on Lisbon rather than the whole trip to keep this shorter.

For those of you concerned about what generative AI tools such as ChatGPT do with your data or those new to the tool, I’m using the Incognito window of the Chrome browser so that I’m not signed into my ChatGPT account. This keeps the results from tracking my prompts (well, at least in theory) and reflecting any past requests. This is also more likely to be what you’d experience if trying this for the first time. Here goes.

After going to chatgpt.com I put into the “Ask anything” field the following prompt:

“I’m planning a trip to Lisbon, Portugal soon. I will be there for three days. Please provide a list of things to do that are not typical tourist activities, that reveal hidden gems, and that allow me to explore these creative interests: urban sketching, knitting, enjoying atmospheric cafes, finding quiet places for journaling and reflecting, and interesting workshops that relate to local artisan specialties.”

Here was the response which took less than ten seconds. From this point on, I’ll continue to write out my comments in italics so you can differentiate them from those of ChatGPT.

ChatGPT’s response for trip planning:

That sounds like an amazing trip! Lisbon is full of charm, and it has a fantastic mix of artistic, quiet, and unique spots that will allow you to get deep into your creative passions. I’ve compiled a list of activities and places that cater to your interests in urban sketching, knitting, journaling, and discovering local craftsmanship—without falling into the typical tourist traps.

1. Urban Sketching & Hidden Architecture

Lisbon is a vibrant city with an eclectic mix of old and modern, perfect for urban sketching.

• Alfama District: Wander through the narrow, winding alleys and you’ll find hidden courtyards, colorful facades, and laundry flapping in the breeze. It’s a sketcher’s paradise with plenty of contrasts—traditional and contemporary architecture blended with street art.
• LX Factory: A trendy area in the Alcântara district, formerly an industrial complex, now home to artists’ studios, galleries, and alternative shops. There’s so much interesting urban texture here to capture.
• Graça Viewpoint (Miradouro da Graça): From this hilltop spot, you get sweeping views of Lisbon. It’s a peaceful place to sketch and reflect, away from the hustle and bustle.

2. Knitting & Textile Enthusiasts

Lisbon has a great local textile culture that you can explore if you’re into knitting and crafts.

• A Parada do Mercado: This is a quaint, hidden yarn shop near Campo de Ourique. It has a wonderful collection of local and imported yarns, plus the owner is very knowledgeable and welcoming.
• Burel Factory: Burel is a traditional wool fabric unique to Portugal, and this factory in the Serra da Estrela region offers workshops where you can learn about the making of this iconic fabric, which is used in clothing, bags, and interior design.
• Arte de Linha: A small but cozy yarn store in the city center, specializing in Portuguese wool and knitting supplies. It’s an excellent spot to pick up some local yarn and chat with fellow knitting enthusiasts.

3. Atmospheric Cafes & Cozy Spots for Journaling

Lisbon’s café scene is perfect for finding spots to relax, write, and enjoy a cup of coffee or tea.

• Café São Bento: A cozy spot near the São Bento Palace, this café has a vintage vibe, great for sitting quietly with a journal and soaking in the atmosphere. The intimate setting makes it feel like a hidden gem.
• Manteigaria: While it’s famous for its pastéis de nata, it’s also a great place for a quiet moment, especially at the location in the LX Factory. You’ll find a peaceful atmosphere perfect for journaling while nibbling on a custard tart.
• Fábrica Coffee Roasters: A minimalist café where you can sip on expertly brewed coffee and enjoy a laid-back vibe. This place is often quieter in the mornings, ideal for journaling or just reflecting.
• Livraria Bertrand: The world’s oldest bookstore, located in the Chiado district. Beyond the books, there’s a small café inside, giving you the chance to sit and write or sketch in a literary haven.

4. Quiet Spots for Reflection and Contemplation

These tranquil locations offer the perfect setting for introspection or just taking in the surroundings.

• Jardim da Estrela: A lovely, less crowded park with benches nestled between lush greenery, a perfect spot for journaling or just being still.
• Jardim Botânico da Universidade de Lisboa: This botanical garden is located slightly off the beaten path. The calm atmosphere, beautiful plant life, and quiet nooks are ideal for reflection.
• Monastery of São Vicente de Fora: While many tourists miss this spot, it’s a peaceful sanctuary with historical value. There’s a serene cloister and a rooftop with amazing views of Lisbon.

5. Workshops and Artisan Experiences

Discover the craftsmanship behind Lisbon’s artisanal traditions with unique workshops.

• Workshop of Portuguese Tiles (Azulejos): Take a hands-on workshop where you can learn about the history and techniques behind the famous Portuguese tiles. You’ll even have a chance to create your own small piece.
• Cork Workshop: Portugal is the world’s largest producer of cork, and there are several places in Lisbon where you can try a cork-based workshop—whether it’s making small goods like wallets or bags, or learning about the sustainable methods behind cork production.
• Ceramics Workshop at Fábrica Sant’Anna: This historic ceramic factory offers pottery workshops where you can learn traditional Lisbon ceramic techniques. It’s a relaxing way to connect with local craftsmanship.
• Lisbon Art & Craft Tours: These tours are designed to introduce visitors to Lisbon’s artisans—potters, weavers, and fabric artists. Some even offer mini workshops, where you can try your hand at traditional crafts.

6. Off-the-Beaten-Path Galleries and Art Spaces

Lisbon has a burgeoning art scene, full of local creators, many of whom offer workshops or experiences.

• Museu de Arte, Arquitetura e Tecnologia (MAAT): Although it’s a museum, it’s known for having some fantastic contemporary art exhibits. The space itself is stunning, and the museum often has workshops focused on design and new media.
• Atelier-Museu Júlio Pomar: A small museum dedicated to the works of local artist Júlio Pomar. The space often hosts intimate art workshops and has an airy, creative vibe.
• Centro de Arte Moderna Gulbenkian: The museum itself is a peaceful space for contemplation, but there are also occasional art workshops and live events that might interest you.

7. Exploring Lisbon’s Artisan Markets

Lisbon has some unique markets where you can find locally made goods and meet artisans.

• Feira da Ladra: Lisbon’s famous flea market in Alfama. While you can find antiques, there’s also a range of handmade and vintage textiles, art, and crafts that can inspire your sketching or knitting projects.
• Mercado de Campo de Ourique: This market offers a mix of gourmet food, artisan products, and local goods. It’s quieter and less touristy than Mercado da Ribeira, so you’ll have a more peaceful experience.

Bonus Tip:

• Join a local art collective or creative group: Some smaller, more intimate art spaces in Lisbon allow visitors to drop in and join group sessions or creative gatherings. Keep an eye out for places like Pensão Amor (a quirky bar/gallery) or The Creative Embassy, which connects creatives and artists through events and workshops.

Lisbon is full of hidden gems that cater to creatives, and the key is wandering off the typical tourist path. Whether you’re sketching the colorful streets, journaling in a quiet park, or learning from local artisans, you’re sure to have a deeply enriching experience. Let me know if you’d like any more details on any of these places or activities!

Summary of the findings

That was the original response. This hopefully gives you a sense of how easy it is to use AI to connect your creative interests (or any interests, really: you could ask about sports, history, food, or other areas as well) to your trip. It would have taken me hours to have pieced together all the insights and recommendations here had I just used a traditional search.

Going deeper

You can stop reading here if you want, since this gets quite long. But if you’re really interested, keep going because next, if there were any areas I wanted more details about, I could ask ChatGPT to expand. Also, I would be sure to look up any of the places of interest using a more traditional Google search or ask Gemini or Claude.ai to confirm that all the places noted are still active businesses. I’ve found out the hard way that not all of ChatGPT’s suggestions are up to date or accurate, so always double check.

In addition, I would then likely ask for links to some of the workshops or directions. But here’s a specific example asking for more yarn shops:

You said:

Please provide additional yarn shops to visit.

ChatGPT said:

Absolutely! Lisbon has a number of charming yarn shops that cater to knitting, crochet, and textile enthusiasts. Here are a few more yarn shops you should check out:

1. Lanas e Linhas

• Location: Rua dos Prazeres 49, Lisboa
• A cozy shop tucked away in the Mouraria neighborhood, Lanas e Linhas is a haven for yarn lovers. They specialize in a wide variety of yarns, from Portuguese and European brands to more exotic fibers. You can find both luxurious and affordable options here. The owner is very knowledgeable, and the shop also hosts knitting and crochet workshops.
• Highlight: Portuguese wool and unique, high-quality yarns.

2. Linha 2

• Location: Rua da Boavista 72A, Lisboa
• A smaller, local yarn shop with a welcoming atmosphere, Linha 2 is known for its selection of premium yarns and knitting accessories. They focus on high-quality fibers and sustainable, eco-friendly options. The shop also has a selection of books for knitting and crochet inspiration.
• Highlight: Eco-friendly, sustainable yarns and a helpful, creative atmosphere.

3. Café do Bairro – Yarn and Café

• Location: Rua de São João da Praça 12, Lisboa
• This is a quirky combination of a café and yarn shop! Café do Bairro is located in the heart of the Alfama district. Besides offering great coffee, they also stock a selection of yarns perfect for your knitting projects. It’s a cozy spot to sit, enjoy a warm drink, and get some knitting done in a charming environment.
• Highlight: Enjoying a coffee while knitting in a unique and cozy setting.

4. Punto y Madeja

• Location: Rua da Madalena 153, Lisboa
• Known for its large selection of yarns, Punto y Madeja offers a mix of classic and modern fibers, including cotton, alpaca, and wool. The shop is quite welcoming to knitters of all levels, and they also have knitting and crochet workshops available.
• Highlight: A wide variety of yarns, including international and boutique brands.

5. A Confeitaria das Lãs

• Location: Rua da Rosa 254, Lisboa
• A delightful yarn store in the Bairro Alto district, A Confeitaria das Lãs has a whimsical atmosphere with a great selection of yarns, including hand-dyed options and more specialized fibers. The store is also known for its friendly and knowledgeable staff who can help you with project ideas or troubleshooting.
• Highlight: Hand-dyed yarns and a creative, warm atmosphere.

6. Tricotô

• Location: Rua da Alegria 26B, Lisboa
• A cozy yarn shop located in the center of Lisbon, Tricotô offers a good variety of yarns, including luxurious options like silk, alpaca, and merino wool. The store also focuses on providing materials for both beginners and seasoned knitters. They often have knitting kits and patterns, so you can easily pick up a project to take home.
• Highlight: Good selection of luxurious yarns and knitting kits for all skill levels.

7. Retrosaria Rosa Pomar

• Location: Rua da Penha de França 99, Lisboa
• Rosa Pomar is one of the most well-known yarn shops in Lisbon, and it’s especially popular with locals. They specialize in high-quality Portuguese yarns, including the traditional Burel wool. The shop has a unique, artisanal vibe and is a great place to learn more about local textile history. They often offer knitting workshops and courses for both beginners and more experienced crafters.
• Highlight: Portuguese yarns, including exclusive and locally sourced fibers, as well as workshops.

8. Lírios e Linhas

• Location: Praça do Comércio 61, Lisboa
• A small but wonderfully stocked yarn shop with a focus on fine yarns from both local and international makers. Lírios e Linhas offers a mix of high-end fibers, perfect for more intricate knitting and crochet projects. The shop also has a great selection of knitting needles and accessories, along with helpful advice for knitters and crocheters.
• Highlight: A refined selection of yarns and a calm, welcoming atmosphere.

9. Armazém das Lãs

• Location: Av. Magalhães Lima 3A, Lisboa
• Armazém das Lãs is a bit more spacious and has a wide selection of yarns for all types of knitting projects. It’s a more traditional yarn store, but you’ll find plenty of options for both fine crafts and more practical, everyday knitting projects. The shop often has yarn sales and promotions, making it a great place to score deals.
• Highlight: A large variety of yarns at affordable prices and great customer service.

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Bonus Tip:

If you’re looking for something specific or want to experience something a bit more offbeat, consider visiting Feira de Artesanato (the Lisbon Craft Fair), which sometimes has stands with local yarn vendors. It’s an excellent way to find unique, handmade fibers, and you can sometimes meet the artisans behind them!

Let me know if you’d like help with directions or any other details on these shops!

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At this point, I might go back and ask for details on the sketching or other options, but let’s go deeper rather than wider here. I’m now asking ChatGPT to map out the yarn shops. Here’s my request, the response, and my follow-up request:

Can you map these yarn shops out on a Google map with directions or at least organized in an easy way to go from one to the other?

ChatGPT said:

I can’t create a live Google Map directly, but I can certainly organize the yarn shops for you in a logical route to follow while you’re in Lisbon. Here’s a recommended walking route with the shops organized by proximity to each other, allowing you to explore multiple yarn stores in a single outing.

Yarn Shop Route in Lisbon

Start in the Baixa and Chiado Area:

1. Punto y Madeja
   • Location: Rua da Madalena 153, Lisboa
   • This is a good starting point because it’s centrally located in the heart of Lisbon.
2. Livraria Bertrand (Optional stop for browsing books and relaxing)
   • Location: Rua Garrett 73-75, Lisboa
   • Since you’re already near the famous Bertrand Bookstore, you can take a break and explore their vast collection of books before heading to the next stop.

Head Toward the Bairro Alto Area:

3. A Confeitaria das Lãs
   • Location: Rua da Rosa 254, Lisboa
   • After exploring the central spots, head toward Bairro Alto, where this charming yarn shop awaits. Bairro Alto is full of character, so it’s worth wandering a bit here as well.
4. Tricotô
   • Location: Rua da Alegria 26B, Lisboa
   • It’s just a short walk from A Confeitaria das Lãs and a great stop if you’re looking for luxurious yarns and kits.

Move Toward the Graça and Alfama Areas:

5. Lanas e Linhas
   • Location: Rua dos Prazeres 49, Lisboa
   • Head towards the Mouraria neighborhood, where this yarn store is located. The route will bring you through the heart of Alfama, a picturesque district with narrow, winding streets.
6. Retrosaria Rosa Pomar
   • Location: Rua da Penha de França 99, Lisboa
   • Located a little further east, in the Penha de França neighborhood, this is a true gem of a store if you want to dive deeper into Portuguese yarns.

End Your Day in the Alcântara/LX Factory Area:

7. Café do Bairro – Yarn and Café
   • Location: Rua de São João da Praça 12, Lisboa
   • After spending your day exploring yarn shops, end on a relaxing note with a coffee or tea at this charming yarn café located in the Alfama district.
8. Armazém das Lãs
   • Location: Av. Magalhães Lima 3A, Lisboa
   • If you still have time and energy, finish your yarn journey at Armazém das Lãs in the Alcântara area. It’s a bit further out, but you can take public transport to get there quickly or enjoy a longer walk through Lisbon’s quieter streets.

Optional (If you want to explore more):

• Lírios e Linhas: Located near Praça do Comércio 61, this is another option, though it’s a bit off the main route.

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Directions Summary (from one shop to the next):

1. Punto y Madeja → Walk 5-10 minutes to Livraria Bertrand → Then head to A Confeitaria das Lãs (15-20 minutes walk).
2. A Confeitaria das Lãs → Walk to Tricotô (5 minutes).
3. Tricotô → Head to Lanas e Linhas (15-20 minutes walk).
4. Lanas e Linhas → Walk to Retrosaria Rosa Pomar (10-15 minutes walk).
5. Retrosaria Rosa Pomar → Take a tram or public transport to Café do Bairro or Armazém das Lãs (20-30 minutes depending on where you go).

I could then go on and ask it to provide the direct Google Map links, but those links don’t copy easily over into Substack, so I’ll leave it at this for now.

Summary of using AI for trip planning

It’s rather scary how easy it is to use AI for trip planning, but also how helpful it can be when you tie your trip planning to your creative or other interests. You can easily go down a lot of rabbit holes generating more details or asking the tool to expand on the lists it gives you.

Some of this will be very familiar to experienced trip planners, but I just heard this week that the vast majority of Americans haven’t used generative AI, and most of my friends are stunned to find out what a great job ChatGPT, Claude.ai, or Google’s Gemini can do for trip planning. However…

After this article was first posted on my Substack at https://stevebrock.substack.com/p/using-ai-for-trip-planning, my wife and I were discussing our upcoming trip so we looked through the recommended knitting stores listed above by ChatGPT. Out of about ten of them, six of them don’t exist, or they don’t show up on Google Maps. That’s a sixty percent (easy math here) failure rate. Now I haven’t gone back to see if some other form of search would uncover ChatGPT’s results, but even if half of the false positives were still invalid, it does raise questions on reliability.

Do I still find the overall results helpful? Yes. It provides a good starting point and connects a number of places that would have taken a lot more time in a regular search on travel blogs and articles. But it only shows that you have to doublecheck what AI gives you. We would have been very bummed showing up and what thought was a cool knitting store only to find it now sells auto parts.

But give it a try and let me know how it works for you.