u/Fancy_Breakfast1020

My boyfriend and I are planning our first trip to Portugal for 10 days in early/mid October. We’re thinking of flying into Lisbon, heading to Madeira, then finishing in Porto before flying home.

I’ve done a ton of research on Reddit, travel blogs, etc., but would love advice from people who have actually been!

1. How would you divide our time?
I’m currently thinking 3 nights Lisbon, 3 nights Madeira, and 2 nights Porto (with the remaining time accounting for travel). Is that enough time in each, or would you rearrange it?

2. Where should we stay?
We’re looking for areas that are safe, convenient for sightseeing/activities, and reasonably priced. Under $200/night would be amazing, but we have some flexibility. We’re fine using Uber/taxis when needed.

I’ve read that Chiado is a good area in Lisbon. Would you agree? What neighborhoods would you recommend in Madeira and Porto? Specific hotel/Airbnb recommendations are very welcome too!

3. What are the absolute must-dos?
We’d love recommendations for things to see, restaurants, experiences, viewpoints, etc. in each destination. I know we might experience some weather since we're entering the rainy season.

I’ve seen mixed opinions on Sintra, and have also heard great things about Cascais, the Douro Valley, Fanal Forest, and Pico do Arieiro/Pico Ruivo.

4. What would you skip?
With only 10 days, we know we can’t do everything. Are there any popular attractions or day trips that you think are overrated or not worth it?

5. How much should we plan vs. leave spontaneous?
Are there things we absolutely need to book ahead (restaurants, tours, hikes, transportation, etc.), especially in October?

A little about us:
We’re looking for a good mix of culture, history, food/wine, and nature, with maybe a mild-to-moderate hike or two. We want to see as much as we can while still having enough downtime to actually enjoy each place rather than constantly rushing around.

Thanks so much! ❤️ 🇵🇹

My boyfriend and I are planning our first trip to Portugal for 10 days in early/mid October. We’re thinking of flying into Lisbon, heading to Madeira, then finishing in Porto before flying home.

I’ve done a ton of research on Reddit, travel blogs, etc., but would love advice from people who have actually been!

1. How would you divide our time?
I’m currently thinking 3 nights Lisbon, 3 nights Madeira, and 2 nights Porto (with the remaining time accounting for travel). Is that enough time in each, or would you rearrange it?

2. Where should we stay?
We’re looking for areas that are safe, convenient for sightseeing/activities, and reasonably priced. Under $200/night would be amazing, but we have some flexibility. We’re fine using Uber/taxis when needed.

I’ve read that Chiado is a good area in Lisbon. Would you agree? What neighborhoods would you recommend in Madeira and Porto? Specific hotel/Airbnb recommendations are very welcome too!

3. What are the absolute must-dos?
We’d love recommendations for things to see, restaurants, experiences, viewpoints, etc. in each destination. I know we might experience some weather since we're entering the rainy season.

I’ve seen mixed opinions on Sintra, and have also heard great things about Cascais, the Douro Valley, Fanal Forest, and Pico do Arieiro/Pico Ruivo.

4. What would you skip?
With only 10 days, we know we can’t do everything. Are there any popular attractions or day trips that you think are overrated or not worth it?

5. How much should we plan vs. leave spontaneous?
Are there things we absolutely need to book ahead (restaurants, tours, hikes, transportation, etc.), especially in October?

A little about us:
We’re looking for a good mix of culture, history, food/wine, and nature, with maybe a mild-to-moderate hike or two. We want to see as much as we can while still having enough downtime to actually enjoy each place rather than constantly rushing around.

Thanks so much! ❤️ 🇵🇹