Portugal Anniversary Trip - Local Tour Company Suggestions?

Posted by Shawna on 12/28/25 06:28 PM

My husband and I are headed to Portugal to celebrate our 25th anniversary this May (2nd week of it mainly). We have hotels and our itinerary lined up but I'm trying to find some suggestions for local tour companies in a few spots. Any ideas? This is a splurge trip so we're open to pricier options than we normally would be.

Day trip to Sintra from Lisbon that would be private (not small group) and include the VIP early entry to Pena Palace.
Catamaran tour that includes a kayak stop or two including into Benagil cave. Preferably in the evening; we're planning to do the Seven Hanging Valleys hike during the daytime that day.
Bonus - we think we have an idea for a company to do a boat trip winery tour in the Douro Valley (staying at a hotel there) but open to other suggestions if folks have done this and liked the company they used. We would be starting in the Valley not starting from Porto.

Thanks for any help folks can offer!

Posted by aulopone

12/28/25 07:48 PM

453 posts

Haven't use them but they have a good reputation, they have group tours but they also have private tours.
https://lisbonriders.com/

Posted by Shawna OP

12/28/25 09:49 PM

103 posts

Thanks! I did see them suggested a few times but they listed on Lisbon in their private tours list.

Posted by aulopone

12/28/25 11:18 PM

453 posts

Some of the smaller tour operators offer customizable private tours, adding these for your research.
https://www.lisbonbeyond.pt/

https://rideforyouportugal.com/about-us/

I'm not making recommendations just providing the info, contact them to determine if they can fulfill your travel needs.

Posted by SandyO

San Franciso Bay Area, USA

12/29/25 01:45 AM

1137 posts

Congratulations Shawna on your 25th wedding anniversary. Been to Portugal in 2023 and 2025 and both times used IGoPortugal: https://www.igoportugal.pt/ for private tours out of Lisbon. The company is very professional and worked with us to craft a trip around our interests. The highlight for us was our guide Carlos Silva. He took the time to get to know us and what was important to make our visits special. It was the little things like making sure my husband went to the best little coffee shop in Lisbon the first time we visited after learning that my husband was a coffee aficionado. (even though it wasn’t on our original itinerary). When we came back last year, he even had purchased some coffee for my husband to enjoy after the tour.

On our last trip, we went to Fatima, Nazare, and Obidos. Carlos made sure that I had time to attend Mass in Fatima as well as explore this miraculous site. In Nazare, we visited a small chapel and had a wonderful seafood lunch, and had more than enough time in Obidos. We were out much longer than the time allotted, but we never felt rushed.

Carlos knows and loves Portugal and brought history and his culture to life. When we go back to Portugal, we will take more tours with IGoPortugal and Carlos.

Posted by debora.go.oliveira

12/29/25 07:48 PM

16 posts

If you're also planning to spend some time in Porto (especially in the Douro Valley), it might be worth considering local operators who prioritize leisurely sightseeing and personalized experiences rather than traditional group tours.

For a relaxed yet immersive exploration of Porto, Tuk Tour Porto is a great option for couples celebrating special occasions. The tours are private, tailored to your pace, and guided by locals who adjust the itinerary as needed—ideal if you're looking for context, perspectives, and flexibility rather than a fixed itinerary.

If you enjoy outdoor activities, Porto Rent a Bike is another excellent option. Cycling along the Douro River in Foz do Douro or between Porto and Vila Nova de Gaia offers a completely different perspective of the city and is easy to combine with visits to wineries, cafes, or a leisurely riverside lunch.

Both experiences often complement a stay in the Douro Valley well, especially if you're already planning a winery visit or a river cruise experience in the region. They don't focus so much on fulfilling requirements, but on enjoying Portugal at a comfortable and personal pace — which seems particularly suitable for a birthday trip.

Posted by Shawna OP

01/02/26 09:11 PM

103 posts

Thank you for the suggestions!

Posted by darkmist1

01/03/26 07:26 PM

170 posts

For your 1st day trip from Lisbon to Sintra , I would highly recommend Jose from Lisbon on Wheels.
My family and I did a private tour with him. He picked us up from our hotel at 9 am and we returned at 7. I customized the tour with Jose to include the National Palace, Moorish Castle, Quinta da Regaleira and the Pena Palace . In retrospect , I would skip the Moorish Castle and spend more time in the Quinta da Regaleira gardens.