For our first trip to Lisbon, we are looking at two Dear Lisbon hotels, which fit our criteria in terms of price and flexible cancellation. We also are extremely interested in finding a good location. Can you please tell me which of these you think is in a better location?

Gallery House, R. de São Bento, 31
or
Palace Chiado, Rua Ivens, 35

Thank you for your help!

For me the more attractive and convenient location would be in the Chiado at Rua Ivens, an easy walk from the Baixa-Chiado metro with nice shops, restaurants nearby.

Thank you Maribel! The reviews of Gallery House say how convenient it is to have Tram 28 stop in front of the hotel, but everything I have read says that that tram is uncomfortably crowded. The metro seems like a better transportation option.

Yes, IME the uber-famous tram 28 is incredibly crowded and pickpockets do a brisk business there. I would avoid it, since it's very hard to grab a seat anyway.

I believe you're traveling with children, so they may enjoy a stop at Gelados Santini, one of Portugal's best ice cream purveyors at Rua do Carmo 9 in Chiado, a two minute walk away! And there's also the ice cream emporium Amorino, not far from the Dear Lisboa Rua Ivens, on shopping street Rua Garret 49.
For yummy take away pastries and pastéis de nata (custard tarts): Pastelaria Alcôa at Rue Garret 37, along with the superb Manteigaria at Rue de Loreto 2, off the Praça Luis de Camões.
This is my favorite shopping/dining area in Lisbon.

Oops! I assumed incorrectly that there would be kids in your group of 5, but adults can certainly enjoy Amorino & Santini!

For wines and creative petiscos, we like By the Wine, the José María Fonseca tasting room--very atmospheric. Open noon- midnight except Mon. (from 6 pm-midnight) at Rua das Flores 21.
By the wine ? Vinhos José Maria da Fonseca ? Vinhos Portugueses

And you'll be near the Teatro São Carlos, where there's Café Lisboa by José Avillez. It's also handy for anytime dining since it's open from noon until 1 am. Of all the many Avillez Lisbon dining destinations, we've enjoyed his Cantinho most, at Duques de Bragança 7, also very close to your suites.

If any of you would like to pick up some high quality Portuguese handicrafts or foods, on rue Ivens 2 there's a branch of A Vida Portuguesa, one stop shopping for everything lovely that's handcrafted in Portugal. And another branch nearby on Rua Anchieta 11.
https://www.avidaportuguesa.com

Those 9 suites are quite handsome and ample with all the amenities that we like. Hope you enjoy Dear Lisbon Palace!

We used to be 5. Now just 2 of us, as the kids have all grown and flown the coop.

Thank you so much for all your helpful recommendations! I am adding them to my notes.