@mjs thank you for the hotel suggestions/locations and details of your trip. Very helpful as we finalize things. Also good to know that the trip to the Douro Valley was not an issue despite the heights involved. Much appreciated!

When I used to live in New Haven there were shuttle services to JFK. Any such services to EWR from your part of Connecticut? Boston otherwise might be an option for you if you happen to have friends or family in the area who could keep your car for you. You can fly direct from Boston to LIS and back from Porto with just a brief stop in Lisbon. Also if you have mobility issues be careful in the rain with slippery cobblestones in Porto and Lisbon. Bring appropriate footgear.

Hi ronniehu,
I did live in Kent for 12 years and before that in Washington, another lovely town in Connecticut's Northwest Corner, but now I live in Madrid. My "day job" requires me
(tough, I know ) to travel extensively all around Spain and Portugal.

When I lived in Kent I took a shuttle to the NY area airports. Is there a shuttle service now?

Yes, as mjs and maitaitom warn, be very, very careful of those cobblestone, the famous calηada portuguesa. Make sure that you bring shoes with thick soles and very good treads. I have shoes that I keep specifically for my Portuguese walking.

In Coimbra, with mobility issues, you'll want to avoid climbing, either up or down, the famous "Rua de Quebra Costas" (Backbreaker's Street), which is a very steep street, a staircase, whitewashed and graffiti-covered that connects the upper town where the University buildings lie to the lower town. Coimbra is another "vertical" city like Lisbon and Porto.
https://www.gpsmycity.com/attraction...et)-45428.html

The reason I used Madomis to arrange a private tour for friends there is that the guide was able to pick up my friends (your same ages) at the rail station, coming in to Coimbra from Porto (or Lisbon) on the Alfa Pendular, take them out to the Roman ruins of Conνmbriga, then to a scenic viewpoint high above the city for a photo op, then to the University for a guided tour, then to a fado house in the afternoon for a short performance before dropping them off at the Quinta das Lagrimas.
The Quinta das Lagrimas recommended them.

Of the Porto hotels I mentioned and have visited, the one I found most impressive, dιcor-wise, was the Le Monumental Maison Albar (also probably the priciest). It's a real jewel box of a hotel with a gorgeous interior, an indoor pool/spa and a gourmet restaurant. Member of Leading Hotels of the World. It sits on Aliados, as does the Intercontinental Palacio das Cardosas, which is more or less a plateau.

The Infante Sagres, the city's first 5-star luxury hotel, also has a beautiful interior, filled with exquisite stained glass, but does sit on a slope, requiring a bit of a climb up or down. It recently changed ownership. It used to belong to Taylor Fladgate but is now owned by Gaw Capital group that owns the Intercontinental and the hotel is managed by the Hospes group.

Cascais would be a good place to stop and relax although not really what I would call a beach town. Nice to stop in Aviero and perhaps take a canal boat ride. We didn't stay overnight in either place, just stopped at Cascais on a tour out of Lisbon that took us first to Sintra and then to the Westernmost part of continental Europe. Our hotel arranged the tour, small van through Hello Portugal, very informative driver and we met up with him in Rossio Square around 8:30 AM or so and headed first to Sintra. We did also stop at Coimbra to tour the university en route to Porto. It was very steep walking from the university down to the historic churches. We enjoyed Guimares very much and we visited as a day trip from Porto.
We were there is mid-June and it was already pretty hot so i would think that May would be ideal weather.

The westernmost point in continental Europe is claimed by Cabo da Roca, on that circular small group or private tour of Sintra-Cabo da Roca-Cascais-Estoril.
Cascais has 3 small urban beaches with the stately Hotel Albatroz facing one, and more expansive beaches in Guincho, popular with surfers and a beautiful walking/biking promenade between the two. It's a popular "beach day trip" from Lisbon since it can be reached easily by commuter train. This distinction of western most point is also claimed by Cabo Sγo Vicente in the western Algarve.


At Cabo da Roca one can get a "certificate" of having visited "land's end". This is. why it's popular on the circular small group tours. It's easier for the mobility challenged than a full day of climbing to visit some of the (now) 5 monuments in Sintra.

This is a typical Lisbon-Sintra-Cabo da Roca-Cascais-Sintra (1 monument, Pena Palace in the late afternoon without so many crowds) small group van tour-
https://lisbonriders.com/group-tours/sintra-cascais/

More great info ...

@mjs, @Maribel and others ... thx for the caution of the challenges of cobblestones and steep streets. Much appreciated and noted!

@maribel, appreciate all the details on hotels and tours. Many good choices, and am confident that we will enjoy those you suggested. THX again!

@madam397, thanks for sharing your experiences in Cascais, Coimbra and Guimares. Looking forward to visiting all three!

Thanks to all the Fodorites who have chimed in! I am very excited about the trip we are planning, and your info has been priceless.

There have been many responses regarding your itinerary but regarding the hills, at least for Lisbon, I posted on this topic a few months ago regarding some of the ways to avoid the hills - How to avoid (some of) the hills in Lisbon - Chiado and Alfama - Fodor's Travel Talk Forums (fodors.com) - we barely even noticed the hills in Lisbon thanks to the elevators and escalators mentioned in my post

Great advice here, and just a note about EWR: Soon United Airlines will have direct flights to the Algarve starting May 24, 2024. It's a time saver if you want to visit there - you can fly into Faro and out of Porto, for example.

We spent this past May in Portugal and thought it was a perfect time. Weather fantastic: warm but not too hot anywhere (including the Alentejo). The jacaranda were still in bloom and WOW are they gorgeous (we noticed them most in Lisbon).

In Porto, we stayed at Vignette Collection Casa da Companhia. I found Porto to be the hardest place to figure out where to stay and i could not have been happier with my choice. Excellent location, quietest hotel room i've ever been in (and we were right next to the elevator and at street level), wonderful indoor pool and rooftop terrace (with small pool) with a stunning view of the Cathedral and ethereal lit up flocks of birds at night... etc. etc. I cannot say enough good things about this hotel.

We spent three nights in Cascais, and loved it -- the Albatroz Hotel.

In Coimbra, don't miss the Fado ao Centre and the Museu Nacional de Machado! We stayed at the Hotel Oslo, and while it is not a highly luxurious hotel, it was nice enough with a great location and a wonderful rooftop terrace with a view.

Perhaps consider flying into Porto, and then going directly to Guimaraes and spending the night there, then heading to Porto by train sometime the next day. It is another hotel change but not an extra trip per se if you are planning a daytrip there anyway. This is how i arrived in Portugal and it was simply a magical start to the trip. I stayed at Hotel da Oliveira.

The Casa da Companhia is really a lovely hotel, too, in a great location. Glad to see a report of it here.

Thank you for all those tips, Skatedancer! It sounds lovely ... will make a point to see those other sights in Coimbra, We are planning a day trip to Guimaraes, although I realize that staying over has many advantages, and a completely different flavor ...

I appreciate your hotel (and itinerary) suggestion for future reference ... I particulatly found it hard to choose hotels -- which makes recommendations like yours and other Fodorites especially valuable. Obrigado!

ronniehu,
While in Porto you might enjoy an evening concert at the Rem Koolhass-designed Casa da Mϊsica concert hall in Boa Vista. We've attended several concerts there....jazz, symphony, choral groups, violin. The tickets are inexpensive and all sight lines are fine, the acoustics wonderful in the main. concert hall, the Sala Suggia.
For music lovers it's a nice way to spend an evening in this great city.
And on you way, you get to see a very fashionable neighborhood of Porto that you as a visitor probably wouldn't see. You don't need to purchase your tickets too far in advance. You could wait until you arrive and your concierge can help you with it.
The full schedule for May isn't up yet although some performances are. Remember that the day comes before the month when looking at the May schedule.