Our flight got in early so we arrived at Terminal J before boarding had started. Waiting area was very organized and there was juice and water available. Called categories in turn starting about 11am and all categories were welcome by 11:30 or so.

Easy to just stroll off the ship and walk right into Old San Juan. The day we were in port the free trolley was running a bit slow and so was crowded - consider a taxi if you aren't wanting to walk and the line at the trolley stop is long.

Old San Juan is wonderful, we had been to Puerto Rico many times but hadn't spent much time there. Hilly with cobblestone streets and some narrow sidewalks, but wear your walking shoes and soak up the centuries-old atmosphere. Lots of online info for DIY walking tours, and many historic buildings have detailed signs telling their stories.

Tender dock is right at the edge of Gustavia's tiny but classy downtown. Fun window shopping, we walked over to Shell Beach, had a lovely swim and then a pricey (but not out of whack with NYC or Hamptons pricing) lunch al fresco under a shade awning with our toes in the sand at Shellona (in what used to be to Do Brazil space).

We rented a car on the spot, no reservation (ask at the Tourist Booth at the base of the cruise dock and they will call a local rep to come walk you to a car, just a couple blocks). Took the suggested clockwise tour of the island. Devil's Bridge is scenic but you will want to be comfortable with gravel/dirt roads for the last mile or so. Nelson's Dockyard (including Shirley Heights etc) a highlight. Roads are pretty well signed but have plenty of potholes, the locals know where the bad ones are so be aware and follow suit. Local practice includes lots of passing, but also folks stopping to let entering traffic in. Allow plenty of time to return to St. John's, traffic can get busy downtown in the afternoon (it was a market Saturday which was probably more traffic than usual).

Took a taxi to The Boatyard and had a lovely beach day, including swimming with the turtles. If you're not a big fan of cheap punch mix, use your "free drink" chit for water and pay for a nice local rum drink.

Rented a car through Cicar online the prior day, they are right at the port and very easy to use. Drove around on our own including the National Park (lots of volcanic activity, excellent and free visitor center), wineries (if you have a car stop at the ones the buses can't fit in), the Manrique Foundation (lots of fun for architecture buffs) and a loop around to the north end of the island and Mirador del Rio. Had a great time in some very interesting and impressive landscape.

Rented a car online through Cicar, very convenient right at the cruise port. Dramatic scenery and - if you do the north end of the island - some pretty twisty roads (car rep suggested south loop - less twisty, more accessible). The national park website is a bit confusing (somehow it was tough to figure out where the visitor center was...but it was super clear on the Cicar map) and you might want a tour to go to the overlooks (otherwise you need a reservation and/or a high tolerance for narrow twisty roads).

Walked to the Fundacion tram stop and took the tram to La Laguna (Trinidad stop). The tram ride is pretty scenic, with views back toward the port and up into the mountains.

It is only about half a block from the tram stop to the historic section of town in La Laguna. You can buy a tram ticket at machines right at the tram stop (or download the app and use your phone as your ticket - not sure if that works for single rides or not). Tram system was new in 2007 or so and is very modern and clean.

Strolled around the picturesque & historic center, enjoyed some wine and cheese at a sidewalk cafe in one of the many small plazas. La Laguna has many historic buildings labelled in Spanish and English, making a self-guiding tour easy. The historic streets are a mix of pedestrian-only and cars/ped. mix, but narrow enough that the cars go pretty slowly and the locals just stay toward the wall if there is a car passing.

Right in Santa Cruz, the hop on -hop off bus does stop right where you meet the Plaza Espana when you exit the cruise terminal (we didn't take it, but there were reps right there)

Took the cruise port shuttle to the center of Funchal, strolled around and tried Madeira wine at a couple of places - the Sao Francisco wine museum is the Blandy's operation, right downtown. D'Oliveras is just uphill from the main square. Took the cable car up to Monte, strolled around and enjoyed the views very much. There is a quickserve cafe with a great view below the Monte cable car station - great place for a glass of wine.