In San Juan, you have the airport next to Isla Verde. Isla Verde is a tourist district with the Ritz Carlton, El San Juan, Holiday Inn Crowne Plaza, and the Hampton Inn (not beachfront but Hampton is about a third less than the others (and there is public beach) which in season run at least $250 a night except for Holiday Inn at $175). Hard to get last minute specials as hotels sell out during the season. There are plenty of non-chain hotels and good deals to be found but I was not in a position to take notes and I didn't stay in that area. Beyond the Verde is the Condado section also along the beach with other hotels and a bit more upscale on the shopping; the Isla Verde neighborhood is lined with Denny's, KFC's and other fast food outlets. Water OK to drink. You can dial 800 numbers to the mainland from the telephones here. There is a 24 hour supermarket in Isla Verde; prices are Manhattan plus 10% and it's just like the mainland. Prices in other supermarkets are about 20% cheaper so groceries here aren't cheap. Rent is cheaper but salaries are lower too. US chains and shopping malls are all over the island; ATM's too; for some strange reason the big two banks are Banco Popular (a local chain) and ScotiaBank from Canada. After Condado is the Caribe Hilton, on its own island (but El San Juan's beach is better says the NY Times), and then you are entering the Old San Juan district. Each of these districts is a short car ride from the other so from Isla Verde to Old San Juan is about 15 minutes drive on local streets. Old San Juan has 3 (2 of which are small) hotels so if you want to stay there you have to be on top of things: El Convento with 60 rooms; Galleria San Juan with 17; and the Wyndham with about 300. 

Old San Juan is a walking area about 7 blocks in length and width; you could walk the perimeter in about 40 minutes; that long because of the changes in elevation and city walls. Driving in the district takes longer than walking. I stayed one night in El Convento, a former convent turned first class hotel, about $250 a night for standard room. The hotel at the turn of the century was sold by the sisters of the convent to the church for $150. Talk about Inflation. During this century the hotel became a garage for garbage trucks, a bordillo and was bought in 1962 by Mr. Woolworth who converted it into a first class hotel. Rooms come with bathrobes, CD player, VCR, very nice wooden furniture and all sorts of pillows. Rooms on each of the 3 floors face the water; the higher the floor the higher the price but all are outfitted the same. Interesting atmosphere with the rooms facing away from an atrium; nicely decorated and very courteous service. I had booked a walking tour but it was cancelled last minute; hotel offered me another tour free of charge and apologized profusely though it wasn't their fault. There is a small pool on the rooftop overlooking the harbor which is a good place to sit drink in hand watching sunset; full continental breakfast and open cocktail bar with daily same-day newspapers from the mainland always available. Cable-TV as we know it is available on the island with all the channels you expect. Dinner in hotel's restaurant was very good but the Italian restaurant Il Perugino across the street has a high reputation for many years and would've probably been a better choice. The 'in" place for young people is the Parrot Club in Old San Juan; I saw it from the outside. The Galleria San Juan is a bed and breakfast overlooking the ocean on the perimeter street between the two forts (San Cristobal and Morro). Rooms start at $90 a night and are decorated like the tropical rainforest; not as luxurious and no food service in-house except for breakfast but definitely a theme place. Sold out the night I wanted and no rooms opened up as of Friday morning. As for the forts, pay $2 to get into one fort and you can see the other one free same day. See both of them. Best views of the area are from the forts. In the center of Old San Juan is a piazza lined with a Marshalls and 24 hour Walgreens pharmacy with high prices. A recommended luncheonette by the travel magazines for a 50's-era experience with good local flavor is Bombanera in Old San Juan; I didn't visit it. 

You can book a walking tour of Old San Juan or just go it yourself. The pedestrian walkway known as Paseo de la Princesa goes along the water from the port where the cruise ships dock to the San Juan Gate (take the walk twice; in the day and at night) which leads into a street going up to El Convento Hotel. Very central. In the early centuries, people got off their ships at the Gate, went up to the Convent to give thanks so it's a walk of history. There is also Casa Blanca, a home of Ponce de Leon right near the Gate. You can get an aerial view with your meal atop the Banco Popular building's Bankers Club a block from the Wyndham which is near the port. Casual dress until 7:30pm. It was booked for private party the day I was there but is recommended by the locals. There is plenty of shopping in the district with outlet stores for all the designers (ie: Polo, Hilfiger); I didn't check them out. There are other little sites to see in Old San Juan (ie La Fortaleza: the Governor's Mansion -- not open on Saturday) and it is enough to keep one busy for a Saturday. Sunset in February is 6:30pm. Weather was 80's during the day; 70's at night; humid but sunny the 3 days I was there. 

Sidetrips: Daytrip to Ponce (pronounced Pon-say) about 75 minutes drive from San Juan by excellent highway. Ponce is the island's second largest city on the other (southern) side of the island; has a city center worth a drive-thru with an interesting looking fire station in the center square. About half an hour out of Ponce further away is Hacienda Buena Vista, a coffee plantation restored to its 19th century glory by the Puerto Rico Conservation Trust. You must make advance reservation but the 1 ½ hour tour shows you nice forests and how the hydraulic power systems worked to run the machines. A nice way to see the island with its mountains and coastlines. Be sure and ask in advance for an English tour if Spanish doesn't do it. Get good driving instructions as it is confusing getting to the Hacienda from the highway. 

Saturday night we went to the El San Juan hotel and casino; park in the public lot across the street for one-fifth the price. Very loud and crowded in this see and be seen place. We went a few minutes down the block to the Ritz Carlton for a more upscale casino and quiet lobby and a late night light dinner where the menu was more agreeable than the El San Juan which had 5 restaurants but no coffee shop. Prices for hotel meals on the island are Manhattan but at least there is no sales tax. Rooms have 9% tax and some hotels such as El Convento tack on a 15% service charge which ups the bill significantly. 

Sunday a visit to El Conquistador country club and golf resort about an hour's drive from San Juan on the eastern part of the island. Built on cliffs overlooking the sea, lunch there is a bviewtific experience and the food of very high quality and presentation. A funicular takes you down to the marina for a boatride to their beach on an island about a mile or two offshore. There is also a public beach; sand is brown and water is very blue. Also a visit to El Yunque tropical rainforest (about 10 minutes closer to San Juan than the resort) to see its visitor center; best visited if you want to hike and see waterfalls and trees, etc on a hike. Not worth it just to see the visitor's center and 10 minute video. 
 

Phone Numbers: 

Galleria San Juan Inn 722.1808 

El Convento 723.9020 

El San Juan Hotel & Casino 800.468.2818 

Hacienda Buena Vista reservations 722.5882 or 284.7020 

Walking Tours / Colonial Adventures (all code 787) 729.0114