We have cruised out of San Juan 9 times (including last week) and our experience is you don't need to stay near the port. We have stayed in Old San Juan, the Condado area, the Isla Verde area and the port area. We have not found a hotel anywhere that offers a shuttle to/from the airport or cruise port. Cab fares are regulated so you don't need to worry about getting overcharged by a cab driver. It's a 20-minute ride from the airport to the Pan-American pier. It doesn't matter how you divide that up. In our experience, we prefer to stay in the Isla Verde area near the airport. It's 5 minutes from the airport and 15 minutes to the cruise port. We think the beaches are the best in Isla Verde and quite often, we can find the best price for hotels in that area. I recommend the Royal Sonesta. It can be a little pricey depending on when you book but it is a gorgeous resort. We now arrive 2 days early in San Juan so we can spend a couple days at the Royal Sonesta before our cruise.