Puerto Rico is one of the best hidden gems the US has to offer. A quick 4-hour flight from NY and less than $300 for a roundtrip ticket and you are swimming in the crystal clear water of the Caribbean.
Here are a few tips for a great Puerto Rico experience.
1. Puerto Rico is a small island. You can reach every point in the island in less than an hour and a half of driving from its capital, San Juan. If you are short on time, make San Juan your base and explore the island from there.
2. It’s the Caribbean, baby! Flip flops and shorts rule. I would bring one pair of Jeans and nice shoes for looking descent when exploring San Juan’s nightlife. Otherwise, dress casualmente.
3. It’s a driving island as public transport will get you nowhere. Enterprise had the best prices I could find. Roads are good and driving is fun, albeit a bit chaotic (for example, after midnight, it is supposedly legal to ignore traffic lights as long as the road is clear.)
Note (for US citizens): I recently discovered that my Continental Chase credit card covers the CDW portion of the car rental insurance, as long as I rented the car using the card. It saves you about $18 a day.
4. Lodging is not as cheap as I expected it to be. Unless you are renting a place for a week or more (vrbo.com has a good collection of vacation rentals), expect to pay ~$100 for a descent hotel. Hotwire got us the San Juan Sheraton for $100 and Priceline got us a cool beach front hotel in Isla Verde for $80.
5. Guidebooks: I am a big Lonely Planet fan, and It’s Puerto Rico guidebook served me well (although it’s wouldn’t hurt to refresh a bit its restaurant data). Most businesses in Puerto Rico have simple websites with their phone listed, and I would recommend calling whenever in doubt.
6. Puerto Rico is part of the US Commonwealth, which practically means it’s part of the US (no passport needed for American travelers).
San Juan Area
1. Old San Juan is one of the most beautiful colonial cities I have seen, with a lively atmosphere and a great vibe. It’s relatively small – 4-5 hours of casual walking will cover most of it’s attractions, but it’s a magical little place with great restaurants and cozy bars. San Juan beaches (Isla Verda, Ocean Park or Candado) are only a 15 minutes drive away, so even if you stay in that area – you’ll find yourself returning to the old city for lazy afternoon strolls and nice dinners.
In general, if you plan to stay a couple of days in the San Juan area and enjoy its beaches, I would recommend staying close to the beach (in Isla Verde or Ocean Park), and driving to the old city for daily/night excursions.