A two-hour drive west of San Juan leads to Puerto Rico's little coastal town of Rincon, where practically everything is negotiable. If you're a musician, try bartering part of your stay with a performance. Save on activities by pooling together new friends you meet on the beach or in the hotel. In Rincon, the bigger the group, the lower the rate.
Do: Learn to surf in one of the world's best surfing destinations. Rincon is also a great spot for seeing the humpback-whale migration in the winter. For an inexpensive lunch, try a hummus bagel and a peanut-butter-banana smoothie at Banana Dang.
Stay: Sunsets are spectacular from the Coconut Palms Inn's studios and one-bedroom apartments ($75 to $125 per night). The grocery store is two blocks away, and local fishermen come to the hotel to sell guests the day's catch.
Getting There: Many major U.S. airlines fly into San Juan, where you can rent a car and drive the modern toll highway to Rincon.