Bailey's Beach is a hollower beachbreak that offers some opportunities for surfers. It's a private beach that was once popular with the Kennedys, but now it mainly sees low crowds thanks to not-so-great parking and inconsistent waves. The spot can get quite crowded during the summer when it's not really surfable, so it’s best to hit it during the cooler months.

The surf here works best with a southeast swell, but you can also catch some waves with swells coming from the east and southwest. The beach can handle swell sizes starting at 2 feet (0.6 meters) and can get decent up to head-high on a mid tide. You can expect both left and right waves, making it suitable for intermediate surfers. The best wind direction is from the north, and it’s rideable during low, mid, and high tides.

Access to the beach can be a bit tricky. One end is public, but parking is a hassle, as you often have to trek from side streets that aren't clearly marked. Keep in mind that there isn’t any surfing in the summer when it virtually never breaks. If you’re looking for a spot with fewer crowds and are okay with variable conditions, Bailey's could be worth checking out.