Pensacola, FL

Mid-September through October is “shoulder season” in western Florida, which makes it the best time to visit Pensacola. During this time—when the weather is moderate and the risk of hurricanes is receding from its late-summer peak—room rates drift down, but activities like surfing or dolphin watching are still at their best. The low season in Pensacola runs from November to February, and is a perfect time to visit for the best price and without crowds of tourists. Wintertime may be chilly, but birdwatching during these months can be an amazing experience. March through early September means peak season in Pensacola. First come the spring breakers, while the summer months draw families looking for beach activities and events like the Pensacola Beach Air Show. Summer days are usually hot, bright, and humid with a chance of hurricanes. Be prepared for skyrocketing prices as well.