Why October Is the Best Time to Visit Key West (Before High Season Hits)

☀️ Perfect Weather Without the Crowds

If you’re wondering what the weather is like in Key West in October, the short answer is: perfect. Daytime temperatures average in the mid-80s, evenings are comfortably balmy, and the ocean feels more like a warm bath than a brisk swim. It’s the kind of tropical climate that lets you spend entire days outside, whether you’re stretched out on the sand, paddling through mangroves, or sipping mojitos on a patio.

Another reason October is such a sweet spot? The crowds. With summer families back in school and winter vacationers still weeks away, you’ll find plenty of space on the beaches, shorter waits at restaurants, and a relaxed, unhurried vibe across the island. It’s the rare travel window where you can feel like a local, without sacrificing sunshine or activities.

🎭 Festivals & Events You’ll Love

October is also one of the most exciting months on the Key West events calendar. The island knows how to celebrate, and two festivals in particular make this month unforgettable.

First up is Fantasy Fest, a week-long extravaganza held in late October. Think Mardi Gras meets tropical masquerade: elaborate costumes, themed parties, parades, live music, and an anything-goes spirit that takes over the island. Even if you don’t dress up, the energy is contagious and the experience is bucket-list worthy.

The Goombay Festival is another highlight, honoring Key West’s Bahamian heritage with street parties, food vendors, live bands, and plenty of dancing. It’s a family-friendly celebration that showcases the island’s cultural roots in a vibrant and colorful way.

And even if you’re not planning your trip around these festivals, October in Key West still has a buzz about it. With live music, art walks, and endless opportunities for nightlife, you’ll never feel like you’re missing out.

💸 Why October Beats November

Travelers who wait until November to visit Key West often find themselves facing higher prices, larger crowds, and less availability. November marks the beginning of the island’s high season, when hotels sell out quickly, flights cost more, and popular activities like sunset cruises and snorkeling tours book weeks in advance.

October, by contrast, offers better value and more freedom. You can secure attractive hotel and flight rates, enjoy wider choices in accommodations, and easily reserve top dining spots and tours without the stress of last-minute competition. For anyone looking to experience Key West at its best, without the high-season premium, October is the smarter move.

🧘 Your Pre-Holiday Reset

Think of October in Key West as the calm before the holiday storm. Before the endless shopping lists, family gatherings, and year-end deadlines, you can gift yourself something far better: time. Slow mornings with Cuban coffee and key lime pie, leisurely bike rides past pastel houses in Old Town, afternoons stretched out in a hammock under the palms, and evenings watching the sky melt into watercolor sunsets.

This isn’t indulgence, it’s a reset. A chance to recharge mentally and physically before the hectic holiday season begins. And because October is a less crowded month, you’ll find yourself moving at a gentler pace, with the freedom to explore (or do nothing at all) on your own terms.

📍 Where to Stay in October

One of the best perks of visiting in October is the variety of accommodations available at reasonable rates. If you love charm and character, boutique inns in Old Town offer lush tropical gardens, intimate pools, and a sense of seclusion just steps from the action. Waterfront resorts, on the other hand, often roll out shoulder-season discounts, letting you enjoy ocean views and resort amenities without the peak-season price tag.

Vacation rentals are another great option, especially for longer stays. Many come with porches perfect for watching sunsets and complimentary bikes so you can cruise around the island at your leisure. In October, you won’t have to settle for what’s left, you can choose the stay that truly matches your style.

🥂 Where to Eat in October

October in Key West is a foodie’s dream. With fewer tourists in town, it’s easier to snag a table at some of the island’s most popular restaurants. That means you can finally check off bucket-list spots like Blue Heaven, famous for its live music and legendary key lime pie, or Latitudes, where sunset dinners feel like private events.

Seasonal specials also shine this time of year. Fresh spiny lobster is a local delicacy you’ll only find in late summer and fall, and bartenders get playful with mango cocktails and rum punches that pair perfectly with balmy evenings. With less hustle and more room to linger, dining in October feels less like a rushed reservation and more like a celebration of island flavors.

✨ The Bottom Line: Visiting Key West in October means warm weather, lively festivals, lower prices, and plenty of room to breathe. Whether you’re here for the parties, the beaches, or the food, it’s one of the best months to experience the island before high season begins.

🎁 Ready to Plan?

We’ll map out your ideal fall trip—totally free, totally custom. You just bring the sunglasses.

Don’t sleep on Key West.