Discover 3 amazing destinations, from hidden anchorages to lively sandbars.
True tropical maritime climate surrounded by the Florida Straits and Gulf of Mexico. Mild winters bring steady trade winds and crystal-clear reef visibility, while summers offer glassy backcountry sandbars. Boaters generally favor the November to May window for the most stable cruising conditions.
annual · Month 7
The biggest boating day of the year. Every sandbar, anchorage, and waterfront spot is packed. Fireworks displays visible from the water across Florida.
annual · Month 7
The two-day sport lobster season, held the last consecutive Wednesday and Thursday in July. One of the busiest boating days of the year in the Keys and SE Florida. July 29–30, 2026.
seasonal · Month 8
The full commercial and recreational lobster season in Florida. August 6 through March 31. Less intense than mini-season but still a draw for diving boaters in the Keys.
annual · Month 9
The last big boating weekend of summer. A favorite for multi-day Keys trips and sandbar sendoffs before the fall.
seasonal · Month 10
Florida stone crab season, the best time for dock-and-dine restaurants serving fresh claws. Peak season is October through January.
annual · Month 11
A major offshore powerboat racing event bringing high-performance boats and spectators to Key West. The harbor gets electric with energy as the world's top powerboat racers compete. November 4–9, 2026.
annual · Month 12
Running 30+ years, Key West's beloved lighted boat parade features local boats decked out in holiday lights cruising past Schooner Wharf Bar and through the harbor. A Keys holiday tradition.
Navigate through Key West Harbor into the tranquil backcountry channels. Drop anchor at Snipe Point sandbar, snorkel the vibrant coral ledges, and cruise back for waterfront conch fritters at sunset.
Sea Bird Marina is a charming, family-owned marina located in the middle keys, just 12 miles west of Islamorada. Known for its friendly and accommodating atmosphere, this marina provides everything a boater might need, including fuel, a bait shop, and easy access to both the bay and ocean. It's a perfect spot for those looking to enjoy great fishing and a laid-back environment, with the added benefit of being well-protected from the elements.
Long Key State Park is a picturesque destination that offers a blend of natural beauty and recreational activities. Known for its scenic hiking trails and excellent birding opportunities, the park provides a peaceful escape with views of both sunrise and sunset. While the park is generally quiet, visitors should be prepared for some noise from nearby highways and construction. The park's clean facilities and helpful rangers enhance the overall experience, making it a worthwhile stop for nature enthusiasts and campers alike.
Outdoor Resorts Long Key is a well-appointed marina nestled between two of the most popular keys, offering a range of amenities for transient and long-term boaters. With its recent updates, including a gym, pool, and various recreational facilities, this marina provides a comfortable and engaging environment for visitors. The marina is known for its quiet and secure atmosphere, with a gated community feel and friendly security staff ensuring a pleasant stay. Boaters can enjoy easy access to fuel, bait, and tackle at competitive prices, making it a convenient stop for provisioning. The marina's proximity to Key West adds to its appeal, offering a strategic location for exploring the surrounding areas.