Boating & Things to Do in Cudjoe Key
Discover 3 amazing destinations, from hidden anchorages to lively sandbars.
Best Time to Visit
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.
Winter (Dec – Feb)
75°F – 79°F73°F – 75°F
Cool offshore breezes, excellent visibility for outer reef snorkeling and wreck diving.
Spring (Mar – May)
80°F – 84°F77°F – 80°F
Prime tarpon migration, calm gulf waters, and ideal conditions for remote island anchorages.
Summer (Jun – Aug)
88°F – 92°F85°F – 88°F
Mirror-flat backcountry waters, quick afternoon showers, and opening of lobster mini-season.
Autumn (Sep – Nov)
83°F – 87°F81°F – 84°F
Quieter anchorages, warm seas, and the return of crisp tropical cruising winds.
Events Calendar
🎆
July 4th on the Water
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.
🦞
Lobster Mini-Season
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.
🦞
Regular Lobster Season
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.
🌊
Labor Day Weekend
annual · Month 9
The last big boating weekend of summer. A favorite for multi-day Keys trips and sandbar sendoffs before the fall.
🦀
Stone Crab Season
seasonal · Month 10
Florida stone crab season, the best time for dock-and-dine restaurants serving fresh claws. Peak season is October through January.
🏁
Key West Powerboat Week
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.
🌟
Key West Schooner Wharf Bar Lighted Boat Parade
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.
Recommended Voyages & Itineraries
Curated RouteFull Day
Key West & Lower Keys Island Cruise
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.
Planned Stops
Key West Historic Seaport→
Snipe Point Sandbar→
Mud Key Sanctuary→
Conch Republic Seafood
Browse by Activity
All Cudjoe Key Destinations
MARINA
Cudjoe Gardens Marina
Cudjoe Key
Cudjoe Gardens Marina is a laid-back marina known for its charter boat services and well-stocked store. It offers essentials like snacks, beverages, live bait, and a clean restroom. However, the boat launch ramp has received criticism for its poor condition and service issues.
SANDBAR
Content Keys Sandbar
5.0
Cudjoe Key
The Content Keys are located due north of Cudjoe Key. They are characterized as unspoiled, tropical backcountry islands with sandy beaches and gin-clear water. Easily accessible from the Middle Keys, they are considered by many to be some of the absolute best, most pristine sandbars in the Florida Keys.
DOCK & DINE
Square Grouper Bar and Grill
Cudjoe Key
Square Grouper Bar and Grill is a vibrant waterfront restaurant known for its American seafood dishes and refreshing cocktails. Located in Cudjoe Key, this spot offers a lively atmosphere, especially on weekends, and a more relaxed vibe during weekdays. It's a family-friendly and romantic destination, perfect for enjoying a meal with a view. The restaurant is accessible by boat with dockage available, making it a convenient stop for boaters looking to dine on the water. With its picturesque setting and delicious menu, it's a must-visit for those cruising through the Keys.