Florida Keys Sailing Charters

High-performance adventure sailing.
Florida Keys sunset Fish in the Florida Keys Beautiful beaches in the Florida Keys Florida Keys weathered boats

Florida Keys Charters

On the southernmost part of the continental United States, kick back and relax in the sun-drenched Florida Keys on Catamaran Surprise.


Endless options await. To the west lies tranquil Florida Bay and the primeval Everglades backcountry. To the east flows the colbalt deep blue water of the Gulf Stream with big fish. Starting out in the north is Key Biscayne with Cape Florida State Park and her magnificent lighthouse, Biscayne National Park with its little gem, Boca Chita Key, then Key Largo with John Pennekamp Coral Reef State Park and Islamorada. Further to the south are the pristine Lower Keys in their natural state of tropical wilderness.


In the two hundred miles from Biscayne Bay to the Dry Tortugas there are innumerable islands, reefs, lakes, bays and beaches for delightful sailing adventures. Drift-dive Sands Cut, snorkel Pennekamp Park, kayak the mangrove labyrinth of Lignumvitae, feed the tarpon, catch the big fish past the reef, check out an underwater lodge, visit a cool museum, spend the night at the National Marine Sanctuary at Looe Key.

Stroll the beach at Bahia Honda State Recreation Area, visit the Windley Key Fossil Reef, see the Turtle Hospital in Marathon, the Blue Hole on Big Pine Key, relive the history of Indian Key and catch a sunset at the famous Mallory Market on Key West with exotic revelry!

Yes, there’s much to do on our Keys Adventure! Its just a question of how much time you can join us for. There are only a few places on earth that offer the brilliance and serenity of the Florida Keys with the outstanding attractions both man-made and natural while cruising an enchanting water world. And we’ve said nothing about the mysterious Everglades where we were registered National Park guides for 10 years!

South Beach to Dinner Key Marina: 7 Nights/8 Days

(Longer or shorter itineraries are available, One-way trips as well)

  • Day 1:  Pick Up Miami Harbor. Afternoon walking tour Miami Beach, Lincoln Street Mall. Evening out on South Beach.
  • Day 2:  Miami to Boca Chita: Visit No Name Harbor, Cape Florida State Park, Key Biscayne. Visit Soldier Key (manatees), visit Boca Chita Key, Biscayne National Park.
  • Day 3:  Boca Chita to Angelfish Creek: Snorkel Boca Chita, Drift-dive Sands Cut.
  • Day 4:  Angelfish to Largo Sound: Traverse Angelfish Creek, sail Hawk Channel. Snorkel Grecian Rocks. Visit  Pennekamp Park’s museum, visit Jule Undersea Lodge.
  • Day 5:  Largo Sound to Indian Key: sail Hawk Channel and snorkel Hen and Chickens Reef or sail out past the reef to deep-sea fish. Explore Indian Key.
  • Day 6:  Indian Key to Lorelei: Sail to Channel 5 Bridge. Cross into FL Bay. Kayak mangrove jungle, feed tarpon, visit Lorelei Beach Bar (option, Seafood Buffet out)
  • Day 7:  Lorelei to Gilberts: visit Sportsman Shop, sail FL Bay, beach at North Nest Keys, visit Gilberts Resort.
  • Day 8:  Return sail up Biscayne Bay to Dinner Key Marina.