Explore the Florida Keys’ Coastline aboard a Fun In The Sun Yacht.
Below we have a few sample itineraries for you to plan your next Florida sailing adventure. The Florida Keys are a perfect charter for both 3-day and weeklong sails. A week-long Florida Keys sailing trip from our South Florida Sailing base includes such destinations as Miami, Biscayne Bay, Key Largo, Islamorada, Marathon, and Key West. You can even sail as far as Fort Jefferson in the Dry Tortugas. If sailing to Key West or the Dry Tortugas you may want to sail the boat one way and drop the boat off in the lower keys.
Upper Florida Keys
Day 1 – Provision in the morning board and depart by 2:00 PM Sail to Miami and spend the night at Dinner Key Marina, Miamarina at Bay Side, Miami Beach Marina, Crandon Park Marina, or anchor in “No Name Harbor” or at Nixon’s Harbor. (18NM)
Day 2 – Depart from the Miami area and sail south down Biscayne Bay, anchor on the inside of Elliott Key (Swim, Snorkel, Beach). Spend the afternoon there and then sail a little further south to spend the night behind Pumpkin Key. (17 NM)
Day 3 – Sail out through Angel Fish Creek into Hawks Channel. Best done at high tide. Entrance and exit are trickiest but in between is plenty of draft. Sail to Craysfort Reef snorkel mid-morning to mid-afternoon. Depart the reef and sail back to No Name Harbor or Miami Beach Marina to spend the night. (17 NM)
Day 4 – Depart early in the morning and sail on back to Fun In The Sun Marina. Unload, clean up and be on your way by 12:00 Noon. (18 NM)
Upper Florida Keys
Day 1 – Provision in the morning board and depart by 2:00 PM Sail to Miami and spend the night at Dinner Key Marina, Bay Side Marina, Miami Beach Marina or anchor in “No Name Harbor”. (18NM)
Day 2 – Depart from the Miami area and sail south down Biscayne Bay, anchor on the inside of Elliott Key (Swim, Snorkel, Beach). Spend the afternoon there and then sail a little further south to spend the night behind Pumpkin Key. (17NM)
Day 3 – Sail out through Angel Fish Creek to the out side. Best done at high tide. Entrance and exit are trickiest but in between is plenty of draft. Sail to Craysfort reef and Elbow Reef snorkel mid-morning to mid-afternoon. Then sail north to Key Largo and pull into Marina Del Mar. Have dinner at a restaurant get off the boat for a while spend the night. (26NM)
Day 4 – Sail southwest on the outside down to Marathon. Full day of sailing. Spend the night at Marathon Marina. (47NM)
Day 5 – Sail out to Sombrero Reef for an early morning snorkel. Then head back northeast and sail to Windley Key. Pull into Holiday Isle Marina (Do not dock at transient dock). Spend the night. (38NM)
Day 6 – Full day sail on the outside up to Government Cut and into Miami, sailing with the Gulf Stream will make for a very fast sail. Choose from the many marinas or moorings to spend the night. (59 NM)
Day 7 – Sail on the outside up to Port Everglades and back to Fun In The Sun Marina. Spend the night on the boat. (18NM)
Upper Florida Keys Family
Day 1 - Provision in the morning board and depart by 1:00 PM Sail to Miami and spend the night at Dinner Key Marina, Miamarina at Bay Side, Miami Beach Marina, anchor in Nixon’s harbor, or in “No Name Harbor” at the southern tip of Key Biscayne. If staying at anchor at No Name Harbor be sure to take time the next morning to check out the nature trails, visit a top 10 beach in the U.S., and climb the historic Cape Florida Light House. All is within walking distance of the anchorage as this is a state park. Also, there is a very good restaurant right at the harbor. Boater’s Grill specializes in Cuban food but has a very eclectic menu and is open early in the morning for breakfast and closes late at night. (25 – 30 NM)
Day 2 – Another option for the morning of Day 2 is to sail the short distance from any of the marinas or anchorages mentioned above over to Hobie Beach and dinghy into the Miami Seaquarium. This will get the kids in the mood for the sailing adventure that lay ahead. Depart from the Key Biscayne / Miami area and sail south down Biscayne Bay, you may anchor on the inside of Elliott Key where you can swim, snorkel, hike and go to a small rocky beach, or stop at Boca Chita where there are BBQ pits, picnic tables, and a faux light house for the kids to climb. Boca Chita is another state park with a manmade harbor and a seawall with cleats. No services on either of these islands, good for just a quick stop and lunch. After lunch sail a little further south to spend the night behind Pumpkin Key or at Wednesday Point in Card Sound. (23 – 28 NM)
Day 3 – The next morning Sail out through Angel Fish Creek to Hawk’s Channel. Sail to Little Grecian Rock Reef, snorkel mid-morning to mid-afternoon. This is where you will find the Christ of Abyss Statue under water. The statue’s spread arms seem to welcome you to the reefs of the Florida Keys. After a great day on the reef, sail to Key Largo and pull into Marina Del Mar or Anchor at Rodriguez Key. If anchored at Rodriguez Key you can dinghy into the pier at Rock Harbor, walk across the street and have dinner at Ballyhoo’s Restaurant where you will find excellent local seafood. (22 – 24 NM)
Day 4 – Sail southwest in Hawks Channel to Hen’s and Chickens Reef. This reef is a very shallow reef, great for kids and is on the inside so conditions are always calmer than the outer reef. After lunch on the boat, depart from Hens & Chickens and sail the short distance to Post Card Marina at Holiday Isle Resort on Windley Key. At this family friendly marina and resort, you will find a great beach, activities for the kids, swimming pool, snorkeling, jet skis, parasailing, banana boat rides, and wonderful restaurants. The Theatre Of The Sea is very close by and has performances for the family. Also, a bit longer cab ride can take you to the Florida Keys Dolphin Research Center on Long Key. There you can have a dolphin encounter, swim with the dolphins, and learn all about these amazing mammals. Spend the night at the marina. (12 – 14NM)
Day 5 – Depart Holiday Isle early and sail the short distance to Indian Key. Pick up a mooring ball at the Indian Key Anchorage. Historic Indian Key is a small island and a state park. There are no services on the island other than ruins from an early 1800’s settlement and a self-guided tour explaining the rich history of the Wrecker’s who settled on the island and were overrun by the native Indians. After a short visit, let the mooring ball free and sail northeast on the outside of the reef allowing the Gulfstream to help you along. If you are making good time, you can always stop at one of the many reefs along the way as they all have recreational day mooring balls open to the public. Sail all the way back up to Rodriguez Key or Marina Del Mar. Spend the night. (21 – 24 NM)
Day 6 – Continue your sail north on the outside of the reef up to Government Cut and into Miami or Old Biscayne Channel and into Upper Biscayne Bay. Sailing with the Gulf Stream will make for a very fast sail. Keep your eyes open for wildlife such as sea turtles, flying fish, and dolphin. Once you get to Upper Biscayne Bay or the Miami area choose from the many marinas, moorings, and anchorages to spend the night. (48 – 55 NM)
Day 7 – Depart from Upper Biscayne Bay or the Miami area and sail on the outside up to Port Everglades and back to Fun In The Sun Marina where you can get a land shower and spend a nice evening in Fort Lauderdale. You can check out the shopping and dining on Las Olas Boulevard or Ft. Lauderdale Beach, go to the Children’s Museum of Discovery and Science or just walk to one of the many fine restaurants close to our facility. Spend your last night on the boat at the marina at Fun In The Sun. (25 – 30 NM) Day 8 – Pack up, clean up, and depart by 12:00 Noon. To add a little excitement, try fishing while you are sailing. It’s a thrill trolling for and catching Dolphin (Mahi Mahi), Tuna, Pompano, Mackerel, and Wahoo, not to mention the occasional billfish. Equipment is available for rent at our base. There is nothing like fresh caught fish for dinner! You can also rent a kayak for island exploration and/or a windsurfer for the water sports enthusiast.
Lower Florida Keys
Sailing from Marathon Key you will experience the many pleasures and sites of the Florida Keys. The unspoiled coral reefs of the Lower Keys have many sites where you can tie up to a mooring ball and snorkel or dive. Hawks Channel provides fantastic sailing, as there is protection from the ocean swells but still great wind.
Day 1 – Depart out of Marathon and sail to Bahia Honda. One of the best anchorage’s in the Florida Keys. Drop your hook near the Old Keys Trestle Railroad Bridge and enjoy the calm natural harbor at Bahia Honda State Park. (12 NM)
Day 2 – Depart Bahia Honda and sail out to Looe’s Key. (6NM) Looe’s Key is a National Marine Sanctuary with great snorkeling and diving. The Reef is from 1 to 80 feet with a great wall for SCUBA. Tie up to one of the mooring balls placed there for your ease of use and also to protect the coral from dropping anchors. After a few hours on the reef head for Newfound Harbor. (5NM) Here you may anchor out or stay at a very exclusive and expensive marina. Little Palm Island Marina offers transient dockage at $7.50 per foot per night with a minimum of $350.00. They have a 5 star restaurant and hotel accommodations, which are very pricey as well. If such an expensive marina is not in your itinerary Newfound Harbor is a great place to spend the night on the hook and there is a restaurant that you can dinghy into.
Day 3 – Depart Newfound Harbor and sail to Key West. (27 NM) Stay at Key West Bight Marina or anchor out in Man of War Harbor. Enjoy the nightlife and shopping in the quaint village of Key West.
Day 4 – Depart Key West and sail to the uninhabited island group of the Marquesas. (26 NM) Enjoy the quite and solitude that this island group offers. Calm waters and nice sandy beaches provide wonderful swimming and relaxation.
Day 5 – Depart the Marquesas and sail back to Key West. (26NM) Stop along the way for some fantastic snorkeling by mooring to the dive buoys on the reef. Spend two nights in Key West to take in all that this “end of the road” destination has to offer.
Day 6 – Explore Key West and maybe do a day sail out to the reef for some snorkeling.
Day 7 – Depart Key West and sail back to Bahia Honda for your last night out on the hook. (33NM)Day 8 – Depart Bahia Honda and sail back to Marathon. (12NM) Arrive early enough to unload, clean the boat and be on your way by 12:00 Noon.
Day 1 – Depart out of Marathon in the evening and sail to the Dry Tortugas. (107 NM) It will take anywhere from 12 to 16 hours to make this passage. You should try to arrive in day light hours so that your approach is easier.
Day 2 – Arrive at the island group known as the Dry Tortugas. This is the most isolated and least visited national park in the United States. You should plan to spend two nights here but if the weather deteriorates be flexible enough to cut it short and head back to Key West. There are no services out on these islands so you should plan to be self sufficient while in this remote area.
Day 3 – Go ashore on Garden Key and tour Fort Jefferson National Monument. This was originally built in the mid 1800’s as a military fort to be used by Union forces during the Civil War. The fort was converted to a prison whose most famous inmate was Dr. Mudd of Lincoln’s time.
Day 4 – Snorkel the reefs surrounding the islands. Go ashore on Loggerhead Key and/or Hospital Key for a cookout, just be sure to clean up well and leave as little of a footprint as possible. Bush Key offers great bird watching from your yacht. Bush Key is a bird sanctuary and landing is prohibited.
Day 5 – Depart the Dry Tortugas early in the morning and sail to the uninhabited island group of the Marquesas. (44 NM) Be careful of Rebecca Shoal on the way and arrive before dark. Enjoy the quite and solitude that this island group offers. Calm waters and a nice sandy beach provide wonderful swimming and relaxation.
Day 6 – Depart the Marquesas and sail to Key West. (26NM) Stop along the way for some fantastic snorkeling by mooring to the dive buoys on the reef. Spend the night at Key West Bight Marina or anchor out in Man of War Harbor. Enjoy the nightlife and take in all that this “end of the road” destination has to offer.
Day 7 – Depart Key West and sail to Bahia Honda for your last night out on the hook. (33NM) One of the best anchorage’s in the Florida Keys. Drop your hook near the Old Keys Trestle Railroad Bridge and enjoy the calm natural harbor at Bahia Honda State Park.
Day 8 – Depart Bahia Honda and sail back to Marathon. (12NM) Arrive early enough to unload, clean the boat and be on your way by 12:00 Noon. There can be variations on some of these itineraries, but all of them show that there is plenty of fun things to do in a 3 Days or a Week of charter in the Upper & Lower Florida Keys. If you would like further information or would like to plan a different Keys or Bahamas trip give us a call and speak with our knowledgeable staff. Cruising guides and Waterproof charts of the different areas are available for sale at our Ship Store and can be sent to you in advance to help you plan your sailing vacation.