Bareboat Yacht Charters Florida: Charter Adventures in Florida


Detailed Adventures


Florida Keys Sailing Highlights

Biscayne Bay: Biscayne Bay is protected by a shoal offshore which makes for smooth sailing and well-protected anchorages. Look for an odd assortment of houses built on stilts, called “Stiltsville.”

No Name Harbor: A short sail to this peaceful anchorage beneath Cape Florida Lighthouse gives you the option of two restaurants to choose from, one in the harbor and the other overlooking the beach.

Elliot Key: Your destination one evening could be Elliot Key or if you are making good time, continue on to round, little Pumpkin Key, which always has a lee side.

Hawk Channel – Key Largo: At the south end of Biscayne Bay/Card Sound is this body of water between the Keys and off-shore reefs. Angelfish Creek is a winding little channel cut through thick mangroves.

Florida Keys Reefs: There are several reefs that have permanent mooring buoys you tie onto without anchoring. Carysfort Reef, the Elbow, and Grecian Rocks are just a few of your choices, and bunched close together, so why not visit them all?

Key Largo: As the south end of Key Largo there are a number of different marinas to choose from: Marina Del Mar to port and Key Largo Harbor to starboard. There is a grocery store and drug store next to an ice cream shop. It’s a short ride to The Fish House, one of the best seafood meals in the Keys.

Rodriguez Key: Why not waste away a day in Margaritaville? You have plenty of time to partake of all the activities at Holiday Isle Resort or you can head out for another day of snorkeling on the reefs.

Lower Matecumbe Key: After passing Hens & Chickens, continuing southwest approximately 6 miles to the north end of Lower Matecumbe Key you will find Indian Key Anchorage. Along the way, you again have a choice of several beautiful reefs for snorkeling: Conch Reef, Davis Reef, and Pickles Reef. If you have never tried snorkeling on a tropical reef before, you will be amazed by the beauty.

Indian Key Anchorage: You can dinghy into the dock at and walk around what used to be a thriving community. This was the Dade County seat from 1836 until 1840 -- when the Indians burned it down. This would be a perfect anchorage to barbecue off the stern of the boat, a great option for dinner.

Alligator Reef: Here you will find plenty of bright and colorful tropical fish on this shallow reef.

Holiday Isle Beach Resort on Windley Key: Here you will find restaurants, arts and crafts shops, sport fishing, wind surfing, parasailing, jet skiing, swimming pools and great beaches…all Florida Key’s style!

Duck Key: Here you will find Hawk’s Key Marina where amenities include fresh and salt water pools, poolside bar, tennis courts and workout room, restaurants and a very popular dolphin shows.

John Pennekamp State Park: This Park, combined with the adjacent Florida Keys National Marine Sanctuary, encompass 178 nautical miles of mangroves, coral reefs and beds of sea grass.

Coconut Grove: Your slip is close to downtown, which is filled with shops, restaurants and clubs.

Bimini Island Chain Highlights

Alice Town: Here you will find friendly people, quaint shops, several bars and restaurants and a beautiful deserted white sand beach on the west side of the island. The Anchorage Restaurant across from the Bimini Blue Water Resort is a great place for dinner or if you would like a spectacular sunset with your meal go to the Bimini Bay Restaurant. Call the Bimini Bay Restaurant and they will send a courtesy van to pick you up.

Bimini Road Anchorage and the Lost City of Atlantis: After leaving Bimini Harbor, turn to the northeast for about three and half (3.5) miles to the rocks just off the hotel marked on the chart. There are wonderful underwater sights to see for all the snorkelers and divers on board. If there are mooring buoys, pick one up, if not, drop your anchor in the white sand.

North Rock: For your evening anchorage, sail northeast two and half (2.5) miles to North Rock and then turn southeast for another two and a half (2.5) miles. From this point motor into the shoreline until you are in eight to ten (8-10) feet of water for anchoring. You may feel like you have the world to yourself while walking this beautiful deserted beach and exploring the mangroves by dinghy.

The Wreck of the Sapona: About two miles south past the Bimini Harbor entrance, between Round Rock and North Turtle Rock you will sail east and southeast clearing the shallow area just east of Turtle Rocks. You will be able to see the wreck of the Sapona, a concrete ship, from quite a distance and this is your intermediate destination today. Anchor anywhere around the ship putting out plenty of anchor rode. The brightly colored fish love to congregate here and if you swim around to the west side of the wreck you can actually snorkel inside the broken hull! Be aware the current runs swiftly at times.

Gun Key Anchorage: From the Sapona sail almost due south until you are just off the rocks north of Gun Cay -- about three and a half miles. At this point, motor along the eastern edge of the sand bar and Gun Cay; the secret to successful anchoring here is to find a sandy spot, drive over it and drop you hook just a head of the sand. Your anchor should drag through the grass and hold in the sand. This is a very popular anchorage so you will often have company here. Gun Cay is an uninhabited island always awaiting a shore party! If you enjoy fishing, this is close to the Bahama bank where the fish are hiding

Honeymoon Harbor: Why not turn on Bahamian time and have a lazy morning swimming and sunbathing. If you would like a more active morning – try taking the dinghy around to Honeymoon Harbor, the white crescent beach at the north end of Gun Cay, for a walk and shell gathering.

Dollar Harbor, South Cat Cay: If your preference is deserted tropical islands, South Cat Cay offers a long rocky and sandy coastline along the western side. You can walk up around the northern tip of the island where there is a white sandy beach.

Wedge Rocks: If you are already in Dollar Harbor, take your dinghy or your boat out to Wedge Rocks for another afternoon of snorkeling. You can either stay at Dollar Harbor tonight or run back to the Gun Cay anchorage. Either location puts you in a good position for your departure to Miami.

Key West to the Dry Tortugas

Seven Day Itinerary

Vessel orientation will be scheduled for 10:00am the following morning. 

If you will be arriving late at the marina, consider an overnight board as an option when checking in after 3:00 pm. Once you check in you will still have plenty of time for provisioning and to get in some sightseeing. 

There are three grocery stores which are located in Key West proper (Publix, Albertson’s and Winn Dixie) They are a ten minute taxi ride from the marina.

Provisioning for the Dry Tortugas must be done carefully. There are no facilities of any kind after you leave Key West, no marinas, no fuel and no fresh drinking water. Be sure to take plenty of food and extra drinking water, more than you think you’ll actually need. You may want to bring a jerry jug of extra fuel, especially if you plan to do a lot of motoring or running a generator. 

Many of our charter guests love Key West so much, they simply day sail and come back to the marina at night. More adventuresome sailors can head out for a trip to the Marquesas and The Dry Tortugas. This itinerary requires advanced navigation skills, prior experience anchoring overnight; and a sense of self-reliance, since you are mostly out of VHF hailing range.

The “Dry Tortugas” were named by early Spanish explorers, due to their resemblance to the sea turtles which were once so plentiful, and the fact that they are “dry”. There is no source of fresh water available.

Though it is not an easy place to get to, once you’re there, we think you’ll agree it’s worth the effort! Part of the appeal of the Tortugas is the remote solitude, natural wildlife and peaceful nature of these islands. The history of abandoned “Fort Jefferson” adds mystery.

Fort Jefferson has a fascinating history and the architecture of this massive structure is amazing. It is well worth a few hours of exploring. Visit the lonely cell of Dr. Samuel Mudd, who was imprisoned here for setting John Wilkes Booth’s broken leg, after he assassinated President Lincoln.

The Dry Tortugas are a National Park, staffed by a few friendly park rangers, and their own water supply is dependent on a cistern system, so you cannot get fresh water from the park, or food. (Some guests however, have reported having great success swapping cold six-packs of beer with the local fisherman, in return for fresh lobster, fish or shrimp!)

Weather is a very important factor when planning a trip to the Dry Tortugas. Listen carefully to the local forecast and check with our Key West manager before leaving.

If weather is not conducive for a trip to the Dry Tortugas, you can always head back through the Keys for a trip in more protected waters. A strong wind from any direction can make this an uncomfortable trip. During the winter months, a strong wind from the north can make this trip downright impossible. Thus, the best time to attempt a trip to the Tortugas is late spring and early summer.


As you depart the marina you will be turning to starboard. Carefully follow the day markers out through the channel. Your course will take you through West channel staying south of Man Key, Woman Key, and Boca Grande.

Approaching the southern tip of the Marquesas Keys, the best anchorage is west of the islands if the prevailing southeast winds are blowing. You can anchor anywhere around the island depending on the wind. Watch the depths carefully as you are approaching the islands.

Distance - 20 miles.

Day 2

Depart the Marquesas in the morning and continue your westerly course, staying south of the Quicksands, Halfmoon and Rebecca Shoals. Track your position carefully as there is a strong north/south current running through the area. Plot your course past the Yellow “O” marker and leave the Red “2” (south and east of Garden Key) to starboard. Cross Southeast Channel using the Green “3” (between Bush and Hospital Key) as your landmark, leaving it to port turn toward the Red “2” and Green “3” (just north of Garden Key). Motor carefully through the channel between Garden and Bush Keys and your anchorage is just south and east of Garden Key. This anchorage is often full and the water shallows quickly as you approach the boundaries. You can also find anchorages southwest and west of Garden Key.

Distance- 45 miles

Day 3

Dinghy ashore and explore Fort Jefferson. Be sure not to leave your dinghy on the beach where the daily sea planes take off and land. Also take a walk or snorkel around the sea wall which creates a “moat” between the fort and the sea, and is brimming with fish. 

Day 4

Take a day trip over to Loggerhead Key. This is a great place to explore and go snorkeling but it does NOT make a good overnight anchorage. You can exit the anchorage at Garden Key either the same way you came in or go out through the channel which is southwest of Garden Key. The anchorage at Loggerhead is east of the island just off the light in the center. From here you can dinghy ashore and walk around the island or dinghy around the southern tip to the reefs off the western side of Loggerhead Key. Before dark, head back over to Garden Key to anchor for the evening.

Use both anchors as the holding ground is “iffy”.

Day 5

Spend another day relaxing and enjoying the Dry Tortugas. Bush Key is protected bird

Sanctuary and during nesting season it is interesting to dinghy slowly around the island

Observing the bird life ashore and all the sea life in the shallow water.

Day 6

It is time to start back to Key West today. Plan on making a stop again at the Marquesas on the way back especially during the winter time when there are limited day light hours. If you make an early start and are making excellent time, you may be able to make it back to Key West. Be sure you can make it to Key West with day light to spare.

Day 7

If you stopped in the Marquesas yesterday, continue on to Key West today. You should

be able to get in early if you want to have some time to explore Key West. Pull into the fuel dock at Oceanside Marina, fuel up and pump out before docking.

Day 8

Your boat is due back today at 10 a.m. Please make sure to bundle your linens, remove trash (trash containers are located at the beginning of the dock), top off the fuel tank and pump out, if you haven’. Please see the charter manager before departing the marina.

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At the Port of Palm Beach · 1177 Avenue C. West Palm Beach, FL 33404. · 800-537-0050 or 561-844-1100 ·

Bareboat Yacht Charters Florida: Charter Adventures in Florida