The word “Key” is derived from the Spanish Cayo, meaning small island. Our watery backyard playground encompasses hundreds of small uninhabited Keys, perfect white sand beaches, and miles of pristine coral fringing tropical reefs teeming with tropical fish. It includes the swath of quiet, small Keys known as the Lower Keys, which include the towns of Big Pine, Summerland, Cudjoe, Sugarloaf & Geiger to name a few. These offer interesting overnight anchorages and ports to visit. And of course fabulous Key West with all that this historic key has to offer. But Key West is only the end of the paved road; the Keys actually don’t end for another 70 miles. Beyond Key West lie a chain of pristine, uninhabited island groups ending at the Dry Tortugas. The Keys’ southern location and relative absence of large-scale artificial lighting at night provide optimal conditions for viewing an unmatched variety of southern constellations, comets, stars and other celestial objects. For the intrepid adventurer the Bahamas, and soon Cuba, are also within our range of sailing charters.

So how much time do you have? Do you want to be close to civilization or leave it behind and sail off to find quiet seclusion? Maybe you want a taste of both? We’ll customize your itinerary pretty much any way you want. Read on for Examples of the Live- Aboard Sailing Vacation itineraries we frequently run.

Westerly Adventure 2 or 3 night itinerary   2 persons  $2595 – $3895
Beyond Key West are several groups of secluded Keys, which include some incredibly beautiful spots to explore. We take a leisurely course towards Woman Key where the water is spectacularly clear and you can lounge in the shallow waters with perfect white sand under foot, walk the beach searching for shells and treasures. After a night at anchor we’ll move on to Boca Grande for lunch, some fishing, snorkeling and more beach combing and end our day at the Marquees Keys where we can check out the Cuban chugs that have washed ashore in attempts to reach US soil. Day three we’ll round the Marquees and make a full day sail along the North side of the chain, passing back through to the Atlantic at Key West harbor before heading back to port.
Easterly Explorer 3 or 4 night itinerary   2 persons   $3895 – $5195
Leave the marina and sail East towards Marathon. Along the way we’ll visit American Shoal with its historic lighthouse, and Looe Key for utterly fantastic snorkeling. We can anchor for the night in Newfound Harbor and take the dingy to shore if you’d like to enjoy a five star meal at the famed Little Palm Island Resort. From there we head towards Bahia Honda State park, whose white sandy beaches and abundant wildlife have frequently earned the area the accolade “one of the most beautiful beaches in America”. We anchor for the night in the shadow of the historic Flagler trestle train bridge. From there we visit Sombrero Reef for more snorkeling and spend the night in the harbor at Marathon.
Atlantic to Gulf Explorer 5 or 6 night itinerary   2 persons   $6595 – $7795
This trip usually includes American Shoal, Looe Key, Newfound Harbor and Bahia Honda. From there we’ll leave the Atlantic waters as we sail under the seven mile bridge into the Gulf of Mexico. There we’ll sail along the line of uninhabited Keys that run all the way back to Key West. The fishing is superb and there are miles of white sand beaches with just the birds and sea creatures as company most of the time. We try to visit the Content Keys, Snipes Key & Mud Keys, where the dingy will be our vehicle into the shallow back country. The trip ends with a night in the historic Key West harbor (subject to slip availability).

The Dry Tortuga NP Voyage – 4 or 5 days  2 persons  $4995 – $5995
Our vessel “Sargasso” is one of the only three sailboats fully licensed by the National Park Service to legally conduct commercial operations within the Dry Tortugas National Park. The Ultimate Expedition! Made up of seven small islands, Dry Tortugas National Park is a truly remarkable place. Home to a multitude of unique birds, vibrant coral reefs, nesting sea turtles, tropical fish and underwater wonders, it’s one of the world’s most unique eco-attractions. Its crown jewel is the historic Fort Jefferson built during the Civil war. Rated the #1 attraction in the Florida Keys by Trip Advisor, visiting the Dry Tortugas is an unforgettable experience. There are only three ways to get there. By a once daily passenger ferry from Key West, sea plane or private charter vessels licensed by the National Park Service. Most people are only afforded a brief taste of this spectacular spot, spending only a few hours on their day trip. There are other companies that run unauthorized Dry Tortugas charters, don’t be fooled by theses unauthorized charter operators as you risk being expelled by park rangers. Check the Dry Tortugas National Park site for authorized vendors.

Sailing to the Dry Tortugas is ideally a fantastic five day adventure, leisurely tripping along the unexploited groups of Keys to get there and back.

Day 1: Departure by no later than 9:00 AM for a leisurely day sail along the various islands with our target being the Marquesas Keys where we’ll overnight. This leg takes approximately six hours. There’ll be plenty of time to swim, snorkel, fish and maybe wander a beach or two before we settle in for the night under the stars.

Day 2: A very early morning departure to make the 50 mile open water jump to the Dry Tortugas, this will take approximately five hours depending on conditions. Our arrival time will dictate what we might be able to squeeze in before securing our anchorage for the night. Our goal is to arrive early enough to take a tour of Fort Jefferson given by the park rangers in the early afternoon. Once the ferry and sea plane depart there will be only a few campers and perhaps a few other boats for the night.

Day 3: A day of leisure to explore the Fort and surrounding areas, fish, snorkel & relax. We’ll make a visit to the isolated island of Loggerhead Key. This is a very special treat as the tourists arriving by ferry or sea plane cannot visit this area, only authorized park operators may get the special day permit which allow us to take you there.

Day 4: On a four day itinerary this day is a 12 hour sail back to the marina. On a five day itinerary we make a leisurely sail to beautiful Boca Grande or Woman Key to enjoy the afternoon snorkeling, fishing and beach combing and another magical night under the stars.

Day 5: Morning departure for Key West where we’ll sail around the harbor before heading back to our marina. Our estimated arrival at the dock is 3:00pm.

• Includes chef prepared gourmet meals, water, assorted soft drinks, coffee & tea. Adult beverages may be brought aboard. There is an additional $100.00 cleaning and pump out fee.

Due to the isolated location it is recommended that participants have a history of completing multi-day sailing trips, sleeping on a moving boat and not susceptible to seasickness. The only opportunity to jump ship and get a quick return to Key West is aboard the once a day ferry from the Dry Tortugas. The Dry Tortuga itinerary is wholly subject to favorable weather and ocean conditions during the scheduled dates. We reserve the right to create an alternate itinerary if the weather or oceans conditions before or during the trip are unfavorable to comfortably sail this route or find safe anchorage.


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