
Florida Keys 7 days sailing itinerary

Itinerary description by day

Day 1
Just east of Key West, Stock Island offers a laid-back, authentic Florida Keys vibe with working marinas, local seafood spots, and a growing arts scene. It’s a great place to dock for the night, enjoy fresh catch at waterfront restaurants, or explore the island’s quirky charm before continuing your sailing adventure. Plan to stay at the dock the first night to provision & prepare for a morning departure.
Distance: 0nm
Duration: 0 hours

Day 2
Marquesas Keys
Depart Key West early and sail straight to the Marquesas Keys. Upon arrival, you can explore two wild beaches on the western side—access to the interior is restricted due to shallow waters and bird sanctuary protections. Navigation requires rounding the southern tip and approaching from the west, where anchorage is available in 8–10 ft depths. A secondary anchorage to the south can be used in northerly winds only; eastern and northern approaches are off-limits due to protected shallows.
Distance: 25nm
Duration: 5 hours

Day 3
Garden Key
Depart the Marquesas after confirming a 72+ hour favorable weather window. An early start ensures arrival at Garden Key in time for an afternoon visit to Fort Jefferson before the ferry departs at 2:00 PM. This 14-acre island features the largest brick structure in the Western Hemisphere, plus a visitor center, campgrounds, and excellent snorkeling. Upon arrival, pay the $15 park fee and register for a free boat permit.
Navigation: Stay south of the Quicksands and shoals. Approach via the northern route, following the marked channel west of Garden Key. Anchor near the fort; shore access is by tender to Dinghy Beach or limited-use dock slips (max 2 hours, first come, first served).
Distance: 40nm
Duration: 8 hours

Day 4
Loggerhead
Just 3 miles from Garden Key, Loggerhead is the largest island in the Dry Tortugas and known for its lighthouse, historic marine lab, and abundant sea turtles. Open for day use only, visitors must stay on marked paths. All buildings and docks are closed to the public. Private boats must check in and file a permit at Garden Key before visiting. Return to the Garden Key for the night.
Distance: 6nm
Duration: 1 hours

Day 5
Boca Grande
An early morning departure is essential, especially in winter when daylight is limited. Predominant easterly winds can slow the return journey, often requiring motor sailing.
Distance: 50nm
Duration: 10 hours

Day 6
Wisteria Island
This Island offers a convenient and scenic anchorage with good holding in sandy bottom. While the island itself is uninhabited and landing is discouraged, it’s a popular spot for overnight stays thanks to its proximity to Key West and protection from easterly winds. Ideal for a peaceful break before heading back to the marina.
Distance: 14nm
Duration: 3 hours

Day 7
Stock Island
Plan to arrive at the marina fuel dock by 5:30 PM to refuel. If you haven’t emptied the holding tanks offshore, use the pump-out station at the dock. Overnight stay at the marina.
Distance: 8nm
Duration: 2 hours
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