Sail the Southwest Florida Coast to the Keys 8 Hours at a Time

Sailing to the Florida Keys 8 hours at a time, or dayhopping, is easy along Florida’s Southwest Coast … sail 10 miles across Charlotte Harbor (between Ft Myers and Sarasota), out Boca Grande Pass, hang a quick left and 126 miles (give or take) we’re in the Dry Tortugas, Key West or Marathon/Boot Key Harbor.

Winterlude Anchored at Ft Jefferson, the Dry Tortugas, Florida Keys

Winterlude Anchored at Ft Jefferson, the Dry Tortugas, Florida Keys

But that 126 miles means an overnight sail and missing out on a lot of fun stops further south, such as Marco Island, Naples, Sanibel Island, Ft Myers Beach and all the wonderfulness of the 10,000 Islands including Everglades City and the Everglades National Park.

As usual on these posts, this link will work much better than the embedded map, I still haven’t figured out why.

Dayhop the Southwest Florida Coast to the Keys!

On the link you’ll find our recommended stops, a photo and a link to a post on that anchorage.

I hope someone finds this information useful and we’ll add to it as we explore north of the Charlotte Harbor Florida Coast (i.e. north of Punta Gorda which is just north of Ft Myers).

Happy day sailing!  If you have comments or would like me to add more information, please leave a comment and share!  Cheers!   Jan


  1. Very timely. We are in Matecumbe Bight and plan to leave for Cape Sable on Wed.

    • Wish we were headed to Cape Sable… we’ve never gotten to anchor there… yet. The wind’s always been in the wrong direction. We’re hopeful this year. 🙂

  2. That is exactly what Sue and I plan to do this year – leaving from our current location in Long Beach, Ms. all the way down. I hit a lot of those places on the way up last year and really enjoyed it. Take care.

  3. Cathy Bradshaw says:

    Thanks Jan as always very interesting adventures!
    Looking forward to seeing you out there……winter 2016
    Stormy Duchess

    • Hi Cathy! Hopefully by winter 2016 we’ll be back out exploring for the full six months we’re on the boat! Looking forward to sharing an anchorage with Stormy Dutchess! Cheers! Jan

  4. Hi again. So glad you share your ventures. Curious…going from Everglades to Marathon is there a channel? We have 6.3′ and am looking for a shorter way than going cleat around keys from east coast to west coast though. Thanks for a response in advance.

    • Hi Cheryl – Moser Channel goes through and under 7 Mile Bridge at Marathon. Other than that, no channel really, but it should be doable. We’ve never had any trouble, but we draw 5.5′. Check your charts to be sure. Cheers! Jan

  5. David Cooper says:

    Hello Jan, just wondering if you are still monitoring this blog? My wife Susan and I are planning a nearly identical trip this winter. We are from Michigan and brought our Seaward 32RK down to Largo at the Island Packet facility for some upgrades and repairs last September. Planning on a month long trip to the Keys with many visitation stops along the way in Feb and Mar. Have a few questions regarding the Intercoastal as far as depths and mast height restrictions along the way. Hoping you are still around and thank you.

    • Hi David! We just bought a trawler & are planning to start The Great Loop soon from Bradenton, so we’ll be headed down Florida’s West Coast. We’re still trying to get the boat ready to go (new anchor chain/rode, updated charts, etc) so not sure exactly when, but soon! Ask away – hopefully I’ll be able to answer your questions. Cheers! Jan

  6. David Cooper says:

    Hello Jan and thank you for your response! Didn’t think you were still monitoring this blog (I was looking for an email). Have been putting together some route planning possibilities and returned to this blog to compare. Low and behold your anchorages between Marco/Sanibel area and the Keys are the two I found possible. What was the draft of Winterlude and how far in towards the mainland were you able to get? Or, is it even worth it?
    I do not want to do a 90 mile trip arriving in the Keys (Marathon or Key West) near or at dark, so anchoring is necessary. What was the bug situation and did you feel safe and secure in both areas? Although we have done a number of Caribbean charters and sailed extensively on the Great Lakes we are new to this area. Concerning the inside route when used, are the mile markers an accurate way for time planning? Thank you again for responding, my wife Susan may join in with some questions as well.

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