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Trailer boat to Florida Keys next Winter

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  • Trailer boat to Florida Keys next Winter

    Wife and I are contemplating a visit to the Florida Keys with our 25 foot cuddy next Winter. The plan is to trailer it down, launch it and leave the truck and trailer parked, then do a 5 night cruise with a mixture of transient slips and quiet anchorages for the overnights. The boat draws 39" of water. I have never been to the are and would love to hear some recommendations of must-see places and must-do activities. Marina and boat ramp recommendations would be great too. We would like to keep our daily distance traveled by boat to under 75 statute miles, but can handle more if there's a good reason for it. We prefer to have shore power while in a slip, but it is not necessary, so we would consider any transient dockage that can handle our draft, the cheaper the better; showers are a must though...

  • #2
    Islamorada..... great drinking place with a fishing problem
    Cheesehead boating the Gulf Coast of FLA 27.51° N, 82.53° W

    1988 Cruisers Rogue 2420 -VP 290 DP now powered by custom 468 - https://forums.iboats.com/forum/owner...988-rogue-2420

    Past Boats
    1970 Wooster Hellion - Merc 9.8
    2002 SeaRay 190BR - 5.0 - A1G2 - "Cheeseheads in Paradise"
    1984 Avanti 170DLI -3.0 stringer- "Ship Happens"

    What’s behind you doesn’t matter.Enzo Ferrari

    Comment


    • #3
      No input other than sounds awesome...
      1979 Carver Montego 2357 | 260 Mercruiser upgraded to Alpha | 2006 Nissan 15hp kicker

      Girls cry and boys fart in front of friends, but girls fart and boys cry in front of true friends.

      Comment


      • #4
        For a shorter tow, I suggest putting in at Tarpon Springs and cruising to Ft. Myers via the Gulf Intracoastal. Sample itinerary:

        After put-in at Anclote River Park near Tarpon:

        Caladesi Island State Park Marina. About 20 miles. Great undeveloped barrier island with fantastic shelling if you like such. No restaurant beside a snack bar. No showers, but does have bathrooms. Docks are $1 per foot with power and water. Try to find that in the Keys!

        Cruise about 35 miles to Ft. DeSoto State Park and anchor.

        Cross Tampa Bay and drop some serious coin at Longboat Key Moorings. If not, there are several marinas and anchorages in the area. About 35 miles.

        Cruise to Aquamarina Palm Harbor. About 40 miles

        Cruise to Captiva and stay at South Seas Island Resort or ‘Tween Waters. Take your checkbook, but if you’re considering Key West, it’s about the same money and less crazy. About 40 miles. On the way, stop at Cabbage Key for a “Cheeseburger in Paradise”. It is the place that inspired the song. If you want to anchor, go farther south and anchor off Ding Darling Wildlife Refuge on Sanibel.

        From there, go to any of the marinas in Ft. Myers. I’ve been to Legacy Harbor. It’s close to everything.

        Rent a car from Enterprise and go fetch your truck and trailer in Tarpon Springs. You’ll have to work to find storage in or near Tarpon. I don’t know how long you can park at Anclote River.

        There are a lot of “No Wake” areas on the Intracoastal so you can’t make as much time as you may be used to.

        If you’re not using Active Captain, start. Unfortunately, Garmin bought it and they’re in the process of screwing up a good thing. Maybe they won’t, but it doesn’t look good.

        Have fun! We did!

        Comment


        • #5
          And we have people along the way...
          1979 Carver Montego 2357 | 260 Mercruiser upgraded to Alpha | 2006 Nissan 15hp kicker

          Girls cry and boys fart in front of friends, but girls fart and boys cry in front of true friends.

          Comment


          • #6
            If you're looking for a crew...sign me up !!
            I'm just a beer-lover with a fishing problem...

            Comment


            • #7
              Originally posted by four winns 214 View Post
              For a shorter tow, I suggest putting in at Tarpon Springs and cruising to Ft. Myers via the Gulf Intracoastal. Sample itinerary:

              After put-in at Anclote River Park near Tarpon:

              Caladesi Island State Park Marina. About 20 miles. Great undeveloped barrier island with fantastic shelling if you like such. No restaurant beside a snack bar. No showers, but does have bathrooms. Docks are $1 per foot with power and water. Try to find that in the Keys!

              Cruise about 35 miles to Ft. DeSoto State Park and anchor.

              Cross Tampa Bay and drop some serious coin at Longboat Key Moorings. If not, there are several marinas and anchorages in the area. About 35 miles.

              Cruise to Aquamarina Palm Harbor. About 40 miles

              Cruise to Captiva and stay at South Seas Island Resort or ‘Tween Waters. Take your checkbook, but if you’re considering Key West, it’s about the same money and less crazy. About 40 miles. On the way, stop at Cabbage Key for a “Cheeseburger in Paradise”. It is the place that inspired the song. If you want to anchor, go farther south and anchor off Ding Darling Wildlife Refuge on Sanibel.

              From there, go to any of the marinas in Ft. Myers. I’ve been to Legacy Harbor. It’s close to everything.

              Rent a car from Enterprise and go fetch your truck and trailer in Tarpon Springs. You’ll have to work to find storage in or near Tarpon. I don’t know how long you can park at Anclote River.

              There are a lot of “No Wake” areas on the Intracoastal so you can’t make as much time as you may be used to.

              If you’re not using Active Captain, start. Unfortunately, Garmin bought it and they’re in the process of screwing up a good thing. Maybe they won’t, but it doesn’t look good.

              Have fun! We did!
              If you want more beer money budget Here is a few things I would change.

              VS longboat key, moor at longboat pass at Jew Fish key. (free) get a bite to eat and drink at the Swordfish Grill or Cortez Kitchen

              vs Captiva, stay in Matlacha at the Anglers in https://anglersinnmotel.com/ Still visit Cabbage key, etc.
              Cheesehead boating the Gulf Coast of FLA 27.51° N, 82.53° W

              1988 Cruisers Rogue 2420 -VP 290 DP now powered by custom 468 - https://forums.iboats.com/forum/owner...988-rogue-2420

              Past Boats
              1970 Wooster Hellion - Merc 9.8
              2002 SeaRay 190BR - 5.0 - A1G2 - "Cheeseheads in Paradise"
              1984 Avanti 170DLI -3.0 stringer- "Ship Happens"

              What’s behind you doesn’t matter.Enzo Ferrari

              Comment


              • #8
                Thanks for the replies. I did some research on transient slip prices and decided the gulf coast makes more sense for our first boating trip to FL. Man, those key slips must be something special... I love the idea of the one-way cruise with the rental car option. We've done something similar to that on Chesapeake Bay and it worked out really well. Please keep the ideas rolling in.

                Comment


                • #9
                  Its the adventure . I do it , drive myself crazy and I live in FL.
                  Four Winns 214 advice is spot on .
                  I have a buddy that trailers his 30 ft boat often too Caladesi Island . We both live Orlando area . .
                  I keep my 30 ft cruiser Cape Canaveral marina . ( have a trailer )
                  I get the bug too get out of Dodge ,and after I do either by water or trailering I question WHY . Deal with expensive marinas, expensive fuel , and the hassle of trailering a boat or going via water ? BUT STILL DO IT .

                  Once you pass ( lets say ) Vero Beach south , heading too Keys pricing gets insane

                  I have stayed few places Keys Prior too Irma .
                  Trailering a 21 ft fishing boat .
                  Perfect few days fishing with guys . Went too Marathon No fancy rooms Common for Keys is old run down rooms .
                  ( 1 ) Coconut Cay , Marathon can tie boat too dock behind room . Nothing fancy . Run down prior to Irma .
                  ( 2 ) Sombrero Resort , has a dock behind condos , last time there boat ramp was in poor condition
                  ( 3 ) Black FInn , clean rooms , has a marina on property .with ramp . . They charge a fee too leave boat at dock . Can leave on trailer and launch .
                  There are many places that offer rooms with ability too tie up just challenging finding a place hundreds of miles away
                  West Coast is easier , lots of places too visit. Clearwater , St Pete Beaches
                  Good luck

                  Comment


                  • #10
                    Cruise out to Dry Tortugas/Fort Jefferson.....anchor/overnight there if you like....beautiful place!

                    Comment


                    • #11
                      Sign up today
                      We are in the keys for 3 months in winter. Our 19' boat is in the canal behind our rental. We get stopped on the water about once a week by the FWC for a fishing license check and boat check. I think because the boat has NY registration. Keep your radio on and listen. Once we heard "This is Coast Guard Key West. We are in pursuit of a vessel (they gave the position 60 miles from us) All vessels are advised to keep clear because live ammunition is being expended." Irma made the deeper areas shallower and the shallow areas deeper .Some channels in the bay used to be 6' deep. Now I kick up sand and I draw 30". Have a good trip. It is nice there.

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