We’ll trailer down to our fav marina in Key West (Stock Island Marina) next month for six weeks (every year for the past 5 or 6 years). Your trailering 2,600 miles for 5 days of boating is hardcore. Artic blasts from the north drop the temps from 82 to 65 for a few days til they pass. Navigation is straightforward, but unforgiving. Nav aid posts may be set in coral rocks that are awash at high tide. Brown is bad. Green water is good. No shortcuts ever until you’ve been there before. Plan to cruise with the sun at your back with polarized sunglasses from sunrise to noon. It’s basically the Caribbean in winter…windy to Small Craft Advisory most every day in the afternoon. Don’t even think about going to Dry Tortugas…10 million lobster pots marked by 3 inch Styrofoam floats that are invisible in the whitecaps. Fine to do it in July, but who wants to be in Key West in July? Take the seaplane there for a trip of a lifetime!
https://stockislandmarina.com/ Key West has great protection from wind and wakes, a heated pool, 5 star resort marina, AC in restrooms/clean showers and laundry, free weekly pumpout by dockhands, free hourly shuttle in to town (though we have our truck there and don’t need it) half price pool bar dinners during happy hour, check DOCKWA there for your rate. Free cancellation up to 48h prior to reservation. $15 to launch at Key West City marina at, Garrison Bight, $10/day for dual axle trailer storage. Have to cruise west then south then east clear around the island, may be rough in the afternoons. Cheaper at Garden marina Cudjoe Key but 20 miles away. Founders Park Plantation key also has trailer storage and ramp. The closest big 6-lane launch ramp with rig storage is Herbert Hoover marina on Biscayne Bay east of Homestead (not in the Keys).
On your way to Key West you will see most every marina from A1A. TugNuts seem to favor Blackfin and Banana Bay (next door) marinas in Marathon, I have no idea why…no beaches, tough ramp, much less attractions and shopping and things to do. We tend to use the boat as a floating RV at this warm locale rather than ‘cruising’ there. 2 years ago we had a 1-day window of calm winds and cruised to Boca Grande key (20 miles 1 way).
Realize you’ll only avg 35-45MPH on A1A from Homestead to Key West with lots of traffic lights. There will be up to 1-2 hour traffic jam where Reagan Expressway dumps into Homestead area at rush hours with construction. We will both be dead for 10 years before this construction is completed, and our kids will be, too.
Check the mfg date on your trailer tires DOT stamp code week/yr and replace them with Goodyear Endurance ST tires if date of manufacture is over 4 years (not date of sale, deterioration starts before and 30% of structural integrity lost in 1 year). We had 4 explosive blowouts (3 on the six-lane portions of I-10) prior to switching in 2017 when they came out and none since.
If you are just looking for a warmer spot, check Calusi Island marina, Goodland, FL. Just north of the Everglades south of Marco Island, direct access off I-75 saves 8 hours driving east and through the Keys with the same weather and has trailer storage with ramp.
Safe Travels,
John