The Course of True Love Never Runs Smooth (Sailing to Miami)

Simons Passage, Grenada to Miami (1500 nm)

6th December 2017

Landing back in Grenada on his last night in the Caribbean Simon was feeling slightly disheartened. It was such an amazing time here with all the people we’d met, many of them now starting sailing journeys through the Windward Islands while we were ending this chapter. Excited for the new adventure awaiting us in the USA but slightly envious of all our friends. Being reunited with Scrumpy who was over the moon to be back with some of his pack helped to lift Simons mood and there wasn’t much time to get all sentimental with so much to do in preparation for the big sail ahead. Little did he know the drama was only beginning to unfold!

Simon at the helm 

Set back number one came in the form of a migraine sending him off to bed at 5:30pm however such an early night resulted in a 4am start giving him plenty of time to begin ticking off jobs. First on the list an 8-mile sail to the capital St Georges for fuel due to problems with the local Prickly Bay fuel dock. Not a major issue as it’s a good place to stock up on food provisions but on route the outside auto-pilot control panel failed, leaving only the inside unit working. This meant continually abandoning the cockpit to adjust the course, which is a bit of an inconvenience. Automatic steering is vital for the 1500 mile passage otherwise its means hand steering the entire 14 days not allowing any opportunity to sleep, basically physically impossible.

Not wanting to anchor out in the bay and pull the chain up single handed the yacht club selling diesel agreed to give Simon a berth for a few hours so he could do a food shop. (Perhaps something he later regretted). Entering into a cul-de-sac of slipways and needing to do a tight 180 degree turn for the only available dock space he slid the throttle from reverse to forward. Except the boat continued to power backwards and no amount of wiggling it made any difference. Now plowing towards a large luxury motorboat with no clue what to do and screaming for the dock master a number of marina stuff luckily came to his rescue. They managed to bridge the gab between the Tudor Rose and 3 other yachts but by the time Simon had switched off the engine the boat was tangled around 3 mooring balls. Spending 40 minutes failing to unravel the mess there was no choice but to jump in the murky manky pooh invested marina water and cut the lines. Finally 2 Dinghies towed him to the pontoon to tie up.

Bye Bye Grenada 

Great, another set back. With a broken engine/gearbox todays planned departure was not looking hopeful. Thankfully it was a straightforward repair and after 2 hours in the engine bay the broken gear linkage was fixed, but there was still the chandlery, customs and supermarket to visit. Simon did his usual ‘run around like a lunatic’ and after a quick chat with Daisy and I he was back on board at 3pm a hot sweaty mess but ready to set sail.

The last 36 hours had been a bit manic but once out of the bay everything relaxed. Being out on the ocean is the perfect calming place to be and to add to Simons inner peace he’d saved a day and a half sailing by doing some further passage routing. The 1500mile trip actually came in closer to 1350 NM. Making his way 10 miles off Grenada and now with plenty of time to think, as the sun set on the first evening the realization of how lonely and isolating this trip would be was beginning to set in.

A map of Simons Passage

So I suspect you are all wondering how exactly does one sail single-handed on a long passage. Well thanks to his handy man skills the Tudor Rose is now fitted out with Automatic Identification System (AIS). It fits to the VHF radio picking up the location and speed of other boats (on AIS) and then shows them on the GPS chart plotter. A bit like you having a Satnav that shows up other cars on the road except it’s for boats. This clever piece of equipment allows Simon to set a warning with a radius of his choosing (in this case 24 miles) so that if another vessel comes within 24 miles of him an alarm goes off. Therefore he can set the autopilot and get some shuteye without the worry of hitting anyone else. Occasionally he has to do a quick visual check for small sailboats and local fisherman without AIS but there aren’t many of these offshore.

The first leg of the trip was 500 nm (5 days) of open water heading North West to the Mona Passage, a 70mile wide channel between Dominican Republic & Puerto Rico. Deemed the easier part of the trip as very unlikely to encounter any small sailing crafts and any large boats or tankers would have AIS by law. Unfortunately there was a distinct lack of wind and with a deadline for mine and Daisy’s arrival the only choice was to motor using a big portion of the fuel supplies.

On day 6 during the second leg (Puerto Rico to Turks & Caicos approx. 2days) things were not looking good when the inside control panel on the Autopilot began failing intermittently. In between hand steering and heaving to (slowing the boats progress & letting it drift) Simon attempted to fix it, after 7 unsuccessful hours he hit it with a hammer out of sheer frustration only for it to start working again. There’s a lot to be said for the ‘give it a good whack’ repair option, it should be listed on the troubleshooting pages of all equipment guides if you ask me.

The third and final leg was through the Bahamas on the home straight to Miami (6 days/650 miles). This brought yet more absence of wind resulting in a pit stop at The Exumas for refueling on day 9. A chore which Simon could have done without but one he didn’t regret once he’d seen how spectacularly beautiful they were with their tranquil turquoise waters. They seemed positively heavenly after nothing but the deep dark depths of rough open water sailing, however the high didn’t last.

The Exumas, Bahamas

For a while we’ve had an ongoing minor issue with the bolts unfastening on the coupling that attaches the propeller shaft to the engine. Shortly after leaving the fuel dock it came apart again only this time all the threads in the coupling had completely worn away. Thinking outside the box, Simon used some Quick Weld putty to secure the nuts back in however this fix wouldn’t hold for long so using the engine would need to be saved for arrival into port and anchoring. Now he was solely relying on the sails to get him there.

The gods must have been watching as he was gifted with 2 days of excellent sailing, but with a day or so to go the wind died off reducing the speed to 2 knots per hour. To top it off the main sail ripped in half and when he arrived at the inlet to the end destination he had 3 knots of tide against him. Thankfully the repaired coupling on the engine held out for the last 4 miles.

Miami skyline 

Having averaged 125 miles per day in the last 24 hours Simon had only gone 70 miles, after 12 days at sea Tudor Rose limped into South Beach. Miami. Surrounded by skyscrapers and apartment blocks Simon was relieved to have made it, all he needed was to be reunited with the rest of the family and the next adventure could begin.

Reunited with his No.1 fan


We are so immensely proud of Simon and his achievement, being at sea alone for so long is not easy, but he did it so that we could continue our journey of discovery without little Daisy being seasick. He is such a loving, caring and selfless person who would do anything to look after his family. We love you Daddy Bear xxx


2 thoughts on “The Course of True Love Never Runs Smooth (Sailing to Miami)

  1. Wow, what a story ! I envy you guys your adventures, your resiliance, imagination and your bravery…. whilst at this stage of daisy’s Life she isn’t likely to recall too much your spirits and determination will un doubtedly rub off on her – it certainly won’t be lost. I wish I had a fraction of your tenacity to do something a wee bit adventurous. Continue to enjoy every second, stay safe and look forward to more images and tales 💜 Deana & Boo x


  2. You’re the youngest old salt we know. Way to go Simon!


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