Sailing Journey: Boat Fit-out and Maiden Voyage

This chapter of the sailing journey guides you through Reality’s fitting-out for her maiden voyage.

Reality is our gorgeous Catalina 470 sailboat purchased in New York. If you want to read about the saga of flying from Australia to buy a boat in New York, check out Sailing Journey: Buying a Boat in New York.

Researching a trucking company

Hassles with brokers trying to buy a boat in New York. Then our bank taking its time to transfer our money. You would think that the next phase of trucking the boat would be relatively painless?

Think again. There always seems to be a glitch on this long stressful journey.

Finding a company with a big enough truck to cart a boat 14-plus-metres and its 16-metre mast isn’t difficult. Everything is trucked by road in the US – it’s not cheap. An escort for the truck is also required. Finally, we find a company.

Although, the company mucks us around for another 2 weeks before the truck finally arrives at Huntington in Long Island.

Hauling out

Heavy snow blankets Huntington over the past few days. And, it’s so cold that when Reality is hauled out, long icicles form on the hull in just minutes.

Packing Reality up for a safe journey includes wrapping the mast and electronics securely. This takes us and another 4 guys more than 4 hours. We work in -8°C temperatures with a wind chill factor of -17°C.

Packing includes craning Reality on to the truck’s long tray then strapping the mast to the side. Everything is secured safely for the extensive 3-day haul to Miami in southern Florida.

Trucking Reality

Huntington, New York to Miami, Florida, USA

Nothing seems to happen on time in the US. Maybe it’s because we’re currently in winter and it’s snowing heavily. Reality’s long journey from Long Island in New York to Miami in southern Florida is scheduled to take 3 days.

Reality leaves Coneys Marine in Long Island on the truck with an escort. We fly to Miami and wait in yet another hotel for her arrival at the boatyard.


Reality’s 3-day scheduled journey takes 8 days. The truck’s trailer breaks down half-way and needs to wait for a part to arrive.

Sunset in Miami, Florida, USA
The only positive about this hotel is this beautiful view.

We also have to wait and still pay hotel costs. I’m on a 3-month visa and time is slipping away. Adding to the pressure is that we must sail below the hurricane belt – Venezuela – by the 31st of May. Otherwise, insurance doesn’t cover the boat. Have I mentioned that it’s an extremely stressful time?

Over 2,250-kilometres later (1,400 miles), we’re ecstatic to see Reality finally come down the road in Miami. Unscathed, tired, and very dirty after her long 8-day journey.

Re-fitting Reality

Our work starts once again…

Gingerly moving Reality onto the travel lift isn’t our job but we wait with bated breath. During this time a boat can be dropped – I’m always on tenterhooks watching this…

After the travel lift moves Reality from the truck to a hardstand spot, it takes loads of time to reassemble everything together again. She also needs a good scrub from her long road trip.

Yet another crane is needed, this time to step the mast…

…we remember to place the obligatory coin underneath the mast for good luck. Then, Reality is moved to another spot in this busy boatyard.


Reality lived on Terra Firma for 18-months before we bought her in New York. A life that included only short sailing passages and racing, so, everything needs checking. It’s just not possible to check every inch of a boat during a pre-purchase survey.

Discovering a hairline crack in a couple of the stainless steel chainplates bolted to the deck, we contact Catalina for advice. Chainplates run through the deck and anchored to a strong point of a boat. The stays (rigging wire) that hold up the mast are fixed to the chainplates. They’re critical as you don’t want the mast falling down!

Catalina needs to make and send us new chainplates. We play the waiting game, again. Although this time, there’s so much to organise for Reality to be ready that it’s not an issue.


Shopping for linen, cookware, and provisioning the boat is time-consuming and very expensive. We buy everything new as haven’t found any opportunity/charity shops in Miami. It’s a little stress release from working on Reality.

Slowly everything is checked and repaired. A final coat of Antifoul paint also goes on. We’re not even allowed to paint our own boat with the boatyard siting insurance reasons. So, another few thousand dollars thrown in the black hole for a sub-standard job as we find out later in Curaçao. What a total rort. Money is vapourising through our fingers as liquid as water!

Catalina 470 fit-out and maiden voyage, Miami, Florida, USA

The boatyard is also closed on weekends – pathetic. One week of working days is lost.

The reason we work on boats ourselves is that we put in 110% effort and then some. And we’re satisfied that the work is done properly. A slip yard cuts corners to make a profit.

The day comes to sling Reality into the water and all goes to plan. Luck is on our side today, finally.

The day comes to sling Reality into the water and all goes to plan – luck is on our side today, finally.

Sleazy hotel

The expensive low-star hotel in a seedy area of Miami is home during all of this work. Unlike Australia, this boatyard doesn’t allow owners to live aboard their boats whilst on the hard siting ‘Insurance reasons’. Although once in the water, we can move aboard.

Spending more than 2 months in hotel rooms, including this last one in Miami with complimentary nasty bed bugs. My body is covered in itchy scabby sores. Moving onto Reality feels surreal and is luxurious. Deciding whether to stay overnight in a marina in Coconut Grove near the mouth of Miami River. Although at USD$120 per night, this is exorbitant when exchanging to Australian dollars and even more expensive than the bug-infested hotel. So, Reality stays at the marina.

More tweaks, fixes, setting everything up then provisioning and we’re ready for another maiden voyage, albeit a little nervous.

Setting sail again

Sailing from Miami to Marathon, Florida, USA

Leaving early in the morning to motor down the Miami River, we soon realise that the buoy system and markers are quickly doing our heads in.

Of course, they’re in reverse to the rest of the world. So, need to stay alert in this busy river and especially as it’s the first real time out in Reality.

Decide to take it slowly over the next couple of weeks to learn Reality’s ropes. Also to make sure that the motor and generator – both of which had issues on commissioning – are now fixed.

The opulence of Cape Florida’s mansions slowly drifts by as we head south to Marathon…

The plan is to set sail for Cuba and the rest of the Caribbean south to Venezuela. But first, there are always formalities to complete when exiting a country.


We can’t leave the US until Reality’s registration transfer papers arrive from Australia.

Weeks after sailing to Marathon, Florida Keys, we’re still waiting for Reality’s new papers. Although, we make use of this time to make sure everything on Reality is working until it’s time for a bus trip to immigration. Need to clear immigration on the day before exiting the US.

Catalina 470, Miami, Florida, USA
Registration transferred

With Reality’s papers finally through it’s time for immigration. Around a couple of hours along the picturesque coral cay archipelago known as Florida Keys and the bus arrives at busy Key West.

With the straightforward formalities over at the U.S. Customs and Border Protection – Key West Port of Entry, the return scenic bus trip to Marathon flies by quickly. It’s such a pretty area and a shame to be whizzing by without exploring, but, it’s time to leave the US.

Bye-bye USA

Today is the very last day of my 3-month US visa. I definitely need to leave the country. The skipper has a 6-month paid visa, so it’s only critical for me to leave.

Yes, it’s taken 3 full long demanding and stressful months, from purchasing Reality in Long Island New York then trucking her to Miami for the re-fit. Sapping most of our energy and with relentless butterflies in my stomach, we leave the US today.

Real maiden voyage

Marathon Florida, US to Varadero, Cuba, Caribbean

Bound for Cuba today and I’m thrilled to be sailing away from the US.

We’ve spent too much time purchasing Reality and also lost 3 months of valuable cruising time.

The hurricane season in this part of the world officially starts on the 1st of June. So, we need to cover around 1,400NM (around 2,300-kilometres) to anchor below this belt. And, head out of Marathon taking the shortest route possible sailing due south, bound for Varadero in Cuba.

Today’s real sail is a short hop of only around 80NM and just enough for a shakedown sail in a new boat.

The freedom of sailing again

The weather is kind and Reality flies along smoothly.

Gliding comfortably at an average of 7-Knots it’s just like letting the reigns of a racehorse go to unleash its spirit. A great boat!

Catalina 470 under sail, USA, Caribbean
Spinnaker purchased months later – doesn’t she look pretty? (Photo credit: Colin Palmer)

Check out this separate post that briefly touches on Sailing from the US to Cuba in Reality during 2008. Continue on this sailing journey with me next week, to see what happens next…

You can also read more about sailing around the Caribbean and south to Venezuela, to explore some of this incredibly spectacular country.

Visit Nilla’s Photography for more global images. More posts at Image Earth Travel.


32 thoughts on “Sailing Journey: Boat Fit-out and Maiden Voyage

Add yours

    1. Hi Traci,
      Congratulations! What’s her name? You’ll love sailing her, so comfortable. How did the sail go? You sound happy with her. 🤗
      Let me know when you’re back in QLD and maybe we can catch up if you have time.
      Fair winds


    1. Thank you for your kind feedback!
      Yes, you are landlocked. Although I no longer live on a boat and a land-lubber these days, I only live about a kilometre from the sea, so it’s a compromise.
      I spent 2 weeks for work in Boulder – beautiful region – returned to Oz just before 9/11.


    1. It was an extremely stressful 3 months Lulu and it was such a relief seeing her round the corner in Miami – we were getting pretty worried about ever seeing Reality again. Yeah, regardless of size, they seem to truck anything and everything in the US!


    1. Ha, ha, that’s a great word for the stressful 3-months in the US buying Reality. Anything that could of gone wrong did, so not a good time.
      Apart from the danger aspect of Venezuela, I would love to return as it’s such a spectacular country with so much to off a traveller. One of my favourite places in the globe is Angel Falls (think I may have mentioned that?).
      I remember you commenting about missing Los Roques due to the region’s dangerous demise – such a shame. Wow, so close to Fabio but yet so far, would have loved Gnocchi on the boat one night. 😉


  1. And you’re off! I didnt realise there was so much to buying, transferring and getting it ready for sailing, but I can just imagine the feeling when you finally set sail and you left the US! xx

    Liked by 2 people

    1. I guess living on Naiad for 20 years and knowing how things work in Australia, we kind of had a rough idea what was involved. Although, not everything, which meant that we learnt the hard way along the way.
      Back in 2008, there wasn’t a ‘guide book’ or many forums on how to buy a boat in the US. Trials and errors.
      Yes, I remember that the feeling was euphoric! Especially, as it was the last day of my US 90-day visa and I’d had a gut full of brokers and shysters. There was so much pressure from everything over those 3 months, it really wasn’t a great time at all. The only good part was sailing away from everything in gorgeous Reality. x

      Liked by 1 person

    1. Ha, ha, yes, dedication but also foolishness to think that this exercise would take less than 3 months. It’s a shame that the crummy hotels weren’t cheap either – you get better value at youth hostels but there weren’t any about and we had some gear to store also…

      The real dedication is building our 1st boat, which took 9.5 years to complete and afterwards, we also extended her!

      Liked by 1 person

    1. It was a great feeling Carol but also a little nervous setting sail in a new boat. Although, it wasn’t such a long sail so if something went wrong, hopefully, it wouldn’t be such an issue. 😉

      Liked by 1 person

  2. That’s some journey! I have some friends that live in upper in New York and that love boating and sailing around. I don’t think they have gone around like this but into Florida where one of them is from is about as far as they go.
    Still what a beautiful but long journey!

    I do have a blogging question for you, if you don’t mind. What company/lab top whatever… do you use to keep up with your blog while traveling? I’m looking to update and I’m asking around!

    Great post!!!

    Liked by 2 people

    1. Hi Skelly,

      Thank you for taking the time to leave me a comment. Yes it was a very long journey but one that I did in 2008. I’ve been writing loads of chapters on the Sailing Journey as I lived on a boat for 21 years.

      As for the blogging question, I do everything myself on the WordPress platform. Of course at the moment, I’m not travelling due to COVID. Although even when I’m travelling, I create drafts of the place/country I’m in and use these as a journal and reminder. Then when I’m stationary somewhere, I update and publish my blogs. I need to have a few weeks’ of posts scheduled in case I don’t have internet but also as it takes me a long time to write and select photos for each post – a lot of work goes into my posts.

      Hope this helps?

      Liked by 1 person

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