In Part 1 I wrote how I went from creating QuickPay for Quicken to selling almost everything to go live on a sailboat in the Caribbean. Now the adventure starts.

We arrive in Sint Maarten

We flew in to the Sint Maarten Airport and promptly made our way to the Simpson Bay Marina. There she was a beautiful Jeanneau 44 foot sailboat. My heart was racing with excitement.

We go shopping for supplies and get our things on board for the 110 mile journey to Virgin Gorda in the British Virgin Isles. (Click on the links for a map of each area)

Comedy of errors

Our first task is to time the opening of the drawbridge so we can get the boat out of the bay and make our way to our first stop in Anguilla.

The bridge only opens twice a day so we should make this first opening in about an hour. So we fire up the engine and the boat broker throws our lines on deck and we are off!

Except I can't remember how to engage the transmission and we are about to hit the boat behind us and then I remember to pull out the little pin on the throttle handle and away we go.

Just out of the dock I see a red buoy and think, ok red right return so let's go to the left of the buoy. Except the French system is opposite and all the sudden the boat comes to a halt and we are stuck in a sandbar. Oh, no! How embarrassing!

I put the boat in full reverse and it just won't budge. But after about 30 minutes of trying it finally breaks lose and I go around the other side of the buoy and head for the drawbridge. Just before we get there it starts to close. We missed it! So now we had to hang out for 8 hours in the bay and get the next opening at 5:30pm.

We finally make it out but then we have to stay the night outside the bay. There are so many boats that I didn't put out enough line for the anchor and at about 2am I get a knock on the boat from someone on their boat saying we are getting too close. Oh man, so now we bring the anchor back up and set it somewhere else with more line this time. After that it was hard to get back to sleep.

Day 2: We are on our way to Anguilla

We got up around 5am and headed off to Anguilla which is about 20 miles away to stay the night. We had a great time sailing and had no problems the whole day.

(Gorgeous sunsets)

Day 3: Up the next morning and off to Virgin Gorda

We woke up around 3am to chart our 90 mile course with no other islands in between. With our gps set we bring up the anchor and set the sails and away we go.

About 40 miles out the wind dies

Everything was great and we were seeing some amazing sword fish jumping. I was thinking it would be awful to be skewered with one jumping over the boat.

We take down the sails and start motoring and I noticed the fuel gauge move to 1/4 tank. That was so strange because it was on full when we left and we didn't use it that much. (Turns out the gauge would read full when there is only 1/4 tank. Oh no!)

After motoring about 10 miles we needed the fuel so we put the sails back up. Here it is getting dark and our GPS loses the signal. I don't say anything and hope it comes back soon because there are no islands in sight.

Finally we see the outline of the island in the moonlight

Luckily it was a full moon that night and we could just make out the outline of the island. It was so dark though by this time and we had to make our way around the south side of the island because our dock is on the other side.

We almost crashed on the rocks

Looking at the charts and looking at what looks like an opening we make are way around. My wife is at the bow and we are still sailing in. Then she says she hears what sounds like jet engines and the depth meter goes off and we are in 13 feet of water and our boat draws nine. Oh no those are waves crashing on the rocks and so we hurry to start the engine and bring the boat around and get away. Wow! That was close!

After going south a little more we see a better opening and make our way around. By this time we are exhausted and a little cranky.

We make it to the entrance to the docks but there is a narrow path cut out of the reef with flashing lights guiding the way. Then all the sudden there are no more lights and so we decide to back on out and go anchor for the night.

What a day!

Day 4: Safe and sound

Morning came quick and in the daylight we can see the path and motor on in to dock. This is where we took the boat out of the water in dry dock to paint the bottom and have cleaned up.

Virgin Gorda is a wonderful island with such nice people. One of our favorite areas is The Baths. We would come back here many times.

Lessons learned

• Check the weather and see if you are in hurricane season. September/ October is not really the best times to be there.
• Top off your fuel even if your gauge says full.
• Make sure you know which side of the buoy you should go on.
• When you anchor be sure you put out enough line/chain and test it.
• If you have a drawbridge to go through give yourself plenty of time to get there.
• Have a high beam light so you can see at a distance in the dark.

Overall we had a great time even though we almost killed ourselves on the rocks we made it!

I have so many wonderful stories to tell about the islands and the island life. Next stop is the US Virgin Islands where we went through so many hurricanes. Hurricane Marilyn was the worst one in 50 years!

That's next time if you like.

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Credits: All photos are mine and the gifs are from Giphy.