#91 Marathon, Florida to Islamorada, Florida

Written by The Crew

Rev writes all the posts as "The Crew" at What Yacht To Do. It's just part of the First Mate duties. That list just keeps growing...

March 7, 2020

Well it’s time to leave Skipjack Marina in Marathon.

A lovely marina and resort.

The hotel looks like it was built in the 50s.

But the pool area was nice.

Even though the restaurant was closed for renovations, the tiki bar at the pool was open for food and drinks.

We got up at a reasonable hour 7ish and started getting the boat ready for a 9:45 a.m. departure.

We had not moved the old gal for two weeks.

We were a little rusty and we were hoping that she wasn’t.

Those engines started up with enthusiasm and I’m sure wondered why we made them wait so long.

Back Down the Skinny Channel

As we left Skipjack slowly, we passed the line of boats of all shapes and sizes on our left.

We passed the Dockside restaurant that we enjoyed several times.

That’s about where the sea of mooring balls and anchorages start.

So. Many. Boats!

Sam tried to follow his bread crumbs out the same way we came in but it was really difficult when there are boats anchored partly in the channel.

We timed our departure for leaving on a rising tide.

Which means that the water is coming in and should be deep enough for us to get through this part.

And it was.

Although we don’t like seeing 3-4 feet under the boat.

So Sam was dodging anchored boats, hugging the green markers (per Navionics/Active Captain) and maneuvering past oncoming traffic.

It was pretty tense.

He had to get so close to an anchored sailboat to avoid an oncoming sailboat that I honestly don’t know how he missed hitting at least one of them.

But he did.

And we had the right of way.

Which shows you that most people behind the big wheel don’t know the rules of the road.

Out There

Once that craziness was over, we made it out to the beautiful green water.

And it was calm.

It was nice.

I couldn’t believe we were in the Ocean.

I had spent a lot of time battening down everything that looked like it would move.

I had certainly learned my lesson from crossing big water in the past.

This was nothing.

So I was a very happy first mate.


I knew before we left that we were going to be anchoring a few times in the coming days.

I had made a few meals for us in preparation.

And I even tried to have a good attitude about it.

But about 45 minutes before reaching Islamorada, the wind and the waves started to pick up a bit.


Just what I need.

In addition, Sam had McGuyver-ed a contraption that I was going to have to get on my belly and attach to the anchor.

Something called a trip line.

It has a fender on one end and is supposed to let us know where the anchor is at all times.

I’m already mad at it.

The Perfect Spot

So the waves are causing white caps and the wind is coming at us from the north.

Sam makes the turn to get closer to shore and the conditions are now right in our face.

Plus, there are many crab pots that we have to dodge.


I’m still trying to have a good attitude.

Anchoring is not going to beat me!

There is a catamaran already stopped there so all we had to do was find a place away from the crab pots, away from the catamaran and away from shallow water.

Sounds easy enough.

After a long while we find what we think is the perfect spot.

I went inside to turn on the windlass switch under a step in the salon.

I go out with the contraption and Sam gives me installation instructions through the headset.

Minor fussing.

Then I proceed to lower the anchor using the windlass.

I step on the pedal.


Oh, don’t tell me the windlass is broken!

I start to mildly freak out.

Just a bit.

Sam finally convinced me to go check the windlass switch one more time.

I didn’t want to but I did.

And yes, that was the problem.

I had turned it off earlier instead of on.


I go back out to the windlass pedal and viola there she goes!

As we go through the motions of lowering the anchor and getting it set, I’m starting to think we may have this anchoring thing down.

Wouldn’t that be awesome?!?

Settling In

So now that we’ve anchored, I start putting the items that I had secured back in their place.

Within a few minutes our boat was once again home.

We usually don’t watch TV while we are anchoring.

Although, Sam had already checked the reception and we only could pick up two Spanish-speaking stations.

So we opened up a bottle of champagne and chatted about a wide variety of topics.

Things like what we think about the snarky comments we get on YouTube and Facebook, what we’re going to do after the loop, what our next boat should be, etc.

I do like that part of anchoring.

Off We Go

After a lovely evening of champagne, chicken wings and chatting, we went to bed early.

But not before we enjoyed the sunset.

It just kept getting better and better.

And then more better.

It was beautiful and a nice reward for getting the anchor set with just a little bit of drama.

Our plan was to get up early and head to Miami.

We had been asleep for about a couple of hours when the anchor alarm went off on Sam’s phone.

He got up to check it and everything seemed to be ok.

Then, at 1:00 a.m., more beeping.

The alarm was going nuts!

Sam went to check it again and found that the anchor had drug about 50-60 feet.

We have a fantastic anchor and have never had any problems.

It may have had something to do with the 24 mph wind we were in but I’m not sure.

I do know we barely got enough sleep.

We’ll have to wait until tomorrow to see what happens.

Our Thoughts

Start YOUR Planning Today

Great Loop Online Courses

Great Loop Planning Starter Kit

How to Lock on the Great Loop

You May Also Like…

Reflections on Two Loops

Reflections on Two Loops

Special Blog Post From Captain Sam Well, it's over! Two loops in three years, one month. It was the most wonderful...


  1. Rewarded with Champagne, chicken wings and that gorgeous sunset!!

    • Yes, we enjoyed our reward very much!

  2. Your adventure never gets old for me. Love ya both! Can’t wait to see you again!

    • Aw, thank you dear! It won’t be long until we are headed your way.

  3. Glad to see the latest post, had wondered how far out into the ocean you had to travel. Hope the weather treats you kindly on your way north and anchorages become easier. after its over you will be able to give lessons. Enjoy the ride

    • Thanks, Buck! The weather was fantastic in the Florida Keys. I’m not sure we will ever get to “instructor” status as far as anchoring but we are going to keep doing it until we get it right!

  4. Love your bits of drama Rev! Makes your blogs and videos so much more interesting!

    Wife and I are still following you two like the CBS Nightly News!

    50’s and 60’s up here in Minnesota. Too heavy for the WYTD hoodie and time to switch into the tee shirt!

    • I would LOVE a drama-free anchoring situation but it’s not happening for me yet! Thanks so much for watching and for grabbing our merch! We really appreciate you.

  5. Great video and blog. We really enjoy them both. And thanks for taking us along around the loop. Sorry you are getting snarking comments. Some people?

    • Thanks so much, Cully! Hope you and Heidi are having a great weekend. I know! Can you believe it? The nerve! LOL

  6. More excitement on the Here’s to Us! BUT, Champagne DOES take the edge off. Thanks for sharing your adventures. Miriam and I had a mini ski vacation to Western New York where we met some long time friends for a few days of skiing with wine and cheese lunches and dinner out. I added another Ski Resort to my list of resorts I have skied to make it 120. HoliMont is a Private Club but recently has opened to the public on midweek days. The slopes were groomed to perfection.

    • Oh, champagne definitely helps! Sounds like you had a great trip. Congrats on #120!


Leave a Reply

Pin It on Pinterest