Making our way to the Florida Keys…


We’ve been on a mooring in Boot Key Harbor (Marathon) for over a week now. It’s time to update our getting here.

After an idyllic calm and starlit night anchored at Ding Darling, we woke early to raise anchor and beat the big powerboats to make it through the “Miserable Mile,” a particularly narrow area of the ICW known for its strong cross currents and large powerboats running it fast, producing damaging wakes. There was very little traffic as we made our way through the area and as we departed the Miserable Mile and made our way towards the bridge and the inlet into the Gulf, we got a very nice push from the river current with our over ground speed reaching 7+ knots. That’s fast for us!

We picked up a mooring at Fort Myers Beach late that morning. Discovering that they now have a weekly mooring deal (basically pay for 6 nights, stay free one night), we decided to sign up for a week rather than the 5 days we had planned. We like Fort Myers Beach for the fresh shrimp markets along the north shore of the harbor and for the 50-cent trolley rides (Ron rides for 25 cents) just about anywhere we want to go around Fort Myers Beach. Another one of the great deals here: the $5 mussels appetizer at Doc Ford’s during happy hour on Monday through Friday. Oh my, we make a meal of these. It’s one of our “got to have’s” at FMB! However, wifi was not great in the area and seems to be a very low priority this season among the restaurants we visited. I was, however, able to stream the U.S. Presidential Inauguration live while hanging out at the Matanza Inn’s laundry room that morning, so I was happy.

The day after arriving at Fort Myers Beach, a cold front came through bringing strong northerly winds. It was good to be in a protected area and to not have to worry about moving in the high winds. We seem to have had a lot of northerly winds ever since that cold front. Interesting.

After a week at Fort Myers Beach, it felt good to move again. At this point, we had made our way off the intercoastal waterway and entered the Gulf of Mexico, where we could actually sail!

We had an easy, slow sail to Naples. I’d forgotten the way that saltwater “sizzles” against Thyme Hyssop & Wry’s hull as she moves through the water. Many years ago, when Auna and Chase were still young kids, we boat-sat friends’ J-40 at a private condo/marina development in Naples during a holiday break. It was fun making our way back, identifying where the boat had been, and remembering a very special family vacation so long ago. Today, Naples has a small mooring field just off the Naples City Dock. They have 12 moorings available, and boaters are limited to no more than a consecutive 4-day stay; maximum 8-nights per month. Also, you must stop at the gas dock for a pump-out before being assigned a mooring. Had we known that, we wouldn’t have waited for the pump-out boat to empty our holding tank at Fort Myers Beach and gotten an earlier start. (Unlike the Great Lakes, pumpouts here in southern Florida are free and very convenient. Many harbors have a pumpout boat that comes to you.)

We spent 3 nights at Naples. We really like Naples: mostly decent and free wifi at the boat on the mooring, very friendly and helpful marina staff, a beautiful town, a very nice grocery about a mile’s walk away, fun pelicans. However, the 3 best deals in Naples (you can find VERY expensive restaurants and shopping, if that’s your thing!):
1. Mooring $10 per night
2. Naples Ships Store (they have something for everyone, and good prices–very fun store to explore)
3. Napoli on the Bay (next to the Ships Store) for pizza by the slice

From Naples, we got another early start and ended up motoring to Marco Island, arriving just about the time the wind began filling in enough to sail. Oh well. Our plan was to head out the next morning for our 2-day trip to Marathon so we needed to make a grocery stop.

At Marco, we again made our way to anchor in Smokehouse Bay, off the Esplanade Marina. Well-populated with upscale homes and shopping, it is probably the best protected anchorage we’ve had in our cruising experience here in southern Florida. In Smokehouse Bay, we are protected from all wind directions. In fact, we rode out a very fierce storm that came through last year while anchored there. And, there is an upscale Winn Dixie (even though my good friend Sue claims that’s an oxymoron) just a short dinghy ride away with its own dinghy dock. We love Smokehouse Bay!


4 thoughts on “Making our way to the Florida Keys…

  1. Smokehouse Bay looks superbly protected on the 11430-3 chart, but no depths indicated. Did you learn of this location from prior knowledge, dinghy soundings, or recommendation? What is the depth in there? Swinging room for more than one? We are taking notes – hope to be there next season…


    • We think we got our information from Active Captain. We first went in there last season when we were in need of a protected anchorage due to heavy weather expected with some high winds for a few days. Our information assured us that there was enough depth as long as we stayed within the marks. There is, though it gets exciting for the person behind the wheel, who is seeing the depth sounder. And yes, there is plenty of room for a few boats. We’ve had no problem with it being crowded. Does this mean you’ve purchased a southern boat?


      • Thank you! I hadn’t thought to check Active Captain. We are actively looking for a “Southern” boat – but will probably miss this winter season…cold and blustery winter in the UP.


Leave a Reply

Please log in using one of these methods to post your comment: Logo

You are commenting using your account. Log Out /  Change )

Google photo

You are commenting using your Google account. Log Out /  Change )

Twitter picture

You are commenting using your Twitter account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s