Dec 27 – Jan 3

Our first week was packed with 3 new anchorages, our first blow on our own anchor, remote island birthday, and trying to snorkel a sunken ship. Whatever we thought the Keys would be like, it definitely was not, but we learned so much.

Here’s our first impression…

Well, before we get there…we jammed a lot into our first week in the Keys. So much that putting together this episode I was surprised by all that we did in 7 days. My memory has this spanning two weeks at least and apparently it was not.

We have a lot of mixed emotions about the Keys. This is the place we experienced at lot of firsts as new sailors. And as a new buddy boat friend more recently said to us…”I’m just ready to done with all the firsts.” We couldn’t agree more. So our time in the Keys is tainted with a lot of first stresses, learnings, scary moments, hard moments, and growing moments. We did manage to have some really awesome and fun experiences. Most importantly, we have met so many amazing people here.

We also made the very wrong assumption that there would be lots of kid boats in the Keys. We were very wrong and learned…they’re all in the Bahamas. A few different boats we met also commented that the Keys are not a fun place with young kids. Lots of snorkeling and beautiful sights, but for a boat with young kids and a dog, it’s not out top choice to cruise now.

We did a lot of unexpected reading about the Keys and it seems pre-COVID the Keys were an awesome place to cruise. Post-COVID, however, the Keys have really gone down hill. Seems like most people jump through the Keys to get good snorkeling in and get out to the Dry Tortugas and up into the gulf.

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Excerpt from letter to home version 01.04.2026

Subject: SV NOBAD Weather fam&friends | Ahoy from Boca Grande Key!

Hello hello Nobad Fam! 

Well, the Florida Keys have been a very interesting place to sail and we are not fans. We have had some really awesome and really not awesome moments, all collectively being added to our sailing journal as we learn and grow in this new life. 

Monday was a really good day. The kids, our buddy boat Amber and I all played in the water around our boats and relaxed. We swam, snorkeled, and paddle boarded. The water was calm and it was a beautiful sunny day. The calm before the storm. The guys had taken off in the dinghy to scout out a new anchorage location for us that was more protected, as strong winds and gusts were going to be rolling in the next day with 2-3 ft swells. Our current location was very unprotected for this weather shift. After they returned, we game planned on when we would leave in the morning to the new anchorage they found, and spent the rest of the evening together playing in the water and eating yummy food, including a fish Jeremy had speared near our boats. We even tied a rope between our buddy boat’s dinghy and our mast and created a sort of catapult. Hit the gas on the dinghy, someone holds the middle of the rope and gets launched into the air. IT WAS SO FUN. Even the kiddos did it. Josh and Jeremy also over inflated one of the paddle boards and then attempted to surf on the paddleboard behind the dinghy. Also a very amusing sight and they were somewhat successful. 

We woke up at 5:30am to warm up the engines and prep the boats to take off. The winds had already started to move in and so had the waves. With only a minor sanfu, Josh and I successfully pulled up our anchor by ourselves and we headed out. We had a momentary scare when we thought we had grounded the boat leaving the channel but quickly got out of it no issue and were soon on our way out of the west side of Key West. *Deep breath* we did it. 

Side note: the Keys are SUPER shallow everywhere. We are slightly at an advantage with a catamaran as catamarans tend to have shallower drafts than monohauls. Draft meaning how much of the boat is below the water level. We are at about 4.5 ft. But even for us, it’s so shallow everywhere, it makes a lot of things tricky. Something we didn’t anticipate. 

Our new anchorage was on the East side of Key West, through an even narrower and shallower channel. Glutton for punishment, but we knew this would be way better for the weather rolling through. However, another panic moment set in when we tried to set the anchor. We were trying  so hard to do it ourselves and tried 3 times. It just wouldn’t take. So we called our buddy boat to rescue us, once again. Jeremy was over in no time helping direct us. We almost grounded the boat twice, we were shooting the gap between tons of shallow areas. Amber was in their dinghy helping as well. It was utter chaos and scary. The wind had officially rolled in and the new location had a really strong current (no waves but strong current). Josh and Jeremy decided we needed to pull out our second anchor and do a “storm anchor” set up. So Josh and I prepped our second anchor while Jeremy kept our boat from moving into danger zones. We accidentally twisted the second anchor up with our bridle (bridle is a rope mechanism you hook to the anchor chain to relieve stress on the anchor chain and spread the stress across the bow of the boat). In an attempt to untangle it, I accidentally dropped the bridle into the water. Yall, the stress was unreal. We finally got everything connected appropriately and BOTH anchors set into the ocean floor. Josh tried to dive and check to confirm both anchors had dug in but the current was too strong. Jeremy suited up in his dive gear and checked for us, confirming we were solid. To say Josh and I felt defeated was an understatement. We felt bad having to call on our buddy boat again to rescue us. And they did without complaint. 

…We rode out the wind and cold weather (low 60s) with knots in our stomachs for the next two days, as we just aren’t used to trusting our anchor yet. And if we did drag anchor, we were going right into our buddy boat and all the other boats anchored behind us. We didn’t sleep much. 

Good news tho, we had a lovely, very simple, New Years. An older gentleman and his wife (Steve and Fran) have their huge catamaran at the marina next to where we anchored. Josh met them in the boat yard a few months prior. They were hauled out for some work and Josh ate dinner with them more than once. They are also friends with our buddy boat. We offered to bring them dinner and it happened to come together for New Years eve. So we made dinner for Steve and his family and brought it over to his huge boat to enjoy company. It was actually really neat. And Steve had grandkids on board, so our kids were over the moon. And those errands we ran the previous day, we borrowed Steve’s truck to run them. Such a good guy. 

On New Years day, we left that anchorage. The weather had cleared and we had a good window to go to a more remote Key. So we packed up the boat and headed to Boca Grande Key, west of Key West. Upon arrival, some things clicked into place for Josh and I. We were becoming very overwhelmed and disappointed by anchorages (which we thought would be our primary way we would “stay” in a place versus a marina). When we arrived in Boca Grande we took a big sigh of relief. This is what we pictured when we thought of anchoring somewhere. A few boats, beautiful beaches, and lots of room. And upon arrival, we finally set our anchor all by ourselves!! Back in Key West, all the anchorages have turned into float trailer parks. They are crowded with derelict boats and people who legit live aboard and do not move and do not take care of their boat. It’s so disappointing. 

We dropped anchor right at sunset, our buddy boat about an hour behind us. I was startled awake at 2:30am to Josh walking out into the cockpit. Upon inquiry, he said he got up to check things and saw that the tide had dropped super low. We were sitting at about 5 ft of water (remember our draft is 4.5ft). We anchored in 11 ft of water. So we got the spotlights out and started checking around the boat for rocks or shallower parts we may ground in. Simultaneously, we saw our buddy boat awake, spotlights out as well. Amber called Josh and said they had actually grounded. So they fired up their engines, got unstuck and we helped guide them to a different part of the anchorage, highlighting the incredibly annoying crab traps. They reset pretty quick after they got out of the shallow area. Never a dull moment. We ended up being fine. They say Boca Grande is the closest thing to the Bahamas in the Keys and we would agree.

We woke up to Raegan turning 9! She loved seeing the beautiful ocean water, breakfast in bed, and opening presents. We made it to the beach and it was bliss. She loved being on an uninhabited island for her bday. Our buddy boat called her over the radio and sang her happy birthday.  The kids think they saw a barracuda and Raegan shouted “best birthday ever!!” So we aren’t totally ruining our kids’ lives with this big life change. 

Our original plan was to continue on with our friends to the Marquesas Key and then on to Dry Tortugas National park. But we decided to stay in Boca Grande. We finally felt a little more settled and we knew there was a beach here that we could go on as a family with our dog (the “beaches” in key west were terrible). So our buddy boat continued on and we stayed and we felt it was the right decision. Someday we will return and hit the dry tortugas (when we have dive and scuba gear of our own). 

The winds shifted last night to coming from the S, so we had a pretty rolly night as our anchorage isn’t protected from southern winds. But the kids slept through it all. I’m still learning to trust the anchor. We did move our boat to deeper waters in anticipation of the weather. But I didn’t sleep much last night. We did wake up to another pretty day here. 

Tomorrow we will prep the boat for sailing again and head back into Key West to refuel and restock our water tanks (can’t wait for our new watermaker to be installed). We plan to stay in Key West for one night and then bounce between anchorages heading east toward Boot Key. We’ve reserved a transient slip at one of the marinas there to ride out another storm anticipated for later this week and because we are attending an event at the end of the month in Hawks Key and need a place to park our boat while we attend (this event is really the only reason why we are in the Keys. That and we thought the Keys would be more like the Bahamas and they are not). It did make us feel better, but also sad, that as we’ve been reading about the area, tons of people talk about the Keys pre-covid being an amazing place for cruisers (like us) and after covid it’s gone completely downhill.  

So onto new adventures and new Keys. Our buddy boat will be doing their own thing as they have lots of friends visiting and other plans. We are desperate for more family/kid boats and hope to see more in the coming weeks. Our plans to go to the Bahamas next month are very up in the air now. We’ve had a lot of learnings out on the water and some big decisions to make on where we sail to next at the end of this month. So stay tuned. 

We love you all and miss you all. To say the homesickness during Christmas and New Years was strong would be an understatement. We are so grateful for our family and friends back home. Thank you for cheering us on. It means more to us than you know. We are so grateful for our Heavenly Father’s continued protection, help and love. We feel it every day and know we have guardian angels watching out for us. 

Ride the t, 

Capt. Josh, 1st mate Sam, and our salty crew