• Molly Gone Wild

Sailing Cristina: Week Two


woman and dog on a sailboat
Experiencing our first bit of stormy sailing.

Our second week of sailing was filled with extremes - frighteningly stormy weather contrasted with gorgeous blue-skied days; utter solitude in Everglades National Park followed by holiday hustle and bustle in Key West; sheltered slips traded in for rough, rolling seas. It was also a week of emotional ups and downs as we settled into the reality of life on Cristina. There were moments of boredom, anxiety, relief, joy, calm, and frustration.


We hoped to spend Christmas at The Perry Hotel & Marina on Stock Island (next to Key West), so we pushed through a number of long days to reach our destination in time. Sailing on a schedule can be challenging, if not foolish, and both Tyler and I began to rethink our imagined itinerary. Sitting on our couch in Sonoma, three months of sailing sounded like more than enough time to explore Florida and The Bahamas but with a better sense for ocean distances, boat speed, weather, and the likelihood of unforeseen delays, Tyler and I have both began to reconsider our planned itinerary. We need to do more research but we may decide to scale back our Bahamas route in order to ensure we actually have time for fun stuff along the way, like snorkeling, paddle boarding, and island exploration.


Day 8: Marco Island to Tiger Key, Everglades National Park


Marco Island proved to one a great stop for errands. In the morning, Tyler dropped me ashore and I took an Uber to Sunshine Ace Hardware to purchase four diesel cans. Cans acquired, we snaked our way out of Smokehouse Bay through winding canals and headed for Rose Marina where we refilled our water tanks and refueled, stashing our new, extra diesel cans on the deck. Unfortunately, the waste pump-out was broken at Rose Marina so we headed south for Caxambas Marina where we struck out again - the pump-out nozzle wouldn’t fit in our tank. By this time, it was midday so we decided to attempt to cut through a shallow channel to save some time. A helpful local said he thought a boat of our draft would make it but, unfortunately, we did not. We narrowly avoided running aground before turning around and exiting the inland waterways. A couple of dolphins shepherded us out into the Gulf.


We motored south to Everglades National Park and anchored off of Tiger Key. Just before sunset, a day-tripping motorboat departed nearby Lulu Key and we were left entirely alone (side note: Lulu Key is just outside the park boundary and allows dogs!). The evening was calm and silent with no sign of the incoming storm. We watched the sunset and the moonrise from our gently swaying deck. The soft pops of snapping shrimp beneath our hull served as our dinnertime soundtrack.


Day 9: Tiger Key to Indian Key, Everglades National Park


We woke early, worrying about the predicted wind and rain. The waves intensified but our anchor held and we enjoyed a leisurely morning on the boat, reading, writing, and doing odd projects. We were anchored in the mouth of a river and the waves continued to pick up as the day went on. Tyler checked the weather, wind, and tides and, absent any extreme predictions, decided we ought to hop down the coast to a more protected spot. As we left our mangrove-lined river mouth, we quickly realized we’d made a mistake. We were met with a terrifying squall; the waves became unwieldy 4 to 5-foot monsters as the wind gusted to 30 knots and above. Then the rain came, drenching us all. Cristina swung and rocked wildly as I clung to Lulu. We hardly spoke, white-knuckling our way south until we finally made it to cover in a small bay behind Indian Key. Perhaps the storm was less frightening than it seemed to us newbies but we quickly vowed to never venture into stormy weather again. We soothed our jittery nerves with a beer and some downloaded Netflix.


Day 10: Indian Key to Little Shark River, Everglades National Park


After a windy yet cozy night at anchor in our bay, we headed south towards Little Shark River. The Gulf was an ominous, murky green despite the storm having mostly blown through. The wind stayed steady at 15 knots but the waves were much, much smaller. We passed three crabbers and hundreds of crab pot buoys, the only other signs of human presence. We anchored and set about our evening activities - I did barre while Tyler organized our front cabin. The sunset left a chill in the air, so we bundled up and heated soup for dinner.

pelicans on a beach
Pelicans huddle together off Everglades National Park.

Day 11: Little Shark River to Marathon Marina, Marathon Key


A note on the Everglades: Before our three nights in the Everglades, I read countless blogs that warned sailors away from the area, mostly because of intolerable bugs. We also met a number of locals who seemed to think the Everglades were not worth seeing. Despite the ominous reports, we were pleasantly surprised to find that we had no issue with bugs other than the one time we briefly went ashore. Perhaps the storm blew them all away, or perhaps the complaints were overblown. Either way, I recommend spending a night or two in the area if your journey takes you by the Everglades - it is a remote and natural place, a reminder of what Florida once was.


In the morning, we said goodbye to Little Shark River and the Everglades and plotted our course for Boot Key. A couple of dolphins accompanied us through murky waters in the morning light. We spent most of our journey dodging crab pots (seriously, you cannot take your eyes off the water in front of you) and finally passed under Seven Mile Bridge around 3:00pm. We called in to see if any mooring balls were still available in Boot Key Harbor - all were taken (they are first-come, first-served) - so we rented a slip for the night at Safe Harbor Marathon Marina. We made excellent use of the marina facilities, doing laundry, taking showers, emptying our trash and recycling, and taking Lulu on many, many walks. We celebrated our arrival in the Keys with mai tais and sunset at the bar next door before returning to Cristina for homemade tacos and Christmas music.

dolphins swimming
Two dolphins off the coast of Everglades National Park.

Day 12: Marathon Marina to The Perry Hotel & Marina, Stock Island


After a productive evening, we left Marathon at 6:50am and headed towards Stock Island. The day started out slow until we hoisted our spinnaker and started making quick progress towards our destination. We arrived at The Perry Hotel & Marina around 3:00pm and were helped to our slip by the extremely welcoming staff. Upon checking in, we were treated to a welcome glass of bubbly and a doggie goodie bag for Lulu - what a treat!


The Perry Hotel & Marina is a sprawling yet charming complex. The Marina offers 288 slips that enjoy easy access to all the amenities of the hotel, including three dockside restaurants, two waterfront pools, two dog parks, walking paths, a healthy vegetable garden, a colorful orchid garden, a coop of guinea fowl, and a small strip of shops. Lulu was particularly delighted to discover the “dog cafe” that sells all sorts of homemade meals, treats, chews, and other goodies. The staff was all incredibly welcoming and helpful and we settled in easily.


After a good bit of exercise, we tucked Lulu into the boat and headed to downtown Key West for some sightseeing. Our favorite way to see and experience a new place is to walk and walk and walk, so we wound our way through the streets as the sun set and the Christmas lights began to glow. We eventually made our way to the quirky Blue Heaven for dinner before heading back to the boat to listen to Christmas music as we stuffed our stockings.


Day 13: The Perry Hotel & Marina


Lulu and I snuck out for a Christmas morning walk and were delighted to discover a manatee grazing along the edge of the marina! The water was crystal clear, allowing us a perfect view of the round, gentle creature. She had a tremendous (healed) scar running down one side of her body where a propeller had chopped its way through her skin. It’s painful to see the trauma we inflict on these creatures and a good reminder of how important it is to heed “slow zones” when boating in Florida. Tyler joined us and we watched the manatee for half an hour - a true Christmas gift!


We celebrated our non-traditional Christmas with banana pancakes on the boat, minimal gifts, many FaceTime calls to family back home, and a luxurious day lounging by the pool. In the evening, we dressed up for an indulgent Christmas dinner at Matt’s Stock Island Kitchen + Bar. The chocolate cheesecake was the perfect way to end the day!

hotel lobby
The charming Perry Hotel & Marina.

Day 14: The Perry Hotel & Marina to Marquesas Keys


Feeling rejuvenated after a day of total relaxation, we prepared for the next leg of our journey - we filled the water tanks, re-furled and stowed the spinnaker, emptied our trash, and tidied the cabin. After one final treat of a latte and baked goods from the onsite coffee shop, Great Lakes Coffee Roasting Co., we left the dock and pointed towards the Marquesas Keys.


The Marquesas Keys form a small ring of vegetated islands about 20 nautical miles southwest of Key West. They are uninhabited and undeveloped, known for their abundant sea turtles and the remnants of Cuban “chugs,” vessels built and piloted by Cubans fleeing the island. We anchored with just enough daylight to take Lulu ashore for a quick potty break and a bit of exercise. As I did my barre workout on the deck, the anchorage began to fill with fishing boats. There was a fight between the crew of two fishing boats (apparently some disagreement about a fishing spot) and lots of motoring and moving about until they finally quieted down. We feasted on fish tacos for dinner - Tyler caught a Spanish mackerel earlier in the day - and gazed at the star-filled sky before bed.


#sailingcouple #sailinglife #liveaboardsailboat

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