top of page
  • Molly Gone Wild

Sailing Cristina: Week One

Updated: Jun 13, 2022

Beach with umbrellas
The view from Provident Oceana Beachfront Suites

We arrived in St. Petersburg, FL, after our 9-day road trip across the country. It was a fantastic cross-country trip but our attention quickly turned to our next adventure: life on our boat! We planned to spend a few days prepping, provisioning, and easing ourselves into ‘boat life’ but weren’t sure how long we would need. In the end, we spent five days docked at the St. Pete Pier, cleaning the boat from bow to stern, fixing things (the bilge, the A/C, the head, the fridge door, some lights, etc.), installing things (solar panels, safety netting for Lulu, new mattress toppers), organizing (food, clothes, books, water, gear, etc.), and testing out some of the gear we bought for the trip (dinghy, paddle boards).

The St. Pete Pier, and downtown, were bustling with holiday events, markets, shoppers, and diners but we were so focused on our tasks that we barely explored the town. Our five prep days blurred together in an endless stream of dog walks, list-making, feeding the parking meter, and trips to Target, HomeGoods, and Trader Joe’s in search of all the kitchen tools, storage containers, home items, and food we would need. As we got closer and closer to finishing our preparations, the anxiety began to kick in - what would it really be like to live on a boat? What would go wrong? Would Lulu adjust to boat life? Would it be nerve-racking? Or maybe boring? My sailing knowledge felt extremely lacking and I worried that I was in way over my head.

While we were outfitting the boat, we stayed nearby in a lovely, spacious condo at Provident Oceana Beachfront Suites on Treasure Island. We stayed in a Gulf-side condo and started each morning with peaceful views of waving sea oats and water lapping at the soft crescent moon of white sand beach. Besides it being a beautiful, relaxing spot, it turned out to be incredibly helpful to have access to a kitchen, laundry machine, and wifi pre-boat departure. We used the condo to easily sort and prep food, wash all the dishes / kitchenware that would go on the boat, run a couple of loads of laundry, repack clothing, and download movies and tv shows. After a long day of sweaty work on the boat, a quick soak in the hot tub and dinner on the breezy rooftop deck were just what I needed. If you’re in the St. Pete area, I highly recommend Provident Oceana as a relaxing vacation spot.

And then all of sudden, we were ready. The fridge was stocked, the lockers were packed to the brim, the bed was made, the solar panels were charging away. We finished our tasks for the day, dropped my car at a storage facility, and then there was nothing left to do but pull away from the dock.

Day 1: St Petersburg

We left our slip at the St. Pete Pier around 4:00pm and motored just south to our friend’s house. As we left, the sun grazed the tops of the downtown buildings, dolphins surfaced just off our bow, and Christmas music wafted off the festive pier. Our friend’s dock was tucked in the back corner of a very (very) shallow bay and we had a few moments of panic thinking we wouldn’t be able to reach it. I watched the depth from the bow while Tyler piloted and kept a sharp eye on the depth finder. Miraculously, we pulled into the dock just as the sun was setting. Still jittery from the excitement of navigating the shallow waters, we cracked a bottle of champagne, ate banh mi sandwiches we’d bought in town, and toasted to the official start of our adventure.

Day 2: St. Petersburg to Longboat Key

After a slightly fitful first night, we downed a quick breakfast of granola and left the dock. We emerged into Tampa Bay and charted a course southwest. We put up the sails and cruised along, passing under the Sunshine Skyway Bridge, along the channel off of Egmont Key, and south around the tip of Anna Maria Island. As we approached Longboat Pass, we realized we didn’t know how to operate the windlass. I frantically googled “how to use the anchor on a Beneteau” while Tyler reassured me he could drop anchor manually if needed. We angled into Longboat Pass and radioed in a request to the drawbridge operator to let us through. Tyler navigated the narrow entrance while I waved to the bridge operator and crossed my fingers that we wouldn’t crash in front of all the stopped cars on the bridge. First drawbridge experience, check!

We tucked into the bay just past Jewfish Key and anchored off of Mar Vista Dockside restaurant. After nervously checking to make sure the anchor held, we took the dinghy ashore at the public boat dock / beach and took a quick walk around the neighborhoods with Lulu. Then, it was back to the boat for dinner (taco salad). After a bit more googling, we figured out the easy answer to why our windlass wasn’t working (we hadn't found the correct switch) and settled in for our first sleep at anchor.

Sailboat at anchor
Anchored in Venice

Day 3: Longboat Key to Venice

We pulled up the anchor and said goodbye to Longboat Key around 7:30am. The wind was a solid 12 knots in the Gulf, so we sailed our way to Venice and arrived around 3:30pm. We anchored just north of the Venice Yacht Club. The heat and humidity kept us on the boat, reading and napping until late afternoon when we finally went ashore. We took Lulu on a walk / run out to South Jetty Beach, where we watched sailboats and dolphins enter the channel, and on to Chauncy Howard Park. Venice beaches don’t allow dogs, so we looked at the sunset from the end of the boardwalk, then returned to the boat for dinner (curried chickpeas and homemade naan) and some reading.

Day 4: Venice to ‘Tween Waters Resort & Marina, Captiva

We set sail at 7:30am and again enjoyed fantastic wind (15 knots) and blue skies all the way to Captiva Island. I know Captiva and Sanibel Islands well - my grandma used to live on Sanibel and my mom studied bottlenose dolphins in the area - and was so thrilled to finally be able to show Tyler one of my very favorite places in the world. For easy access to the islands, we decided to spend the night at ‘Tween Waters Island Resort & Spa on Captiva. It turned out to be the perfect home base for exploring!

We paid $140 for one night which gave us access to dockage, water, electric, pump out, and all resort amenities including, pools, hot tub, spa, and free bikes. There was free coffee in the marina store in the morning and plenty of space to walk Lulu on the property. We arrived just before sunset and tucked Lulu safely in the cabin (we felt safe leaving her on board because we were securely docked). Tyler and I walked up the beach as the sun set in a brilliant coral-colored blaze. We had dinner at the Bubble Room, a quirky, one-of-a-kind restaurant that was a childhood favorite of mine. The food is standard island tourist food but the decor, tropical drinks, and extravagant cakes make it a must-visit. The best part: instead of bread and butter to start, they bring a basket ladder with their famous ‘Bubble Bread’ (cheesy garlic bread) and cinnamon rolls. After stuffing ourselves, we walked home in the dark on the beach, stopping to hide from a brief rainstorm at one point.

woman walking on beach at sunset
Captiva Island at sunset.

Day 5: Captiva to Sanibel

We started the day with a manatee sighting just off the bow of our docked boat. It was Tyler’s first manatee! Then, we enjoyed a dip in the pool and hot tub at ‘Tween Waters before loading up our bikes for a trip down to Sanibel Island. We did a 17-mile out-and-back, visiting my grandma’s old house and enjoying some of Sanibel’s top-notch bike paths. We even stumbled upon the Sanibel Police coaxing a massive alligator off the bike path. Quite exciting!

After one final swim in the pool, we departed ‘Tween Waters and motored south on the Intra-Coastal Waterway. Dozens of pontoon boats and luxurious motor yachts sped past us as we lazily made our way to the mouth of Tarpon Bay. We dropped our anchor, blew up the paddleboards, and journeyed into the mangrove canals of Ding Darling National Wildlife Refuge. Lulu rode the front of my board like a champ and only slipped off twice.

In the evening, as the moon rose, two dolphins circled our boat, feeding. The soft, moist puff of their breaths broke the moonlit silence as their fins glinted in the shadows. We could hear them rush through the water at times, clearly chasing something yummy. It was at that moment that I began to understand the magic of living a life on the water, sharing space with elusive and captivating wildlife.

tropical hotel pool
The pool at 'Tween Waters Island Resort & Spa.

Day 6: Sanibel to Captiva

We left the boat just before 8:00am and took the dinghy into the boat ramp at Tarpon Bay. It was low tide, so we had to pull the boat across the sandbar at Shallow Cutoff. Technically, Tarpon Bay does not have a dinghy dock, so if you attempt this you must be able to pull your dinghy out of the water and put it in the parking lot. They call it a ‘reverse launch’ and it costs $15.00 (unless you rent bikes from them, then it’s free). Lucky for us, our dinghy is tiny, so we had no problem pulling it ashore and locking it to the bike rack. The staff at Tarpon Bay Explorers were super helpful and accommodating, and sent us on our way with two comfortable bikes.

We pedaled along Wildlife Drive in Ding Darling National Wildlife Refuge, looking for birds and other creatures. If you go, try to time your visit at low tide when the birds are out on the sandbars. We saw countless herons, egrets, ibises, a brilliant flock of white pelicans, and a handful of neon pink Roseate Spoonbills. If you’re traveling with your pup, you’ll be happy to know that dogs are allowed on Wildlife Drive as long as they are on a leash (6 feet or less). Lulu spent most of the time riding in Tyler’s bike basket.

After our visit to the Refuge, we pedaled around to do some errands, stopping at Ace Hardware, Bailey’s General Store, and Spoondrift for lunch. Then, it was back to the boat. Sanibel is connected to the mainland via a low-clearance causeway, so we had to motor back up to Captiva to exit through Redfish Pass. We motored up to the marina at South Seas Island Resort for diesel (filling the tank for the first time was surprisingly nerve-racking) and saw a mom and baby dolphin just off the gas dock. Then, we dropped anchor just offshore of Chadwick Bayou.

I strung Christmas light on our boat as the sun set and, just as I finished, heard the unmistakable sounds of Christmas music drifting across the water. I could see lights dancing on the water in the distance and, after investigating with the binoculars, realized that there was a small holiday boat parade puttering along the shore of the island. What a sweet, festive surprise!

mangrove sprouts
Mangroves sprouting in J.N. Ding Darling National Wildlife Refuge.

Day 7: Captiva to Marco Island

After two and a half wonderful days exploring Captiva and Sanibel, we set off once again. We left at 6:45am for a long day of motoring south (no wind). Our destination was Smokehouse Bay at Marco Island. To enter the bay, we navigated narrow, shallow channels past countless impressive mansions. Compared to Captiva and Sanibel, Marco Island is extremely crowded and developed (high rises and motor yachts everywhere) but Smokehouse Bay was quiet and protected. We dropped anchor, then went ashore in the dinghy. The Winn Dixie just behind Smokehouse Bay has a dinghy dock available to customers. I went for a short, sweaty run while Tyler and Lulu played in the park, and then I did a quick grocery shop.

We chugged back to the boat in our very full dinghy, passing a dolphin in the channel. Christmas lights glittered from the surrounding condos and we relaxed in the cool evening air. We’d made it through our first week of sailing life!

136 views0 comments

Related Posts

See All


bottom of page