The Beginning of Many Wanderingkeller Adventures: Learning to Bareboat Cruise on a 40-foot Catamaran with Offshore Sailing School

One of our plans for retirement is to buy a sailboat and cruise around enjoying the ocean breeze and beautiful sunsets, letting the winds and our whims decide where we spend our next day, week or month. As a young boy I often dreamed of owning a boat and always thought it would be a 60 foot power yacht. Not growing up on boats I realized that this was a dream (an expensive one at that). The more realistic and perhaps more adventurous, older, me realized a sailboat is not only more economical but the thrill of harnessing the wind appealed to me. My wife was initially a little skeptical and the teenage boys were less than impressed with 7 knot cruising but once I got them on the boat and we heeled the rail in the water the boys were hooked. How did I get the wife on board? Well the first time we sat on the hammock on the front of the Fountaine Pajot 40 and watched the sunset with the breeze, a glass of wine and pure quiet, she was hooked.

As I said earlier neither my wife nor I grew up with boats. We own a small pontoon boat which is perfect for beaching on the sand bar, tubing, fishing and watching the fireworks (my favorite thing to do), but is basically a floating cork with an engine. Fun, but limited. If we were going to really make a go of it we needed some training on the water and initially took a local ASA keelboat class in Maryland. This was a perfect way to get our feet wet and learn the ropes. The real goal, however was to bareboat in the British Virgin Islands and beyond. For that we needed some real water time on a bigger boat. This is where Offshore Sailing School came in. Offshore Sailing School was started by Steve and Doris Colgate 55 years ago and has over 150,000 graduates. All instructors are certified by the Central Sailing School, unlike many programs that are independently run and variable in the abilities of their instructors. With Offshore Sailing you get a great instructor every time and ours (Kelly) was no different. They have many classes that allow you to either go slow or to do a fast-track class that allows you to get many certifications in a packed week. We tested out of our basic keelboat since we had done that with ASA and decided to take a fast track to cruising class (103,104 and 114) in 6 days instead of the 8 if we would have needed to do the 101 as well.

They have schools in Tortola, Scrub Island, Captiva Island, St. Pete, Cape Coral and Ft. Myers which allows them to have year round training sites.

The school sent us all our materials months in advance so we could study and prepare on our own time for what we needed to know. This allowed us to have more focus on the actual sailing aspect and less classroom time when we arrived. There was also a pretest we took online to ensure that we, and everyone involved, had completed the reading and were ready for the class. This is a nice touch as it keeps people who didn’t do the proper pre-work from slowing down and impeding the groups learning during the class. Our class was just us and another couple, plus our instructor Kelly.

We flew into Tampa, took an Uber to Saint Petersburg and stayed at the Hampton Inn & Suites St. Petersburg/Downtown. We got in the afternoon before our class began, so we were ready to do some exploring and took the short walk to the marina to begin our week of adventure and learning. The hotel was well-appointed and right near the marina and many restaurants downtown. We explored the main drag and ate lunch and dinner on the strip. We got to bed early knowing we were in for a long week.

Day 1- Monday

The first day on the boat was immediately down to business as my wife and I challenged the basic keelboat test. We took the basic keelboat test and then spent some time reviewing what we were going to learn, important points we needed to know and explored all of the boat’s functions and equipment. We checked the bilge pumps, explored all the holds and bilge areas, checked the oil, filled up the water tank and identified all the breakers, safety equipment, and necessary charts. We got all the provisions put away and got ready to shove off after a briefing and a little pre-work. The couple we were on the boat with had done the two day basic keelboat class prior to this fast-track class and found it excellent.

Our boat for the Class was a Fountaine-Pajot 40 foot sailing catamaran named the Oasis. She had air conditioning, plenty of refrigeration/freezer capacity and all the navigation equipment one would expect on a well-appointed boat. The bedrooms and bathrooms were very comfortable even for the 6-foot 4 inch sailor who was part of the class. There was plenty of space to stow the gear and I couldn’t have been happier with our luck in getting to spend the week on this fine sailing vessel.

Kelly did most of the driving the first hour or so explaining the lay of the land, important channels and where it was safe to play around. This became important for our last two days when we would do a solo sail from the marina. After that, we each took turns motoring towards our destination in Manatee River. This was a great anchorage that was quiet and peaceful. It was also near the end of Tampa Bay by the Gulf of Mexico where we had lots of room to sail and practice our skills.

Dinner was on the grill on the back of the boat with dolphins swimming by and a beautiful sunset.

Day 2- Tuesday

Today we spent much of the day sailing in the bay practicing our tacking, jibing, and pinching skills (pinching, which on a catamaran isn’t that close to the wind and holding a course). We also took turns working the sheets as couples to get the communication practice we needed to be effective teams. Kelly took a lot of time this first day working us all through the different roles on the boat making sure everyone was comfortable in each role. He made sure that the women spent some extra time to make sure the guys didn’t take all the fun away. He was patient but made sure we kept our skills sharp and efficient. This was a great day of relaxed but purposeful practice that got us all feeling more confident.

We spent the night in Manatee River again as it was a perfect anchorage given the wind direction and the ability to anchor close to shore making for a quiet and still spot to spend the night. We set the anchor this night as team and it went off without a hitch. After a great meal of shrimp and fresh fish we had a few glasses of wine and hit the rack early.

Day 3- Wednesday

We awoke early and had a quick breakfast before taking the second of the four tests we would take on the trip. We pulled up the anchor and headed out into the Gulf for some practice in higher winds and more rocky seas. This trip was cut a bit short as the ladies got a little queasy from all the rocking and rolling so we headed back into the stiller waters of the Bay. We sailed out to where based on the predicted winds we would anchor for our solo sail in Boca Ciega Bay near the Days Inn. After getting a good line in the channel and practicing anchoring a few times in this location we headed off to Longboat Key for the night. This gave us a chance to go through two drawbridges and practice calling the bridge tender operators.

The channel beyond the second bridge is narrow and staying on the windward side is paramount, but with Kelly’s support and trust we navigated and successfully docked at Longboat Key where we ate on land at the Mar-Vista Restaurant. The food was excellent and the venue was beautiful. After dinner we went back and had a few drinks on the boat prior to turning in.

Day 4 – Thursday

We awoke to a beautiful sunrise of all the boats floating in the anchorage and had a hearty breakfast of bacon and eggs.

After breakfast we took our final two tests and headed back toward our home base marina and worked on man overboard drills and mooring and docking in a nearby marina. We motored into our home base marina and hooked up our shore power prior to heading out for a dinner on land at Stillwaters Tavern and a short walk to stretch our legs.

It was early to bed since we had our solo sail the next day so all of us wanted to be sharp and maximize our opportunity to practice and gain confidence without our instructor Kelly who departed before dinner to head home and sleep in his own bed.

Day 5- Friday

We awoke early and ate breakfast while underway as we shoved off and made our way out into Tampa Bay to practice our skills. Each couple took turns jibing and tacking as the others spent time inside relaxing and eating some lunch. After we all felt confident, we set sail for our overnight anchorage in Boca Ciega. We took turns sailing until we reached the entrance channel for our overnight spot where we fired up the motors and dropped sail to motor into our home for the night. After arriving we dropped anchor made sure we had plenty of scope and the anchor was well set and then broke open a bottle of wine to toast our accomplishment on the day.

Dinner that night was shrimp, steak, rice and vegetables as well as a few more glasses of wine as we watched the sunset and we remarked how much we had learned and how great our instructor Kelly was.

Day 6- Home Again

We got up early again and headed out the channel and back to home base to dock the boat and get our graduation certificates. The winds were strong and we battled waves as we made way against the wind and surf back to the marina.

We docked at a T-dock to pick up Kelly as the wind was howling and none of us wanted to end the week badly with an accident getting into a tight slip between numerous expensive boats.

Kelly got us safely in the slip, we tied the boat off and plugged in the shore power. We washed off the boat, filled the water tanks, disposed or boxed up left over provisions and got all our stuff up on deck. Kelly presented us with our certificates, we took a few photos to remember our experience and stepped onto shore much more competent and confident sailors then we stepped on 6 days prior.  

Final Thoughts

Offshore Sailing School far exceeded our expectations as far as the quality of vessel we were on, teaching style and ability of our instructors, convenience of the booking and material review process, food provided, as well as the fun we had all while learning a lot.

For anyone looking to learn how to sail, Offshore Sailing School is really the way to go as we went from knowing very little besides the absolute basics to feeling confident enough to go it alone with the family. Upon getting home, we booked a short trip in the Keys out of Key West with Dream Yacht and an 8 day sail in the BVIs with the Moorings (graduates of the OSS Bareboat class get 10% off). We have completed both those trips and I will say our class definitely prepared us well for all we would need to do. This trip was a great start for many new adventures to come.

10 thoughts on “The Beginning of Many Wanderingkeller Adventures: Learning to Bareboat Cruise on a 40-foot Catamaran with Offshore Sailing School

  1. That sounds like a great class. I’d love to own a boat someday, even if it is just something to take out on a lazy river.

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  2. Great read. Learning how to sail is very high up on my list. A good buddy of mine used to own a 24-footer and is thinking about buying a bigger yacht. I’m trying hard to push him to do so.

    I was particularly interested in the bit about convincing the missus as this is going to be one of my big challenges when I’ll finally ask her to go sailing with me haha…

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  3. What a great experience, this intensive class seems like the perfect way to learn the ropes (pun intended!). I love sailing but not sure I’d ever be brave enough to do this. Sailing around retirement sounds amazing!

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