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4659

St. Petersburg, Florida

A Learn-To-Sail-Vacation

hosted by Intelligent Sailing School
  • 2025: Oct 5 - 31
  • 4 - 6 Days
  • 101 / 103 / 104 / 118

Destination

This trip takes place starting in St Petersburg, where you can enjoy and find out what St Pete is a top destination vacation hub, sail during the day and then be a tourist go to the beach , hit the Dali museum, walk the pier, watch the Rowdies – its all here for you to enjoy, or just sail and go on a trip to Gulfport or Downtown Tampa, the choice is yours. When you arrive we will bring you to your yacht for your personalized experience. Find out why Intelligent Sailing is the perfect location to learn to sail.

Sailing in St. Petersburg, Florida, offers a unique and enjoyable experience for a variety of reasons. Here are some top reasons why St. Pete is such a great place to set sail:

Beautiful Scenery

St. Petersburg is known for its stunning waterfront views. The sparkling waters of the Gulf of Mexico, Tampa Bay, and the surrounding islands provide an idyllic backdrop for any sailing adventure. Whether you’re cruising along the shoreline or venturing into open waters, the scenery is always breathtaking.

Perfect Sailing Conditions

The weather in St. Petersburg is generally ideal for sailing. With warm temperatures year-round, moderate winds, and calm seas, sailing in St. Pete can be a smooth and relaxing experience. The area enjoys around 361 days of sunshine annually, so there’s a high chance you’ll get perfect weather during your trip.

Vibrant Waterfront Community

St. Petersburg has a thriving marina district, with plenty of places to dock, explore, and enjoy local restaurants, shops, and bars. The city is home to one of the best waterfronts in Florida, with marinas, waterfront parks, and a vibrant downtown area – and for beach-lovers, you will be minutes away from some of the nation’s top beaches.

Relaxation and Adventure

Whether you prefer a leisurely sail with a picnic or a more adventurous sailing experience, St. Pete offers both. You can choose from day sails, sunset cruises, or even multi-day charters that allow you to explore more of the Gulf Coast.

Rich Maritime History

St. Pete has a rich maritime culture and history, with museums, historical landmarks, and opportunities to learn about the area’s sailing past. The St. Petersburg Yacht Club’s Sailing Center is a great place to get involved in the local sailing community and learn more about the history and culture of the area.

With so much to offer, St. Petersburg is a fantastic destination for sailors of all types. Whether you’re seeking relaxation or adventure, sailing here provides an unforgettable experience.

CERTIFICATIONS

This learn-to-sail vacation with Intelligent Sailing School includes three certifications. Choose from the following course combinations:

101, 103, 104 – 6 Days
101, 103, 118 – 4 Days (less than the listed fee)
103, 104, 118 – 6 Days

Already have some of these certifications? We’ll customize a course to fit your needs.

Learn more about the available certifications:

¤ ASA 101 | KEELBOAT SAILING 1
¤ ASA 103 | COASTAL CRUISING
¤ ASA 104 | BAREBOAT CRUISING
¤ ASA 118 | DOCKING ENDORSEMENT

SAMPLE ITINERARY

Day 1
EMBARK
  • Start time between 0900 to 0930.
  • Provision stowage. Chart work. Classroom work on the boat.
Day 2
TAMPA BAY
  • Sail in Tampa Bay. Get to see why Tampa Bay offers safe sailing. The bay is 400 square miles, we will show you were you can sail and where you never want to “are we aground?” Don’t worry this will never happen, we know our waters and so you will also
Day 3
GULFPORT MARINA
  • Depart 0900 – Harborage Marina to Gulfport Marina. Approximately. 22 nm. Estimated time underway: 4-5 hours (running at 5 knots per hour). Add undocking and docking: 6 hours total. Route – Harborage to Skyway Bridge. Skyway Bridge to Gulfport Marina via Skyway Channel and ICW. Classroom work (whilst underway).
  • Sailing, ICW, bascule bridge, marina reservations, marina docking/shore power hook-up. Chart next day’s route. Walk to City of Gulfport for dinner, shopping, drinks.
Day 4
HARBORAGE MARINA
  • Depart 0900 – Gulfport Marina to Harborage Marina, (stopping for anchorage simulation (1hr)) while preparing and cooking lunch and having lunch (.45hr) @ Point Pinellas Cove: 27 42.10 N / 82 40.25 W. Approximately 22.5 nm. Estimated time underway (including anchorage/lunch): Route – Gulfport Marina to ICW. ICW to Anchorage, Anchorage to ICW. ICW to Harborage Marina.
  • Bascule bridge opening, tight ICW channel, anchoring simulating a 12hr Anchor-watch system, marina docking/shore power hook up. Classroom work (whilst underway). Chart next day’s route.
Day 5
TAMPA BAY
  • Depart 0900 – Harborage home port, Sail in Tampa Bay or Sail to downtown Tampa
  • Relax easy sail day in Tampa Bay or push yourself and sail to Downtown Tampa – The choice is yours
 
Day 6
DISEMBARK
  • Leaving dock, heading back or temporary docking at a fuel dock and pump out station, re-fueling, pump out, returning to home marina, docking/shore power hook up.

Please Note. This itinerary is meant to serve as an example of what a 5-night sailing journey aboard Chronos, exploring the stunning Balearic Islands of Spain, may entail. However, it is important to note that the actual itinerary is subject to change due to weather conditions or circumstances beyond our control.

AVAILABLE BOATS
  • Jeanneau 490 - "Go Bold" boat - The crown jewel of the fleet, the "i.S 51"Designed for luxurious cruising, offering a spacious three-cabin. two-head layout, high-end finishes, and advanced sailing capabilities.
  • Jeanneau 410 - "Go Bigger" boat - the "i.S 42"Perfect for advanced training, family trips, or small group outings with more onboard amenities in a three-cabin, two-head layout.
  • Bavaria 38 - "Go Big" boat - the "i.S 38"Offers enhanced comfort and space for training and short cruises to week long trips in a three-cabin, two-head layout.

    Our "GO" fleet - Go Bold, Go Bigger, Go Big each have a layout of 3 cabins and 2 electric fresh-water heads, these yachts makes for a perfect vacation for you and your family, all while you learn to sail on brand new boats. Our yachts are fully-loaded with air conditioning. Our professional Captains will 'hold your hand' during the entire length of your course or vacation or day sail; you will be in safe hands and have the experience of a lifetime. We have a variety of courses to choose from outside of a day sail, We have options both with or without ASA certification – all depending on what you'd like. We will give you a wonderful and comfortable experience to remember.
  • Standard Fleet Boats Ranging from 32-35 feet in length. Sail the "i.S 32" or "i.S 34." Ideal for day sailing, basic training, and coastal cruising in a two-cabin, one electric fresh-water head layout.

    Monohulls not for you? Try out "Go Cat" boats. Sail the "i.S 38C" - email us to fin out more... Go Cat!

PHOTOS

Testimonials
Where do I start? In short, Intelligent Sailing, Inc. (i.S.) has made my lifelong dream of sailing come true. I was searching for a sailing school that offered the majority of American Sailing Association (ASA) courses with live aboard accommodations on the monohull and catamaran sailboats. I visited several sailing schools and none of them had the total “Big Boat” bundles I was looking for at a reasonable price, until I attended an i.S. Open House in St. Petersburg, Florida. Marty is the founder/owner of i.S and he runs a great organization with an outstanding fleet of sailboats. He has a vast selection of highly qualified sailing instructors for every ASA course. I did the complete yachtsman package (ASA 101, 103, 104, 105 online, 106, 114 and the 118) over a period of 2 months. I was able to live on the yachts with family and friends who participated in some of my training. I had one on one private instruction at my own pace, which was awesome! I would be remiss, if I didn’t mention both of my instructors by name. I had Captain Andy and Captain Wayne who are both very proficient and professional at what they do as U.S.C.G. Licensed Captains. In closing, I knew nothing about sailing and now I have the required knowledge and most of all, confidence in sailing a 51 foot monohull and a 45 foot catamaran sailboat. Don’t put it off any longer, just commit yourself by starting your sailing adventure dream and do it with Intelligent Sailing, Inc. You won’t be disappointed and it’s money well spent! So, what are you waiting for?
 
Joseph

ADDITIONAL INFORMATION

The base starting price is private training based on one person, and we would never bundle you with strangers. It would be just you and the Captain, all to yourself. Want to bring someone? You should—you can add additional people for as little as $645 per person. Bring the family and enjoy a trip to remember.

Why Choose Intelligent Sailing?

Here are a few aspects that consistently pop up in reviews that people seem to love:

1. Professional and Friendly Instructors:

Many reviews rave about the instructors being not only highly knowledgeable, but also incredibly approachable. Sailors mention how the instructors are patient, thorough, and make learning fun, especially when explaining complex concepts. One review said:
“The instructors were amazing! They really took the time to explain everything clearly, and their passion for sailing was contagious. I felt so confident and safe, and I’ve learned so much!”

2. Excellent Fleet of Boats:

The fleet of modern, well-maintained boats is frequently mentioned in reviews as a key highlight. Sailors appreciate how each boat is kept in top condition, making for a safe and smooth sailing experience.
“The boats are beautiful and in excellent condition. It’s such a pleasure to sail on a new, well-maintained yacht—makes all the difference!”

3. Tailored and Flexible Learning:

Another aspect that comes up in positive reviews is the personalized approach. Whether it’s sailing lessons, charters, or the membership program, people love that everything is tailored to their skill level and needs.
“The ability to tailor my experience to my specific goals made all the difference. The flexibility with the membership options was fantastic, and I never felt rushed or overwhelmed.”

4. A Great Community:

People also enjoy the community aspect of Intelligent Sailing. It’s not just about learning or chartering—it’s about connecting with other sailors and sharing the love for the water.
“Being part of this community has been an incredible experience. Everyone is so welcoming and passionate about sailing. It’s more than just learning; it’s about building relationships with people who share your passion.”

5. Great Location:

Many reviews mention the location in St. Petersburg, which is ideal for sailing with beautiful weather and calm waters. Reviews frequently mention how much fun they have exploring the area and sailing around the bay. Tampa Bay is also home to one of the nation’s top airports, and you are near top beaches, theme parks, museums, and countless other recreational activities
“The location in St. Pete is perfect. The waters are calm, and the weather is great for sailing year-round. Every time I sail, it’s an unforgettable experience!”

  • Learn-To-SailOct 5 – 31, 2025
  • from $3,835 USD per person
  • 101 / 103 / 104 / 118

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