Have it all... it's easier than you think!

Do you dream of one day captaining your own boat and sailing off on a grand adventure around the tropics? It's never to soon to get started! Simple Sailing offers both ASA certified sailing lessons and weekend getaway packages that can be combined into one fantastic adventure! Have an awesome hands-on experience learning to sail, while also enjoying a vacation in paradise...

There are few things in life more rewarding than sailing from tropical destination to destination, forging your own adventure on the high seas, while enjoying the immense beauty of our oceans.

At Simple Sailing, we offer customizable 2-3 day charter packages that are perfect for weekend excursions and certified ASA sailing classes that range from intro to advanced sailing and navigation. These packages can be combined as a great way to enjoy a fantastic vacation while also getting hands-on experience sailing and learning the skills you need for future expeditions. 

Our Fleet

We have a robust fleet of boats, many with amenities for overnight excursions. Even if you're just starting to learn the basic's and not heading out to sea, we can accommodate your needs...

Train the basics in the morning on one of our small crafts...

Take a break to enjoy downtown St. Petersburg and it's wonderful selection of food and entertainments

then return to stay on one of our yachts...

There's no need for a hotel!

If you would like more information on booking a weekend excursion with sailing lessons contact us today!


List of classes we offer


Basic Keelboat Sailing

Class: ASA101
Price: $425.00
Prerequisites: None
Description: Demonstrated ability to skipper a sloop-rigged keelboat of approximately 20 to 27 feet in length by day in light to moderate winds and sea conditions. Knowledge of basic sailing terminology, parts and functions, helm commands, basic sail trim, points of sail, buoyage, seamanship and safety including basic navigation rules to avoid collisions and hazards. Auxiliary power operation is not required.

Basic Coastal Cruising

Class: ASA 103
Price: $475.00
Prerequisites: Basic Keelboat Sailing (ASA101) Certification
Description: Demonstrated ability to skipper a sloop-rigged auxiliary powered (outboard or inboard engine) keelboat of approximately 25 to 35 feet length by day in moderate winds and sea conditions. Knowledge of cruising sailboat terminology, basic boat systems, auxiliary engine operation, docking procedures, intermediate sail trim, navigation rules, basic coastal navigation, anchoring, weather forecast interpretation, safety, and seamanship.

Bareboat Chartering (Intermediate Coastal Cruising)

Class: ASA 104
Price: $495.00
Prerequisites: Basic Keelboat Sailing (ASA101) and Basic Coastal Cruising (ASA103) certifications.
Description: Demonstrated the ability to skipper a sloop-rigged, auxiliary powered (inboard diesel engine) keelboat of approximately 30 to 50 feet in length during an extended cruise in coastal waters in moderate to heavy winds and sea conditions. Knowledge of provisioning, galley operations, boat systems, inboard engine operation, maintenance procedures, advanced sail trim, coastal navigation including basic chart plotting and GPS operation, mooring with multiple anchors, weather interpretation, and dinghy/tender operation.

Cruising Catamaran

Class: ASA 114
Price:  $1,025.00
Prerequisites: Basic Keelboat (101) and Basic Coastal Cruising (103). The Bareboat Charter Standard (104) is also a prerequisite and can be attained either by itself prior to BBC Multihull (114) or in conjunction with BBC Multihull (114). In either case, ALL MATERIAL IN BOTH STANDARDS (104 & 114) MUST BE TAUGHT AND TESTED BEFORE 114 CAN BE AWARDED.
Description: An advanced cruising standard for individuals with cruising experience. The individual can act as skipper and crew of a 30-50 foot multihull sailboat by day in coastal waters. The standard includes those skills unique to a 30-50 foot multihull.

Coastal Navigation

Class: ASA 105
Price: $350.00
Prerequisites: None
Description: Able to demonstrate the navigational theory required to safely navigate a sailing vessel in coastal or inland waters. There is no Sailing Skills part to this Standard and practical application of this sailing knowledge is found in the Advanced Coastal Cruising Standard.

Advanced Coastal Cruising

Class: ASA 106
Price: $850.00
Prerequisites: Basic Keelboat Sailing, Basic Coastal Cruising, Bareboat Chartering and Coastal Navigation Certifications
Description: Able to safely act as skipper and crew of a sailing vessel about 30 to 50 feet in length. This is a day and nighttime Standard in coastal and inland water, in any weather.

Celestial Navigation

Class: ASA 107
Price: $~~~~~~
Prerequisites: None
Description: Able to demonstrate the Celestial Navigation theory required to safely navigate a sailboat on an offshore passage. The practical application is conducted in the Offshore Passagemaking Standard.

Docking Endorsement

Class: ASA 118
Price: $325.00
Prerequisites: None
DescriptionAble to safely and efficiently dock an auxiliary powered (single inboard or outboard engine) sailboat. Knowledge of basic auxiliary power theory, engine and steering controls, proper use of dock lines, crew communication and safety.

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About Our Services...

Simple Sailing Charters and Sales is based out of Saint Petersburg Florida. We love sailing and the sea, so it's a pleasure to help bring the craft into new lives. We offer weekend excursions, sunset cruises, weddings, and corporate team-building exercises. (captained or self-driven) We are also an American Sailing Association School offering a selection of courses from basic coastal cruising to advanced celestial navigation and catamaran cruising. For all your sailing needs we are ready to help! Give us a call today!