Enjoy our capable sailboats. Our local knowledge will present the best in local sailing fun. Restaurants, scenic opportunities, historical venues and local boating sites will all be available for your reference. The local cruising area is detailed and routes and waypoints are available for the GPS chart plotter. Click on the picture of our Hunter 29.5 below for more information.

  • Hunter 29.5
    Our Hunter 29.5 is the "all around" sailboat. Not too big and not too small. We have sailed them up the East Coast as far North as NYC and have spent months in the Florida Keys. It's a very different design with only one door on the head compartment, all the rest is open giving maximum room. ...
Checkout time is 9am. All sailboats must be back no later than 1 hour before sunset or 5pm whichever is sooner.

All charter rates are subject to state sales tax. Sailboats and rates are based upon availability and subject to change without notice. Weekends and holidays may be at a higher rate.

While we are great dog and cat lovers, pets are NOT allowed aboard SmarterSail vessels.

Charter Requirements

To reserve or use SmarterSail boats you must:

  • be 25 years old have executed the Rental Agreement and paid all moneys due SmarterSail.
  • if you are born on or after January 1, 1988 you are required to complete an approved boating safety course and obtain a Florida Boating Safety ID Card.
  • hold ASA 103 (Basic Coastal Cruising) and/or equivalent, recent training / coastal experience is required for day charters for the Hunter 295.
  • hold ASA 104 (Bareboat Chartering) and/or equivalent training/coastal experience to charter the Hunter 295 overnight away from the base.
  • ASA certificates to be provided by Renter and a copy kept on file with SmarterSail.
  • have successfully completed the on-the-boat familiarization and checkout.

Damage Deposit

SmarterSail will maintain a credit card authorization in the amount of $1,000 as a damage deposit. Amounts will not be charged against the card unless SmarterSail equipment boats and/or equipment is damaged or lost. 


If the charter is cancelled by us due to impending weather, I.e. a pending major storm or the boat is unavailable due to damage or maintenance; we will gladly re-book your charter at the next available opportunity with no penalty.

All of our locations offer the ability to sail in heavy weather, up to 20 knots, and anything less than a wind advisory 20+ knots can be sailed successfully. Usually, wind advisories of 20 knots or greater last less than 24 hours. Subject to availability, and at additional expense, we can provide you with a Captain to teach you heavy weather sailing.

On the other hand, if you are required to cancel due to personal circumstances, it must be recognized that we may lose the charter income for the period if we are unable to re-book the boat on very short notice. Thus, if the charter is cancelled more than 30 days in advance, we will rebook without penalty. A cancellation of less than 30 days notice will result in forfeiture of your days. SmarterSail management will be the sole arbiters of this decision.


On-the-boat familiarization and check-out is required for each sailboat model rented. This checkout is typically 1 hour and covers the operation of the sailboats, equipment and sailing area. This is not sailing instruction. If additional time is required for proficiency it will be charged at the standard rates. Sailors who receive their ASA certification from SmarterSail will be qualified to charter our boats with an abbreviated checkout based on proficiency.