Sailboat Cruises in Siesta Key, Florida

A hidden gem located just off the central western coast of Florida, and about 55 miles south of Tampa, Siesta Key is an eight-mile long barrier island that offers all of the advantages of tropical island living, but with easy access to the mainland via two separate bridges that direct connect it to Sarasota. For those who love sailing, Siesta Key offers access to several different options for sailing cruises or charters, whether for the day, or for just a few hours.

  1. Key to the City

    • With a sailing program that includes both sailing charters as well as sailing instruction, Key Sailing offers a number of cruises around Siesta Key and Sarasota Bay. Customers who go with Key Sailing will enjoy the water on a 41-foot Morgan Classic II called the "Key Breeze," captained by Janet Hamel Solomon. Solomon, who was raised in Sarasota, knows its waters well, and has been sailing them all her life. Joining Solomon on deck is husband U.S. Coast Guard Master Captain Tim Solomon, who as an ordained and licensed minister, can even marry guests on board, or simply renew their vows.

      The Key Breeze not only offers outstanding views of Siesta Key, the boat carries the key to the city itself, as it was once awarded to Solomon's father. Cruises include afternoon and sunset cruises and custom charters, with sights including dolphin-watching, celebrity homes, the Ringling Causeway Bridge, and the Sarasota skyline. The Key Breeze is documented and insured for up to 12 passengers at a time for maximum comfort, with prices ranging from $45 for sunset sails, to $150 per person for eight-hour day sails.

      Key Sailing
      Docked at Marina Jack's
      P.O. Box 51173
      Sarasota, FL 34232
      941-720-8487
      siestakeysailing.com
      keysailing@comcast.net

    Enterprising Sailing

    • Another local option for sailing the waters of Siesta Key and the waters off Sarasota is Enterprise Sailing Charters, which offers views of local waterways, wildlife, sights and islands via a 41-foot ketch with three sails from Captain Justin. Enterprise Sailing includes cruise options from short two-hour cruises, to daytrips, sunset cruises and more. Destinations include Siesta Key, Sarasota, Bradenton, Anna Maria Island, Longboat Key, Lido Key and the waters of the Gulf. Prices begin at $40 per person for two-hour cruises including Siesta, Bird and Lido Keys, to $70 for four-hour cruises, and a host of other options. Enterprise also offers discounts for those with kids 12 and under for family sails, and food and (non-alcoholic) beverage are included in the price.

      Enterprise Sailing Charters
      2 Marina Plaza
      Sarasota, FL 34236
      941-951-1833
      sarasotasailing.com

    A Spindrift View of Sarasota Bay

    • A final option for local sailors wishing to experience Siesta Key is Spindrift Yacht Charters, which sails its guests from Longboat Key, Siesta Key and Sarasota to the nearby waters of the Gulf of Mexico. Options include offshore fishing packages, as well as bay and backwater exploration, cruises past some of the area's most palatial homes, and sunset cruises on the "Spindrift," a 45-foot Morgan Ketch.

      The Spindrift's cruising prices for a minimum three and a half-hour charter start at $350, with $75 for each additional hour, and for a maximum of six passengers, although the vessel is licensed for up to 12 passengers.

      Spindrift Yacht Charters
      410 South Gulf of Mexico Drive
      Longboat Key, FL 34228-4010
      941-383-7781
      spindrift-yachts.com