Entries by Captain Mac

Uncharted Waters

WINTER 2020/21 CORONAVIRUS UPDATES – Olde World Sailing Line Schedules Dear Guests – The Coronavirus has presented global challenges to us all unlike any in modern memory.   Challenges in personal life, business and community commerce, and professional interactions – truly uncharted waters for everyone.  Following the guidance of the respected health officials we will all […]

Phase I Reopening Plan for Olde World Sailing Line

­­­PHASE I REOPENING PLAN Olde World Sailing Line Beginning March 1, Olde World Sailing Line discontinued sailing operations as prescribed by U.S. health experts.  After reopening briefly from August – October, we have suspended sails again due to the widespread surge in coronovirus cases in the U.S. When health officials indicate it is safe to […]

A VIP Guest Experience – from 98Rock Baltimore

We were thrilled to welcome Sarah Fleischer aboard Lionheart this January.  She is an on-air personality at 98Rock from the Greater Baltimore area.  Check out her Blog at 98Rock Online. All Aboard Matties! Just getting away from the “Polar Vortex” for 6 days to Clearwater,Florida was wonderful in itself but a real highlight of out […]


 The winter months in Central Florida are some of the most beautiful months of the year. The air is crisp and clear as well as the waters of Tampa Bay as summer algae dissipates. This year November and December have provided us many spectacular sails, brilliant sunsets, and abundant wildlife encounters.  As many of you […]


Proposals on a Private Sailing Yacht Spectacular sunset sailing, steady predictable winds, and comfortable temperatures – all the wonderful things we love about Tampa Bay and Gulf Coast sailing in the fall. Apparently Cupid has an affinity for the season as well. The past few months have been a great time for marriage proposals aboard […]

Tampa Bay Sailing Eco Tours

Sailing Tampa Bay – One of Florida’s Most Productive Natural Habitats One of the most profound pleasures of sailing on beautiful Tampa Bay is the abundance of sea life we encounter. Tampa Bay is Florida’s largest estuary – an enclosed body of coastal waters with one or more rivers flowing into it, opening to the […]

Tampa Sailing Tours

Olde World Sailing Line You haven’t seen the Tampa Bay Area until you’ve seen it from the sea. Get a preview from our video… Make your reservation today…Click Here!