Sail Old San Juan

Sail Old San Juan offers unforgettable sailing experiences on the sparkling waters of San Juan Bay, Puerto Rico. Led by U.S. Coast Guard licensed captains, this boutique sailing company specializes in intimate group adventures and private charters aboard performance racing sailboats. Whether you're seeking a leisurely daytime cruise, an exhilarating spinnaker adventure, or a romantic sunset sail, Sail Old San Juan delivers authentic Caribbean sailing with a personal touch. Their fleet is designed for excitement and comfort, capable of reaching impressive speeds when conditions allow. The company caters to couples looking for a special experience, families wanting quality time together, and groups of friends seeking adventure. With flexible scheduling and customizable itineraries, they accommodate groups up to 6 passengers on day charters. The Spinnaker Adventure Sail is their signature experience, where skilled crew members unfurl the asymmetrical spinnaker to catch the trade winds—this is when guests truly experience sailing at its finest. All sails depart from the picturesque Paseos de San Juan area, offering stunning views of Old San Juan's colorful colonial architecture and the broader San Juan skyline. The atmosphere is relaxed yet thrilling, combining the peaceful rhythm of sailing with the excitement of being on open water. Whether it's your first time sailing or you're an experienced sailor, Sail Old San Juan makes every moment memorable.