First, we sail to the paradise Island of Icacos aboard the modern, 51 ft. sailing catamaran,  SPREAD EAGLE II!  The brisk 40 to 50-minute sail to the protected anchorage off of this uninhabited Spanish Virgin Island is beautiful... More

Experience the magic of exploring the marine world at a stunning beach in San Juan. Join this beginner-friendly adventure led by a professional guide in small groups of up to 10, ensuring a personalized and high-quality experience... More

Hop aboard and join us for a captivating journey on a sunset pontoon boat tour, exploring the timeless allure of San Juan Bay, the historical gem of Puerto Rico. Our Sunset Tour offers a perfect fusion of cultural exploration, a... More

Discover the beauty of the Caribbean on a 4-hour tour to the stunning Icacos Island. This trip offers the perfect blend of relaxation and adventure with two exciting stops: one for snorkeling among vibrant marine life and another ... More

Discover San Juan, Puerto Rico aboard a 37-foot catamaran sailboat while enjoying complimentary mimosas, house rum punch, and other drinks in moderation (not a booze cruise type open bar). Take in the panoramic views on this pleas... More

Sailing is authentic to San Juan culture- having a conversation with a local, the power of the wind, the peace from no engine noise, no crowds, no fake pirates, no crowds, no need to scream. We sail aboard a real racer cruiser (J3... More

Sit back, relax and take in the amazing sights of historic San Juan Bay with picturesque sunset lighting. This 2-hour sail aboard a 37ft catamaran sailboat completely powered by the wind is the perfect setting for a romantic momen... More

Private, AM. PM. or Sunset, sailing around the San Juan Bay and Harbor of Old San Juan, Puerto Rico. (Prices already include all taxes and fees) This sightseeing, sailing tour will pass historical, Old San Juan Forts and views o... More

Get more time, See more do more!, More Space! Welcome aboard your private water tour aboard a choice between a 37 foot sailboat ot a a high performance Powerboat. Enjoy complimentary local drinks. Your personal tour guide and Pro ... More

Authentic sailing is culture, having a conversation with a local, with the power of the wind, no engine noise, no crowds, no fake pirates, no stray cats, no crowds, no need to scream . . . we sail sideways, aboard a real racer-cru... More

Experience the magic of exploring the marine world at a stunning beach in San Juan. Join this beginner-friendly adventure led by a professional guide in small groups of up to 8, ensuring a personalized and high-quality experience ... More

Looking for a travel experience that goes beyond the ordinary? Black Octopus Tours offers more than just sightseeing, we craft unforgettable journeys designed to thrill, inspire, and connect you with the heart of every destination... More

First, we sail to the paradise Island of Icacos aboard the modern, 51 ft. sailing catamaran,  SPREAD EAGLE II!  The brisk 40 to 50-minute sail to the protected anchorage off of this uninhabited Spanish Virgin Island is beautifu... More

We are the only excursion that allows you to drive the boat during this private excursion. We are the only boat that sails in the dark, at night, wait till you see that sky and moon.!!... More

Come aboard the comfortable Janise Lagoon 380 for a memorable voyage in the beautiful waters of the Caribbean Sea. Great for birthdays and any special private event. Come experience first class service by our professional and frie... More

Come aboard the comfortable Janise Lagoon 380 for a memorable voyage in the beautiful waters of the Caribbean Sea ending in an amazing sunset setting. Great for engagements, and any special private event. Come experience the 1st c... More

Our experienced USCG Captain and crew will make sure you experience the most beautiful and secluded spots of the Jobos Bay National Estuarine Research Reserve (JBNERR) in the comfort and privacy of our 36-foot sailboat fit for six... More

Come aboard the comfortable Janise Lagoon 380 for a memorable 8-hourfull day charter in the beautiful Spanish Virgin Islands. Come experience first class service by our professional and friendly crew. Our great reviews have positi... More

On this trip we offer you a sailboat trip experience during 4-hours tour from the coast of Fajardo to one (1) selected Island (Icaco Island or Palomino Island). Customers can swim and enjoy themselves on each island. In some cases... More

On this trip we offer you a sailboat trip experience during 6-hours tour from the coast of Fajardo to two (2) different destinations: Icaco Island and Palomino Island, in combination with snorkeling, swimming experience and much m... More