San Juan
Sailing Trips & Tours

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Our most recommended San Juan Sailing Trips & Tours

  • From Fajardo: Full-Day Culebra Islands Catamaran Tour

    1. From Fajardo: Full-Day Culebra Islands Catamaran Tour

    Discover an area off the beaten path on this full-day catamaran tour to the Cordillera Islands. Departing from Puerto Del Rey Marina in Fajardo, the 45-50 minute journey on the high-speed catamaran will take you to the beautiful Cordillera Islands, off the coast of San Juan. Upon arriving at the Cordillera Islands, the captain will decide which beach will have the best conditions for the day, usually Flamenco or Culebrita beach. Spend the afternoon swimming, snorkeling, beachcombing, sunbathing, or relaxing on the roof deck. Throughout the day, the bar on board the catamaran is open for all guests with Piña Coladas, Rum Punch, sodas, iced teas, and juices. A sumptuous buffet lunch is served on board, including fresh fruit, freshly baked bread, sliced meats, sliced cheeses, salads, chips, and cookies.

    The island was so beautiful! It a long commute that I really didn’t care for. It was an hour bus ride from my hotel to the location. Then, it was an hour boat ride to the private island. If you get motion sickness, I highly recommend buying motion sickness medicine and sit outside the boat for the ride. Once you get to the island, you forget about everything. The staff was friendly and very helpful if you are not a swimmer. It was open bar which I loved! And the snack they gave was pretty good. 10/10 recommendation.

  • Fajardo: Icacos Deserted Island Catamaran & Picnic Cruise

    2. Fajardo: Icacos Deserted Island Catamaran & Picnic Cruise

    Board the Barefoot IV catamaran and set sail to the remote island of Icacos, just off the coast of Fajardo. Icacos is the perfect place to enjoy the white, sandy beaches and the clear blue waters of the Caribbean Sea. After a leisurely sail to Icacos, drop anchor 50 feet from the beach with crystal clear blue water for easy disembarking. Swim in the beautiful warm water or sunbathe on a white sand beach. Take advantage of beach toys such as volleyball, football, beach paddles, and floatation devices provided by the crew. If you bring your own snorkeling equipment, choose to explore a wonderful coral reef that is home to beautiful tropical sea life.  Take a break for lunch with a complimentary packed lunch box, with a turkey or veggie wrap or sandwich, pasta salad, chips, cookies, and fresh fruit to enjoy on the beach. Quench your thirst with soda, water, and tropical drinks provided wi...

    Wonderful day and well worth every penny! The service and experience were above and beyond expectations.

  • San Juan Mini Boats

    3. San Juan Mini Boats

    The most complete tour for those explorers who would like a glimpse into San Juan's captivating history, have an adventure in the waters of the harbor at the helm of your own boat and stop to learn the highlights of the city’s history. You will take the helm of a 13' inflatable boat that you will get to operate during the entire tour. Appreciate Condado and the Puerto Rico Convention Center. After a short stop where the guide will point out these areas of interest, the fleet will cruise along the southern shores of the Islet towards the Historic District. On your way there, Old San Juan will rise in front of you in the distance and you will admire Fort San Cristobal, the largest fort built by the Spaniards in all the Americas, the cruise ship ports with the green mountains to the south and the Rainforest to the southeast. Along the way, you will feel the warm Caribbean breeze and may sp...

    My family and I really enjoyed the whole experience and definitely will do it again.

  • San Juan: Old San Juan Sunset Cruise

    4. San Juan: Old San Juan Sunset Cruise

    Climb aboard the beautiful Amazing Grace in Old San Juan and get enchanting views of the cultural city and sites around the bay. Marvel at the 16th-century citadel of Castillo San Felipe del Morro and the official residence of the governor of Puerto Rico at La Fortaleza. Sip soft drinks and cocktails under the sun and avail of the services of a local guide. The Amazing Grace is a topsail schooner representative of the traditional American sailing crafts that fought the British in the War of Independence. The beautiful sailing vessel flies seven sails that can be used in different combinations to suit the wind conditions, making for a fun journey out at sea.

    Kudos to the exceptional crew who took their time to provide a lot interesting details about San Juan and PR; who made sure the cruise ran smoothly; took the extra mile to turn this trip into an interesting one for our 6-yo; and always smiled. Highly recommended.

  • From Fajardo: Icacos Island Half-Day Catamaran Trip

    5. From Fajardo: Icacos Island Half-Day Catamaran Trip

    Spend a day in the sun on a 6-hour trip, with lunch and speciality drinks includes, taking you out on the clear waters of the Caribbean and along the Fajardo coastline aboard a catamaran. Set sail in the morning from Puerto del Rey Marina, the largest and best-kept marina in the Caribbean. On board the catamaran's deck you will enjoy beautiful views of the mountains in the El Yunque National Forest, as well as the beaches along the Fajardo coastline. After a comfortable sail of about 45 minutes, you will anchor at one of the small deserted islands and cays off the northeast coast of Puerto Rico. Normally it is the island of Icacos, but the captain will sometimes head to Cayo Lobo or Palominos if the conditions are better for the day. Once you arrive, step off into shallow water and spend the next 2 hours walking on the beach, beachcombing, and swimming in the crystal clear waters. Re...

    This is a must do when here in Puerto Rico. The transportation was on time, the crew on the boat was phenomenal and the waters are fantastic. The food was good and the unlimited drinks were even better

  • From San Juan: Bioluminescent Bay Boat Tour

    6. From San Juan: Bioluminescent Bay Boat Tour

    Climb aboard and set sail towards a nearby sandbar. Upon arrival, chill out on the beach and soak up the glorious Puerto Rican sunshine then take a stroll along the picturesque boardwalk.

    As evening draws near, watch the sunset across the ocean before dining a delicious dinner of fresh fish, chicken, or vegetable tacos at a local restaurant.

    After dinner, and once night has fallen, cruise to the bioluminescent bay where you will be amazed by the glowing landscape that awaits.

    At the bay, jump in the water to really experience this unique phenomenon, which is a true feast for the eyes. Enjoy some free time to swim and play in the water and admire the striking glow of the microorganisms that surround you.

    At the end of an unforgettable day, dry off on the boat then sit b...

    This tour was so much fun! I loved that it was a small group, and our guide was really helpful and personable. Definitely recommend bringing two bathing suits if you can swing it, as there are plenty of opportunities to change. Loved it!

  • Old San Juan Sailing Tour

    7. Old San Juan Sailing Tour

    Climb aboard the "Amazing Grace" topsail schooner and cruise around Old San Juan. Take in the enchanting views of the cultural city from a different perspective. See the sites around the bay, including El Morro, La Fortaleza and Paseo de la Princesa, and listen to interesting facts about the landmarks from a local guide.  Feel a part of history as you sail aboard a vessel like those that fought the British in the War of Independence, and in 1812 as ships of the U.S. Navy and as privateers. Look up at the 7 sails that can be used in different combinations to suit the wind conditions, making for a fun sailing adventure.

    I WISH I Can give this tour a 10+++++++ star. not only was the captain and his crew amazingingly, 100% humorous but they new their sh*t. They're welcoming, loving, humorous and, you, for sure, can see that they love what they do. You will leave like this but come back like this . IF you haven't done this yet please do. Trust us. You won't regret it. TOO THE CREW: Thank you so much for the experience. we will treasure this moment forever. BAGA .

Other Sightseeing Options in San Juan

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What people are saying about San Juan

Overall rating

4.8 / 5

based on 291 reviews

If it’s your first time in PR, or you’re just looking for things to do I 100% suggest doing the Bio Bay Tour! Be warned, it is an all day event, so plan ahead with extra clothes, a towel, etc. The tour is such an amazing experience from start to finish. Educational, entertaining, and also relaxing. There’s no way to describe the breathtaking view that is the Bio Bay, it’s certainly something you have to see for yourself, but I can tell you it’s spectacular and worth every penny. Our guide was hilarious and fun spirited which made the whole day even better. 10/10. Do yourself a favor and book a tour!

It was so much fun! We weren’t able to go to Flamenco but we still made it to the island and were swimming in The same waters. The staff was super friendly and the drinks were flowing! Be sure to bring some cash to tip&I might sure they take PayPal if not !!!! They deserve it.

This tour was so much fun! I loved that it was a small group, and our guide was really helpful and personable. Definitely recommend bringing two bathing suits if you can swing it, as there are plenty of opportunities to change. Loved it!

Our tour guide was amazing!! She is super sweet and told us everything we needed to know. I would definitely recommend to my friends and family

All I have to say this experience was off the hook