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San Juan, Puerto Rico Sailing trips & boat tours

Our most recommended San Juan, Puerto Rico Sailing trips & boat 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 50-55 minute journey on the high-speed catamaran will take you to the beautiful Cordillera Islands, off the coast of Fajardo. 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 onboard the catamaran is open for all guests with Piña Coladas, Rum Punch, sodas, iced teas, and juices. A sumptuous lunch is served on board, including fresh fruit, chicken salad or veggie wraps, salads, and chips.

From Fajardo: Icacos Island Full-Day Catamaran Trip

2. From Fajardo: Icacos Island Full-Day Catamaran Trip

Spend a day in the sun with lunch and specialty 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 1.5 hours walking on the beach, beachcombing, and swimming in the crystal clear waters. Return on board to enjoy your pre-packed lunch. Sodas, water, and juices are also available, and those with a taste for the sweeter things in life will want to sample the specialty piña coladas and tropical rum punch. When you have eaten your fill, the boat will head a short distance out and anchor over the reef for another 1 or 2 hours of swimming or relaxing. A leisurely sail back to Marina Puerto del Rey will bring you back to the dock, with plenty of time to enjoy your afternoon and evening in Fajardo.

San Juan: Old San Juan Sunset Cruise

3. 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.

From San Juan: Bioluminescent Bay Boat Tour and Hot Springs

4. From San Juan: Bioluminescent Bay Boat Tour and Hot Springs

Embark on an adventure to a bioluminescent bay on this trip from San Juan. See the hot springs, feast on a hot dinner in a local restaurant, and visit a sand bar, before heading out to the bay and swimming in the luminous water. After pickup from your hotel, relax on the drive to the southwest and the first stop at the hot springs. From there you will dine on fresh fish, chicken, or vegetable tacos at a local restaurant. After dinner, you will visit the sand bar 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 back and relax on the journey to your accommodation.

Old San Juan Sailing Tour

5. 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.

Frequently asked questions about San Juan, Puerto Rico

What top attractions are a must-see in San Juan, Puerto Rico?

The must-see attractions in San Juan, Puerto Rico are:

What are the best day trips and excursions from San Juan, Puerto Rico?

The best day trips and excursions from San Juan, Puerto Rico are:

El Yunque National Forest

Other Sightseeing Options in San Juan, Puerto Rico

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What people are saying about San Juan, Puerto Rico

Overall rating

4.8 / 5

based on 291 reviews

We were not able to go to Culebra due to rough seas. We went to an island closer to Fajardo and the marina. Boat ride was probably 20-25 minutes. It was still fun and the crew was fantastic. Snorkeling was average. Company credited back some money due to the itinerary change. It was a good way to get out on the water and we enjoyed the day.

This was an amazing experience. There were shuttles bringing us from different parts of the island to the location. The boat and the staff were perfect.

Guides Diego and other team members were really friendly and made our entire trip really pleasant and memorable. It was worth it

I have been on your tour several times & always have enjoyed each time

Very nice experience! Beautiful waters and nice beaches!