The sailing scene in San Juan delivers some of the Caribbean’s most rewarding maritime experiences. The practical traveler will find three standout options:

First, the Culebra island catamaran excursion combines high-speed sailing with world-class snorkeling spots.

Second, the intimate sunset cruise past El Morro and San Cristóbal forts offers the best photography opportunities and historical context.

Third, private sailing tours provide hands-on experience at the helm while watching for marine life.

We especially love the sunset cruise for its unbeatable value – combining history, views, and refreshments in a single outing.

The Culebra trip stands out for serious snorkelers who want to maximize their time in pristine waters.

Let’s explore the top sailing tours in San Juan and what makes each special.

Key Points

  • The Culebra Snorkeling Tour by Catamaran offers a high-speed cruise, snorkeling, and beach relaxation, with a buffet lunch and cocktails.
  • The San Juan Catamaran Sunset Sail provides an intimate sunset experience with breathtaking views, complimentary drinks, and a 99% traveler recommendation.
  • The Private Sailing Excursion From San Juan allows you to learn sailing basics, enjoy scenic views, and potentially spot dolphins.
  • The Fajardo Private Island-Hopping Sailing Tour includes an open bar, guided snorkeling and paddle boarding, and exploration of vibrant reefs.
  • The Private Sailing and Snorkeling Tour in Puerto Rico offers a customizable schedule, full open bar, and snorkeling equipment with an exceptional 5.0 rating.

Culebra Day Trip by Catamaran From Fajardo

Culebra Day Trip by Catamaran From Fajardo

For those seeking an unforgettable day on the water, the Culebra Snorkeling Tour by Catamaran from Fajardo is a must-try experience.

With over 2,240 reviews and a Badge of Excellence, this high-speed catamaran cruise whisks travelers to the stunning Culebra island for swimming, beach combing, and sunbathing.

The morning begins with snorkeling at the Carlos Rosario or Luis Peña underwater nature reserves, offering a glimpse into the vibrant marine life.

Afterwards, guests can relax on the pristine beaches of Flamenco or Culebrita, soaking up the sun.

The tour includes a delicious buffet lunch with tropical cocktails, fresh fruit, and gourmet salads, ensuring a well-rounded day of adventure and leisure.

Moderate physical fitness is required, and the tour isn’t recommended for pregnant travelers or those with certain medical conditions.

Read our full review: Culebra Day Trip by Catamaran From Fajardo Review
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San Juan Catamaran Sunset Sail With Drinks Included

San Juan Catamaran Sunset Sail With Drinks Included

Travelers seeking a captivating sunset experience on the waters of San Juan Bay can embark on the San Juan Catamaran Sunset Sail With Drinks Included.

This intimate small-group cruise, limited to just six passengers, offers breathtaking views of the coastline, including iconic landmarks like El Morro Fort and San Juan Gate.

With 515 reviews and a 99% traveler recommendation, the 2-hour cruise provides a professional captain and guide, as well as complimentary drinks, including rum punch, sparkling wine, and beer.

Guests can enjoy the relaxing atmosphere and informative commentary on Puerto Rican history.

While snacks and dinner aren’t included, passengers are welcome to bring their own.

The cruise departs from the San Juan Bay Marina, with check-in required at least 20 minutes before departure.

Participants must remove their shoes before boarding, and the experience isn’t recommended for those with certain medical conditions or mobility challenges.

Read our full review: San Juan Catamaran Sunset Sail With Drinks Included Review
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Private Sailing Excursion From San Juan

Private Sailing Excursion From San Juan

Embarking on a private sailing excursion from San Juan offers travelers a chance to experience the city’s stunning coastline from a unique vantage point. Rated 5.0 with a 94% recommendation, this private tour allows small groups of up to 6 to enjoy a flexible, half-day cruise with Captain Jimbo, known for his intuitive, knowledgeable, and engaging style.

The tour includes hotel pickup, safety gear, coolers, and ice, ensuring a comfortable and well-equipped experience. While not wheelchair accessible, the tour welcomes infants and service animals.

Passengers can learn sailing basics and even steer the boat, gaining a hands-on understanding of the activity.

Beyond the scenic views of San Juan’s forts and city lights at sunset, the tour offers the chance to spot dolphins and customize the experience to the group’s preferences.

Consistently praised for its family-friendly appeal and Captain Jimbo’s hospitality, this private sailing excursion promises a memorable and relaxing way to explore the city from the water.

Read our full review: Private Sailing Excursion From San Juan Review
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Fajardo Private Island-Hopping Sailing Tour With Open Bar – San Juan

Fajardo Private Island-Hopping Sailing Tour With Open Bar - San Juan

Beyond the scenic private sailing excursions from San Juan, travelers can also embark on an island-hopping sailing adventure from Fajardo. The “Puerto Rico Private Sail: Island Hopping, Snorkeling, Open Bar” tour, provided by Sandy Bottoms Sailing, offers a full day of exploration and relaxation.

The 5-star rated experience departs from the Puerto Del Rey Marina, where guests will board the sailboat and enjoy a variety of beverages and locally-inspired appetizers. The open bar features Puerto Rican coffee, fresh juices, beer, rum, and more.

Throughout the day, the crew will guide participants in snorkeling and paddle boarding, allowing them to discover vibrant reefs and encounter marine life like sea turtles and dolphins.

Guests consistently praise the expertise and hospitality of Captain Arturo and first mate Christy, who create an engaging and personalized journey. With a moderate fitness level required, this sailing tour is a perfect way to take in the beauty of Puerto Rico’s islands while indulging in local cuisine and drinks.

Read our full review: Fajardo Private Island-Hopping Sailing Tour With Open Bar – San Juan Review
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Private Sailing and Snorkeling Tour in Puerto Rico With Open Bar

Private Sailing and Snorkeling Tour in Puerto Rico With Open Bar

Departing from the Puerto Del Rey Marina, the private Puerto Rico sailing and snorkeling tour offers a personalized and immersive experience for guests.

With a maximum of 6 participants, the tour promises an intimate adventure away from large crowds. Led by an experienced captain, guests can enjoy a customizable schedule and destination, whether it’s sailing to Icacos or Palomino Island.

The tour includes a full open bar stocked with local beer, rum, vodka, tequila and white wine, as well as a spread of appetizing snacks like fresh baked bread, cheese platters, and guacamole.

Snorkeling equipment, paddle boards, and other water toys are provided, and the crew offers basic instruction for those new to the activities.

The well-maintained boat and hospitable staff create a relaxing atmosphere, as confirmed by the tour’s exceptional 5.0 rating from 33 glowing reviews.

For a seamless, all-inclusive Puerto Rico sailing adventure, this private tour is an excellent choice.

Read our full review: Private Sailing and Snorkeling Tour in Puerto Rico With Open Bar Review
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The Sum Up

The best sailing experiences in San Juan offer a diverse range of options, from day trips to private excursions. Travelers can enjoy the scenic beauty of Culebra Island, admire the sunset over the ocean, or explore remote islands and snorkel in the clear waters. These sailing tours provide an unforgettable way to experience the natural wonders of Puerto Rico’s coastline.