San Juan’s sailing scene combines Caribbean waters, historic views, and island adventures.
The most worthwhile excursions include the Culebra snorkeling catamaran tour – perfect for nature lovers and swimming enthusiasts.
Along San Juan Bay, sunset sailing tours offer postcard-worthy views of colonial fortifications.
We especially love the intimate 37-foot catamaran trips, which provide just the right mix of sightseeing and relaxation, with drinks included.
For social butterflies, the Fajardo yacht gatherings create memorable evenings on the water.
Check these top-rated sailing tours in San Juan:
Key Points
- The Culebra Snorkeling Tour by Catamaran offers a scenic ferry ride and access to pristine underwater reserves, accompanied by a buffet lunch.
- The Historical San Juan Bay Sunset Sailing Tour provides an intimate 2-hour cruise with knowledgeable guides and light refreshments.
- The San Juan Catamaran Sunset Sail With Drinks Included offers a personalized 2-hour cruise with stunning views of Old San Juan during sunset.
- The Real PR Yacht Party Mix & Mingle in Fajardo presents a lively yacht party experience with alcoholic beverages and lunch.
- These sailing experiences in San Juan cater to various preferences, from snorkeling adventures to sunset cruises and exclusive yacht parties.
Culebra Snorkeling Tour by Catamaran From Fajardo
Although Culebra is just a short ferry ride away from Fajardo, the Culebra Snorkeling Tour by Catamaran offers a hassle-free way to experience this island paradise. Rated 4.6 out of 5 based on over 2,240 reviews, this tour provides a blend of relaxation, snorkeling, and beach time.
You’ll visit the Carlos Rosario or Luis Peña underwater nature reserves and enjoy the pristine beauty of Flamenco Beach or Culebrita.
The tour includes a delicious buffet lunch featuring tropical cocktails, fresh fruit, and gourmet salads, meats, and more. Snorkeling equipment, beverages, and gratuities are all provided.
The spacious catamaran can accommodate up to 60 passengers, ensuring a comfortable and laid-back atmosphere.
With moderate physical fitness required, the tour isn’t recommended for pregnant individuals or those with serious medical conditions.
However, if you’re an able swimmer looking for an exceptional snorkeling experience in a stunning tropical setting, this Culebra adventure is well worth considering.
Read our full review: Culebra Snorkeling Tour by Catamaran From Fajardo Review
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Historical San Juan Bay Sunset Sailing Tour
Embarking on the Historical San Juan Bay Sunset Sailing Tour provides a unique opportunity to experience the rich history and breathtaking scenery of Puerto Rico’s capital city.
This 2-hour tour, rated 4.5 out of 583 reviews, departs from the San Juan Bay Marina at 5:00 PM and accommodates up to 6 passengers. Along the way, you’ll enjoy light refreshments, bottled water, and optional alcoholic beverages as you witness the stunning sunset over the bay.
The tour offers an intimate and informative experience, with knowledgeable and friendly guides providing historical insights. Reviewers praise the beautiful views and atmosphere, though some note booking issues and lack of clear instructions.
While not wheelchair accessible, the tour may accommodate infants on laps. Be aware of the 275 lb weight limit and arrive at least 10 minutes early, as departures are prompt.
With potential weather-related cancellations, it’s recommended to book directly with the company for the best service and clarity.
Read our full review: Historical San Juan Bay Sunset Sailing Tour Review
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San Juan Catamaran Sunset Sail With Drinks Included
The San Juan Catamaran Sunset Sail offers a captivating 2-hour cruise along the picturesque San Juan Bay. Accommodating a maximum of 6 passengers, you’ll sail aboard a 37-foot catamaran with a professional captain and guide. Complimentary drinks, including sparkling wine, rum punch, and soft beverages, are provided in moderation.
During the tour, you’ll take in stunning views of Old San Juan and its historical landmarks as the sun sets over the horizon. The intimate group size and relaxing atmosphere create a personalized experience. Reviewers praise the friendly and knowledgeable crew, who are happy to offer recommendations for dinner in Old San Juan after the cruise.
This tour departs at either 5 PM or 5:30 PM, depending on the time of year, from the San Juan Bay Marina. Guests are required to check-in 20 minutes prior to departure.
While the experience isn’t wheelchair accessible, it’s a great option for those seeking a peaceful, picturesque sail in San Juan.
Read our full review: San Juan Catamaran Sunset Sail With Drinks Included Review
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Real PR Yacht Party Mix & Mingle
Indulge in a lively yacht party experience with the Real PR Yacht Party Mix & Mingle event. Located at the Villa Marina Yacht Basin in Fajardo, Puerto Rico, this 11 AM event offers a maximum of 24 travelers a chance to mix and mingle on the water.
The package includes alcoholic beverages, lunch, bottled water, soda, and gratuities, ensuring a carefree celebration. However, keep in mind that transportation is available at an additional cost, and the meeting location may vary depending on the vessel.
While the overall rating is 3.0 based on 4 reviews, some guests have reported a disorganized experience, poor venue choice, and inadequate drinks. On the other hand, others have praised the great service and energy.
The hosts acknowledge the variability of nightclub attendance and emphasize the importance of enjoying the experience regardless of crowd size. Whether you’re seeking a lively party or a more intimate gathering, the Real PR Yacht Party Mix & Mingle event provides a unique opportunity to experience the charm of Fajardo’s waterfront.
Read our full review: Real PR Yacht Party Mix & Mingle Review
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Recap
Experience the best sailing adventures in San Juan. Explore the stunning Culebra Island on a snorkeling tour, witness the historic San Juan Bay at sunset, or enjoy a lively catamaran party with drinks. Whichever you choose, you’re sure to make unforgettable memories on the serene waters of this beautiful Caribbean destination.