San Juan is a fantastic place for sailing — thanks to its calm waters, historic landmarks, and stunning sunsets. The city’s bay is small enough to explore intimately, yet vibrant enough to make each trip feel special. We’re particularly taken with the San Juan Catamaran Sunset Sail with Drinks Included, a relaxed, small-group cruise perfect for unwinding after a day of sightseeing, and the Icacos Luxury Sailing Catamaran, which offers an all-day adventure blending snorkeling, beach time, and luxurious comfort. Both tours showcase the region’s beauty from the water, with options for every taste and budget. If you want a taste of Puerto Rican history combined with sailing, the San Juan Historical Bay Daytime Sailing Tour is a perfect pick. It’s an authentic experience on a wind-powered boat with great views of Old San Juan.
If you’re considering a trip focused on snorkeling and beach time, the Culebra Snorkeling Tour by Catamaran stands out for its high ratings and extensive reviews. Whatever your preference, these options cover everything from romantic sunsets to family-friendly adventures, all designed to help you experience Puerto Rico’s waters in style.
Quick Overview
The list below highlights some of the best sailing experiences in San Juan, varying from quick sunset cruises to full-day luxury trips and historic bay tours:
– San Juan Catamaran Sunset Sail with Drinks Included
– Historical San Juan Bay Sunset Sailing Tour
– Icacos: Luxury Sailing Catamaran All Inclusive Beach and Snorkel
– San Juan Historical Bay Daytime Sailing Tour
– Culebra Snorkeling Tour by Catamaran from Fajardo
1. San Juan Catamaran Sunset Sail with Drinks Included
At number 1 on our list, the San Juan Catamaran Sunset Sail with Drinks Included offers a charming and intimate way to enjoy the evening. For about $119 per person, you’ll hop aboard a small, 6-passenger boat for a roughly 2-hour cruise around San Juan Bay — perfect for couples, small groups, or anyone looking for a peaceful way to end the day.
What sets this tour apart is its personalized experience. The crew warmly welcomes you aboard, and the small size ensures personalized attention. During the sail, you’ll enjoy stunning views of Old San Juan, with landmarks like El Morro Fortress and San Juan Gate passing by. The highlight is the sunset itself — a prime time to capture photos or simply soak in the changing light. You can sip complimentary rum punch or sparkling wine as the sky turns shades of pink and orange.
This cruise is praised for its relaxing atmosphere and friendly crew, making it ideal for travelers who want a quiet, scenic experience without loud music or heavy waves. Since it stays within the bay, there’s no worry about rough seas, making it suitable for all ages.
Bottom line: A romantic, low-key sunset cruise that’s perfect if you want a quick, memorable way to see San Juan from the water while enjoying drinks and good company.
2. Historical San Juan Bay Sunset Sailing Tour
At number 2, the Historical San Juan Bay Sunset Sailing Tour offers a slightly more relaxed but equally picturesque evening experience for around $115. This tour is great for travelers desiring a comfortable, education-oriented sunset cruise.
The racer-cruiser sailboat glides through the calm waters of San Juan Bay, passing close to the Fort San Felipe del Morro, which makes for spectacular photo opportunities. The captain shares commentary on the region’s history and landmarks, enriching the experience beyond just the scenery. Along the way, you’ll spot the busy harbor activity and possibly dolphins playing in the wake — a bonus for nature lovers.
This tour’s small group cap of six ensures plenty of space to relax and chat with fellow travelers. The complimentary drinks, including sangria, add a festive touch to the scenic views. Guests have raved about the intimate atmosphere and the captain’s engaging storytelling. The timing at sunset highlights the best lighting for photographs, and the relaxed pace makes it suitable for first-time sailors or those simply looking for a peaceful escape.
Bottom line: Perfect for history buffs and photo enthusiasts who want an elegant, informative cruise with a laid-back vibe and sunset views.
3. Icacos: Luxury Sailing Catamaran All Inclusive Beach and Snorkel
Ranking third, the Icacos Luxury Sailing Catamaran is a full-day adventure that costs around $195 per person. It’s the most extensive trip on our list, offering roughly six hours of luxurious relaxation and active fun.
This tour features a 54-foot catamaran with amenities like shaded areas, private restrooms, and a fully stocked open bar serving unlimited tropical drinks and water. The itinerary includes visiting secluded spots in the Cordillera Cays, where you can snorkel amid coral reefs and swim in calm, crystal-clear waters. The boat is equipped with water slides and ample lounging space on daybeds, making it ideal for families or groups seeking comfort and adventure.
Guests rave about the friendly crew and the gorgeous scenery, with many calling it a “perfect day.” The snorkeling at hidden beaches is especially popular, as well as the authentic Puerto Rican lunch served on board. Some reviews note the boat’s clean, modern facilities and the well-organized schedule, making it a great value for a full-day trip.
Bottom line: This all-inclusive, high-end day trip is best suited for travelers wanting a blend of snorkeling, beach time, and luxury — a true Caribbean-style feast for the senses.
4. San Juan Historical Bay Daytime Sailing Tour
Number 4, the San Juan Historical Bay Daytime Sailing Tour offers a more relaxed, 2-hour sail for around $99. It’s perfect if you want a calm, wind-powered cruise that emphasizes authentic sailing rather than motorized tours.
This experience uses just the wind, avoiding noisy engines, and offers a peaceful ride through the bay. Passengers get views of Old San Juan, the San Cristobal Fortress, and even the Goat Island lighthouse. The captain points out landmarks along the way, sharing insights into the local history and maritime culture. The small group size enhances interaction and ensures personalized service.
Reviewers appreciate the informative narration and the laid-back pace, with many noting the chance to spot dolphins while sipping on beer or sangria. The experience is especially suited for travelers seeking a relaxing, scenic adventure with a touch of history, all aboard an authentic sailboat.
Bottom line: Great for those wanting a quiet, educational sailing experience with a focus on traditional sailing and local sights.
5. Culebra Snorkeling Tour by Catamaran from Fajardo
Finally, the Culebra Snorkeling Tour by Catamaran ranks as one of the most popular options, with over 2,500 reviews and an average rating of 4.5. For roughly $180, this full-day trip offers a chance to explore some of Puerto Rico’s best beaches and coral reefs.
Starting with a high-speed catamaran from Fajardo, you’ll cruise to Culebra, stopping at Carlos Rosario or Luis Peña reef for snorkeling among colorful marine life. The tour includes a buffet lunch with rum punch and piña colada, perfect for recharging after swimming. In the afternoon, you’ll relax on deserted beaches like Flamenco or Culebrita, soaking up the sun and enjoying the calm Caribbean waters.
Reviews highlight the professional crew, the beautiful reefs, and the comfortable boats. Many mention how the snorkeling was the highlight, with the added benefit of visiting less crowded beaches. The optional transportation from San Juan makes it accessible for travelers staying in the city, though the long drive to Fajardo is worth it for the scenery and experience.
Bottom line: A full-day, snorkeling-focused adventure perfect for underwater lovers and beach loungers, especially if you enjoy a lively, well-organized trip.
How to Choose Your Perfect Sailing Adventure
Choosing between these sailing experiences depends on your interests, budget, and time. For a romantic sunset, the San Juan Catamaran Sunset Sail is unbeatable. If you want a more educational or historic vibe, the San Juan Historical Bay Daytime Sailing offers insight and scenic beauty.
For those looking for luxury and active fun, the Icacos Catamaran combines snorkeling, lounging, and a fully stocked bar in one luxurious package. Budget travelers or those with more time may prefer the full-day Culebra Snorkeling Tour, which offers a comprehensive taste of Puerto Rican waters and beaches.
Practical tips: Book early during peak season (winter months) and consider your fitness level — some tours involve swimming or walking on beaches, while others are more relaxed. Also, check the weather forecast since many trips are weather-dependent.
Final Thoughts
San Juan’s sailing options provide a diverse range of experiences — whether you’re after a quick sunset toast, a full day of snorkeling and lounging, or a historical sailing adventure. For a romantic evening, the small, intimate sunset cruises are ideal. Families and adventure seekers will love the all-day luxury catamaran excursions with snorkeling, water slides, and delicious food. Meanwhile, history enthusiasts will appreciate the authentic, wind-powered bay tour.
No matter your choice, each of these trips offers a unique way to see Puerto Rico from the water. Remember to book in advance, especially for popular excursions like the Culebra snorkeling tour, and always check the weather forecast. These sailing adventures are a perfect way to add a special touch to your San Juan vacation, combining relaxation, scenery, and a splash of sea adventure.