There’s something undeniably magical about watching the sun dip below the horizon, especially when you’re on the water, sails billowing in the Caribbean breeze. Puerto Rico, with its stunning coastline and vibrant marine life, offers some of the most breathtaking sailing adventures, which are one of the best things to do in Old San Juan. Whether you’re looking to celebrate a special occasion, looking for something to do before you head to the Old San Juan bars, or seeking a romantic getaway, these sunset sailing tours in Puerto Rico promise to make your vacation unforgettable.
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1. San Juan Historical Bay Sunset Sailing Tour
Imagine gliding along the waters of San Juan, the setting sun casting a golden glow over the historic Castillo San Cristobal and Castillo San Felipe del Morro that stand guard over the bay. The San Juan Historical Bay Sunset Sailing Tour takes you on a two-hour journey into the heart of Puerto Rico’s past, all while enjoying the modern-day luxuries of complimentary drinks and captivating stories shared by your captain. With a small group setting, it feels like your own private viewing of San Juan’s majestic beauty as day turns into night.
- Duration: 2 hours
- Meeting point: 482 Av. Manuel Fernández Juncos, San Juan
- Start time: 05:00 PM
2. Full day private La Parguera Snorkeling and Bio Bay Sunset Tour
Enjoy an all-day adventure with the Private La Parguera Snorkeling and Bio Bay Sunset Tour. Visit small islands on the southern coast of Puerto Rico, enjoy snorkeling in the clear waters, and enjoy a breathtaking sunset experience. At the end of the day you will also get to witness the natural wonder of bioluminescent waters!
- Duration: 8 hours
- Meeting point: San Juan Marriott Resort & Stellaris Casino
- Start time: Multiple options
3. Sailing Afternoon Charter in Fajardo
For a personalized sailing experience, the Janise Sailing Afternoon Charter in Fajardo whisks you away from the crowds into the serene beauty of the Caribbean Sea. As the sunset hues fill the sky, you can enjoy the luxury of having a vessel all to yourselves, complete with amazing service. It’s perfect for marking a special occasion or simply indulging in the luxury of the moment.
- Duration: 3 hours
- Meeting point: Puerto Del Rey Marina, Fajardo
- Start time: ~2:30 PM
4. San Juan Catamaran Sunset Sail
There’s something about being on a catamaran, feeling the sway of the waves and the salt on your skin, that says ‘this is the life’. The San Juan Catamaran Sunset Sail embraces this vibe, offering a blissful two-hour escape. Enjoy some rum punches or sparkling wine as you watch the coastline drift by, and the sunset skies setting in.
- Duration: 2 hours
- Meeting point: On the dock behind Qué PezCa’o, San Juan
- Start time: ~05:00 – 5:30 PM
5. Private Scenic Excursion from San Juan
Want to choose your own adventure? Sail around the bay on a Private Scenic Excursion from San Juan with Captain Jimbo and crew. You can bring your own drinks, go snorkeling if weather permits, and enjoy the scenes of the Old San Juan harbour and bay.
- Duration: 2-3 hours depending on tour
- Meeting point: 482 Av. Manuel Fernández Juncos, San Juan
- Start time: Multiple time slots
Not a fan of sailing? Here’s a great Old San Juan sunset boat cruise option.
San Juan Sunset Harbor Boat Ride
For those who prefer to soak in the urban skyline with a touch of sea breeze, the San Juan Sunset Harbor Boat Ride offers a front-row seat to the enchanting evening spectacle of Old San Juan. As the city lights begin to twinkle, you’ll enjoy panoramic views of landmarks like Paseo De La Princesa and La Fortaleza. Refreshments and friendly banter with the crew add to the experience, making it a perfect casual yet captivating evening activity.
- Duration: 1.5 hours
- Meeting point: San Juan Bay Marina, or pick up from select hotels
- Start time: ~05:00-5:30 PM
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Aaron is one of the co-founders of The Dharma Trails. His background in marine eco tourism and writing have blended together to create the eco travel platform read by users around the world.
