Going sunset sailing in Puerto Rico is one of the best things to do in Old San Juan, you can enjoy the stunning coastline and snorkel with vibrant marine life. Watching the sun dip below the horizon, especially when you’re on the water, sails billowing in the Caribbean breeze, is the perfect way to practice mindfulness, or spend a moment in gratitude. Whether you’re looking to celebrate a special occasion, looking for something to do before you head to one of the many Old San Juan bars, these sunset sailing tours in Puerto Rico promise to make your vacation unforgettable.
This post may contain affiliate links, which means I may earn a commission if you click a link and make a purchase. As an Amazon Associate, I earn from qualifying purchases.
Summary of the top Sunset Sailing in Puerto Rico Tours
| Name | Duration | Meeting Point | Price | Where to book |
|---|---|---|---|---|
| San Juan Historical Bay Sunset Sailing Tour | 2 hours | San Juan | From $119 | Check availability |
| San Juan Catamaran Sunset Sail | 2 hours | San Juan | From $109 | Check availability |
| Full day private La Parguera tour | 8 hours | San Juan Marriott Resort & Stellaris Casino | From $799.99 | Check availability |
| Sailing Afternoon Charter in Fajardo | 3 hours | Fajardo | From $229 | Check availability |
| Private Scenic Excursion from San Juan | 2-3 hours | San Juan | From $595 | Check availability |
Table of Contents
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
- Price: From $119
2. San Juan Catamaran Sunset Sail
What better way to enjoy sunset sailing in Puerto Rico, then on a Catamaran, overlooking Old San Juan with a drink in hand. There really is 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 that’s perfect for a romantic getaway. 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
- Price: From $109
3. Full day private La Parguera Snorkeling and Bio Bay Sunset Tour
Want to go on a longer trip that includes a sunset sailing in Puerto Rico experience? Enjoy an all-day adventure with the Private La Parguera Snorkeling and Bio Bay Sunset Tour. Visit the 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
- Price: From $799.99
4. Sailing Afternoon Charter in Fajardo
Want a private sunset sailing in Puerto Rico experience? The Janise Sailing Afternoon Charter in Fajardo offers a personalized experience, whisking 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
- Price: From $229
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, beaches and bay.
- Duration: 2-3 hours depending on tour
- Meeting point: 482 Av. Manuel Fernández Juncos, San Juan
- Start time: Multiple time slots
- Price: From $595
Not a fan of sailing? Here’s a great Old San Juan sunset boat cruise option.
San Juan Sunset 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 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
Looking for more information on Puerto Rico?
Like this article about Sunset Sailing in Puerto Rico? Pin it!
