Category San Juan Bay Sunset Sails

San Juan · SAN JUAN BAY SUNSET SAILS

The 13 Best San Juan Sunset Sails

13 reviewed

There is no better view of the old city than from the water as the sky turns pink. These are the best sunset sails on San Juan Bay: which pour drinks, which keep it small and quiet, how long you are out, and what each costs, so the only thing left is where to sit.

Icacos Island Catamaran Day Sail from Fajardo

Icacos Island Catamaran Day Sail from Fajardo - The Morning Sail: Fajardo Coastline Views and El Yunque in the Distance

1.Icacos Island Catamaran Day Sail from Fajardo

★★★★★★★★★★5.0 · 1,483 reviews · from $140Our pick

Six-hour catamaran day sail from Fajardo to Cayo Icacos for snorkeling, swimming, deli lunch, and rum cocktails with East Island Excursions.

“A beautiful and relaxing day trip to Icacos Island. Everything is super organized and efficient with the best captain and crews. You don't need to worry about a thing once you step onto the boat, and the island is absolutely gorgeous!”

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San Juan Sunset Harbor Boat Ride

San Juan Sunset Harbor Boat Ride - Getting There Without Stress: Pickup, Meeting Point, and Timing

2.San Juan Sunset Harbor Boat Ride

★★★★★★★★★★4.5 · 1,320 reviews · from $109

San Juan Bay sunset cruise with Old San Juan views, rum punch and local beer, snacks, and music. Pickup options, about 90 minutes.

“This was a lovely way to spend a couple hours. It was informative, beautiful, and fun! The views were amazing, the education on PR and the sites was informative and it was a blast!”

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Historical San Juan Bay Sunset Sailing Tour

Historical San Juan Bay Sunset Sailing Tour - The 2-hour route: calm bay water, then close-in harbor views

3.Historical San Juan Bay Sunset Sailing Tour

★★★★★★★★★★4.5 · 710 reviews · from $115

Small-group San Juan Bay sunset sail past El Morro with captain stories, photo stops, and included beer, sangria, and rum punch.

“Beautiful evening! Ivan was wonderful! Very knowledgeable and friendly! Great drinks! We enjoyed every second! Highly recommend! Thank you Ivan!”

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San Juan Catamaran Sunset Sail with Drinks Included

San Juan Catamaran Sunset Sail with Drinks Included - San Juan Bay at Sunset: Views of El Morro and San Juan Gate

4.San Juan Catamaran Sunset Sail with Drinks Included

★★★★★★★★★★5.0 · 622 reviews · from $119

Small-group San Juan sunset catamaran with drinks included. Sail past El Morro and San Juan Gate for a chill, scenic 2-hour cruise.

“Catamaran smaller than I imagined. Also catamaran could use some updates. Hector and Nicola were informative . I thought the engine was a bit noisy. It was a nice two hours.”

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La Parguera Bio Bay Boat Ride and Swimming w/ San Juan Transport

La Parguera Bio Bay Boat Ride and Swimming w/ San Juan Transport - La Parguera Village Time: Food and a Quick Sense of Place

San Juan Bay Day Sail with Drinks Included

San Juan Bay Day Sail with Drinks Included - The Crew Makes It (Captain Rafa and Francisco’s Style)

La Parguera Glowing Bioluminescent Bay Boat Tour from San Juan

La Parguera Glowing Bioluminescent Bay Boat Tour from San Juan - Appetizers and sunset timing in La Parguera (not just a quick stop)

Puerto Rico: Bio Bay Swim and Sunset Charter or Late night tour

Puerto Rico: Bio Bay Swim and Sunset Charter or Late night tour - The biobay swim: 30 minutes of pixie-dust lighting

Sail Away: Private Scenic Excursion from San Juan

Sail Away: Private Scenic Excursion from San Juan - The 2–3 Hour San Juan Bay Route: From Harbor Work to Old San Juan Sights

Private Old San Juan Bay Boat Sunset-Night Cruise

Private Old San Juan Bay Boat Sunset-Night Cruise - La Fortaleza stop: governors’ palace from the water

San Juan Bay Private Tour with Drinks and Tapas: 4+ people

San Juan Bay Private Tour with Drinks and Tapas: 4+ people - Getting to Caribbean Fishing Academy Charters without stress

11.San Juan Bay Private Tour with Drinks and Tapas: 4+ people

★★★★★★★★★★5.0 · 40 reviews · from $166

Private San Juan Bay boat tour with real sailing or power cruising, homemade sangria, charcuterie, and history views for up to 6 people.

“We did the sunset sailboat ride and it was amazing! We got to see the history of Old San Juan while enjoying homemade sangria and a charcuterie board. The captain was also very accommodating and made sure everyone was comfortable. He was also very accommodating to our dietary restrictions. Would definitely recommend!”

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Janise Sailing Afternoon Charter in Fajardo, Puerto Rico

Janise Sailing Afternoon Charter in Fajardo, Puerto Rico - Price and Value: What $229 Per Person Gets You

Private Sunset Escape: Sailing an Island Paradise

Private Sunset Escape: Sailing an Island Paradise - Isla Palominos: Swim Time, Island Time, and the Sunset Payoff

13.Private Sunset Escape: Sailing an Island Paradise

★★★★★★★★★★5.0 · 6 reviews · from $399

A private sunset sail from Fajardo to Isla Palominos for up to 6 people, with swimming options, photos, and a calm island vibe.

“Our family of 6 booked this sunset cruise through Viator (but you can book directly through Encanto boat tours) after our sailboat cruise earlier in the week was canceled due to weather. We had a great experience with Jamille as our boat capRead more”

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