San Juan
A sunset sail is the lazy highlight of a San Juan trip, and I collected my favorite boats for it. They slip out of San Juan Bay and put El Morro’s walls in view right at golden hour. The bay stays calm even when winter swell pounds the north coast.
Experience stunning San Juan sunsets from the water with a 1.5-hour boat ride featuring scenic views, drinks, snacks, and engaging commentary—perfect for a relaxed yet memorable evening.
Most Popular★ 4.5“The tour was great. It was a lot of moving parts and it was physically tiring, but it was worth it. We saw a lot of the rainforest. The beach was really nice with good food options and drink options in the tour of old…”
★★★★★★★★★★
1,320 reviewsFrom $109.00by Rico Sun Tours
Set sail on a serene sunset journey by San Juan Historical Bay, where breathtaking views and personalized service await, creating an unforgettable experience.
★ 4.5“We had a very relaxing sunset sail. The crew (Joe the Captain and Carlos the mate) were very knowledgeable and fun to listen to. Good drinks, wonderful scenery, and smooth sailing meant to a memorable time!”
★★★★★★★★★★
710 reviewsFrom $115.00by Sail San Juan Bay
Discover Old San Juan’s charm during a 2-hour sunset walking tour, with expert guides, stunning views, and insider tips perfect for first-timers and history lovers alike.
★ 5.0“Antonio is exceedingly warm and full of facts., not to mention bilingual and insightful. While there is plenty to say and learn about old San Juan, he was gracious about taking many questions that came up from his fascinating comments. I Read more”
★★★★★★★★★★
634 reviewsFrom $39.00by Patria Tours Puerto Rico
Lose yourself in the mesmerizing beauty of San Juan's sunset as you set sail on a catamaran, but be prepared for the unexpected surprises that await.
★ 5.0“Absolutely beautiful sail! The crew guys were so friendly & it was the perfect end to our PR vacation!”
★★★★★★★★★★
622 reviewsFrom $119.00by Sail PR
Keen travelers embark on a captivating culinary adventure in Old San Juan, where tantalizing flavors and hidden gems await, leaving them hungry for more.
★ 5.0“Tour guide did a fantastic job interesting and informative but was doing a lot of coordination of the tour on the fly. Not the fault of the guide at all but for the money spent didn't feel the value was there. Would recommend this at…”
★★★★★★★★★★
559 reviewsFrom $179.00by Spoon
Tantalize your senses with a San Juan Bay Day Sail With Drinks Included, as we uncover the thrilling features and benefits of this unforgettable adventure.
★ 5.0“Fantastic boat tour! If you take the time to read all the info/directions they send, the boat will be easy to find. Weather looked a bit questionable, but they kept us updated and luckily we were able to go out on the water. Very informative…”
★★★★★★★★★★
502 reviewsFrom $99.00by Sail PR
Experience a thrilling dinner suspended high above Old San Juan, with stunning sunset and city lights views, gourmet cuisine, and a lively atmosphere.
★ 4.5“Great experience! Staff are the best! Do not book if you’re afraid of heights and ruin other peoples experiences, good vibes only! Food was amazing, and presentation on point! It’s a lot of fun, scary, but fun! Music the entire time with a full course…”
★★★★★★★★★★
326 reviewsFrom $159.00by FlyDining Puerto Rico
Experience Puerto Rico’s bioluminescent bay and sunset with a swim, guided boat ride, and stunning views—perfect for adventure seekers and nature lovers alike.
★ 5.0“Don’t forget your towel or a dry shirt or jacket in case the boat ride home is chilly once you’re wet. Otherwise everything AMAZING!!!! Coolest experience ever! I would do it again and take more people!”
★★★★★★★★★★
258 reviewsFrom $65.00by Mareaito Charters
Experience a scenic sunset salsa class on Puerto Rico’s beaches, perfect for beginners and culture lovers seeking fun, views, and authentic vibes.
★ 4.5“The teacher did a great job breaking down the steps, encouraging us, and making sure everyone “got” it. She was fun and knowledgeable. The setting was stunning! A wonderful experience.”
★★★★★★★★★★
208 reviewsFrom $29.00by Salsa Tours PR
Experience San Juan's beauty on a 2-hour daytime sailing tour aboard an authentic sailboat, with stunning views, knowledgeable guides, and local wildlife spotting.
★ 4.5“We were really looking forward to this boat trip, but unfortunately, it didn’t meet our expectations. The boat was much smaller than advertised, which made the experience less comfortable. They also promoted multiple drinks, but we only rRead more”
★★★★★★★★★★
173 reviewsFrom $99.00by Sail San Juan Bay
Mystify your senses and unlock a world of adventure with a private sailing excursion from San Juan, where the possibilities are endless.
★ 5.0“Everything was great. The captain was very friendly, and since it was our first time on a sailboat he made the experience very nice!”
★★★★★★★★★★
138 reviewsFrom $494.00by Sail Snorkel Party inc.
Experience luxury on a Puerto Rico catamaran cruise with all-inclusive food, drinks, snorkeling, and beach stops. Perfect for relaxing adventurers.
★ 5.0“Would do it again! Amazing staff and service. Took care of us the whole time from the beginning until the end”
★★★★★★★★★★
96 reviewsFrom $195.00by Sail Getaway
Experience stunning sunsets and historic sights on a private Old San Juan bay boat cruise. Enjoy Champagne, snacks, and expert insights in a relaxed setting.
★ 5.0“We had a fantastic time! Carlos was great and very informed about the area. We were able to see great views and a beautiful sunset.”
★★★★★★★★★★
44 reviewsFrom $349.00by Encanto Boat Tours
Discover Puerto Rico’s stunning west coast with this full-day tour from San Juan, featuring scenic stops, cultural sights, and a breathtaking sunset at Rincón Beach.
From $400.00by Transport and Experiences Puerto Rico
San Juan packs rainforest, glowing water, and 500 years of history into one small corner of Puerto Rico; start here.