San Juan Bay: Catamaran Sunset Sail with Drinks & Guide

Summary

Drift past San Juan’s old city walls as the sun dips low and laughter carries across the bay

You’ll slip off your shoes and step onto a breezy catamaran for two hours of sunset sailing around San Juan Bay—with drinks included and a local guide pointing out stories behind La Fortaleza and city gates. Expect laughter, real conversation, golden light on old stone walls, and one of those rare pauses where everything feels easy.

What’s the experience like?

“No shoes on board,” our captain grinned, waving a hand at the pile of sandals by the dock. I wobbled onto the catamaran barefoot—felt weirdly freeing, actually. The deck was warm under my feet and the air smelled like salt, sunscreen, maybe a little bit of rum from somewhere behind me. We pushed off just as the sky started to soften around the edges, that hour when Old San Juan looks almost painted. There were six of us total—just enough for easy conversation but not so many you’d feel lost in a crowd.

I didn’t expect to laugh so much. Our guide (I think her name was Carla?) pointed out La Fortaleza as we sailed past—she called it “the second oldest executive mansion in the Americas,” but honestly I was more distracted by the way the light hit those blue-and-white walls. Someone tried to say “Puerta de San Juan” in Spanish and butchered it; Carla laughed and gave us a quick pronunciation lesson, which turned into a running joke every time we passed another landmark. There was sparkling wine if you wanted it, or cold beer—rum punch too, which tasted like summer vacation and made me wish I could bottle that exact flavor for home.

The breeze picked up as we circled back across San Juan Bay. You could hear music drifting from shore—some salsa maybe? Or just people talking loud over dinner plates. For a minute nobody said anything at all; we just watched the city glow gold and pink against the water. I still think about that silence sometimes—how rare it is to find quiet with strangers who don’t feel like strangers anymore. So yeah, if you’re after a day trip in San Juan with something softer than sightseeing buses and louder than a hotel bar… this sunset sail kind of sneaks up on you.

Step-by-step itinerary

Day 1 — Sunset sail and sightseeing in San Juan

• Board 37ft catamaran sailboat
• Sail around San Juan Bay
• View San Juan Gate from water
• See La Fortaleza from water
• Enjoy complimentary drinks onboard
• Relax and watch sunset views

Top questions

How long is the San Juan catamaran sunset sail?

The sunset sail lasts approximately 2 hours from departure to return.

Are drinks included on this sunset cruise?

Yes, complimentary beer, rum punch, sparkling wine, and rum & coke are included in moderation for guests 18+.

Where does the catamaran sail during the tour?

The route circles historic San Juan Bay with views of landmarks like La Fortaleza and Puerta de San Juan from the water.

Is there a minimum age to join or drink?

The minimum drinking age is 18 years old; minors must be accompanied by an adult.

Do I need to remove my shoes before boarding?

Yes, all guests are required to remove their shoes before boarding; they’ll be stored safely on the boat.

How many people are allowed per booking?

A minimum of 2 people per booking is required; maximum group size is 6 guests per cruise.

Are there physical requirements for this tour?

This tour isn’t recommended for travelers with spinal injuries or poor cardiovascular health; basic mobility is needed to board.

Is transportation included to reach the boat?

No hotel pickup is provided but public transportation options are available nearby for easy access to departure point.

What’s included

Your evening includes two hours sailing aboard a 37ft catamaran around San Juan Bay with a professional local captain and guide leading stories along the way. Complimentary drinks—beer, rum punch, sparkling wine—are served in moderation throughout your trip before returning to shore just after sunset.