San Juan Bay: Small Group Sailing Tour & Drinks

Summary

Sail old san juan bay with locals for fort views and fresh breeze

You’ll board a real sailboat in San Juan Bay for a small group sailing tour with local drinks included. Expect up-close views of Old San Juan’s forts, stories from your captain, and moments where you forget about everything except the wind and sea spray. If you’re lucky, dolphins might show up too.

What’s the experience like?

The first thing I noticed was how quiet it got once we left the dock — just the slap of water against the hull and that soft creak of ropes. Our captain, Luis, handed me a cold beer and grinned like he’d done this a thousand times (he probably has). I kept looking back at Old San Juan, those blue-and-yellow houses stacked up behind the walls. The wind picked up fast, so we tilted sideways — honestly, more than I expected. It felt weirdly freeing not to hear an engine or see any big tour groups crowding around.

At one point Luis pointed out Castillo San Cristobal and started telling us about pirates (the real kind, not the ones in costumes). You could smell salt and something sweet from shore — maybe fried plantains? There were only five of us on board, so it felt more like tagging along with friends than being on a “tour.” Someone asked about La Fortaleza and he told us that’s where the governor lives, but also joked about how nobody ever sees him. I tried to say “Bahía de San Juan” in Spanish; Luis laughed at my accent but gave me a thumbs-up anyway.

I didn’t expect to feel so relaxed. The sun hit the water just right as we passed by Goat Island’s little fort — nothing fancy but somehow memorable. We even spotted dolphins for half a minute (or maybe they were just big fish — hard to tell). By the time we turned back toward the marina, I was salty-haired and happy. It wasn’t luxury, but it was real sailing — you know?

Step-by-step itinerary

Day 1 — Sail and view Old San Juan landmarks

• Board J30 sailboat
• Sail San Juan Bay
• View Old San Juan seaward side
• See Castillo San Cristobal fortress
• Pass Goats Island little fort
• View La Fortaleza Governor's Mansion
• Enjoy complimentary drinks onboard
• Take photos of San Juan Bay

Top questions

How many people are on the San Juan Bay sailing tour?

The maximum is 6 people per sailboat.

Are drinks included on this sailing trip?

Yes, beer, sangria, rum n coke, and bottled water are included.

What sights do you see during the tour?

You’ll see Old San Juan from the water, Castillo San Cristobal, La Fortaleza, Goat Island’s fort, and San Juan Bay itself.

Is there a bathroom on board?

Yes, there’s a toilet and cabin on the J30 sailboat.

Is hotel pickup included?

No hotel pickup; you meet at San Juan Bay Marina.

What should I wear for this sailing tour?

Smart casual clothing is recommended; expect some spray from the water.

Can infants join this sailing tour?

Infants can join but must sit on an adult’s lap.

Is this suitable for travelers with health issues?

It’s not recommended for those with spinal injuries or poor cardiovascular health.

What’s included

Your day includes all taxes and fees covered plus bottled water and local drinks like beer, sangria or rum n coke while you sail past Old San Juan’s famous forts in a small group setting before returning to shore at San Juan Bay Marina.