San Juan: FlyDining Sunset & Night Dinner Over Old Town

Summary

Suspended dining in San Juan as sunset fades to city lights

You’ll float above Old San Juan at sunset or under city lights, savoring a four-course dinner with drinks included. Local guides keep things fun—and safe—as you watch rooftops glow gold or twinkle at night. Expect laughter, maybe a little nervousness at first, but mostly just that giddy feeling of doing something truly different.

What’s the experience like?

I’ll never forget the first second my feet left the ground—suddenly we were dangling above Old San Juan, seatbelts snug, forks in hand. The breeze caught the scent of grilled steak and ocean salt at once, which is not something you expect together. Our guide, Javier, grinned and checked everyone’s harnesses again (he must’ve done it three times already). Someone behind me laughed nervously and I realized my own hands were gripping the table a little too tightly. It’s not scary exactly—just… different. You look down and there’s nothing but air between you and the cobblestones.

We picked the 5:30 slot for that golden hour light—honestly, I’d do it again just for how the sun hit the rooftops. The city glowed all honey-colored while we started on some roasted chicken thigh (tender, with this peppery kick I’m still thinking about). There was a vegetarian dish too—my friend tried to ask what was in it in Spanish and our server just smiled and winked. I loved that nobody rushed us; even though you’re up there for about an hour or so, time feels weird when you’re floating. At some point I stopped worrying about my napkin blowing away and just watched the sky change.

By dessert (some creamy thing I can’t pronounce), the city lights had started flickering on below us. It’s wild—cars moving like tiny toys, music drifting up from somewhere near the plaza. Javier pointed out El Morro glowing in the distance and told us how they used to light bonfires on those walls centuries ago. Maybe he made that up? It sounded true enough after a glass of bubbles. Anyway, if you’re looking for a dinner that’s actually memorable—not just another meal—I’d say this FlyDining thing over San Juan is worth every slightly shaky bite.

Step-by-step itinerary

Day 1 — Sunset and city lights dinner experience

• Arrive 30 minutes before seating
• Take off within 15 minutes of seating
• Enjoy 4-course gourmet meal
• Watch sunset or city lights
• Choose from main dish options
• Optional upgrade to premium drinks

Top questions

What time does FlyDining over Old San Juan start?

There are three seatings: 5:30 PM (sunset), 7:30 PM, and 9:30 PM (city lights).

Is food included in the FlyDining experience?

Yes, your booking includes a four-course gourmet meal with options like steak, mahi mahi, chicken thigh, pork chop, or vegetarian dishes.

Are drinks included during dinner?

House beverages such as sparkling bubbles, sodas, and juices are included throughout your meal.

Is FlyDining wheelchair accessible?

Yes, all areas and surfaces are wheelchair accessible.

How early should I arrive before my scheduled time?

Please arrive at least 30 minutes before your scheduled seating.

Where is FlyDining located in San Juan?

The experience takes place at their new location over Old San Juan; check your confirmation for details.

Can I upgrade to an open bar?

You can upgrade to a top-shelf open bar with premium spirits and craft cocktails from expert mixologists.

How long does each FlyDining session last?

The dining experience lasts about an hour per seating.

What’s included

Your evening includes a four-course gourmet meal with house beverages like sparkling bubbles, sodas, and juices served throughout; friendly local guides handle safety checks; choose from three seating times; upgrade to premium cocktails if you want; everything happens high above Old San Juan—with all accessibility needs covered too.