Puerto Rico Is Getting 7 Flights a Day from Miami on American Airlines This Winter 

It’s the busiest time of year — and American Airlines is making it easier than ever to get to Puerto Rico. This festive season, the airline is ramping up service on one of its most in-demand Caribbean routes, increasing to seven daily flights between Miami and San Juan. The expanded schedule begins December 18 and runs through January 5 — bringing more options, more flexibility and more lift into the heart of the Caribbean.

For travelers heading home, escaping the cold, or simply chasing the rhythm of the holidays in Old San Juan, this move makes one thing clear — Puerto Rico is a priority.

More Flights, More Reach

American Airlines is no stranger to San Juan. But seven daily flights from Miami — that’s a statement. It’s part of the airline’s largest-ever winter schedule from South Florida, with more than 170 additional daily departures added across the region and peak service to 73 Latin American and Caribbean destinations.

San Juan stands out. With seven frequencies per day, travelers will have nearly round-the-clock options to get to the island — whether for a last-minute getaway or a long-anticipated return.

Why Puerto Rico, Why Now

The increase isn’t just about volume — it’s about timing. The holiday season is one of the busiest periods for travel to Puerto Rico, especially for those visiting family or taking advantage of the island’s warm weather and cultural festivals.

The expansion also reflects San Juan’s rising profile as a Caribbean hub — not just a destination, but a gateway. With connections, cruises, and increasing hotel development, Puerto Rico is having a moment — and American Airlines is leaning in.

The Bigger Picture

Miami is central to American’s Caribbean network — and this winter, it becomes even more important. Alongside the expanded San Juan service, American is adding routes and flights across the region, from the Dominican Republic to Mexico. But Puerto Rico is leading the way in daily lift — and likely, in passenger volume.

The Takeaway

If you’re planning a holiday trip to Puerto Rico, the skies just got friendlier. Seven daily flights from Miami mean better timing, fewer layovers, and a smoother path to the island. Whether you’re headed for Nochebuena with family, ringing in the New Year in Condado, or just chasing 80 degrees in December — there’s a seat for you.

Where to Stay in Puerto Rico Right Now

O:live Boutique Hotel — San Juan

A Mediterranean-inspired escape in the heart of Condado, O:live Boutique Hotel is a refined sanctuary for adults. Each of the 15 suites is uniquely designed with handcrafted details, rainfall showers, and private terraces — some with plunge pools. The rooftop offers a saltwater pool with panoramic views, while the hotel’s signature restaurant, Sage, delivers upscale steakhouse fare in a sultry setting. This is romance, intimacy, and design-forward luxury — right where you want to be. While the O:live brand is growing, this is still the OG. 

Royal Isabela — Isabela

Set on 1,800 acres of preserved land atop dramatic Atlantic cliffs, Royal Isabela is a place where nature leads. The resort’s 20 freestanding Casitas come with private plunge pools, spacious terraces, and sweeping ocean views. Guests can play the world-class golf course carved through coastal dunes, dine at the farm-to-table Jota Restaurant, or explore quiet trails and organic gardens. This is luxury on Puerto Rico’s wild northwest — deliberate, unspoiled, and unforgettable. This is one of the best-kept secrets in the golf world. 

Caribe Hilton — San Juan

Caribe Hilton is where the piña colada was (apocryphally) born — and where timeless beachfront vibes live on. Tucked on a 17-acre oceanfront oasis between Old San Juan and Condado, the resort features nine restaurants and bars, a private beach, spa, tennis courts, and tropical bird-filled gardens. Rooms and suites offer contemporary Caribbean style with views of the Atlantic or verdant grounds. Families, couples, and conference travelers alike will find their corner of paradise. I love this resort for family vacations. 

Looking for a San Juan getaway? Here’s our guide to the best places to stay in Puerto Rico’s capital.