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Puerto Rico is the best of many worlds — it has its own culture, beautiful beaches, isn’t too far from the US mainland and doesn’t require a passport for US citizens. Puerto Rico has a lot in common with some of its Caribbean neighbors, but it makes for an easier family trip since you don’t need to get passports for the whole family, deal with customs and pay a bunch of international taxes just to visit.

Bright, pastel colors of houses in a neighborhood of San Juan, Puerto Rico. Photo by Ken Wiedemann / Getty Images
San Juan, Puerto Rico (Photo by Ken Wiedemann / Getty Images)

What to See in San Juan

If you do make the trip, San Juan has plenty of attractions to keep a family busy for days. Here are some ideas:

Explore Old San Juan

The forts, including Castillo San Felipe del Morro, and other historical structures of Old San Juan are a UNESCO World Heritage site and are especially popular with active families. My wife and I spent most of a day exploring these aspects of Old San Juan.

Castillo San Felipe del Morro
Castillo San Felipe del Morro, also known as Fort San Felipe del Morro or El Morro Castle, is a 16th-century citadel in San Juan, Puerto Rico. (Photo by felixairphoto / Getty Images)

The neighborhood also has plenty of (pretty touristy) shopping areas. We aren’t big shoppers, but we did enjoy a stop at Casa Cortes Chocolate bar in Old San Juan that would be a hit with the little ones.

Casa Cortes Chocolate Bar (Photo by Dan Miller)

There are also two free trolley routes that you can take around Old San Juan. They make various stops throughout the old part of San Juan and are a good way to get around. Note that they are just trolleys — there are no guides or any kind of explanatory audio or text offered. The “red” City Hall route takes you along Old San Juan’s shopping areas while the “blue” El Morro route reprises some of the shopping stops along with visits to Fort San Cristobal and Castillo San Felipe del Morro.

Visit the Condado Neighborhood

If you’re staying in Condado, where many of the points hotels are located, it’s about a $20 taxi ride to Old San Juan. My wife and I stayed at the Hyatt House San Juan, which is in the Miramar neighborhood between Condado and Old San Juan. We walked from our hotel to Old San Juan, which was about 45 minutes one-way.

Hyatt House San Juan

The Hyatt House San Juan is 12,000 Hyatt points per night and is a great place for families. Not only does it offer free breakfast, but rooms feature a full kitchen and there is a grocery store nearby. Condado is the main “touristy” area of San Juan and almost all of the chains have beachfront properties there. There are also many restaurants that serve Puerto Rican and other Caribbean food. When Carolyn and I were there, we ate twice at the Hacienda Don Jose, which had a great view of the ocean from our table.

Where to Stay in San Juan

There are a ton of points hotels in San Juan, Old San Juan and beyond. If you’ve got a Marriott Category 5 free night certificate from a card like the Marriott Bonvoy Boundless Credit Card or Marriott Bonvoy Business™ American Express® Card you will be spoiled for choice. You can choose between the Sheraton Puerto Rico Hotel & Casino (Category 5), the Sheraton Old San Juan Hotel (Cat 4) or the AC Hotel San Juan Condado (Cat 4). The La Concha Renaissance San Juan Resort and San Juan Marriott Resort & Stellaris Casino are now Category 6 hotels.

 

Image courtesy of the San Juan Marriott Resort & Stellaris Casino

World of Hyatt points can be used at the Hyatt House San Juan or Hyatt Place San Juan/City Center from 12,000 points per night or the Hyatt Place San Juan/Bayamon from 8,000 points.

Wyndham also has properties on the island: TRYP by Wyndham Isla Verde, Howard Johnson by Wyndham San Juan Centro Cardiovascular and, outside San Juan, the Wyndham Grand Rio Mar Puerto Rico Golf & Beach Resort. All Wyndham hotels cost 15,000 points per night, but check cash prices, which are usually quite affordable at TRYP and the Howard Johnson hotels.

Hilton loyalists have a range of options, from the Caribe Hilton (currently being renovated but will be available for bookings in spring 2019; from 46k to 50k Hilton Honors points per night) and Condado Plaza Hilton (open but currently being renovated) to the DoubleTree by Hilton Hotel San Juan (from 47k to 60k points), Embassy Suites by Hilton San Juan Hotel & Casino (from 48k to 60k points), El San Juan Hotel Curio Collection (70k points per night through much of the year) and the Hampton Inn & Suites San Juan (60k points per night most of the year).

Luxury hotels include The Ritz-Carlton, San Juan and the InterContinental San Juan from 50,000 IHG Rewards Club points per night. Beyond San Juan, you can consider the St. Regis Bahia Beach Resort (Marriott Category 7), which reopened after completing $60 million repairs and renovations in December 2018. This property should be better than ever once any reopening kinks are worked out.

Image courtesy of St. Regis Bahia Beach
Image courtesy of St. Regis Bahia Beach

Spots to Check Out Beyond San Juan

While Southwest Airlines only flies to San Juan in Puerto Rico, you can rent a car and explore the rest of the island. While still recovering from the effects of 2017’s Hurricane Maria, the island is getting back on its feet. There are a variety of places that make good day trips from San Juan. Here are a few:

  • Bioluminescent bay — either Laguna Grande (about an hour’s drive from San Juan) or La Parguera (a two- to three-hour drive depending on your route)
  • El Yunque National Forest on the northeast part of the island
La Mina Falls in El Yunque National Forest,
La Mina Falls in El Yunque National Forest, Puerto Rico. (Photo by Alisha Bube / Getty Images)
  • Cabo Rojo Lighthouse — set on the limestone cliffs above the Caribbean Sea on Los Morrillos Peninsula (about three hours from San Juan by car)
  • Ponce — on the island’s southern coast, this city has a pretty old town, waterfront boardwalk and plenty of bars and restaurants (a 90-minute drive from San Juan)

Bottom Line

Puerto Rico is a no-brainer vacation destination for any family that earns a Southwest Companion Pass. It’s a quick trip from points south and it’s nearly always bright and sunny. It’s a US territory so there’s no need to worry about money conversions, passports, international data plans or language barriers (many locals speak both English and Spanish).

So what do you think? Will you take advantage of this Southwest Companion Pass promotion to fly to Puerto Rico in 2019?

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Featured image by felixairphoto / Getty Images

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