Trip Report: Puerto Rico

With snow in the forecast for Philadelphia, the timing for a getaway to San Juan couldn’t have been better timed. As my plans were being foiled again by Omicron for a week in NYC, it seemed brighter days were ahead.

A good friend and fellow advisor, Alle Pierce and I have been plotting a getaway for some time. Finally, our schedules synced and a girls warm getaway plan was in the works.

Touching down at the airport and walking through the jetway, I could already feel the warmth. We decided to rent a car to get around and be flexible. What we didn’t realize, four days was just not enough time to do all the things we wanted to do.

St. Regis Bahia Beach Resort

As we drove up the lush green winding road to the St. Regis Bahia Beach Resort, we found the perfect oasis to start the trip and decompress from city life.

The property sits on 480+ acres of land, including a secluded beach with stunning views of the Atlantic Ocean, exotic wildlife sanctuary, 18-hole golf course, water sports or just pamper yourself with a custom spa day in our Iridium Spa.

Every day was topped off at 6 pm for when the sun meets the night with a daily St. Regis tradition of sabering a bottle of champagne. Naturally, we felt right at home with this custom.

The following day we spent time by the pool in the cabana and took a break for massages, which was an incredible treat with Prosecco happy ending - ha. We sat and sipped in the open air relaxation area.

Fairmont El San Juan Hotel

Back in the hustle of San Juan and area that leads into Old San Juan, we settled into the historic Fairmont. The beach-front hotel was recently taken over by the Hilton, however, if you ask any local, they’ve always had a connection with the property growing up from proms to nightlife. That remains and the scene is more boisterous than our previous hotel. Two places, two very different vibes, and the ideal traveler for each.

We settled in after a hotel site tour at the pool-front cabana with a bottle of rose to quench our thirst and create my very first reel, which will probably be my last. Let’s be honest. I need expert supervision and director & producer Alle Pierce (follow her).

Later that night, we sat at the historic lobby transported us back in time with its 7,000 crystal chandelier, original wood-carved ceilings, statement oval bar and live entertainment speakeasy — who’s hosted the likes of Frank Sinatra, Sammy Davis, Liza Minnelli and Nat King Cole. We enjoyed some of the bartenders speciality cocktails and sushi bites, while striking up conversations with some of the locals and guests before going out on the town.

Take Time Old San Juan

The following day we meandered through the colorful streets of Old San Juan. With the uneven streets and cobble stone, wear comfortable shoes. Give yourself plenty of time to walk within the walls and see each fort.

It’s enjoyed strolling the streets and ducking into shops, restaurants and bars on our colorful journey, eyeing all the architecture and flanked by the historic fortresses. Got some great art from the “Handcraft Store” - one of my favorite souvenirs to take home everywhere I go.

We dropped into La Factoria cocktail bar, #32 in The World's 50 Best Bars 2019, which is a must visit — be sure to explore the speakeasy behind the door. After cocktail hour, we head over to Condado for a real treat at José Enrique restaurant with absolutely delicious Puerto Rican fare.

It is pretty easy to get around San Juan by Uber, however, when you venture beyond, sort out your arrangements with your hotel or rent car.

On my last visit, I was on the opposite side of the island in Rincon, which is a completely different vibe and trip style. If you’re to a flip flop, surfer vibe with boutique properties only. Very chill and beautiful.

Oddly enough, I spent my March 6, 2020 birthday there. Upon my return March 10th things were escalating quickly and the following day, it was declared a global pandemic.

If you’re interested in me reserving any hotel, let me know. As an advisor, I can make sure the staff looks after you and secure perks with my network.

Other Must Sees:

  • Vieques - an island just of the coast, home to the Bioluminescent Bays and wild horses

  • El Yunque National Forest (not far from St. Regis Bahia Beach Resort)

  • Rincon - the side of the island creates the perfect break for surfers

An amazing resource and navigate each region of Puerto Rico, visit Discover Puerto Rico.




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