San Juan, Puerto Rico (solo)
January 2026
Minnesota winters are no joke and can be very draining. This winter I decided to prioritize self-care and take a much needed sea-sand-sun break. Puerto Rico had long been on my list, especially since it's one of the few Caribbean destinations with nonstop flights from Minneapolis–Saint Paul. When I saw a Delta flight deal online, I did not hesitate!
I visited a few weeks before Bad Bunny swept the Grammy Awards and performed in the SuperBowl Halftime Show. It was great to get more context about the island and its people before all the media headlines. Puerto Ricans are U.S. citizens, but continue to grapple with complicated post-colonial reality like so many other Caribbean communities.
Ocean Park
I needed relaxation so decided to stay in San Juan and not rent a car. Ubers are safe, inexpensive, and abundant. I felt safe walking around the Old San Juan, Condado, and Ocean Park neighborhoods, but it is important to be vigilant after dark and avoid certain areas of the city altogether.
I stayed in the Ocean Park neighborhood, which I would recommend without hesitation. It offers a beautiful beach, safe quaint neighborhood, plenty of delicious food close by, and proximity to the airport.
Several blocks closest to the beach have gated access for additional security. I stayed at Numero Uno Beach House and loved having a small kitchen in my room where I could store fresh fruit and prepare breakfast, which I enjoyed in the cozy inner courtyard. The hotel has beach chairs and café service. Every morning I would just walk up to the beach with my cup of delicious Puerto Rican coffee and sip it watching the turquoise waves roll in.
Having a kitchen also gave me a chance to experience a small slice of everyday life in San Juan. I enjoyed stopping by a nearby supermarket to stock up on fresh fruit, coffee, and breakfast essentials.
The beach at Ocean Park has large, powerful waves. When I wasn’t tussling in the surf, I was lounging and watching locals walk their dogs, surfers catch waves, and kiteboarders take advantage of the steady breeze.
The highlight of the neighborhood is Kasalta, a cafe and bakery serving the most delicious quesitos and empanadas. I also visited La Cueva del Mar for fresh seafood, and Berlingeri for vegan fare.
Old San Juan
While I spent most of my time on the beach in Ocean Park, I visited Old San Juan twice. I visited on the morning of my second day and returned on my final afternoon to watch the sunset from El Morro.
Old San Juan, or the historic city within the walls, is compact and walkable. Flanked by two fortresses (Castillo San Cristóbal to the east and Castillo San Felipe del Morro to the west) and a cruise port in the south, the old town is full of charm. Pastel-colored Spanish colonial houses and narrow cobblestone streets made me wonder if I was still in the United States after all.
I started my explorations by visiting the eastern fortress of San Cristobal for the 360 views of the ocean, the harbor, and the city. The castle features an exhibit on the tumultuous history of the island. Originally inhabited by the indigenous Taíno people, the island was colonized by the Spanish. After centuries of back-and-forth and the Spanish-American war, the island was ceded to the United States in 1898, and the residents received American citizenship in 1917.
View through the embrasure
As the heat of the day intensified, I left the castle to find some shade in the old streets. The city is full of colorful murals, cosy courtyards, old trees and ornate facades. I stopped at Cuatro Sombras cafe for a delicious cold brew and a quesito, a wonderful local cream cheese pastry. For lunch I visited Deaverdura, a bustling traditional spot with a chalkboard menu and delicious pina coladas (thank you, Puerto Rico, for inventing what must be the most famous tropical drink in the world!)
La Perla Neighborhood
Two days later I returned to Old San Juan in the afternoon. I did a bit of souvenir shopping at Spicy Caribbee and enjoyed a refreshing treat from Señor Paleta in the shade of a giant mango tree. As I walked down to Paseo de la Princesa, I spotted a large iguana sunning itself on the old city wall.
I followed the path beneath the city wall until I reentered the city at the historic Puerta de San Juan. I kept walking west toward the expansive grounds of the San Felipe del Morro castle passing the community cats sanctuary and park. I reached the fortress just in time to enjoy the sunset (and a sighting of another iguana) from the high ground. The cruise ships were just leaving port, the fresh ocean wind was in my hair, and the sun was warm. As the sun slowly set, I made my way back down into the city.
Cruise ship passing the Morro Citadel
I ended my night at La Factoria, a famous bar with true Puerto Rican hospitality, imaginative and memorable cocktails, and a relaxed elevated vibe. Cheers, San Juan!
Culebra
Culebra is a small island off the eastern coast of Puerto Rico, famous for its Flamenco beach, consistently ranking in the world’s best beaches lists. Visitors can either fly to Culebra or take the ferry from Ceiba before exploring the island by car. I was by myself and had limited time, so I opted to visit via an organized day tour. I booked a group tour with East Island Excursions, and they organized a pickup from my accommodations in Ocean Park.
From the port, it was an hour-long ride on a large ocean-going catamaran. The crew served drinks while we enjoyed the sea spray from the back deck.
Once on Culebra, our first stop was to snorkel in a cove at the Cayo Luis Peña, followed by a deli lunch served while anchored in the cove.
After lunch and relaxing on the catamaran roof, we made our way to our final destination, Flamenco beach.
The catamaran anchored offshore, and we had several hours to swim and relax. Flamenco Beach is stunning with powdery white sand and unbelievably clear turquoise water. The crescent shaped bay is large so it doesn’t feel crowded and there are no beachfront hotels or resorts.
Sadly, it was time to head back. Tired from a full day of sun and sea, I snoozed on our way back in, lulled by the rise and fall of the catamaran on the waves.
Flamenco Beach
