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Destination Spotlight: Old San Juan

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Destination Spotlight: Old San Juan

In this episode, Christopher and Ashleigh share their love for Old San Juan, Puerto Rico. They discuss the history, attractions, challenges, and their favorite places to stay and eat in this beautiful, historic city.

History and Attractions in Old San Juan

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Founded in 1496, Old San Juan is the oldest European established city in the U.S. It was originally a walled, fortified city with the purpose of military defense. Many parts of the old wall and several iconic fortresses like El Morro remain today.

Top attractions include:

  • El Morro and San Cristobal forts - Offer great views and fascinating history
  • Paseo de la Princesa - Beautiful walkway with a light display at Christmastime
  • Calle Fortaleza - Street in front of Governor's Mansion with decorations throughout the year
  • Free walking tours - Great way to see hidden gems and learn history
  • Poet's Passage art gallery - Beautiful and colorful paintings of Old San Juan
  • Puerto Rican Arts and Crafts - Handmade local items
  • No beaches - Closest are outside the old city
    • Challenges of Visiting Old San Juan

    Some difficulties travelers may encounter include:

    • Very crowded when cruise ships are in port
    • Extremely hot and humid in the middle of the day
    • Not car-friendly - Parking is limited and driving is difficult
    • Frequent power outages
    • Restaurants can get very busy

      • Tips: Book morning and evening activities to avoid mid-day heat. Have a backup quick meal option and make reservations for dinner. Rent a car only for non-San Juan portions of your trip.

      Favorite Hotels

      Christopher and Ashleigh love Hotel El Colonial in Old San Juan. It's adults only, has a free open bar, and is located in their favorite part of the city.

      Other good options are Hotel El Convento or unique Airbnbs right in Old San Juan.

      Favorite Restaurants and Food

      Recommendations for breakfast/lunch:

      • Cafeteria Mallorca - Traditional Puerto Rican mallorca bread sandwiches
      • Chocobar Cortez - Chocolate-infused coffee, milkshakes, and more

        • Dinner favorites:

        • La Madre - Modern Mexican with great margaritas
        • La O - Tapas and Pizzas
        • El Viejo Almacen - Argentinian food near the governor's mansion

          • Classic Puerto Rican dishes to try: Churrasco steak, mofongo (mashed plantains), tostones (fried mashed plantains), Popsicles from Señor Paleta.

          And be sure to try Puerto Rican coffee! Cafe Cuatro Sombras, Finca Cielitos, and Café Cola'o were recommended.

          Let Christopher and Ashleigh know if you have any other Puerto Rico tips!

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