All-inclusive road trip to explore the cultural gems of southern Puerto Rico, with local stops, iconic sites, and flexible experiences guided by a friendly local.

PRICE: From
$270
per person

 

Embark on a full-day cultural road trip from San Juan to the historic southern city of Ponce, known as “The Pearl of the South.” Travel through picturesque towns such as Caguas, Cayey, and Juana Díaz, with curated stops designed to immerse you in Puerto Rico’s rich culture and history.

Enjoy an authentic food experience at Guavate, home of the island’s famous “pork highway,” where local lechoneras serve traditional roasted pork and other Puerto Rican delicacies. From there, continue to Juana Díaz, a town deeply rooted in Taíno ancestry and known for its vibrant Three Kings Day Festival.

Your journey culminates in Ponce, where you’ll explore the city’s iconic Downtown Plaza, stroll past neoclassical architecture, and taste the local charm — including a visit to a famous ice cream parlor that’s been serving locals for over 25 years. Optional stops include the Ponce Art Museum, the Music Museum, or the historic Castillo Serrallés, a former rum estate with panoramic views.

The itinerary is fully customizable based on your group’s vibe. Whether you’re a foodie, a history buff, or just want to soak in local culture, this experience is tailored to feel less like a tour and more like a road trip with your Boricua friend. Travel in comfort, skip the tourist traps, and uncover Puerto Rico’s southern soul.

• Explore the historic streets and plazas of Ponce with a local guide.
• Enjoy flexible, personalized stops based on your group’s vibe.
• Taste authentic Puerto Rican food in Guavate (pork highway).
• Optional visits to the Ponce Art Museum or Serrallés Castle.
• Hosted by a local — this isn’t a tour, it’s a cultural road trip.

Includes:
Transportation (gas and tolls)
water
One alcohol shot when you follow “City of Rums” on Instagram
Smoke-friendly for private tours
Photos
Concierge
Towns- San Juan – Caguas – Cayey – Juana Diaz – Ponce
Gratuities
Extra food and drinks (available for purchase)
lunch

 

 

Explore thousands of upcoming events, local tours, top restaurants, and the best places to stay in Puerto Rico. You can also check out our dedicated city guide for San Juan.

 

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