Planning a trip to Puerto Rico but don’t know where to start? This pocket-size guide lays out the perfect 14-day itinerary, taking you from historic streets to pristine beaches, lush rainforests, and charming coastal towns. Whether you’re into adventure, culture, or just want to unwind, this plan covers San Juan, Vieques, Ponce, Rincón, Cabo Rojo, and more—all while making the most of your time. Plus, we’ve included the best places to stay for a stylish and comfortable experience. Ready? Let’s dive in!
Day 1-3: San Juan – History, Food & Nightlife
- Explore Old San Juan (Castillo San Felipe del Morro, colorful streets, local shops)
- Enjoy beach time at Isla Verde or Condado
- Visit Piñones for street food and ocean views
- Experience La Placita for nightlife
Day 4: El Yunque & Luquillo Beach
- Hike through El Yunque Rainforest
- Swim in waterfalls (La Mina, Juan Diego Falls)
- Relax at Luquillo Beach & try local kiosks
Day 5-6: Vieques – Bioluminescent Bay & Secluded Beaches
- Ferry or flight to Vieques
- Explore Playa Negra, Caracas, or La Chiva
- Kayak the Bioluminescent Bay at night
- Stay at a boutique hotel or guesthouse
Day 7-8: Ponce – Art, Culture & Coffee Country
- Walk through Ponce’s historic center (Parque de Bombas, Plaza las Delicias)
- Visit the Museo de Arte de Ponce
- Take a day trip to Jayuya (coffee farms, Toro Negro rainforest)
- Enjoy local cuisine at El Negocio de Panchi
Day 9-10: Rincón – Surf & Sunset Views
- Drive to Rincón, the surf capital of Puerto Rico
- Beach hop: Domes Beach, Sandy Beach, Steps Beach
- Watch the sunset at Punta Higüero Lighthouse
- Try fresh seafood at La Cambija
- Optional: Whale watching (seasonal)
Day 11-12: Cabo Rojo & Guanica – Hidden Gems & Nature
- Visit Playa Buyé & Playa Sucia (breathtaking views)
- Hike to Cabo Rojo Lighthouse
- Explore Guánica Dry Forest (UNESCO Biosphere Reserve)
Day 13-14: Back to San Juan & Relaxation
- Return to San Juan for a spa day or shopping
- Final dinner at a fine dining spot (1919 Restaurant, Marmalade)
- Depart from Luis Muñoz Marín Airport
Where to stay in Puerto Rico?
- The Weekender by Otium (modern design, saltwater pools, 24/7 concierge, exclusive experience)
- Otium Vacation Rentals (chic, fully equipped apartments in prime locations)
Book now at stayotium.com and get 20% OFF booking 2 months in advance using code SAVEMORE at checkout.