The Perfect Puerto Rico Itinerary

I am visiting Puerto Rico for the first time in many many many years this upcoming July. As I am planning my upcoming vacation, I wanted to create the perfect itinerary. Well here it is…
Day 1: Arrival and Settling into Paradise
- Arrive in Style
Begin your luxury journey by flying into San Juan, where private airport transfers await to take you to one of Puerto Rico’s most luxurious resorts. Consider staying at Condado Vanderbilt Hotel, a historic property known for its elegant rooms and oceanfront views, or the ultra-modern Dorado Beach, a Ritz-Carlton Reserve, offering a serene and private beach escape. - Fine Dining Welcome Dinner
Start your stay with an exclusive dinner at 1919 Restaurant in the Condado Vanderbilt. Enjoy world-class cuisine prepared by a Michelin-trained chef, with the freshest local ingredients, while overlooking the Atlantic Ocean.
Day 2: Private Tours and Cultural Exploration
- Private Helicopter Tour
After a relaxed breakfast, take off on a private helicopter tour to see Puerto Rico from above. Fly over the lush landscapes, waterfalls, and hidden beaches, giving you a bird’s-eye view of the island’s natural beauty. - Explore Old San Juan
Once back on the ground, embark on a private, guided tour of the charming streets of Old San Juan. Visit landmarks like El Morro Fortress, and enjoy the colorful colonial architecture while learning about Puerto Rico’s rich history. Your guide will tailor the tour to your interests, offering personalized insights and experiences. - Dinner at Marmalade
For dinner, head to Marmalade, a trendy yet refined restaurant in Old San Juan. This place is known for its innovative menu and superb wine pairings, offering a multi-course tasting experience you won’t forget.
Day 3: Relaxation and Wellness
- Private Beach Day
For day three, unwind with a private beach experience. Spend the day at Dorado Beach, a Ritz-Carlton Reserve, where you can relax in a luxury cabana, enjoy personalized beachside service, and indulge in rejuvenating spa treatments right on the sand. - Exclusive Wellness Experience
For the ultimate luxury experience, treat yourself to a bespoke spa day at the Spa Botanico at Dorado Beach. This tranquil retreat offers personalized treatments, from massages using organic local ingredients to holistic wellness therapies that will leave you feeling revitalized. - Dinner at La Casita Blanca
End your day with a home-style dinner at La Casita Blanca, a hidden gem in the suburbs of San Juan. While not ultra-modern, it offers a welcoming ambiance and authentic Puerto Rican flavors, ideal for a relaxed yet refined evening.
Day 4: Adventure and Discovery
- Private Yacht Charter
On your final day, embark on a private yacht charter to explore the stunning coastlines and nearby islands like Culebra or Vieques. You’ll be able to snorkel in crystal-clear waters, enjoy water sports, or simply bask in the sun on the deck of your luxurious yacht. - Lunch on the Water
Enjoy a gourmet lunch prepared by a private chef onboard, featuring freshly caught seafood and locally-sourced ingredients, paired with fine wines. - Evening Farewell Dinner at José Enrique
Return to San Juan for a farewell dinner at Cocina Abierta. This restaurant combines upscale dining with local flavors. The food is undeniably world-class.
Day 5: Departure
- Relax Before You Go
Before heading home, enjoy a leisurely breakfast at your hotel and spend the morning relaxing by the pool or indulging in one last spa treatment. When it’s time to leave, enjoy a private transfer back to the airport, reminiscing on the unforgettable experiences of your Puerto Rican getaway.
I can’t wait to visit the beautiful Caribbean island of Puerto Rico.