At the center of this program is the San Sebastian Street Festival in Old San Juan.  Our participation in the San Sebastian Street Festival will include the opening ceremony, parades, arts and crafts exhibits and live music entertainment in different plazas.

The main site for the program will be Old San Juan. Called "La Ciudad Amurallada," (The Walled City), Old San Juan was founded in 1521. In 1508 Juan Ponce de León founded the original settlement, Caparra, behind the almost landlocked harbor just to the west of the present metropolitan area. The settlement was abandoned and moved to the site of what is now called Old San Juan. San Juan is one of the biggest and best natural harbors in the Caribbean and is the second oldest city in the Americas.   

During our first day our Program Leader and a Puerto Rican architect will lead a full day walking tour through the narrow streets of Old San Juan to experience five centuries of Spanish Caribbean history. We will become acquainted with significant architectural features of the city, historical sites, forts, plazas, cultural centers, fountains, museums, and galleries and with Old San Juan lively people's cultural life and idiosyncrasy. 

In addition to our participation in the main venues of the San Sebastian Street Festival, we will expand on our understanding of Puerto Rican culture when will visit the Museum of Art of Puerto Rico, a modern five-story structure in a 1920 neo-classic building.  The Museum supports Puerto Rico's 500 years old tradition in painting, sculpture, graphics, ceramics, folk art, photography and other contemporary media; nothing like art history to learn the history of a nation. 

We will get a glance at contemporary arts visiting the Puerto Rican Contemporary Art Museum.  Founded in 1984, the Puerto Rican Museum of Contemporary Art was the result of collaboration between a number of generous artists and the civil society to create a collection of a variety of art forms and contemporary art expressions. 

To experience Puerto Rican dance and music we will explore night entertainment venues. 


  • Five nights accommodations at El Convento Hotel in Old San Juan 
  • Full American breakfasts
  • Welcome and farewell dinners
  • Ground transportation and drivers’ tips
  • Guided walking tour of Old San Juan with Puerto Rican architect
  • Guided visits to the museums in itinerary and El Morro Castle 
  • Guided visits to the San Sebastian Street Festival venues 
  • Reading and websites suggestions to learn about PR before departure
  • Online orientation meeting before departure


  • Airfare to/from San Juan
  • Transportation from/to San Juan International Airport 
  • Meals:  4-L, 3- D 
  • Gratuities for maid and bellman
  • Trip interruption and cancellation insurance 


Amongst the cobblestone streets, restored buildings from the sixteenth and seventeenth century, and the charm of a district in Puerto Rico that has existed for more than four hundred and ninety years, tourists often loose themselves in an ocean of attractions. They come here to explore the history of Old San Juan, try their hand at the casino, take walks along the picturesque beaches and explore the noteworthy sights and attractions, such as the Plaza de San Jose, Plaza del Quinto Centenario and Plaza de Armas. But in January, they come to take part in a tradition that is rooted in the culture of Puerto Rico, the San Sebastian Street Festival.

The annual celebration of the San Sebastian Street Festival has been taking place for more than fifty years. It is a festival that was created for the local community, giving artists and handcraft traders the opportunity to exhibit their work, as well as to bring business to the area. The plan worked better than expected, as within a few years thousands of tourists flocked to Puerto Rico to attend the San Sebastian Street Festival, creating a lucrative tourist industry and bringing business and prosperity to an almost forgotten district.

During the day, the streets of Old San Juan are jam packed with people, food stalls, live music, artists, craft exhibits and vendors. The only way to reach San Sebastian Street is on foot as no vehicle of any kind will be able to make it through the mass of festival enthusiasts. It is an eventthat is looked forward to all year and the parades of color and noise attract thousands of spectators who come to see the parade participants in their vibrant costumes and traditional vejigantes masks.

SanSe Festival

First day of the San Sebastian Street Festival. Opening parade of the cabezudos and comparsas.


  • Arrive in San Juan, Puerto Rico, Luis Muñoz Marin International Airport 
  • Transfer to hotel on your own 
  • Check-in at hotel
  • Welcome Dinner   

DAY 2 

  • Breakfast 
  • Walking Tour of Old San Juan 
  • Lunch 
  • San Sebastian Street Festival Opening ceremony and dedication of the Fiestas de la Calle San Sebastián. 
  • Dinner or optional tours  

DAY 3   

  • Breakfast
  • Visit to Museum of Art of Puerto Rico
  • Lunch
  • San Sebastian Street Festival Over 350 artisans will be displaying and selling works at Cuartel de Ballajá, plazas and along    San Sebastian Street
  • Dinner or optional tours  

DAY 4 

  • Breakfast
  • Visit to the Contemporary Museum of Art
  • Lunch
  • San Sebastian Street Festival – music presentations at different plazas 
  • Dinner or optional tours


  • Breakfast​
  • Free time for optional tours and visits to museums and galleries
  • Lunch
  • San Sebastian Street Festival – music presentations at different plazas
  • Farewell Dinner   


  • Breakfast
  • Check-out 
  • Transfer to airport on your own


A landmark monument to the Conquistador Age and one of the most historic hotels in Old San Juan Puerto Rico, Hotel El Convento in San Juan, Puerto Rico showcases a timeless aura of Old World charm and splendor. Befitting its origins as a Carmelite convent more than 350 years ago, our splendid Puerto Rico luxury hotel is a loving restoration of Spanish Colonial architecture and design. All 58 elegant rooms are adorned with rich wooden beams, handcrafted tiles, carved chairs, velvet settees, and antique chests. Our colorful past at El Convento in San Juan includes highlights such as:  

  • Named the premier "Small Luxury Hotel" in Puerto Rico
  • Daily Manager's reception, serving a variety of wine and a variety of international cheeses on La Veranda terrace
  • Plunge pool and heated jacuzzi, offering breathtaking views of San Juan Bay
  • 24-hour fitness center, with free weights, treadmill, elliptical trainer, and stair climber, offering guests unlimited use
  • One restaurant serving cuisine ranging from tapas to traditional Puerto Rican fare
  • Library, with access to our business center  


  • Free and fast WI-FI 
  • Plush bathrobes and slippers 
  • Goose-down pillows 
  • Flat-panel 37" LCD TV 
  • Bose radio 
  • ADA compliant rooms
  • Cordless telephones
  • Spacious work desk 
  • Hairdryer, iron, and ironing board 
  • In-room safe 
  • Refrigerator, with complimentary bottled water 
  • Premium Alto Grande coffee with a two cup coffeemaker
  • 24-hour guest services
  • In room dining available for breakfast, lunch, and dinner
  • Aromatherapy, facials, and manicures available upon request
  • Coin operated laundry; equipped with washer, dryer and soap dispenser
  • Herb Garden with fresh herbs and fruit, used in delicious cocktails at the bar and in signature dishes