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.

Many might think that as night falls, while the artists start to pack up their stalls and the municipal workers come in to clean the streets, that the festival is over for the day, but they would be wrong. It can be viewed as the calm before the storm. At night, the massive stage that has been set up sets the musical and rhythmic tone for dancers to show off their best salsa and merengue moves, drinking beer and partying the night away.

The San Sebastian Street Festival is a lively and energetic event that sets Old San Juan on fire. It is a magnificent blend of art, rhythm, entertainment and enjoyment that starts when the sun rises, and gains more momentum when it sets. The festival has become one of the vital tourist attractions in Puerto Rico, a time for dance and laughter.

San Sebastian Street Festival (SanSe) 

January 15-20, 2020
Registration Deadline – July 1, 2019

At the center of this program is the 2020 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.

Called "La Ciudad Amurallada," (The Wall City), 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. 

To explore visual arts in Puerto Rico 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. Then, 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. Those involved decided to form a non-profit institution whereby local artists could display their art and the public could be exposed to a variety of art forms and contemporary art expressions. Known locally as the Museo de Arte Contemporáneo (MAC), all the art collected by the museum officially belongs to the people of Puerto Rico. The Puerto Rican Museum serves not only to educate but to preserve and document art from Puerto Rico, the Caribbean and Latin America from 1940 to the present.

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


  • Five nights accommodations at the Casa Blanca Hotel
  • Welcome and farewell dinners
  • Ground transportation and drivers’ tips
  • Guided walking tour of Old San Juan with Puerto Rican architect
  • Guided visits and entrance fees to the Museum of Art of PR, Museum of Contemporary Art of PR and El Morro Castle 
  • Guided visits to the San Sebastian Street Festival venues 


  • Airfare to/from San Juan (hotel check-in time is 3 pm)
  • Transportation from/to San Juan International Airport (estimate $20 plus a $1 per bag, each way)
  • Meals: 5-B, 4-L, 3- D (estimate $10-15 for breakfasts and lunches and $20-30 for dinners)
  • Gratuities for maid ($1 per person, per day) and bellman ($5.00 per person)
  • Trip interruption and cancellation insurance 
  • Optional tours 


$ 2200 per person in a double room 
$ 2600 single room 



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

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. Parade of Cabezdos
  • Dinner 

DAY 3              

  • Breakfast
  • Transfer to Museum of Art of Puerto Rico
  • Visit toMuseum of Art of Puerto Rico
  • Transfer to hotel
  • Lunch
  • San Sebastian Street Festival

       Over 350 artisans will be displaying and selling works at Cuartel de Ballajá, plazas and along  

       Calle San Sebastian

  • Dinner 

DAY 4             

  • Breakfast
  • Transfer to the Contemporary Museum of Art
  • Visit to the Contemporary Museum of Art.
  • Transfer to hotel
  • Lunch
  • San Sebastian Street Festival – music presentations at different plazas 
  • Dinner 


  • Breakfast
  • Los Cabezudos Parade 
  • See optional tours, museums and galleries to visit
  • Lunch
  • San Sebastian Street Festival – music presentations at different plazas
  • Farewell Dinner and Flamenco 


  • Breakfast
  • Check-out 
  • Transfer to Luis Muñoz Marin International Airport on your own



The tour starts with an afternoon pickup from select hotels in San Juan. Then proceed on to Cataño, the facility also known as Casa Bacardi. What is now the world’s largest rum distillery was founded in Cuba in 1862, before moving to Puerto Rico in 1936. Savor a handcrafted rum cocktail in the building’s pavilion before moving on to learn about the company history and distilling process. Continue with an interactive exhibit detailing the lineage of this celebrated spirit brand and family-owned business. Check out a re-creation of the company’s original operation in Cuba, and admire artifacts and photos showcasing the brand’s unique heritage. Take a few minutes to sniff different varieties of rum before heading to the bottling plant for an overview of fermentation and production. Before you leave, peruse the gift shop for a few rum and Bacardi-themed souvenirs.


This Puerto Rico food tour offers an intimate introduction to the dishes and flavors that make the country’s cooking so unique.  Start your tour at 3pm from a central meeting point in the atmospheric neighborhood of Old San Juan. 

As you proceed on foot to your first tasting, immerse yourself in the area’s breathtaking French and Spanish architecture, some of which is more than 500 years old, listening as your guide explains the history of the location. After arriving at your first tasting stop, have a few delicious bites and learn about the diverse culinary influences, including Spanish, African and indigenous cuisines, that give Puerto Rican food its distinctive flavor. 

During your excursion you’ll sample sofrito, a delicious sauce often used as a base for other Puerto Rican dishes, and learn how to make mofongo, a local staple dish made with fried plantains. Top that off with rice and beans, Puerto Rican rum, and enjoy something extra sweet for dessert. Finish your gastronomic adventure with our handy guidebook and map, plus the knowledge and know-how to explore the colorful colonial architecture of Old San Juan.