Puerto Rico: Colonization Today
A 28-day academic program tracing colonialism, resistance, and cultural identity from San Juan to Vieques, the coffee highlands, and the southwest coast
Colonialism, Resistance, and Identity Across Puerto Rico
An Island-Wide Curriculum
This student travel program circumnavigates Puerto Rico's main island over four weeks, with daily lectures that connect each location to its history. In San Juan, the focus is colonial history, status politics, and Afro-Caribbean resistance. On Vieques, students learn how 60 years of U.S. military use shaped the island's land and communities. In the coffee highlands of Adjuntas and Jayuya, they work on a farm, visit the Caguana Ceremonial Ball Courts, and engage with Taíno heritage that predates colonization by centuries. In Rincón, food sovereignty and agroecology frame discussions about Puerto Rico's food system. Three built-in rest days provide space to absorb it all.
Culture, Music, and Community Across the Island
The program pairs its academic structure with direct cultural engagement. In Loíza, Puerto Rico's center of Afro-Caribbean traditions, students participate in bomba dance and drumming workshops, hear oral histories from Black community elders, and visit the studio of Samuel Lind, one of the island's most celebrated Afro-Boricua artists. A full day in San Juan traces reggaetón from its roots in marginalized communities to its role in Puerto Rican identity worldwide. Grassroots organizing runs throughout the program — from The Happy Givers' mutual aid work in Vega Baja to community-led sustainability projects and hurricane recovery conversations.
Day-by-Day Itinerary
Twenty-eight days across Puerto Rico — from San Juan's colonial history and Afro-Caribbean traditions to Vieques, the coffee highlands, and the southwest coast. Every element of this itinerary can be adjusted to fit your program's learning objectives.
Day 1: Arrival in San Juan
Arrive in San Juan, transfer to the hotel, and settle in after your flight.
Lodging: Hotel Dreams Miramar, San Juan
Day 2: Orientation and San Juan Walking Tour
The program begins with an orientation session covering safety guidelines, group dynamics, and daily life in San Juan.
Head out on a walking tour through the city, pausing for conversations about Puerto Rican identity and what it means to live here today. A welcome lunch follows. The afternoon is free for rest or personal exploration before regrouping for dinner.
Lodging: Hotel Dreams Miramar, San Juan
Day 3: Old San Juan — Colonial History and El Morro
Travel 20 minutes to Old San Juan for a full day of history and culture. The morning opens with a lecture on colonial histories and status politics. After lunch in the old city, explore El Morro, the fortress overlooking the bay, and learn about its role across centuries. The afternoon brings time to walk the colorful streets, plazas, and cultural landmarks, including a stop at La Princesa street.
Lodging: Hotel Dreams Miramar, San Juan
Day 4: Piñones Mangroves and Environmental Justice
Head to Piñones to explore the mangroves and attend a talk on environmental justice. A lecture follows on ecological colonization and land dispossession, connecting nature to broader struggles over land and rights.
Lodging: Hotel Dreams Miramar, San Juan
Day 5: U.S. Imposition and the Museum of the Americas
The morning begins with a lecture on U.S. imposition and cultural resistance — how identity and power have been negotiated over time. In the afternoon, visit the Museo de las Américas, where art and history come together across its collections.
Lodging: Hotel Dreams Miramar, San Juan
Day 6: Old San Juan — Afro-Caribbean Resistance
Return to Old San Juan. The morning lecture explores Afro-Caribbean resistance in Puerto Rico, placing emphasis on histories often overlooked. After lunch, participate in a bomba dance class, hear oral histories from Black community elders, and engage in conversations on race and colonialism.
Lodging: Hotel Dreams Miramar, San Juan
Day 7: Journaling and Decolonization
The day opens with a lecture considering how to break the chains of colonization and what decolonization means in practice. After lunch, the afternoon is dedicated to reflective field journaling and group check-ins. Additional time is available for journaling, small group circles, or academic advising sessions.
Lodging: Hotel Dreams Miramar, San Juan
Days 8-9: Vieques Island
Travel up to four hours to Vieques Island, passing through coastal landscapes along the way. Upon arrival, attend a lecture on the lasting effects of U.S. military occupation, with a focus on food, sovereignty, and land. The afternoon is open for relaxation — the beach, walking the town, or taking in the island's slower pace.
The following morning is yours to rest, enjoy the beach, or experience the island at your own pace. After a final lunch on Vieques, begin the trip back to San Juan.
Lodging: Hotel in Vieques
Day 10: Return to San Juan
Return to San Juan, reflecting on Vieques' history and landscape along the way. The rest of the day is for settling back in.
Lodging: Hotel Dreams Miramar, San Juan
Day 11: El Yunque Rainforest
Travel an hour into the mountains to El Yunque, Puerto Rico's tropical rainforest. A lecture guides you through themes of ecology, colonialism, and Indigenous stewardship, connecting the natural world to broader histories. Lunch is enjoyed in the area, surrounded by lush greenery. The afternoon is free for exploration or rest.
Lodging: Hotel Dreams Miramar, San Juan
Day 12: Beach Day
A slow day. Sleep in, take care of laundry, and spend the afternoon on the beach.
Lodging: Hotel Dreams Miramar, San Juan
Day 13: Rest Day
After several full days, this one is reserved for rest and personal time. Explore San Juan at your own pace, take care of errands, or recharge before the final stretch of activities.
Lodging: Hotel Dreams Miramar, San Juan
Day 14: Carmelita Vega Baja and The Happy Givers
Travel about an hour to Carmelita Vega Baja to visit The Happy Givers. A workshop on mutual aid and resistance economies explores how communities organize to support one another. In the afternoon, participate in reflective activities focused on hurricane recovery and grassroots organizing. The day ends back in San Juan with a farewell dinner at a local restaurant.
Lodging: Hotel Dreams Miramar, San Juan
Day 15: Ponce and the Road South
Travel south with a mid-morning stop in Guavate, the famous "Pork Highway." Taste Puerto Rico's iconic lechón asado (roast pork) while learning about food, festivity, and cultural tradition in this mountain community. Continue to Ponce, known as the "Pearl of the South." After lunch, explore architectural landmarks, plazas, and cultural institutions that showcase Ponce's artistic heritage before heading to the mountains for a stay at an eco lodge in Adjuntas.
Lodging: Eco Lodge, Adjuntas
Day 16: Adjuntas and Coffee Country
Adjuntas is Puerto Rico's "coffee capital." Begin with a guided nature walk, observing how the forest supports both biodiversity and local economies. Visit a coffee farm to learn about cultivation, roasting, and the global politics of coffee. The day ends with a dip in the pool and dinner at the lodge.
Lodging: Eco Lodge, Adjuntas
Day 17: La Parguera and the Southwest Coast
Travel west to La Parguera, a coastal village known for its mangrove keys and bioluminescent bay. After checking into your hotel, attend a lecture on the environmental impact of coastal tourism. The afternoon is free to walk the village or swim from the dock.
Lodging: Hotel, La Parguera
Day 18: Cabo Rojo and Bio Bay
Hike in Cabo Rojo's wildlife refuge, home to limestone cliffs and salt flats. Lunch overlooking the Caribbean. In the afternoon, head by boat to Cayo Caracoles to snorkel and learn about mangrove ecology. After dinner, witness La Parguera's bioluminescent bay.
Lodging: Hotel, La Parguera
Day 19: Rincón and Food Sovereignty
Drive north along the coast to Rincón, famous for surf culture and sunsets. Stop for lunch before continuing to Finca Dos Hermanos, where a lecture on food sovereignty and agroecology frames your farm visit. Learn from local farmers about resilience and adaptation in the Puerto Rican food system.
Lodging: Hacienda Gripiñas, Jayuya
Day 20: Finca Dos Hermanos — Farm Work
Spend the day working alongside farmers — tending crops, preparing meals, or supporting community projects. The evening features a group reflection circle connecting food, land, and cultural identity.
Lodging: Hacienda Gripiñas, Jayuya
Day 21: Caguana Ceremonial Ball Courts
A short drive to the historic Caguana Ceremonial Ball Courts. Attend a lecture on Taíno heritage, cultural memory, and Indigenous resistance. Share lunch at the site and spend the afternoon walking the ceremonial grounds and learning about their significance.
Lodging: Hacienda Gripiñas, Jayuya
Day 22: Return to San Juan
Drive back to San Juan, stopping at lookout points along the Cordillera Central. Lunch en route highlights mountain cuisine. After arriving in San Juan — having now circumnavigated the main island — the afternoon is free for rest, journaling, or catching up on assignments.
Lodging: Hotel Dreams Miramar, San Juan
Day 23: Loíza — Afro-Boricua Culture
Journey east to Loíza, Puerto Rico's center of Afro-Caribbean traditions. Participate in a bomba dance and drumming workshop, meet mask-makers, and share a traditional lunch. A discussion on African heritage and cultural pride rounds out the day before returning to San Juan.
Lodging: Hotel Dreams Miramar, San Juan
Day 24: Samuel Lind Studio Visit in Loíza
Return to Loíza to spend the day at the home and studio of Samuel Lind, one of Puerto Rico's most celebrated artists. Lind's work embodies Afro-Boricua identity, spirituality, and cultural pride. Through a guided tour of his studio, see paintings, sculptures, and prints that highlight themes of bomba, community, and ancestral memory. A conversation with the artist (if available) or local guides provides context about how art functions as both cultural preservation and political resistance. The afternoon allows time for sketching, journaling, or quiet reflection.
Lodging: Hotel Dreams Miramar, San Juan
Day 25: Rest Day
Catch your breath and get ready for the last stretch of the trip.
Lodging: Hotel Dreams Miramar, San Juan
Day 26: Reggaetón, Economy, and Cultural Impact
Spend the day in San Juan exploring reggaetón's roots and its transformation from underground movement to global phenomenon. Begin with a discussion on the genre's origins in marginalized Afro-Caribbean and urban communities, tracing influences from reggae, hip-hop, and bomba. Walk through neighborhoods that shaped early reggaetón culture, pausing at murals and community spaces that celebrate its pioneers.
In the afternoon, shift to the present with a seminar on the economic and cultural impact of Bad Bunny's recent residency in Puerto Rico — how his concerts have boosted the local economy, spotlighted independent businesses, and redefined Puerto Rican identity on the world stage. The group reflects on how music functions as cultural resistance and economic empowerment. Dinner features a playlist curated by local youth highlighting emerging reggaetón artists.
Lodging: Hotel Dreams Miramar, San Juan
Day 27: Santurce and Isla Verde
The morning begins in Santurce, San Juan's vibrant arts district. A guided walking tour takes you through Calle Cerra, where murals tell stories of identity, protest, and resilience. Meet local artists and cultural leaders who are reimagining public space through community art projects. A discussion frames Santurce's creative scene within broader conversations about gentrification, resistance, and cultural autonomy. Lunch at a local café.
In the afternoon, head to Isla Verde for beach time. Swim, relax, and reflect on the morning's lessons. Group activities may include journaling or small reflection circles.
Lodging: Hotel Dreams Miramar, San Juan
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