Old San Juan, Puerto Rico — vibrant colorful colonial streets, cobblestone, pastel buildings — Puerto Rico Thanksgiving Retreat 2026
🦃 Thanksgiving 2026 · Nov 26 – Dec 1 · San Juan

PUERTO RICO THANKSGIVING

A Culinary & Cultural Journey Through San Juan

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THANKSGIVING WEEKEND RETREAT — November 26 – December 1, 2026

6 days · 5 nights · Dream Inn, Old San Juan · Culinary & Cultural Immersion

The Experience

Trade Autumn for Island Warmth

This isn't your typical Thanksgiving. An immersive 5-day retreat in San Juan combining world-class dining, authentic Puerto Rican culture, movement, and connection. From acclaimed restaurants and hidden gems to speakeasies and curated cultural experiences — limited capacity for intimacy and authenticity.

Solo and repeat guests welcome. Celebrate gratitude through elevated dining, vibrant culture, and unforgettable moments in Puerto Rico's most dynamic neighborhoods.

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Dates

Nov 26 – Dec 1, 2026

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Duration

6 Days · 5 Nights

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Stay

Dream Inn, Old San Juan

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Style

Culinary & Cultural Immersion

What's Included

  • ✓Accommodations at Dream Inn, Old San Juan
  • ✓Curated restaurant reservations
  • ✓Local guidance & cultural immersion
  • ✓Movement & connection activities

Not Included

  • —Airfare
  • —Personal alcohol
  • —Shopping & personal extras
  • —Optional activities
Dream Inn San Juan — striking red geometric lattice facade

Dream Inn

Dream Inn San Juan — lobby with woven wicker chairs and tropical plants

The Lobby

Epicuro Chef's Table — chef plating dishes at the open kitchen

Epicuro Chef's Table

“For adults seeking cultural immersion, elevated dining, and genuine connection. This is the real Puerto Rico — not the tourist version.”

— Xavier Marzan · X-Cursions in Motion

⭐ Dining Spotlight · Epicuro Chef's Table

Epicuro Chef's Table

Intimate 12-Seat Chef's Table · 5-Course Tasting Menu · Santurce, San Juan

One of the most extraordinary dining experiences in Puerto Rico — a 12-seat chef's table encircling an open kitchen where you watch every course being prepared right in front of you. Monthly rotating five-course tasting menus with wine pairings. Rated 5.0 on OpenTable — Best Overall, Best Food, Best Service, Best Ambiance, and Best Value in all of Puerto Rico.

Epicuro chef plating dishes at the open kitchen — textured stone plates with artful presentations, guests watching from the 12-seat chef's table, crystal chandeliers and moody lighting

The Chef's Table

12 seats · Open kitchen · 5-course tasting menu

Epicuro table setting — wooden charger plates on concrete table, crystal wine glasses, linen napkins, Laguiole steak knives, menu card

The Setting

Two chefs plating dishes at Epicuro — white chef coats, rows of beautifully plated dishes with colorful garnishes

The Kitchen

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Location

316 Avenida José de Diego · Santurce, San Juan, PR 00909

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Experience

12-Seat Chef's Table · Open Kitchen · 5-Course Tasting Menu · Wine Pairings

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Price

$175 per person · Monthly rotating menu · Reservations required

Epicuro's intimate 12-seat chef's table encircles an open kitchen where you watch every course being prepared. Monthly five-course tasting menus with thoughtful wine pairings create a warm, special-evening atmosphere. Smart casual dress code. A highlight of the Thanksgiving retreat dining experience.

“Epicuro is one of those once-in-a-lifetime dining experiences. Twelve seats around an open kitchen, watching every course come to life right in front of you. A must on every Puerto Rico trip.”

— Xavier Marzan · X-Cursions in Motion

🍍 Pineapple Award · #1 Place to Stay

Dream Inn

Boutique Hotel · Ocean Park, San Juan · Your Home Base

Xavier's all-time #1 place to stay in Puerto Rico — earning the Pineapple Award 🍍, his highest personal honor. Approximately 8 stays and counting — it genuinely feels like home. A boutique hotel steps from the beach in one of San Juan's most vibrant neighborhoods. Ocean Park sits between Condado and Isla Verde, with direct beach access, the best local brunch spots, and pickleball courts at Parque de Barbosa just around the corner.

Dream Inn San Juan — striking red geometric lattice facade on the hotel exterior against a bright blue sky with tropical greenery

The Exterior

Dream Inn San Juan — lobby with woven wicker chairs, wooden reception desk with Dream Inn logo, tropical plants and surfboard

The Lobby

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Location

2009 McLeary Street, Ocean Park, San Juan, PR

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Neighborhood

Ocean Park · Between Condado & Isla Verde · Steps from the beach

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Awards

40+ hospitality awards · 30+ architectural awards · 4.9/5 rating

Dream Inn is your home base for the Thanksgiving retreat. An award-winning boutique hotel offering a peaceful, tranquil space in the heart of Ocean Park — one of San Juan's most walkable, vibrant neighborhoods. Direct beach access, local brunch spots within walking distance, and the kind of atmosphere that makes you feel like you belong here.

🍍 Pineapple Award🏖️ Beach Access~8 StaysFeels Like HomeBoutique HotelOcean Park

What's Nearby

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Ocean Park Beach

Steps from the hotel — one of San Juan's most beautiful, less-crowded beaches.

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Pickleball at Parque de Barbosa

Courts just around the corner — connect, compete, and enjoy the island breeze.

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Numero Uno Beach House

Toes-in-the-sand breakfast with ocean views — walking distance from Dream Inn.

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Lela's Eatery

Famous guava and cheese French toast — a bright, airy neighborhood kitchen nearby.

“Dream Inn is where I stay every single time I'm in Puerto Rico. About 8 stays now — it genuinely feels like home. The location, the vibe, the beach steps away — this earns the Pineapple Award 🍍.”

— Xavier Marzan · X-Cursions in Motion

🍍 Pineapple Award · Xavier's #1 Restaurant

Santaella Restaurant & Bar

Puerto Rican Nouvelle Cuisine · Chef José Santaella · Santurce, San Juan

Xavier's all-time #1 restaurant in Puerto Rico — earning the Pineapple Award 🍍, his highest personal honor. Chef José Santaella trained under Ferrán Adrià, Eric Ripert, and Gary Danko. Bold, creative New Puerto Rican cuisine with tapas-driven menus rooted in local ingredients and world-class technique. The octopus is legendary. Xavier returns every single trip.

Santaella tuna tartare — vibrant red tuna cubes with cream dots, sesame seeds, chives, and crispy crackers on a white rectangular plate

Tuna Tartare

Santaella cocktail — golden martini with herb garnish on a Santaella-branded napkin, candlelight, warm speakeasy atmosphere

The Cocktail

Santaella cocktails — two craft cocktails beside the red Santaella menu, one with mint garnish, one martini with lavender, warm amber bar lighting

The Bar

Santaella red cocktail — bright red drink with dried citrus garnish and black straws on a Santaella napkin

Red Santaella

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Location

219 Calle Canals, Santurce, San Juan, PR 00907

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Cuisine

Puerto Rican Nouvelle · Tapas · Local & International Ingredients

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Contact

(939) 221-0575 · josesantaella.com

Chef José Santaella trained under three of the world's most celebrated chefs — Ferrán Adrià at elBulli, Eric Ripert at Le Bernardin, and Gary Danko at Restaurant Gary Danko — and brought that world-class technique home to Puerto Rico. The menu is tapas-driven, designed to be shared and combined into a full meal. The bar program is equally serious — cocktails that match the ambition of the kitchen.

“Santaella is the one. Every single trip to Puerto Rico — I'm going. The octopus, the tapas, the bar — Chef Santaella trained under the best in the world and brought it all home to the island. This earns the Pineapple Award 🍍.”

— Xavier Marzan · X-Cursions in Motion

🍸 Old San Juan Nightlife · La Factoría

La Factoría

Puerto Rico's Premier Cocktail Bar · Old San Juan

La Factoría is where it all started for Puerto Rico's cocktail renaissance. Multiple rooms, each with its own vibe — La Facto (the Front Bar), Vino (wine bar), El Shingaling (the Salsa Room with live band La 51), El Final (neon-lit late-night room), El Desvío (hidden 10-seat candlelight bar), and La Cubanita (old bodega next door). Live salsa starts at 10 PM in the Shing A'Ling room.

La Factoría Front Bar — rustic run-down chic interior with long wooden bar counter, string lights, checkered floor, red couch, Hijos de Borinquen wall art, and warm ambient lighting in Old San Juan

La Factoría

The Front Bar · Run-down chic · Old San Juan

Hijos de Borinquen — guests gathered at La Factoría's front bar with string lights, exposed beams, and warm ambient lighting in Old San Juan

Hijos de Borinquen

El Desvío — La Factoría's hidden 10-seat candlelit bar with candles, flowers, and warm amber lighting on a rustic wooden counter

El Desvío

Furtivo cocktail overhead — craft cocktail garnished with dried citrus and mint on a patterned carpet

Furtivo Cocktail

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Location

148 Calle San Sebastián, Old San Juan, PR 00901

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The Rooms

La Facto · Vino · El Shingaling · El Final · El Desvío · La Cubanita

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Hours

Opens daily at 11 AM · First-come, first-served · No reservations

El Shingaling is the Salsa Room — live salsa and jazz with the house band La 51, founded by Tempo Alomar and Roberto Roena. The music starts at 10 PM and the energy doesn't stop until close. This is where our Old San Juan bar crawl ends — and where the real night begins.

“La Factoría is where the cocktail revolution started in Puerto Rico. Multiple rooms, each with its own soul. The Shing A'Ling room with live salsa is how we end every night in Old San Juan.”

— Xavier Marzan · X-Cursions in Motion

Experience Puerto Rico This Thanksgiving

November 26 – December 1, 2026 · Dream Inn, Old San Juan · Limited capacity for intimacy and authenticity. Reach out to reserve your spot.

X-CURSIONS IN MOTION · Puerto Rico Thanksgiving 2026 · Est. 2012