Retiro Trips

Join us on our small group trips

Stress free travel with fellow travelers - just pack your bags!

  • A street scene viewed through a large archway, with an art market on the sidewalk featuring paintings and drawings, and historical buildings with balconies and shutters in the background.

    Spain - Sept 2025 Madrid/ Barcelona CLOSED

    6 nights/ 7 days

    $2,899/ shared room $3,699/ own room

    Two iconic cities. One seamless journey.
    Discover the heart of Madrid and Barcelona with a curated small group trip featuring an authentic paella dinner, a lively flamenco show, guided city walks, a tapas tour, beach day and boutique stays. Every detail is planned — so you can simply enjoy the rhythm, flavor, and soul of Spain.

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  • A brick sidewalk lined with trees and residential buildings, with an American flag hanging outside one of the buildings, and fallen leaves on the ground.

    Weekend In Boston - Oct 2026

    2 nights/ 3 days

    Fall in love with Boston this October.
    Join us for a cozy autumn weekend in one of America’s most historic (and charming) cities. Wander cobblestone streets, take in crisp harbor views, and soak up the season’s best — from colorful foliage and warm cider to iconic landmarks and local eats. Perfectly timed for peak fall vibes, with everything thoughtfully planned for a relaxed, memorable escape.

    COMING SOON →
  • Split view of two scenes: on the left, an ornate classical marble fountain with sculptures, and on the right, a hillside of colorful buildings overlooking the sea.

    Italy- June 2026 Rome/Amalfi Coast

    6 nights/ 7 days

    $3,775/ shared room $4,550/own room

    An effortless escape through Italy.
    Indulge in a thoughtfully curated journey from Rome to the Amalfi Coast — where every detail is handled, from boutique stays and private guides to elevated dining and exclusive experiences. Travel in style, connect deeply, and savor Italy.

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  • A pink stucco house exterior with a dark wooden door, a decorative white angel face above the door, a lantern light fixture above the angel, shadows of palm leaves on the wall, two utility meters in a small recessed area, and a window with a black wrought iron railing.

    Mexico - Feb 2026 CDMX/ San Miguel De Allende

    7 nights/ 8 days

    A vibrant journey through culture, color, and charm.
    Experience the best of Mexico with a thoughtfully curated adventure from dynamic Mexico City to the artistic heart of San Miguel de Allende. Enjoy private museum tours, artisan markets, and authentic culinary moments — all with boutique accommodations and seamless travel between cities. Bold, beautiful, and deeply inspiring.

    Coming Soon →