Retiro Trips

Join us on a small group trip

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 2026 Madrid/ Barcelona

    6 nights/ 7 days - Sept 6th - 12th

    $3,225/ shared room $3,875/ 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.

  • Summer Time Chi - August 2026

    Enjoy a fun and stylish summer getaway in Chicago, filled with a mix of relaxation, exploration, and memorable experiences. This curated itinerary offers a balance of city highlights, social moments, and time to unwind. Explore vibrant neighborhoods, enjoying great food and drinks, and taking in the energy of the city, with flexibility built in for personal preferences and spontaneous plans!

  • 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/ Salem - 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.

  • 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 2027 Tulum/ Merida

    7 nights/ 8 days

    Experience a thoughtfully planned getaway exploring the beauty and culture of Tulum and Mérida. This journey blends relaxation, local experiences, and light exploration, offering a well-balanced mix of scenic surroundings and cultural highlights. Enjoy coastal views, historic charm, and curated stops along the way, with time built in to unwind and explore at their own pace.

  • 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- 2027 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.