What's the plan

Fri, Apr 24

The Adventure Takes Flight

Your Iberian adventure begins! Board your overnight flight from the US to Madrid. As the engines roars and you rise above the clouds, imagine the tapas, the flamenco music, the castles, and coastlines that await. Sleep well—tomorrow, Spain welcomes you!

Day 1 – Sat, Apr 25

(Madrid) — ¡Bienvenidos a España!

Step off the plane and into the vibrant heartbeat of Spain’s dazzling capital. A private coach whisks you past grand boulevards, royal plazas, and neighborhoods alive with energy. Pause for your first Spanish flavors over breakfast in the gardens of El Retiro, then enjoy a little siesta after settling into your stylish 4-star hotel Emperador in the heart of the city. As evening falls, enjoy a guided stroll through Madrid’s city center before gathering for a festive welcome dinner at La Cuenca—where Asturian cuisine pairs perfectly with crisp northern cider, setting the tone for the unforgettable journey ahead.  

Day 2 – Sun, Apr 26

(Madrid) — Markets & Midnight Rhythm

Wake up to chocolate and churros, then dive into the buzzing El Rastro flea market, where stalls brim with antiques, art, and curiosities. The afternoon is yours—wander museums, sip vermouth, or simply people-watch in a plaza. As night falls, the air crackles: an electrifying flamenco show at Las Tablas, where guitars wail, dancers stomp, and dinner is a feast for every sense.

Day 3 – Mon, Apr 27

(Toledo) — Echoes of Three Cultures

A short coach ride brings you to Toledo, the City of Three Cultures. From the panoramic viewpoint, the city unfolds like a living museum standing atop of a mountain surrounded by the Tagus river. Step into history with a visit to the serene Synagogue of Santa María la Blanca, followed by a guided walk through the winding lanes of the Jewish Quarter, where heritage lingers in every stone and courtyard. Then marvel at the soaring Cathedral of Toledo—a Gothic masterpiece often called the crown jewel of Spain’s cathedrals, where sunlight pierces stained glass to illuminate centuries of art, faith, and grandeur. Over lunch near Zocodover Square, taste Castilian flavors before discovering a traditional sword-making forge, where Toledo’s legendary steel has armed warriors for centuries—and supplied the silver screen with iconic blades featured in Conan the Barbarian, Highlander, Xena, Hercules, Gladiator, Zorro, Alexander, and Eragon. You’ll return to Madrid carrying Toledo’s spirit with you.

Day 4 – Tue, Apr 28

(Madrid) — Royal Majesty & Paella Dreams

Step into a world of royal grandeur with a guided visit to Madrid’s magnificent Royal Palace / Royal Galleries —a treasure chest of chandeliers, frescoes, and opulent halls that once hosted kings and queens. Every room whispers of empire, ceremony, and splendor. Afterward, a leisurely stroll delivers you to Casa de Valencia, where golden saffron and the freshest seafood unite in a paella worthy of its legend. The afternoon is yours: sip sangria on a sun-drenched terrace, shop the bustling Gran Vía, or lose yourself in the vibrant rhythm of a city that never fails to surprise.

Day 5 – Wed, Apr 29

(Madrid → Cáceres) — Into the Medieval Past

Bid farewell to the bustle of Madrid and set out west toward Cáceres, a UNESCO World Heritage city that feels like stepping back in time. Its cobblestone streets, fortified walls, and medieval towers have guarded centuries of history—and even served as filming locations for Game of Thrones. After checking into your hotel, the evening is yours to slow down—sip local wine, explore at your own pace, and let the golden glow of Cáceres at sunset work its magic.

Day 6 – Thu, apr 30

(Cáceres → Lisbon / Belém) — Golden Age of Discoveries

Wave goodbye to Spain as we cross into enchanting Portugal. By lunchtime, you’ll be savoring the rich flavors of Portuguese cuisine in Lisbon enjoying a panoramic city tour and a visit to the magnificent Jerónimos Monastery. The evening is yours to wander through the city’s sunlit streets, breathe in the Atlantic breeze, and let Lisbon’s golden glow welcome you.

Day 7 – fri, may 1

(Lisbon) — A city of light & soul

This morning, we’ll set out on a guided walking tour through Lisbon’s historic heart — winding alleys, elegant squares, and hilltop views that capture the city’s timeless charm. In the evening, we’ll gather for a special dinner accompanied by an unforgettable fado performance, where heartfelt melodies and candlelit ambiance reveal the true soul of Portugal. Transfers are included for your comfort.

Day 8 – Sat, May 2

(Sintra, Cabo da Roca & Cascais) — Palaces & the Edge of the World

Sintra welcomes you like a fairytale—misty hills crowned with whimsical palaces. At Cabo da Roca, stand on the windswept cliffs of Europe’s westernmost point, gazing at the endless Atlantic. Lunch in Cascais brings coastal charm before returning to Lisbon for a sparkling farewell dinner with champagne—celebrating friendships, memories, and the journey of a lifetime.

Day 9 – Sun, May 3

(Lisbon) — Até Logo, Iberia

After breakfast, a private transfer whisks you to the airport. As you board your flight, your camera roll overflows, your suitcase is heavier with souvenirs, and your heart is lighter with joy. Iberia has left its mark—these are memories that will live with you forever.

Trip Overview

  • DATES: Apr 25 – May 3, 2026.   9 days | 8 nights
  • START:  Madrid (4 nights) – Arrive in Madrid by 10:00 AM on Apr 25, (Requires an overnight flight on Apr-24)
  • END: Lisbon (3 nights) – Depart back from Lisbon to the US on May 3
  • OTHER CITIES VISITED: Toledo (day trip), Cáceres (1 night), Sintra/Cascais (day trip)
  • GROUP SIZE: Target 30 travelers
  • THEME: Culture, food, fun, art and iconic sights without the guesswork
  • PACE: Moderate walking; some cobblestone streets & hills (Lisbon/Toledo)

Pricing

Included:

  • 8 nights at 4-star hotels per itinerary (Madrid, Cáceres and Lisbon)
  • 18 meals: daily buffet-style breakfast at the hotels, 6 lunches and 4 dinners
  • Private coach transfers & excursions as listed
  • Trip host + on site Licensed English-speaking local tour guides & headsets as listed

Cities and Visits:

  • MADRID:  Retiro park, El Rastro shopping, Royal Palace, Plaza Mayor, Debod Temple, Flamenco show with dinner and drinks
  • TOLEDO:  Day tour – Synagogue of Santa Maria la Blanca, Jewish quarter, Toledo’s Gothic Cathedral, Visit to authentic sword forge and more.
  • CÁCERES:  Visit to the ancient city with local tour guide
  • LISBON:  Visit to the historic center with local tour guide, Belém, Jerónimos Monastery, Fado show with dinner and drinks
  • SINTRA/CASCAIS: day tour to the enchanting cities of Sintra and Cascais

Not Included:

  • International flights
  • Tips, personal expenses, optional activities
  • Travel insurance (strongly recommended)
  • Optional add-ons will be offered on tour!

 From $2,995 per person (after early-bird rebates)

  • Taxes included
  • Based on double occupancy