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Discover Spain: Madrid, Granada & Seville — Tracing the Roots of St. Augustine

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The Empire, the Inspiration, and the Gateway

How Three Spanish Cities Built a Florida Town

 Discover the Spain That Shaped St. Augustine


For centuries, Spain has been woven into the streets, architecture, and stories of St. Augustine. From the coquina walls of the Castillo de San Marcos to the courtyards, arches, and plazas that give the city its character, traces of Spain are everywhere. But to understand those connections, you have to cross the Atlantic and stand where the story began.


Join us on a journey through Madrid, Granada, and Seville as we trace the roots of Spain's empire and the people, places, and traditions behind America's oldest continuously occupied European settlement.


We begin in Madrid, the seat of royal power. In 1561, just four years before St. Augustine was founded, Madrid became Spain's capital. From here, monarchs and royal councils governed territories across Europe, the Americas, Africa, and Asia. As we walk its plazas and older streets, we'll look at how decisions made in this city reached thousands of miles across the ocean and changed life in a small garrison town in Florida.


From Madrid we head south to Granada. Here we'll step inside the Alhambra, the hilltop palace complex the Nasrid rulers built over the 13th and 14th centuries. As we move through its courtyards, gardens, and tiled halls, you'll start to recognize something. The horseshoe arches, the carved detail, the cool inner courtyards built around water — these are the same ideas Henry Flagler's architects borrowed in the 1880s when they built the Hotel Ponce de Leon and the Hotel Alcazar back home, the buildings you now know as Flagler College and the Lightner Museum. Stand in the Alhambra and the St. Augustine you've walked past your whole life suddenly makes sense. In the evenings, you'll have time to wander Granada's old neighborhoods, work your way through its tapas bars, and catch flamenco beneath the caves of Sacromonte.


Our journey ends in Seville, the city that connected Spain to the New World. This was the gateway. Explorers, merchants, soldiers, and settlers passed through here on their way between Europe and the Americas, and ships returned carrying silver, gold, and reports from across the Atlantic. We'll spend time at the Archivo General de Indias — the archive that still holds the original colonial records of Spanish Florida, the paper trail historians used to reconstruct St. Augustine's earliest years. We'll also visit the cathedral and the Alcázar, walk the old riverside quarters, and see where Spain's empire was organized, financed, and run. The link between Seville and America's oldest city is something you can stand inside here.


Along the way we'll share long meals, find local traditions, and leave you plenty of time to explore at your own pace alongside a small group of fellow travelers who care about history, food, and the real story of a place. This isn't a checklist of sights. It's a trip built to show you how Spain's past still lives in St. Augustine today.


Whether history, architecture, food, or culture brought you here, this is a side of Spain few travelers get to see.


Come curious. Leave connected.


And maybe come home seeing St. Augustine in a whole new way.

See what’s included, pricing, and travel dates.

Trip Overview

Date: October 19-27, 2027

Price: $2,999 (based on double occupancy, single supplement available)

Duration: 9 days, 8 nights
Starting Point: Madrid
Ending Point: Seville
Group Size: 14-20 guests

Pace: Relaxed, immersive experience
Activities: Guided city walks, food experiences, cultural highlights
What’s Included:

✅ Digital Guidebook including customized Google maps with restaurants, pubs, live music, & museums
✅ 8 nights in comfortable hotels
✅ All breakfasts + Welcome Dinner

✅ Historic Walking Tour in Madrid

✅ Private Alhambra Tour in Granada
✅ Culinary experience in Seville
✅ All group transportation within Spain
✅ Small group setting for a more personal experience

What’s Not Included:
❌ Flights to and from Spain
❌ Meals during free time
❌ Travel insurance (highly recommended)
❌ Personal expenses and optional activities

Reserve Your Place

Itinerary Breakdown


Day 1: ¡Bienvenidos a España!

  • Welcome dinner with the group
  • Free evening to explore or relax

Day 2: Imperial Madrid

  • Guided walking tour through the Madrid of the Habsburgs, where the empire was governed and decisions were made that reached across the ocean to Florida
  • Free afternoon and evening to explore on your own

Day 3: South to Granada

  • Coach from Madrid to Granada, arriving by early afternoon with time to settle in
  • Welcome to Granada tapas happy hour
  • Free evening to explore on your own

Day 4: Inside the Alhambra

  • Private guided tour of the Alhambra
  • Free afternoon to rest or wander
  • Sunset dinner followed by a flamenco performance in the caves of Sacromonte

Day 5: Granada, At Your Own Pace

  • A full free day to discover Granada your way
  • Step inside the Cathedral, browse the market stalls, and lose an afternoon in the streets of the Albaicín

Day 6: On to Seville

  • Coach from Granada to Seville
  • Welcome to Seville food tour with our local friends
  • Free evening to explore on your own

Day 7: The Alcázar & the Cathedral

  • Private guided tour of the Royal Alcázar and Seville Cathedral
  • Free afternoon and evening to explore at your own pace

Day 8: The Archive of the Indies

  • A private Archive of the Indies experience, standing with the original records of Spanish Florida
  • Free afternoon and evening to explore on your own

Day 9: ¡Hasta Pronto!

  • Breakfast included, but no group activities today
  • Fly home from Seville, or carry on by train to Córdoba, Cádiz, or Madrid
  • Easy connections across Europe from here for anyone not ready to head home just yet

Why Choose Europe With Friends

Stress-Free Travel

Unforgettable Experiences

Stress-Free Travel

 We've planned (almost) everything so you can simply enjoy. 

Small Groups

Unforgettable Experiences

Stress-Free Travel

 More personal experience with like-minded travelers. 

Local Connections

Unforgettable Experiences

Unforgettable Experiences

Meet locals, explore historic districts, and experience authentic Spain. 

Unforgettable Experiences

Unforgettable Experiences

Unforgettable Experiences

Enjoy Spanish cuisine, rich traditions, and timeless cities. 

Copyright © 2025 With Friends Travel Group LLC |  With Friends Travel Group LLC is registered with the State of Florida as a Seller of Travel. Registration No. ST45748  

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