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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.
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
Itinerary Breakdown
Day 1: ¡Bienvenidos a España!
Day 2: Imperial Madrid
Day 3: South to Granada
Day 4: Inside the Alhambra
Day 5: Granada, At Your Own Pace
Day 6: On to Seville
Day 7: The Alcázar & the Cathedral
Day 8: The Archive of the Indies
Day 9: ¡Hasta Pronto!

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

More personal experience with like-minded travelers.

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

Enjoy Spanish cuisine, rich traditions, and timeless cities.
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