Mediterranean Vacation Spots I Plan Most Often
The Mediterranean offers a depth of regional history, food, art, architecture, and local traditions that rewards slower, more intentional travel.
My primary focus is Italy vacation planning — helping couples and families experience everything from iconic cities like Rome and Florence to regional treasures like Tuscany, the Amalfi Coast, and Venice.
I also plan trips to other Mediterranean destinations like Greece, Spain, and Portugal.
Rather than offering a fixed list of destinations, this page highlights examples of regions I work with most often. Every itinerary is custom, shaped around the people traveling and how they want to experience a place.
How to Use This Page
Think of these destinations as starting points, not prescriptions.
They reflect places where I have planning depth and firsthand experience, and where thoughtful pacing and cultural exploration tend to work especially well for couples and families.
If the place you’re dreaming of isn’t listed here, that doesn’t mean it’s off the table. We’ll always start with what matters most to you.
Italy Vacation Planning: Cities, Regions & Cultural Experiences
Italy offers an incredible range of experiences — from historic cities and hill towns to regional food traditions that vary widely from place to place.
Trips here often balance art, architecture, and history with time to slow down and enjoy everyday life. Italy works especially well for couples and families who want depth without feeling rushed, and for travelers returning to Europe who want to go beyond the highlights.
Common Italy itineraries I plan include combinations like Rome and the Amalfi Coast, Tuscany and Umbria, or the classic trio of Rome, Florence, and Venice. First-time visitors often focus on iconic cities, while returning travelers tend to explore regions like Puglia, Sicily, or the Italian Lakes.
The country’s compact size and excellent train network make multi-destination trips manageable, though I typically recommend staying at least 3-4 nights in each location to avoid feeling rushed. Italy’s regional food traditions—from Tuscan bistecca to Sicilian street food—are often highlights for families and couples alike.
Greece Vacation Planning: Islands, Ancient Sites & Cultural Exploration
Greece blends ancient history with a rhythm of daily life that encourages you to linger.
Depending on interests, trips may include archaeological sites, villages and small towns, or one or more islands chosen for their character rather than popularity. Greece is a strong choice for travelers who value cultural context, beautiful settings, and a relaxed pace. Popular combinations include Athens with islands like Naxos, Paros, or Crete, or mainland explorations of the Peloponnese with its Mycenaean ruins and coastal villages.
Spain Vacation Planning: Energy, Food & Local Character
Spain offers a vibrant mix of regional identity, food culture, and everyday life.
Itineraries often focus on cities and regions with strong local character, balancing lively culture with moments of calm. Spain works well for couples and families who enjoy energy and variety, while still wanting time to slow down and experience a place more deeply. Common itineraries pair Barcelona with coastal towns, Madrid with historic Toledo, or extended stays in Andalusia exploring Seville, Granada, and Córdoba.
Portugal Vacation Planning: Historic Cities & Coastal Towns
Portugal is often overlooked, but it offers rich cultural experiences with a slower, more intimate feel.
Trips here may highlight historic cities, coastal towns, and local traditions that invite exploration on foot. Portugal is a great fit for travelers who appreciate cultural depth without feeling overwhelmed, and it pairs well with Spain for longer itineraries. Many travelers focus on Lisbon and Porto, though the Douro Valley wine region and coastal Algarve also offer compelling experiences for couples and families.
And Beyond
These destinations reflect the core of my current planning focus and where I offer the deepest guidance.
If you’re interested in Mediterranean Europe more broadly — or have a specific place in mind — we can talk through how it fits with your interests, timing, and travel style.
Common Questions About Mediterranean Destinations
How do I choose between Italy, Greece, Spain, and Portugal?
The best destination depends on your interests, travel style, and timing. Italy offers the richest mix of art, history, and regional food culture. Greece combines ancient sites with island relaxation. Spain brings vibrant energy and strong regional identities. Portugal offers cultural depth with fewer crowds and a more intimate scale.
For first-time visitors to Mediterranean Europe, Italy and Greece tend to offer the most accessible combination of culture and infrastructure. Spain and Portugal work especially well for travelers who’ve already experienced Italy or who want a slightly slower pace.
Can I combine multiple countries in one trip?
Yes, though I generally recommend focusing on one or two countries for trips under 14 days. Quality of experience matters more than passport stamps. A well-paced 10-day Italy trip often feels more satisfying than a rushed tour through four countries.
For longer trips (14+ days), combinations like Spain and Portugal or Greece with one or two Italian destinations can work well if planned thoughtfully.
Let’s Talk About What Fits You Best
If you’re considering a Mediterranean trip and want help shaping it into something meaningful — rather than piecing it together on your own — a planning call is the best place to start.