Skip to content
🌿 Planning a Greece trip? Grab my free Greece Starter Guide →
  • Home
  • DestinationsExpand
    • Athens
    • Crete
    • Mykonos
    • Santorini
  • Explore GreeceExpand
    • Greece Travel Tips
    • ItinerariesExpand
      • Santorini Itinerary
    • Travel Resources
  • Plan My TripExpand
    • Itinerary Review
  • About Me
  • Contact
Pyrgos village Santorini
Welcome to

The Olive Suitcase

Yassas! Hello and welcome! If you love traveling in Greece, you’re in the right place. We’re excited to share our Greece travel tips and stories with you.

What will you find here?

About the blog

Dreaming of Greece but overwhelmed by the planning?
You’re in the right place. I’m Rachel, a Greece-obsessed travel planner who’s turned decades of experience into stress-free guides that actually help.

Whether you’re craving turquoise waters, cozy tavern nights, or a trip that finally feels easy, I’ve got you. Let’s make Greece the trip you never stop talking about.

Meet Rachel
1

Woman in a bright red dress and white cover up sits on a stone step in front of a tall wooden door at Rethymno Fort in Crete. She wears a wide brim hat and sunglasses, with terracotta pots and pink flowers on either side, highlighting the historic stone architecture of the fortress.

You planned the whole trip. But does it actually work?


You’ve got the flights booked, the hotels reserved, and a color-coded spreadsheet you’re lowkey proud of.

But something still feels off. Is the pacing right? Will the ferries actually work? Did you miss something obvious?

I’ll review your full itinerary, catch the problems, and tell you exactly what to fix before you land.

Expert eyes on your plan. Delivered in 7 days. $129.

“Rachel provided insight I would have never thought of. She took so much worry and anxiety out of our trip.” — Michael, USA

Get My Itinerary Reviewed →

Digital mockup of a Santorini itinerary on a smartphone screen, showing a photo of white-washed buildings with blue domes overlooking the sea. Text highlights features like a day-by-day Santorini plan, clickable Google Maps, tested tours and restaurants, and mobile-friendly design.

Stop Googling. Your Santorini Plan Is Already Done.

You’ve got 20 tabs open and you’re still not sure you’ve got it right.

I’ve already done the research, tested the routes, and built the plan that actually works on the ground.

A 5-day itinerary designed like an app, not a PDF you read once and lose.

Clickable maps, real restaurant picks, and days that flow without backtracking.

Instant download. $39. Less than one dinner in Santorini.

“Planning for Greece is a full-time job. This guide makes it a five-minute checkout instead.” — Aleah, USA

Get the Santorini Plan →

A scenic coastal village in Greece with white and terracotta-roofed buildings clustered along the shore, surrounded by lush green hills and calm blue waters dotted with small boats. Overlaid text reads “Travel Guide: GREECE,” representing a Greece travel guide cover from The Olive Suitcase.

Stop Researching. Start Planning.

Grab the free Greece Starter Guide and get 30 insider tips, a realistic packing list, and the travel resources I actually use, all in one place.

No more tab overload. Just clarity.

You’ll also get Greece travel tips and trip planning ideas delivered to your inbox. Unsubscribe anytime.

Start Exploring Greece!

Travel By Destination

Scenic view of the main harbor at Chania with the mountains of Crete in the background.

Crete

Athens Food Crawl through busy Monastiraki Square with Acropolis in the background

Athens

Platis Gialos Beach Overlook Mykonos

Mykonos

3 blue domes of Oia Santorini

Santorini

What’s new?

START HERE!

  • An open map of Greece lies on a wooden desk with islands circled in red including Corfu Naxos Santorini and Crete. A notebook pen and closed book sit nearby suggesting travel planning. The handwritten circles highlight popular Greek islands for a planned trip.

    How to Choose Which Greek Islands to Visit (Without Regret)

    Posted onFebruary 21, 2026February 21, 2026 UpdatedFebruary 21, 2026
  • Simplified map of Greece divided into administrative regions including Central Macedonia, Thessaly, Epirus, Peloponnese, Attica, Crete, and the North and South Aegean. Each region is shown in a different color with clear labels marking mainland areas and island groups. The image provides an easy visual overview of how Greece is geographically organized by region.

    How Greek Island Regions Actually Work (And Why It Changes Your Itinerary)

    Posted onFebruary 20, 2026February 20, 2026 UpdatedFebruary 20, 2026
  • A person writes in a notebook that reads Plan Trip to Greece with bullet points Choose region and Pick islands on a wooden desk. Nearby are a tablet displaying a map of Greece, a Greek flag, sunglasses, a straw hat, a cup of coffee, a passport, and a ferry ticket labeled Greece. The image shows travel planning essentials for organizing a trip to Greece.

    How to Plan a Trip to Greece Without Losing Your Mind

    Posted onFebruary 14, 2026February 21, 2026 UpdatedFebruary 21, 2026
  • Orange kayaks rest on the black pebble shore at Mesa Pigadia Beach in Akrotiri, Santorini with calm blue water stretching out toward anchored sailboats. The image shows a quiet Santorini adventure spot where volcanic coastline meets the Aegean Sea under a clear sky.

    5 Santorini Adventure Tours to Book If You Want More Than Sunsets

    Posted onFebruary 7, 2026February 7, 2026 UpdatedFebruary 7, 2026
  • Couple standing on a white rooftop in Santorini, Greece, with the woman looking back while holding the man’s hand, surrounded by white Cycladic buildings and a stunning cliffside view of the Aegean Sea.

    The Best Private Tours in Santorini, Worth the Splurge

    Posted onJanuary 27, 2026February 4, 2026 UpdatedFebruary 4, 2026
  • A romantic sunset dinner overlooking the Aegean Sea in Santorini, featuring two glasses of chilled Santorini wine, a carafe, and a plate of grilled meats and vegetables on a table with a small olive tree centerpiece.

    Best Santorini Wine Tours for First-Time Visitors (Top 3)

    Posted onJanuary 25, 2026February 3, 2026 UpdatedFebruary 3, 2026
Explore

Santorini

If you’ve ever dreamed of blue rooftops and golden sunsets, Santorini’s probably on your bucket list. This island really lives up to the hype, from its cliffside villages to its fresh seafood.

Let me show you exactly how to get the most out of every sun-soaked corner, even if you only have a few days. Expect clear tips, some fun stories, and answers to the questions you forgot to ask.

Explore Santorini!
3 blue domes of Oia Santorini
Oia, Santorini
view on oia in santorini 2021 08 31 10 31 58 utc
Santorini Sunset
Discover

Mykonos

There’s nothing quite like waking up to the Aegean breeze in Mykonos.

From fresh-caught seafood by the water to boutique shopping nestled in bright alleys, the island has a bit of everything.

Whether you’re here for fun or a slow escape, you’ll find it has more to offer than just a party scene. I’ll guide you through the best activities, cozy cafés, and can’t-miss beaches. Come with me and see what makes Mykonos unforgettable.

Explore Mykonos!
  • a white building with red doors and a bell tower Mykonos Greece

    Mykonos Villages Guide: Quiet Corners, Hidden Gems & Planning Tips

    Posted onJanuary 10, 2026January 10, 2026 UpdatedJanuary 10, 2026
  • Best Restaurants in Mykonos, Where to Eat Well

    Best Restaurants in Mykonos, Where to Eat Well

    Posted onJanuary 3, 2026January 3, 2026 UpdatedJanuary 3, 2026
  • Outdoor dining area of Katerina’s Restaurant & Cocktail Bar in Little Venice, Mykonos, with white tablecloth-covered tables set along a balcony overlooking the Aegean Sea. The sunset casts a golden light across the water, capturing the romantic, seaside ambiance the venue is known for.

    Katerina’s Restaurant and Cocktail Bar Mykonos Review

    Posted onNovember 28, 2025November 28, 2025 UpdatedNovember 28, 2025
My Socials

Follow Me!

  • Facebook
  • Instagram
  • Pinterest
  • YouTube
Browse my site!

What are you looking for?

Facebook Instagram YouTube
  • Home
  • About
  • Contact
  • Privacy Policy
  • Affiliate Disclosure
  • Terms of Use

© 2026 The Olive Suitcase - Kadence Child Theme by Sarah Pasiuk

Manage Consent
To provide the best experiences, we use technologies like cookies to store and/or access device information. Consenting to these technologies will allow us to process data such as browsing behavior or unique IDs on this site. Not consenting or withdrawing consent, may adversely affect certain features and functions.
Functional Always active
The technical storage or access is strictly necessary for the legitimate purpose of enabling the use of a specific service explicitly requested by the subscriber or user, or for the sole purpose of carrying out the transmission of a communication over an electronic communications network.
Preferences
The technical storage or access is necessary for the legitimate purpose of storing preferences that are not requested by the subscriber or user.
Statistics
The technical storage or access that is used exclusively for statistical purposes. The technical storage or access that is used exclusively for anonymous statistical purposes. Without a subpoena, voluntary compliance on the part of your Internet Service Provider, or additional records from a third party, information stored or retrieved for this purpose alone cannot usually be used to identify you.
Marketing
The technical storage or access is required to create user profiles to send advertising, or to track the user on a website or across several websites for similar marketing purposes.
  • Manage options
  • Manage services
  • Manage {vendor_count} vendors
  • Read more about these purposes
View preferences
  • {title}
  • {title}
  • {title}
  • Home
  • Destinations
    • Athens
    • Crete
    • Mykonos
    • Santorini
  • Explore Greece
    • Greece Travel Tips
    • Itineraries
      • Santorini Itinerary
    • Travel Resources
  • Plan My Trip
    • Itinerary Review
  • About Me
  • Contact