Greece Vacation Packages & Greek Islands Tours

Santorini sunsets, Mykonos beaches, Athens history, and Crete coastline — custom Greece vacations planned by a certified advisor with a personal connection to Greece.

Plan Your Greece Trip

Greece offers one of the world's most rewarding vacation experiences — ancient history, dramatic island scenery, legendary hospitality, and some of the finest food in Europe. Working with a certified Connecticut travel advisor who knows Greece personally means a better-designed itinerary, fewer logistics headaches, and a trip that goes beyond the highlights.

I plan Greece vacations — land tours, island-hopping itineraries, and Greek isles cruises.

Kelly Bonatsakis, certified travel advisor at Vacations by Kelly

From Kelly

A Personal Connection to Greece

Greece is not just another destination for me — it is part of my heritage. I am of Greek descent, and I have toured Greece firsthand. That personal and cultural connection shapes every Greece itinerary I build.

On the cruise side, I have personally sailed on Celebrity Eclipse as well as multiple Royal Caribbean ships, including Anthem of the Seas, Oasis of the Seas, Symphony of the Seas, Independence of the Seas, and Freedom of the Seas. That firsthand experience means I can give you an honest picture of what a Greek isles cruise actually feels like from deck, not just from a brochure.

I am CLIA and IATA certified and affiliated with World Via / Travel Leaders.

Why Book a Greece Vacation Through a Travel Advisor?

Greece rewards careful planning. Island-hopping logistics — ferry schedules, airport connections, port timing — can quickly become overwhelming when you are piecing it together yourself. An advisor who knows the destination handles the complexity so you can focus on the experience.

I match each client with the right type of Greece vacation: whether that is a relaxed two-island stay in Santorini and Crete, a deeper mainland-plus-islands itinerary including Athens, or a Greek isles cruise that covers multiple ports in one trip. The best itinerary depends on your travel style, timeline, and who you are traveling with.

I coordinate flights, airport transfers, guided tours, and ferry crossings — and I am available before, during, and after your trip if anything needs adjusting.

Infinity pool overlooking the sea at a Mediterranean resort

Cruise ship deck overlooking the open sea

Greek Isles Cruise or Land Tour: Which Is Right for You?

A Greek isles cruise is one of the most efficient ways to experience multiple islands in a single trip. Ships call at ports like Santorini, Mykonos, Rhodes, and Corfu within one itinerary, with your accommodations traveling with you between stops. Celebrity Cruises and Royal Caribbean both offer Mediterranean itineraries with Greek island ports, and having sailed both lines personally, I can advise which ships and itineraries provide the best Greek coverage.

A land-based Greece tour offers more time per location and more flexibility. You can spend several nights in Santorini, take the ferry to Crete at your own pace, and build in time to explore without a ship's schedule constraining you. For travelers who want depth over breadth, this is often the stronger choice.

Many clients do a hybrid — a cruise anchoring the Greek islands portion, combined with a few days in Athens before or after. I help you think through the trade-offs based on your travel party and priorities. I also plan cruise vacations to other destinations if you want to compare options.

The Greek Islands: Where to Go

Each island has its own character. Here is a high-level picture to help you start thinking about where to go and how long to stay.

Santorini

Santorini is one of the most visually iconic places on earth. The caldera-top villages of Oia and Fira, whitewashed architecture, and dramatic sunset views are genuinely as striking as the photographs. It is a top choice for couples and honeymooners. The island is compact, and its main appeal is atmosphere, wine, and scenery rather than nightlife or extensive beach culture.

Mykonos

Mykonos is known for its cosmopolitan energy, vibrant nightlife, and beautiful beaches. The Chora — the old town with its iconic windmills and narrow alleys — is charming during the day; by evening the island comes alive. It is a popular destination for groups and travelers looking for a lively social scene alongside genuine Cycladic beauty.

Athens

Athens is the essential starting point for most Greece itineraries. The Acropolis and the Parthenon remain one of the world's great historical sites, and the neighborhoods below — Plaka, Monastiraki, Syntagma — offer excellent food, markets, and layers of history. Most travelers spend two to three days in Athens before heading to the islands.

Crete

Crete is Greece's largest island and one of its most diverse. It offers ancient Minoan ruins at Knossos, dramatic gorges, excellent beaches along both the north and south coasts, and a distinctive food culture. Crete rewards longer stays and suits travelers who want more than a purely scenic experience.

Which Greek Island Is Right for You?

A quick reference for matching your travel style to the right destination.

Greek islands and mainland destinations at a glance
Destination	Best For	Vibe
Santorini	Couples, honeymoons, sunset seekers	Dramatic caldera views, romantic and atmospheric
Mykonos	Social travelers, beach lovers, nightlife	Cosmopolitan and lively with iconic Cycladic charm
Crete	History, hiking, varied scenery	Diverse and unhurried — Greece's largest island
Rhodes	History and beach combined	Medieval old town meets long sandy coastline
Corfu	Lush greenery, relaxed pace	Verdant island with distinct Venetian-influenced character
Athens (mainland)	First-timers, history lovers	Ancient monuments alongside a vibrant modern city

Not sure which destinations to combine? Send me a message and I will help you build the right itinerary.

Greece Vacation Planning: Common Questions

When is the best time to visit Greece?

Late spring (May to early June) and early fall (September to October) are generally the most pleasant times to visit. The weather is warm and sunny, the crowds are thinner than peak summer, and prices tend to be lower than in July and August. Peak summer is the busiest period — particularly in Santorini and Mykonos — with high heat and higher prices. Shoulder-season travel often makes for a better overall experience.

How many days do you need for a Greece vacation?

Most travelers benefit from at least ten to fourteen days, which allows time in Athens plus two or three islands without feeling rushed. A shorter trip of seven to eight days works well if you focus on one or two locations. If you are doing a Greek isles cruise, the ship's itinerary sets the pace, and you will typically visit four to six ports over seven to ten nights.

Is island hopping in Greece difficult to arrange on your own?

It is doable, but can be surprisingly complex. Ferry schedules, port locations, luggage logistics, and timing connections between islands all require careful coordination — and schedules change seasonally. An advisor who knows the routes helps you avoid common pitfalls, like choosing a ferry crossing that is longer or rougher than expected, or booking a tight connection at a busy port that is hard to make.

Is Greece an expensive destination?

Greece is generally more affordable than many Western European countries, but costs vary significantly by island. Santorini and Mykonos are among the pricier destinations in the Mediterranean, with elevated accommodation and dining costs at peak season. Athens and Crete tend to offer better overall value. A well-planned Greece trip can work across a range of budget levels, depending on island selection, travel timing, and accommodation tier.

More Vacation Planning Resources

I plan a full range of vacations for Connecticut travelers. These pages cover the most popular destination types I work with.

Cruise Vacation Planning — Greek isles cruises and beyond, with lines I have personally sailed.
All-Inclusive Resort Planning — Caribbean and Mexico resorts if you are looking for a more traditional beach vacation.
Glastonbury, CT Travel Agent — Learn more about my certifications and how I work with clients.
About Kelly — My background, affiliations, and approach to travel planning.

Ready to Plan Your Greece Vacation?

Whether you are dreaming of a cruise through the Greek islands, a land tour anchored in Athens and Santorini, or a combination of both — I will build an itinerary around your travel style and handle every detail.

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