Greek island hopping by gulet cruise in 2027 follows the same Saturday-to-Saturday format that made 2025 and 2026 fully sold out across all Sail in Greece routes. With 2027 dates now open for booking from May through October, early reservations are available on all six routes –Ionian, Zante, Rhodes, Mykonos, Harmony, and 18-39s -at 2027 prices that represent significant savings versus last-minute bookings.
Whether you’re planning a relaxing island escape, an adventure with friends, or your first sailing holiday in Greece, booking early gives you the widest choice of departure dates, cabins, and routes. Sail in Greece continues to offer authentic gulet cruises that combine stunning islands, crystal-clear waters, local cuisine, and unforgettable experiences that are difficult to replicate on larger cruise ships.
Why Plan Your 2027 Greek Island Cruise Early (2026 was fully sold out)
Demand for Greek island cruises has continued to grow every year. Following fully booked departures throughout the 2025 and 2026 seasons, many travellers are already securing their preferred dates for 2027.
Booking early provides several important advantages. You’ll have access to the full selection of departure dates between May and October, greater flexibility in choosing cabin types, and access to the best available prices before demand increases.
Unlike large cruise ships that visit crowded ports, Sail in Greece’s traditional gulets explore quieter bays, hidden beaches, charming fishing villages, and authentic Greek islands. Since each gulet accommodates a limited number of guests, availability naturally becomes limited much earlier than many travellers expect.
If you’re travelling with family, friends, or as part of a group, early reservations also ensure everyone can stay on the same departure.
The 6 Greek Gulet Cruise Routes Available in 2027
Sail in Greece offers six carefully designed itineraries, each providing a different perspective of the Greek islands while maintaining the company’s signature Saturday-to-Saturday cruise format.
Ionian Island Hopping (Corfu, Kefalonia, Ithaca, Zante)
The Ionian Cruise is one of the most popular routes for travellers seeking a balance of relaxation, sightseeing, swimming, and authentic Greek culture. Guests explore beautiful islands including Corfu, Kefalonia, Ithaca, Lefkada, Paxos, and Zante while enjoying daily swim stops in crystal-clear waters.
This itinerary is perfect for couples, families, and first-time visitors looking to experience some of Greece’s most picturesque islands.
Zante & Ionian Cruise (Kefalonia, Meganisi, Ithaca)
The Zante Cruise combines dramatic coastlines with peaceful island villages and famous natural attractions. Highlights include Kefalonia’s turquoise beaches, Meganisi’s quiet harbours, Ithaca’s legendary history, and the vibrant atmosphere of Zakynthos (Zante).
Travellers enjoy a mix of scenic sailing, local tavernas, optional excursions, and opportunities to swim in secluded coves that are only accessible by boat.
Rhodes & Dodecanese Cruise (Symi, Chalki, Tilos)
The Rhodes Cruise explores the beautiful Dodecanese islands in the southeastern Aegean Sea. Guests discover colourful harbours, medieval towns, peaceful villages, and crystal-clear anchorages throughout islands such as Symi, Chalki, Tilos, and Rhodes.
History lovers particularly enjoy this route because of its combination of ancient architecture, traditional island life, and impressive coastal scenery.
Mykonos & Cyclades Cruise
The Mykonos Cruise showcases the famous Cyclades island group, combining iconic destinations with lesser-known gems. Travellers experience whitewashed villages, blue-domed churches, lively waterfronts, and spectacular sunsets while exploring some of Greece’s most photographed islands.
The itinerary offers the perfect balance between vibrant nightlife, cultural exploration, relaxing beaches, and traditional Greek hospitality.
Harmony Cruise (Saronic Islands)
The Harmony Cruise explores the beautiful Saronic Gulf, located close to Athens. Islands such as Aegina, Poros, Hydra, and Spetses offer charming waterfront towns, historic landmarks, beautiful walking streets, and relaxed island living.
This route is ideal for travellers looking for shorter transfer times from Athens while still enjoying an authentic sailing experience through some of Greece’s most elegant islands.
18–39s Party Cruise
Designed specifically for younger travellers, the 18–39s Cruise combines island hopping with social experiences, beach parties, water activities, nightlife, and unforgettable memories.
Guests enjoy the same stunning sailing experience while meeting like-minded travellers from around the world. It’s an excellent choice for solo travellers, groups of friends, and anyone looking for a lively atmosphere alongside beautiful Greek scenery.
Best Months for a Greek Cruise in 2027 (with pricing guide)
The Greek sailing season runs from May through October, with each month offering something different.
May marks the beginning of the season, featuring pleasant temperatures, quieter islands, and attractive early-season pricing.
June offers warm weather, longer days, and ideal swimming conditions while remaining less crowded than peak summer.
July and August are the busiest months. Travellers enjoy consistently sunny weather, vibrant nightlife, and lively island events. Due to high demand, these months usually command premium prices and sell out first.
September is considered one of the best months for sailing. The sea remains warm after summer, temperatures become more comfortable, and popular destinations become less crowded.
October provides a peaceful end to the sailing season, with mild weather, beautiful sunsets, and excellent value for travellers seeking a quieter experience.
As a general guide, departures in May and October are typically the most affordable, June and September offer excellent value, while July and August represent peak-season pricing due to demand.
For current weather conditions and seasonal climate information, you can also refer to the Official Greek National Tourism Organisation.
What’s Changed for 2027 -New Destinations, Fleet Updates
The 2027 season continues Sail in Greece’s commitment to delivering authentic small-group sailing experiences while maintaining the high standards that have made previous seasons so successful.
Guests can expect carefully maintained traditional gulets, experienced local crews, flexible swim stops depending on weather conditions, and continuously refined itineraries designed to maximise time on the water and time exploring each destination.
Operational improvements, guest feedback, and itinerary refinements continue to enhance the overall experience while preserving the relaxed atmosphere that defines a Sail in Greece holiday.
As additional updates become available for the 2027 season, they will be reflected across individual cruise pages and departure schedules.
How to Book Your 2027 Greek Gulet Cruise (deposit, process)
Booking your 2027 cruise is simple.
- Choose the cruise route that best matches your travel style.
- Select your preferred departure date between May and October.
- Complete your reservation online.
- Pay the required deposit to secure your cabin.
- Receive your booking confirmation and travel information.
- Complete the remaining balance according to the payment schedule before departure.
Because 2025 and 2026 departures reached full capacity, booking early is strongly recommended, especially for July and August departures and for travellers requiring multiple cabins.
If you’re unsure which itinerary is right for you, the Sail in Greece team can help recommend the best route based on your travel preferences, budget, and group size.
Frequently Asked Questions
Is 2027 booking now open?
Yes. Sail in Greece has opened bookings for the 2027 season, with departures scheduled from May through October.
Why should I book early?
Previous seasons sold out well in advance. Early booking gives you access to the widest choice of dates, cabins, and pricing.
Which cruise route is best for first-time visitors?
The Ionian Cruise is often recommended for first-time visitors because it combines beautiful scenery, relaxed sailing, charming villages, and iconic Greek islands.
Are meals included on board?
Meals and onboard inclusions vary depending on the selected cruise. Please refer to the individual cruise page for complete details before booking.
How much deposit is required?
The required deposit and payment schedule are shown during the booking process and may vary depending on the selected cruise and departure.
Start Planning Your Greek Island Adventure
A gulet cruise remains one of the most rewarding ways to discover Greece. Instead of rushing between crowded ferry terminals or visiting only the busiest tourist destinations, you’ll wake up each morning surrounded by the sea, swim in secluded bays, enjoy authentic Greek cuisine, and explore islands at a relaxed pace.
With 2027 departures now available and previous seasons selling out completely, early planning provides the best opportunity to secure your preferred itinerary and travel dates. Whether you’re dreaming of the Ionian Islands, the Cyclades, the Dodecanese, or a lively social sailing experience, Sail in Greece offers a route designed for every type of traveller.
Start planning today and make 2027 the year you experience the Greek islands from the deck of a traditional gulet.
