The Greek Islands offer one of Europe’s most enchanting cruise experiences, blending ancient history, sun-drenched beaches, and timeless island charm. While large vessels flock to hotspots like Santorini and Mykonos, luxury small ship cruises Greek Islands provide a more intimate and authentic way to explore. These boutique voyages access secluded harbors and lesser-known gems unreachable by bigger ships, giving travelers a deeper connection with Greece’s diverse island culture.
From the whitewashed villages of Paros to the sacred ruins of Delos, each stop offers something unique. Most small ship cruises Greece depart round-trip from Athens or include destinations like Italy, Croatia, or Turkey, extending the adventure beyond the Aegean. Sailing season runs from May to October, with early booking recommended due to limited availability. If you’re looking for a relaxed yet luxurious way to discover Greece, these curated cruises deliver exceptional experiences, stunning scenery, and the freedom of effortless island-hopping.
1. SeaDream Yacht Club
SeaDream Yacht Club offers an ultra-luxury experience ideal for travelers seeking luxury small ship cruises Greek Islands. Founded in 2001 by Atle Brynestad, also the founder of Seabourn Cruise Line, SeaDream is a family-owned company operating two award-winning mega-yachts: SeaDream I and SeaDream II. With the philosophy “It’s Yachting, Not Cruising®”, SeaDream provides a casually elegant alternative to traditional cruising. These yachts feature ocean-view suites, inclusive fine dining, a golf simulator, spa treatments, water sports, and even mountain bikes for onshore exploration.
Designed to access intimate ports unreachable by larger ships, these small ship cruises Greece focus on immersive experiences and exceptional service. From May to October, SeaDream sails through the Mediterranean, including the Greek Islands, with overnight stays in select yachting harbors. With a highly attentive crew and a guest-focused atmosphere, SeaDream delivers personalized, pampered voyages that keep guests returning again and again. Discover Greece in unmatched style aboard SeaDream.
2. Windstar Cruises
Windstar Cruises offers a truly immersive way to experience the world, especially through its small ship cruises Greece and beyond. With vessels accommodating just 148 to 342 guests, Windstar blends casual elegance with world-class service, earning recognition as Travel + Leisure’s Best Midsize-Ship Ocean Cruise Line in 2022. Their signature luxury small ship cruises Greek Islands include round-trip voyages from Athens, visiting enchanting ports like Crete, Santorini, and Rhodes.
The onboard experience is intimate and personalized, with access to hidden bays and complimentary watersports via the ship’s private marina. Windstar offers two distinct yacht styles: the classic Wind Class sailing yachts and the all-suite Star Plus Class. Each stateroom and suite is designed for comfort with Egyptian linens, marble bathrooms, and L’Occitane products. With over 2,000 authentic shore excursions and regionally inspired cuisine prepared with fresh, local ingredients, Windstar connects guests to cultures in unforgettable ways. This is not just cruising — it’s transformative travel by sea.
3. Ponant
Ponant Cruises is the epitome of refined elegance at sea, offering luxury small ship cruises Greek Islands with a distinctly French touch. Founded in 1988, Ponant has become a pioneer in boutique cruising, combining cultural richness with modern innovation. Its chic fleet includes the stylish Explorer Class yachts and elegant Sister Ships, all operating small ship cruises Greece from April to October. These itineraries range from iconic stops like Mykonos and Santorini to exclusive gems such as Hydra, Limnos, and picturesque Symi—destinations unreachable by large vessels.
With passenger capacities kept intentionally low, Ponant delivers a near-private yacht experience. The French art of living is expressed through gourmet cuisine, intuitive hospitality, and elegant design. Onboard amenities include luxurious spas, fitness areas, panoramic lounges, a theatre, and serene pool decks. Multilingual crews provide personalised service with impeccable attention to detail, making every moment on board feel bespoke.
4. Sea Cloud Cruises
Sea Cloud Cruises offers a sailing experience unlike any other—an enchanting return to the golden age of windjammers. Sailing aboard one of their majestic tall ships, such as the legendary Sea Cloud, Sea Cloud II, or the modern Sea Cloud Spirit, is like stepping into a timeless voyage where the rhythm of the wind and waves dictates each day. These fully rigged three- and four-masted ships, with sails hoisted entirely by hand, provide an authentic and awe-inspiring spectacle at sea.
With a maximum of just 136 guests, Sea Cloud Cruises delivers an intimate, yacht-like ambiance. This small scale allows access to charming, lesser-known ports like Paxos, Spetses, Milos, and Patmos—hidden gems far beyond the reach of large cruise ships. Onboard, guests enjoy the warmth of a close-knit community, where classic seamanship, respect for local cultures, and a deep appreciation of nature are central to the experience.
Destinations span the sun-kissed Mediterranean, the diverse landscapes of the Canary Islands and Morocco, the untouched beauty of the Azores and Madeira, and the breezy, idyllic Lesser Antilles. Whether exploring picturesque old towns or simply enjoying life under sail, each journey with Sea Cloud Cruises transforms travel into a soulful and memorable experience.
5. Silversea
Silversea pioneered the concept of all-inclusive luxury small ship cruises, and are widely acclaimed for their impeccable personal service and diverse itineraries. Their classic fleet ranges from the 296-guest Silver Wind to the 608-guest Silver Spirit, both offering refined experiences on small ship cruises Greece is known for.
They offer a range of luxury small ship cruises Greek Islands-bound, with itineraries typically including well-known destinations such as Mykonos, Santorini, Rhodes and Corfu. Most voyages are round-trips from Athens or end in Venice, with durations from 7 to 14 nights running between April and October in 2025 and 2026. Some select itineraries also operate in winter, revealing the Greek Islands in a refreshingly tranquil and different light.
6. Seabourn
Seabourn offers one of the most refined luxury small ship cruises Greek Islands-bound, with an ultra-modern fleet comprising 458-guest sister ships and the elegant Encore and Ovation, each accommodating 604 guests. Known for their private yacht-like ambiance, Seabourn ships are designed by Tihany Design and offer all ocean-front suites—most with private verandas. Guests enjoy intuitive service, world-class dining, complimentary premium spirits, fine wines, and signature experiences like Caviar in the Surf® and Evening at Ephesus.
Seabourn’s small ship cruises Greece itineraries include 14-night journeys featuring destinations like Santorini, Patmos, Kos, and Symi, as well as ports in Malta, Turkey, and Sicily. Select sailings also explore Croatia, Slovenia, and even stretch as far as Dubai. Expedition voyages on Seabourn Venture introduce immersive excursions with expert-led Zodiac tours, nature walks, and submersible dives. With included Wi-Fi, entertainment, gratuities, and curated shore experiences, Seabourn defines luxury exploration on both classic and expedition journeys, blending comfort with adventure on every voyage.
7. Crystal Cruises
Crystal Cruises offers an exceptional all-inclusive experience with award-winning service, luxurious accommodations, and world-class dining. Since their relaunch in February 2023, they have elevated personalized service across their elegant fleet. The 606-guest Crystal Symphony and 740-guest Crystal Serenity sail through the Mediterranean from May to October, visiting iconic destinations such as Mykonos, Santorini, and Katakolon—gateway to ancient Olympia. Designed for discerning travelers, Crystal Cruises blend comfort, sophistication, and cultural discovery seamlessly. Ideal for those seeking small ship cruises Greece-bound, they offer immersive journeys that highlight the region’s charm, history, and coastal beauty with unparalleled elegance and attention to detail.
8. Emerald Cruises
Emerald Cruises offers one of the finest luxury small ship cruises Greek Islands bound, aboard the sleek and stylish Emerald Azzurra. This superyacht-style vessel combines elegance and intimacy with top-tier features, including an infinity-style pool, al fresco Sky Bar, wellness centre, and a watersports marina perfect for exploring the coves of the Aegean. Operating from April to October 2025 and 2026, itineraries include iconic destinations like Mykonos and Santorini, cultural treasures such as Delos and Rhodes, and hidden gems like Paros and Lefkada’s Nydri. With the option to extend your journey with stays in Athens, Emerald Cruises delivers a refined yet relaxed experience designed for travellers who appreciate comfort, history, and immersive adventure.
