Explore Iraklia, Amorgos and Koufonisia with cavern dives, wreck diving and island hopping across the Small Cyclades.
This Small Cyclades sailing and diving itinerary from Paros combines island hopping, advanced diving experiences and authentic Greek island culture in one immersive week. Starting from Paros, the route explores some of the most remote and unspoiled islands in the Cyclades, including Iraklia, Amorgos, Dryma, Antikeri and Koufonisia.
The itinerary is designed for travelers looking to combine sailing in the Cyclades with diving, featuring a variety of underwater experiences such as cavern dives, reef exploration and a unique World War II plane wreck dive. Each day alternates between sailing, diving and time at anchor in protected bays with clear waters and excellent visibility.
Beyond diving, the cruise includes visits to traditional villages, local tavernas and quiet anchorages rarely reached by mass tourism. Islands like Iraklia and Kato Koufonisi offer a slower pace of life, while Amorgos adds cultural depth and scenic landscapes.
Life on board follows a relaxed rhythm, with time for swimming, sunbathing and enjoying the surrounding nature. This Greece sailing and diving holiday is ideal for those seeking a balance between adventure, exploration and authentic island experiences in the Small Cyclades.
Itinerary
Day1
Paros Check-in, Briefing and First Evening
Your Small Cyclades sailing and diving holiday from Paros begins with check-in at 17:00. After boarding, you will settle into your cabin and meet the crew and fellow guests.
A detailed briefing follows, covering safety procedures, onboard routines and the diving plan for the week. Equipment is checked and prepared, and provisioning is organized for the days ahead.
In the evening, take time to explore Paros town, known for its whitewashed streets and lively harbor atmosphere, before enjoying a welcome dinner in a traditional Greek taverna. This first evening introduces the relaxed rhythm of the cruise.
Day2
Pantieronisia Cavern Dive and Iraklia Island
After breakfast, sail toward the remote Pantieronisia islands, an uninhabited group ideal for cavern diving in the Cyclades.
The first dive of the week takes place in a natural underwater cavern, where light filters through rock formations creating unique visual effects. The site is known for its clear visibility and calm conditions.
After the dive, anchor in a sheltered bay for swimming, snorkeling and lunch on board. In the afternoon, sail to Iraklia Island, one of the most peaceful islands in the region.
The evening is spent ashore in the village, with dinner in a local taverna offering simple and authentic Greek dishes.
Day3
Alimia Plane Wreck Dive and Amorgos Sailing
The day begins with a highlight dive at the WWII plane wreck in Alimia Bay, one of the most interesting dive sites in the Small Cyclades. The wreck lies in clear waters and is surrounded by marine life, offering a combination of history and underwater exploration.
After the dive, sail toward Amorgos Island, stopping at Nikouria Bay for a swim and lunch in calm waters.
Arrival in the Aegiali area provides time to explore traditional villages, walk along the harbor and enjoy dinner ashore. Amorgos is known for its authentic character and scenic landscapes.
Day4
Dryma and Antikeri Islands, Cave Diving and Remote Anchorage
A short sail leads to the isolated islands of Dryma and Antikeri, offering one of the most exclusive diving environments in the Cyclades.
The dive focuses on a colorful underwater cavern, with rock formations, light contrasts and excellent visibility. After the dive, the afternoon is spent relaxing at anchor in a completely untouched setting.
In the evening, a beach barbecue is organized on a small natural strip between the islands. The night is spent at anchor under the stars, far from any port, offering a unique off-grid experience.
Day5
Reef Dive and Kato Koufonisi
Sail toward the Koufonisia islands, stopping at an offshore reef for a lively dive rich in marine biodiversity. The area is known for its abundance of fish and clear waters, making it suitable for both experienced and intermediate divers.
After the dive, continue to Kato Koufonisi, one of the least developed islands in the Cyclades. Its turquoise waters and minimal human presence create a peaceful environment ideal for relaxing.
Dinner is enjoyed ashore in a small traditional taverna run by one of the few resident families.
Day6
Coastal Sailing and Return to Paros
Begin the return journey toward Paros, with a relaxed sailing day along the Cycladic coastline.
Stops are made in selected bays for swimming and lunch, depending on weather conditions. The final destination is Piso Livadi, a small fishing port with a local atmosphere.
Guests may visit the nearby village of Prodromos, known for its narrow streets and traditional architecture, before enjoying a final dinner ashore.
Day7
Disembarkation in Paros
After breakfast, disembarkation takes place, marking the end of your Small Cyclades sailing and diving experience. Guests can continue exploring Paros or travel onward.
Note
This Cyclades sailing and diving itinerary is designed to remain flexible. Routes, dive sites and stops may vary depending on weather conditions, sea state and visibility, ensuring the best possible experience both above and below the water.
Cruise price details
Yacht - Catamaran 45ft
Sailing Yacht for Comfortable Mediterranean Cruises
This classic sailing yacht is designed to offer a balance between reliable sailing performance and onboard comfort, making it an excellent choice for a relaxed sailing holiday in the Mediterranean.
The layout includes 4 double cabins, with a recommended capacity of up to 6 guests to ensure more space and a comfortable onboard experience. There are 2 bathrooms with showers, along with a stern shower for easy access after swimming or water activities.
The interior features high quality wood finishes, creating a warm and traditional atmosphere, with good headroom, practical storage solutions and well ventilated cabins suitable for extended stays on board. The saloon benefits from natural light, enhancing everyday comfort during the cruise.
Outdoor spaces are designed for both sailing and relaxation, with a spacious cockpit and wide deck areas ideal for sunbathing and enjoying the sea. The yacht also offers easy access to the water, making it perfect for swimming, snorkeling and marine exploration.
This yacht is ideal for travelers looking for an authentic sailing experience, combining classic design, comfort and a smooth sailing experience along coastal destinations.
Yacht
Model
1983 Catamaran 45ft
Length
14 m
Yacht services
Tender size
14 m
Air conditioning
Yes
Accommodations
Max guests
6
Double cabins
3
Bathrooms
3
Private Bathrooms
Yes
Crew
1
Chef on board
No
Other facilities
VHF DCS
echo sounder
laptop
internet access
CD stereo
DVD
Cabins
Double Standard Cabin
2
cabin capacity
double bed
private bathroom
air conditioning
Cruise activities and tips
Travel organizer tips
What to pack for a sailing holiday?
Pack smart for your yacht charter: choose a soft bag instead of a hard suitcase, bring lightweight layers, reef-safe sunscreen, and non-slip shoes for onboard use. A couple of swimsuits and motion sickness remedies can also make a big difference. Each boat has limited storage, so pack light, but wisely! Need help building the perfect list? Read our full guide: What to pack in a suitcase for a yacht charter
What’s a Typical Day Like on a Yacht Charter?
Start your day with a swim in a quiet bay, sail to hidden beaches or seaside villages, and enjoy a slow lunch on deck. Afternoons mean snorkeling, sunbathing, or exploring ashore. As the sun sets, your boat anchors in a scenic cove or near a harbor, ready for a relaxed dinner and a night under the stars. Curious about the full experience? Discover more in our guide: What’s a typical day like on a sailing holiday?
Who Handles Cooking and Cleaning on a Yacht Charter?
On skipper-only charters, guests usually share cooking and cleaning duties, think salads, pasta, and good teamwork. If there's a hostess, light meals and tidying are included, but it's still a casual, collaborative vibe. On fully crewed yachts, you’ll enjoy full service with a chef and crew managing everything. Want to know what’s included in your setup? Read the full guide: Who takes care of cooking and cleaning on a sailing charter?
What Happens in Case of Bad Weather During a Sailing Holiday?
Summer sailing holidays rarely face major weather issues, but when the sea gets rough, skippers adjust the route for your safety. Expect protected bays, marina stops, or a change in plan. These moments often lead to unexpected gems: local towns to explore, time to relax on board, or cozy dinners ashore. Curious about how crews handle these changes? Read the full FAQ: What to do in case of adverse weather conditions or changes to the itinerary
