Board at Pera Gialos and sail to Kounoupa for a moonlit dinner and sunset framed by Astypalaia’s castle. This five-hour evening cruise mixes relaxed dining, starry returns, and close-up coastal views.
Board at Pera Gialos and sail to Kounoupa for a moonlit dinner and sunset framed by Astypalaia’s castle. This five-hour evening cruise mixes relaxed dining, starry returns, and close-up coastal views.
The sun slides along the castle walls as the yacht slips from Pera Gialos, the decks warming under a last golden hour. Guests lean on the rail with a welcome cocktail in hand, the Aegean breathing steadily around them as the coastline recedes and Kounoupa’s low silhouette grows against the horizon.
Verified experiences and guided adventures in the surrounding area.
Operated by Astypalea VIP Yachting · Pera Gialos, Astypalaia, South Aegean
The sun slides along the castle walls as the yacht slips from Pera Gialos, the decks warming under a last golden hour. Guests lean on the rail with a welcome cocktail in hand, the Aegean breathing steadily around them as the coastline recedes and Kounoupa’s low silhouette grows against the horizon.
Astypalaia sits where Cycladic white meets Dodecanese ruggedness; the island’s history is written in Venetian ramparts and maritime lanes that have steered sailors for centuries. Geologically, volcanic and limestone strata shape jagged coves and shallow reefs—features that make the short sail to Kounoupa scenically dramatic and safe for evening anchoring. Local culture here is quietly maritime: modest tavernas, fresh cheeses and simple seafood are the language of celebration.
On this five-hour cruise travelers can expect a relaxed, romantic itinerary: a 45-minute sail from Pera Gialos, cocktails and light plates on arrival, sunset views framed by the castle, and return under star-pinned skies. The boat provides onboard restrooms and seating; lighting and soft music set a low-key mood for dinner on the island.
Practical notes: bring a light windproof layer for the cooler post-sunset sea, non-slip shoes for boarding, and motion-sickness remedies if you’re prone. Reservations are advised in high season; check the cancellation window (24 hours) and confirm departure from Pera Gialos. For photographers, low light yields dramatic silhouettes—arrive early to claim a rail-side spot and charge devices before you leave shore.
easy.
5 hours.
Suitable for all fitness levels; involves brief standing and boarding steps
The cruise departs from Pera Gialos port (main harbor) and returns to the same port at the end of the evening.
Yes—small plates, local cheeses, fresh fruit, and a main dish are served on the island, plus a welcome drink on board.
Infants are allowed but must sit on an adult’s lap; the trip is generally suitable for all ages with basic safety precautions.
Full refund available if cancelled at least 24 hours before departure; trips may be cancelled for bad weather or insufficient travelers.
Astypalaia’s Chora is dominated by a Venetian castle and masonry that reflect centuries of Aegean trade and island defense; maritime routes since antiquity shaped local life.
Visitors should avoid anchoring on seagrass beds and respect dark-sky conditions to protect marine life and nesting zones; local operators often follow low-impact practices.
Astypalea VIP Yachting operates guided outdoor trips and adventures with an emphasis on safety, stewardship, and memorable experiences.




The sun slides along the castle walls as the yacht slips from Pera Gialos, the decks warming under a last golden hour. Guests lean on the rail with a welcome cocktail in hand, the Aegean breathing steadily around them as the coastline recedes and Kounoupa’s low silhouette grows against the horizon.
The sun slides along the castle walls as the yacht slips from Pera Gialos, the decks warming under a last golden hour. Guests lean on the rail with a welcome cocktail in hand, the Aegean breathing steadily around them as the coastline recedes and Kounoupa’s low silhouette grows against the horizon.
Astypalaia sits where Cycladic white meets Dodecanese ruggedness; the island’s history is written in Venetian ramparts and maritime lanes that have steered sailors for centuries. Geologically, volcanic and limestone strata shape jagged coves and shallow reefs—features that make the short sail to Kounoupa scenically dramatic and safe for evening anchoring. Local culture here is quietly maritime: modest tavernas, fresh cheeses and simple seafood are the language of celebration.
On this five-hour cruise travelers can expect a relaxed, romantic itinerary: a 45-minute sail from Pera Gialos, cocktails and light plates on arrival, sunset views framed by the castle, and return under star-pinned skies. The boat provides onboard restrooms and seating; lighting and soft music set a low-key mood for dinner on the island.
Practical notes: bring a light windproof layer for the cooler post-sunset sea, non-slip shoes for boarding, and motion-sickness remedies if you’re prone. Reservations are advised in high season; check the cancellation window (24 hours) and confirm departure from Pera Gialos. For photographers, low light yields dramatic silhouettes—arrive early to claim a rail-side spot and charge devices before you leave shore.