calypso boat rental

Your Private Cruise from Sifnos – Tailored Just for You

At Calypso, we make every sea journey unique. Our private boat cruises with skipper let you explore the Aegean your way — from hidden coves and sea caves to Sifnos’ stunning coastline — all with the warm hospitality that defines our team.

️ Ready to sail?

Choose your preferred cruise below, pick your boat, select your date, and book online to secure your spot on board.

We in the Calypso team are here to make your time on the water safe, joyful, and truly unforgettable.

Our RIBs

IMG-20240701-WA0001
tender-boat-services
thetis_aerial
1
thetis_koufonissia

Fost Matrix RIB Black Edition

lefkippi_aerial
IMG-20230905-WA0000-1079x650
IMG-20240709-WA0003
IMG-20240608-WA0007

Fost Matrix RIB white Edition

Cruises

Milos Cruise

Milos (Half Day – Famous Cruise)

see our cruise
Poliegos

Poliegos (Half Day)

see our cruise
Sifnos (Half Day)

Sifnos (Half Day)

see our cruise
Polyaigos – Kimolos (Half Day)

Polyaigos – Kimolos (Half Day)

see our cruise
Milos (Half Day) Sarakiniko

Milos (Half Day) Sarakiniko

see our cruise
Serifos (Half Day)

Serifos (Half Day)

see our cruise
Folegandros (Half Day)

Folegandros (Half Day)

see our cruise
Antiparos (Half Day)

Antiparos (Half Day)

see our cruise
Milos (All Day)

Milos (All Day)

see our cruise
Sifnos (All Day)

Sifnos (All Day)

see our cruise
Milos NorthWest

Milos NorthWest (Half Day)

see our cruise

Choose Your Cruise Duration:

Half-Day Cruise (5 hours)

Morning Cruise: 09:00 – 14:00

Afternoon Cruise: 15:00 – 20:00

Full-Day Cruise (9–11 hours)

Our full-day trip allows you to visit more isolated islands and spend more time at each stop if you're looking for more time to explore, relax, and fully immerse yourself in the Cycladic seascape. Ideal for longer lunches at beachside tavernas, long swims, or beach hopping.

A Sea Experience that Recharges Body & Soul

Spending a day at sea is not just a holiday treat — it’s a gift to your well-being. The benefits are many:

  • The sea breeze and salty air clear your mind and uplift your mood
  • The gentle rhythm of the waves helps you relax and recharge
  • And, of course, sunlight boosts your vitamin D and your spirit
  • Swimming in natural waters activates your body and improves circulation

What’s Included in Every Cruise

With Calypso, comfort comes standard. All our private cruises include:

  • Chilled refreshments & bottled water
  • A delicious cheese and fruit platter
  • Professional skipper with deep knowledge of the area
  • Friendly, relaxed atmosphere — we welcome you like friends, not clients
  • Snorkeling gear available on request (All included in the price – no hidden extras)