Adults enjoy a luxury family sailing holiday with full crew service

Prepare yourself for total relaxation! With Crossing the Sea you can rest assured you are in for a summer experience where we have thought of everything. Whatever you like to do best on holiday, you can do with Family Sailing. Would you rather relax on a private beach under designer sunshades, sip cocktails on the deck of your yacht or go off to explore the islands? Just let your crew know and they will set up the beach, mix you a drink or suggest walking tracks for you. You are free to decide.
  • CTS Family Sailing Holidays Greece Adults food
  • CTS Family Sailing Holidays Greece Adults tea
  • CTS Family Sailing Holidays Greece Adults food

  • Boatique... Boat + Boutique

Our boats have been designed like boutique hotels, down to the very last detail! Carefully selected Italian-design choice linens and tableware provide a touch of elegance to every setting. We also provide daily housekeeping services and mid-week linen changes.
  • CTS Family Sailing Holidays Greece Adults Sailaxing
  • CTS Family Sailing Holidays Greece Adults Sailaxing
  • CTS Family Sailing Holidays Greece Adults Sailaxing

  • Sailaxing ... Sailing + Relaxing

Our Family Sailing crew have one goal when it comes to looking after our adult guests: relaxation from sunrise to sunset! We find deserted beaches to set up luxurious buffet lunches for you to indulge in the perfect luxury beach-picnic. If you feel like something more active try your hand at water skiing, canoeing, banana boat rides, snorkelling, stand up paddle boarding, windsurfing, sea-scooters, or fishing.
  • CTS Family Sailing Holidays Greece Gourmit
  • CTS Family Sailing Holidays Greece Gourmit
  • CTS Family Sailing Holidays Greece Gourmit

  • Gourmit ... Gourmet + Italy

Italian cuisine is always a crowd pleaser and we offer you a truly gastronomic experience made from the best ingredients and flavours with everything sourced fresh and in season. You will sample traditional Italian cuisine with a touch of modernity to please even the most discerning of palates.
  • CTS Family Sailing Holidays Greece Seascovery
  • CTS Family Sailing Holidays Greece Seascovery
  • CTS Family Sailing Holidays Greece Seascovery

  • Seascovery... Sea + Discovery

Make the most of the fact that the kids are having a great time under the watchful eye of professionals and have an adventure of your own! Each boat has its own skipper so you are free to sail around the bays and coastline to explore as you like. There is also an organised excursion where you can discover the island by quadbike or scooter for a change of pace.

  • CTS Family Sailing Holidays Greece Staffcooning
  • CTS Family Sailing Holidays Greece Staffcooning
  • CTS Family Sailing Holidays Greece Staffcooning

  • Staffcooning... Staff + Cocooning

At Crossing the Sea we pride ourselves on attention to detail and thinking of what you want before you even realise it for yourself! Your floating boutique hotel with luxury Italian linens and tableware sets the scene, while your crew make sure all your needs are met. Our team are always ready to set up on an empty beach for you with designer sunshades and loungers or if you want to make your way onshore and have a picnic lunch all you have to do is ask and the team will prepare a basket for you.