• Sign up
  • Log in
Sailsquare
      • All Greece
      • Ionian Islands
      • Cyclades
      • Dodecanese
      • Saronic Islands and Athens area
      • All Italy
      • Northern Sardinia
      • Aeolian Islands
      • Aegadian islands
      • Tuscany
      • Liguria
      • Pontine Islands
      • Amalfi Coast
      • All Spain
      • The Balearic Islands
      • Andalusia
      • Catalunya
      • Galicia
      • Valencia
      • All Caribbean
      • BVI - British Virgin Islands
      • Antigua and Barbuda
      • Cuba
      • Grenadines & Martinique
      • Guadeloupe
      • Bahamas
      • Belize
      • All Indian Ocean
      • Bali
      • The Maldives
      • Mauritius
      • Seychelles
      • Corsica
      • French Riviera and Porquerolles
      • Brittany and Normandy
      • Split Archipelago
      • Kornati Islands
      • Turkey
      • French Polynesia
      • Norway
      • Adventure
      • Courses & regatta
      • Day trips
      • Flotilla
      • Offshore
      • Sport & wellness
      • WWF Sailing Cruises
      • Whole boat with skipper
      • All inclusive
      • Crewed
      • Catamaran
      • Gulet and sailing ship
      • Monohull
      • Mediterranean
      • Families
      • Couples
      • Solo Travellers
      • Exotic
      • Whale watching
  • Rent a boat
  • Call us
    +44 20351 44220
    • ITA
    • FRA
    • DEU
    • ESP
  • You have 0 messages!
  • 0 new alerts for you!
  • Message area
  • Holiday wishlist
  • My profile
  • Edit account
  • Log out
      • All Greece
      • Ionian Islands
      • Cyclades
      • Dodecanese
      • Saronic Islands and Athens area
      • All Italy
      • Northern Sardinia
      • Aeolian Islands
      • Aegadian islands
      • Tuscany
      • Liguria
      • Pontine Islands
      • Amalfi Coast
      • All Spain
      • The Balearic Islands
      • Andalusia
      • Catalunya
      • Galicia
      • Valencia
      • All Caribbean
      • BVI - British Virgin Islands
      • Antigua and Barbuda
      • Cuba
      • Grenadines & Martinique
      • Guadeloupe
      • Bahamas
      • Belize
      • All Indian Ocean
      • Bali
      • The Maldives
      • Mauritius
      • Seychelles
      • Corsica
      • French Riviera and Porquerolles
      • Brittany and Normandy
      • Split Archipelago
      • Kornati Islands
      • Turkey
      • French Polynesia
      • Norway
      • Adventure
      • Courses & regatta
      • Day trips
      • Flotilla
      • Offshore
      • Sport & wellness
      • WWF Sailing Cruises
      • Whole boat with skipper
      • All inclusive
      • Crewed
      • Catamaran
      • Gulet and sailing ship
      • Monohull
      • Mediterranean
      • Families
      • Couples
      • Solo Travellers
      • Exotic
      • Whale watching
  • Rent a boat
  • Call us
    +44 20351 44220
    • ITA
    • FRA
    • DEU
    • ESP
  • ITA
  • FRA
  • DEU
  • ESP
Crewed yacht sailing holidays & cruises

Crewed yacht sailing holidays & cruises

Get on board of a vacation with crew and live the sea without thoughts. Whether you choose a sailboat, a catamaran or a gulet, comfort and gulet, comfort and well-being will be the first place for a holiday of absolute relaxation. vacation of absolute relaxation.

  • Sailing Holidays
  • Crewed

FLEXIBLE CANCELLATION.

Stress-free booking: you can cancel up to 24 hours before departure!

  • 12 reviews

    Easter in Catamaran between Genoa, Camogli and Portofino, Santa Margherita, Sestri Levante

    from 7 April - 3 nights
    Liguria Italy
    3 people interested
    in this holiday
    297€ Per person
  • 1 review
    almost
    confirmed

    Easter and Easter Monday in Ventotene, Ischia and Procida on 14m sailboat

    from 8 April - 3 nights
    Pontine Islands Italy
    Join in on this experience!
    437 421€ Per person
  • 1 review
    almost
    confirmed

    Easter and Easter Monday in Ventotene, Ischia and Procida aboard a 22m maxi sailing yacht

    from 8 April - 3 nights
    Pontine Islands Italy
    Join in on this experience!
    626 613€ Per person
  • 29 reviews
    almost
    confirmed

    Ready to set sail? Magical places await you! - HOSTESSES on board

    from 8 April - 7 nights
    Ionian Islands Greece
    Join in on this experience!
    462€ Per person
  • PREMIUM 17 reviews
    confirmed

    TORTOLA Dream Premium - 8 days in catamaran ALL INCLUSIVE with hostess / cook

    from 8 April - 7 nights
    BVI - British Virgin Islands Caribbean
    Join in on this experience!
    2.175€ Per person
  • PREMIUM 17 reviews
    confirmed

    EXUMA Dream Premium - 8 days in catamaran ALL INCLUSIVE with hostess / cook

    from 8 April - 7 nights
    Bahamas Caribbean
    Join in on this experience!
    2.140€ Per person
  • PREMIUM 17 reviews
    confirmed

    Dream Premium - 8 days in catamaran ALL INCLUSIVE with hostess / cook

    from 8 April - 7 nights
    Grenadines & Martinique Caribbean
    2 people interested
    in this holiday
    1.890€ Per person
  • PREMIUM 17 reviews
    confirmed

    ABACO Dream Premium - 8 days in catamaran ALL INCLUSIVE with hostess / cook

    from 8 April - 7 nights
    Bahamas Caribbean
    Join in on this experience!
    1.945€ Per person
  • PREMIUM 17 reviews
    confirmed

    PHUKET Dream Premium - 8 days in catamaran ALL INCLUSIVE with hostess / cook

    from 8 April - 7 nights
    Phuket, Krabi and Phi Phi Islands Thailand
    Join in on this experience!
    1.520€ Per person
  • PREMIUM 17 reviews
    confirmed

    GUADELOUPE Dream Premium - ALL INCLUSIVE catamaran with hostess / cook

    from 8 April - 7 nights
    Guadeloupe Caribbean
    Join in on this experience!
    1.925€ Per person
  • PREMIUM 17 reviews
    confirmed

    ST. BARTH Dream Premium - 8 days in catamaran ALL INCLUSIVE with hostess / cook

    from 8 April - 7 nights
    Saint Martin Caribbean
    Join in on this experience!
    1.980€ Per person
  • PREMIUM 17 reviews
    confirmed

    BORA BORA Dream - 8 days in catamaran ALL INCLUSIVE with hostess / cook

    from 8 April - 7 nights
    French Polynesia Pacific Ocean
    Join in on this experience!
    1.890€ Per person
  • 1
  • 2
  • 3
  • 4
  • 5

Why you should book a holiday with Sailsquare?

Location point above a wave

The leading sailing holiday marketplace

25,000+ happy travellers, and 10,000+ holidays in 110 destinations worldwide.

Two people with sailor hats

Get onboard solo, with your family, or your friends

Reserve a single spot, a cabin, or a whole boat just for you and your friends or family.

A boat with a magnifier above it

Discover who’s already onboard

Introduce yourselves online, get to know each other onboard, and go home with a bunch of new friends.

Two coins with a currency on top

Sailing holidays that suit all budgets

Rumour has it that sailing holidays are only for the rich or well-connected. With Sailsquare, that's no longer true. Come and discover a world you never thought was accessible!

Reviews - Crewed yacht sailing holidays & cruises

748 reviews
20 / 10
Maddalena S.

Maddalena S.

review about The Caribbean dream with Skipper & Hostess. December 2022

8 / 10
The trip was exciting, with pristine and beautiful landscapes. I thank Dom for the competence and seriousness and Patricia for her availability and great culinary ability: she spoiled us every day. Thank you! I highly recommend it to get out of the usual travel patterns in the hotel, to see new horizons with admiring eyes. Good wind!
Alice F.

Alice F.

review about LAST MINUTE! - Catamaran cruise to the SEYCHELLES - Cook on board! November 2022

10 / 10
5 stars and even more in Pier Paolo!!! Skipper and fantastic person, who managed with his professionalism, competence and sympathy to make this week even more indimentìcabile! He accompanied us with laughter and wonderful stories in these enchanted places; with simplicity it has always allowed us to make a group with cheerful evenings and chats, or to leave us to contemplate a little the landscapes immersed in our thoughts; also able to solve some small unexpected or to create valid alternatives, always meeting everyone's needs, always transmitting tranquility and security! I cannot fail to mention Claudia who, with her delicious dinners, delicacies and lots of laughter, pampered us throughout the trip!!! All the right ingredients to enjoy the Seychelles even more... Paradise beaches, an aquarium for everyone, surreal landscapes ...
Niklas T.

Niklas T.

review about IBIZA and FORMENTERA: 1 week sailing with cook on board! August 2022

10 / 10
We had a truly fantastic holiday with Olmo and Margerita and can recommend it to everybody looking for a nice and relaxing sailing vacation! Olmo is a very knowledgable sailor, with whom you feel safe at all times and who is also happy to teach about sailing, if desired. Margarita is a very fun person and a great cook. They knew the area very well and adjusted the trip to our preferences, so that we had the best possible experience. Furthermore, are very nice and easy-going people, so that you like to spend time with them beyond the sailing. The boat is also nice and comfortable.
Raffaele P.

Raffaele P.

review about A week in the Aeolian Islands aboard a Sun odyssey 49! Sea, relaxation and trekking August 2022

10 / 10
After a stormy start due to the weather we spent a wonderful holiday, the boat has large interior spaces and Francesco is experienced and reliable, he managed to satisfy us on all our requests. Thank you!!!
Stefano  B.

Stefano B.

review about Cruise for two between the Dalmatian islands (Croatia) - ALL INCLUSIVE August 2022

10 / 10
A week among crystal clear waters, suggestive coves, romantic towns, ancient hermitages, relaxation and good company. All sailing on a sailboat rich in history captained by Cesare, a very capable and experienced skipper, who will tell you endless anecdotes and stories of the sea. In addition, if you wish, it will involve you in the different aspects of navigation. Together with him you will meet Carla, his companion and precious assistant in all the maneuvers that, with her sunny sympathy, kindness and constant good humor, is a fundamental presence on board. Every day, between one bath and another, you can enjoy the excellent dishes prepared for you: Cesare has even prepared the tagliatelle made by boat ... with a rolling pin!!! In short, thanks guys! We had a really good time, the Dalmatian islands are gorgeous and sailing with you was a beautiful experience. Good wind! Maria Cristina & Stefano
Nino C.

Nino C.

review about Splendid 16-meter yacht in the Aeolian Islands - Hostess on board August 2022

10 / 10
Very nice boat, helpful and courteous crew. Positive holiday to the maximum, certainly to be recommended
Antonio R.

Antonio R.

review about Seven days cruise to the Pontine islands: sea, sun and relaxation August 2022

10 / 10
First Sailing Experience. Leonardo is a person who lives the sea at 360 degrees, he transmits this visceral passion. Visited all the corners, coves and seabed of each island. Too bad only for not having gone to Ventotene and being back 2 days before, but this does not have weight from him but from adverse weather conditions . I conclude by saying that surely as in any family after several days many in a small space can be born some friction, but with a good dose of adaptation also passes. Lucky to have found another very nice and friendly couple.
Giorgio  M.

Giorgio M.

review about Cruise between Pontine and Flegree on a luxurious maxi sailing yacht of 22 meters August 2022

10 / 10
Great trip reliable and confident skipper. Friendly and welcoming hostess. Boat with large outdoor spaces for pleasant moments of conviviality. The kitchen is also excellent.
Carla A.

Carla A.

review about Exploring Ionian Greece and Salento - Hostess on board - Embarkation and disembarkation in LEUCA August 2022

10 / 10
I have just returned from my holiday with Gianni to the Ionian islands of Greece. What can I say? He and Giovanna were wonderful. Gianni is a true connoisseur of the sea. Together with my travel companions we lived an experience of joy and safety. He made us discover lovely places with joy and availability. He and Giovanna cooked for us, accompanied us on excursions and we also learned a few more secrets about the winds and navigation. Giovanna amazing! Goliardic and playful climate always. I recommend to everyone!
Matteo P.

Matteo P.

review about Ibiza y Formentera - Not just nightlife! Nature, magic and relaxation - Hostess on board August 2022

10 / 10
Roberto is a skipper very prepared and attentive to customer care. I would recommend him for any crossing as he is a guarantee of safety and passion for what he is doing. With him we had the opportunity to see the true face of Ibiza: the non-commercial one but of the 70s hippies, to be clear. An itinerary between Ibiza and Formentera made of magical views, interesting coves and cozy brains with the characteristic bongos.
Alessia C.

Alessia C.

review about July 15-21 Egadi islands week with skipper and mariania / hostess July 2022

10 / 10
Unique experience! Breathtaking scenery on board Rebelle, a brand new boat equipped with all comforts: from the coffee maker to the air conditioning for the hottest nights. The professionalism, competence, grace and hospitality of Clelia (the skipper) and Simona (as a sailor) made this experience unforgettable. Felt thanks to them, to my fellow adventurers and to the splendid Sicilian views :)
Marco C.

Marco C.

review about Discovering Northern Sicily from Milazzo to Marsala - Hostess on board July 2022

10 / 10
The places visited were wonderful, the company on board excellent. Thanks to the high experience and professionalism of Massimo (and Martina) the holiday was beautiful and will be unforgettable. Quiet navigation, stops without problems, excellent cuisine (I will always remember the dishes prepared - spaghetti mussels and clams, pasta with sardines, zucchini oil and pecorino cheese and many others). The welcome on board was impeccable.
Serena B.

Serena B.

review about The Great Beauty of the Maddalena Archipelago and Southern Corsica. Cook on board! July 2022

10 / 10
It was a fantastic week and very relaxing. With the group a beautiful harmony was created and I felt good from the first moment. An added value was certainly the sleep in the harbor for most of the nights: waking up in a bay and immediately taking the first dip before having breakfast has no equal. Thanks then to Claudio and also to Barbara, for being a cook attentive to my celiac needs. I hope there are other opportunities to travel together!
Gennaro G.

Gennaro G.

review about LAST MINUTE - A week to discover Wild Sardinia July 2022

10 / 10
Top week! The skipper Simon was fantastic, he immediately put us at ease and always shared with us the best itinerary often satisfying our requests ... with a lot of patience! We shared lunches and dinners always with so much joy and he taught us the key maneuvers to enter and exit the ports and often helped him with sails. Sleeping in radda is a unique experience... we lived in close contact with nature... what can I say?... super experience!
Elisa V.

Elisa V.

review about Between Tuscany and Corsica: infinite well-being - cook on board! July 2022

10 / 10
It was an unforgettable week aboard Kikko, a wonderful boat, very spacious and kept like a jewel, which exudes the passion for the sea that only three fantastic people like Daniele, Mariapia and Andrea can infuse. Daniele is an excellent captain, with him you always feel in good hands, thanks to his experience and his ability to keep the situation under control with a smile on his face. Mariapia is an exceptional cook, she delighted us throughout the week with dishes that are always different and able to satisfy everyone's tastes. Andrea is a very nice guy who at sea, despite his young age, has experience to sell. Together, they make an exceptional trio but above all a sweet family that makes all guests feel at home and in total relaxation. For lovers of water sports, the boat is super equipped and you can experience wonderful places in an even more adventurous way. Thank you for this wonderful experience! Elisa and Michele
Anastasia C.

Anastasia C.

review about Comfort & Relax aboard a 20-meter Sailing Yacht - Skipper & Hostess July 2022

10 / 10
Top Holiday! Where to start... it was a unique experience! We started from Tropea, and then passed by Panarea, Lipari, Filicudi, Vulcano and Stromboli. We could admire breathtaking landscapes and coves! Our snorkleing was accompanied by some great and healthy food prepared with care by Rodolfo and Massimo (Captain of Excellence) who managed to meet all our culinary needs. The icing on the cake? definitely the crew! We met fantanistic people. We laughed and danced aboard the lovely Alysia! Extra-recommended experience.
David D.

David D.

review about Eolian Sailing- Max 4 guest for exclusivity and relax - Hostess on Board June 2022

10 / 10
I would do this interesting and wonderful adventure with Adele and Mark again and again and recommend it to my loved one without hesitation! From delicious food with great cocktails, to playing dolphins, loving dadjokes from Mark, shared nightly adventures in the dinghy and Adele's care for us and the right music, to the fight of the crabs vs. jellyfish, everything was just perfect. We go home with the feeling of having taken family holidays with Adele and Mark and being teenagers again. Again and again!
Enrico D.

Enrico D.

review about French Riviera from Imperia to Villefranche ... Hostess on board June 2022

10 / 10
Vittorio and Giulia are two exquisite and genuine people, who have made the boat a life choice. They put the comfort of the guests at the center of their attention throughout the cruise, never missing anything and delighting us with their stories. Despite some small inconveniences (not due to them, and that can always happen at sea), they have always been able to manage the situation in the best way. A mention also to the boat, which is a nice gem, always clean and with the plus of private bathrooms. I can't wait for the next adventure with them!
Elena S.

Elena S.

review about Weekend among the pearls of the archipelago with hostess on board June 2022

10 / 10
Fantastic experience, what to say elba always beautiful but this time in particular, the skipper Edoardo and his partner Irene were very good I dare say of the travel companions albeit short. Edoardo very good and self-confident in steering the boat and Irene an excellent assistant but above all cook. Experience to be redone as soon as possible Everything above all expectations
Lorena S.

Lorena S.

review about Ready to set sail? ... prepare your bags and we'll take care of everything else! .. Magical places await you - Hostess on board June 2022

10 / 10
With Andrea in first place, competence and safety at sea. From a human point of view a very special person for the attention he has towards his guests and the ability to better cope with any situation or request. A beautiful week of carefree and fun. Thanks to him and his collaborators, Alessandro and Susanna, see you soon guys!!
Marco S.

Marco S.

review about June 2nd in the Egadi Islands relaxation and fun on a 16-meter boat (private bathroom) with * Hostess May 2022

10 / 10
Super!
Daniela D.

Daniela D.

review about For a day feel like a pirate of the Caribbean aboard the catamaran, Captain Marco's sailing ship May 2022

10 / 10
What can I say! A very pleasant first experience in the company of Marco and his wife!! My husband and I should have had travel companions but at the last we found ourselves exclusive guests of the tour ... We sailed, chatted, laughed, sunbathed and slept in absolute freedom. We were greeted by a good aperitif which was then followed by an excellent lunch and also a good snack. We felt pampered until sunset and to conclude this beautiful adventure we also thought of the dolphins spotted in packs along the way back ... Thanks Marco!! Good wind and to the next adventure!
Giuseppe B.

Giuseppe B.

review about The Gargano and the Tremiti April 2022

10 / 10
Thank you guys for welcoming us in your boat with all its comforts and the precautions reserved for us you have made us this Easter special. Everything was perfect... The ability of andrea and his partner to sail even with sea always formed in maximum tranquility and carefree the enchanted places visited at the tremiti the walks in the villages evenings and dinners on the boat spent in joy with the fantastic companions ... leave an indelible memory and new true friendships Thank you for the wonderful holiday I highly recommend to try all these beautiful emotions
Marco B.

Marco B.

review about Tartare, prawns and bubbles in Santa Margherita Ligure - all inclusive April 2022

10 / 10
Beautiful sailing experience, exciting chats, great food and above all many bubbles! Giorgio is a very pleasant, helpful and empathetic person: he managed to involve and make people with significantly different backgrounds and experience feel at ease on board (newbies, experienced skippers and "amateur" enthusiasts) so that everyone could make the most of the experience. His is a spacious, clean, brand new boat full of comfort (heating, privacy guaranteed by the excellent closed cabins, soft and spacious mattresses, hot shower in the cabin and on the platform ... not to mention the delicious delicacies that he cooked us in the amazing overhead oven!). I recommend to everyone and hope to repeat the adventure soon!
Trustpilot

Customer Support

Would you like some support using the platform? We've (almost) always got the answers!

Call us at +44 20351 44220 Check out our Help page

Can't find the perfect holiday for you?

Use our free holiday concierge tool - and let us find your dream sailing experience for you!

Let's find it together!

Why choose a sailing vacation with hostess or crew

  • Do you want to enjoy an all-round relaxing vacation, without having to think about anything? On board these vacations you will find a crew who will brighten up your stay.
  • Find the perfect vacation for you: choose a vacation with a hostess who will take care of the all-round service or choose a vacation with an on-board chef who will prepare the best local dishes for the guests.
  • Enjoy the vacation you've been dreaming of for a long time after a year of work: devote your time only to having fun and relaxing, without having to lift a finger.
  • Are you planning your vacation with children and don't want to have any thoughts other than enjoying time with your family? A vacation on a boat with a crew is ideal!

The best destinations for a sailing vacation with crew

.

Sailing vacations with hostess or crew in the Mediterranean: discover the wonders of our sea, following the advice of the skipper, perhaps sipping a cocktail prepared by the staff on board. You'll be spoiled for choice for a cruise on a sailing boat or catamaran or gulet with family, friends or new people met on board. Marinas and marinas, historic and lively villages, islands full of small restaurants or almost deserted islands, waters from green to turquoise, wide beaches and hidden coves: a boating vacation in the Mediterranean offers everything!

In Italy the best destinations are the Tuscany from whose coast to reach the island of Elba and the Giglio but also the Corsica. The Northern Sardinia, trendy and exclusive, but also the wild Southern Sardinia, or the Aeolian Islands, the Egadi Islands, the Pontine Islands and the Amalfitan Coast.

Do you prefer to go abroad? Choose a sailing vacation with hostess or crew in Croatia or in Greece, choosing a custom itinerary among the dozens and dozens of islands. But that's not all: Côte d'Azur, Corsica, Balearic Islands are all fantastic experiences, surpassed perhaps only by a vacation aboard a gulet in Turkey with crew for maximum comfort!

Hosted or crewed sailing vacations in the Caribbean: sailing on a catamaran in the Caribbean is the best way to enjoy the winter sea in Martinica, Grenadines, Cuba, Antigua and Barbuda, British Virgin Islands, Guadeloupe: excellent sailing conditions and a unique atmosphere characterize each island of the archipelago. Whether by catamaran or by sailboat, in the Caribbean your skipper will take you to explore small deserted bays even in high season, so that your cruise will be a unique and unforgettable experience.

Crewed: best destinations

  • Italy (327)
  • Caribbean (197)
  • Greece (115)
  • Indian Ocean (112)
  • Pacific Ocean (61)
  • Spain (41)
  • Thailand (28)
  • Croatia (18)
  • France (15)
  • Albania (2)

Other travel ideas

  • Monohull (2987)
  • Whole boat with skipper (2806)
  • Crewed (917)
  • All inclusive (895)
  • Catamaran (633)
  • Day trips (402)
  • Courses & regatta (282)
  • Gulet and sailing ship (143)
  • Sport & wellness (134)
  • Offshore (110)

Let's talk Sailsquare

Huffpost Sailing Today Yahoo!
Sailsquare press review

Sailsquare

  • Team
  • Careers
  • Press Room
  • Press Releases
  • Sustainable Tourism
  • General Terms & Conditions
  • Privacy

Travellers

  • Contact & Support
  • Blog
  • Customer Reviews
  • Sailsquare Concept
  • Ambassador Program
  • Traveller policy

Skippers & Businesses

  • List a holiday
  • Contact & Support
  • Provider Policy
  • Code of Conduct

Follow us on

Facebook Instagram Youtube Sailsquare blog

Secure online payments

Mastercard Visa America Express Apple Pay

Top Destinations

  • Italy
  • Greece
  • Aeolian Islands
  • Tuscany
  • Northern Sardinia
  • Ionian Islands
  • France
  • Pontine Islands
  • Caribbean
  • Aegadian islands
  • Lake Garda
  • Liguria
  • Cyclades
  • Croatia
  • Indian Ocean
  • Spain
  • The Balearic Islands
  • French Riviera and Porquerolles
  • Gulf of Naples
  • Sicily
  • Amalfi Coast
  • Seychelles
  • Split Archipelago
  • French Polynesia
  • Grenadines & Martinique
  • Dodecanese
  • The Maldives
  • Saronic Islands and Athens area
  • Corsica
  • Canary Islands

Top Travel Ideas

  • Adventure
  • Catamaran
  • Courses & regatta
  • Day trips
  • Flotilla
  • Gulet and sailing ship
  • Monohull
  • Offshore
  • Sport & wellness
  • Whole boat with skipper
  • All inclusive
  • Crewed
  • WWF Sailing Cruises
© 2023 Sailsquare Srl - Società Benefit • All rights reserved - VAT 07860990964