header cover

All Inclusive Sailing Holidays & skippered cruises

Experience an all-inclusive sailing holiday, pay the initial fee and forget about galley costs and skipper's services. Services offered by the skipper. The ideal way to be carefree once on board and keep your daily expenses under control.

64

experiences

cover image
avatar image
Antiparos Discovery Schooner Tour - Despotiko - Blue Lagoon

Duration:

1 day - 0 nights

Greece:

Cyclades

Give this experience a try!

€130

Per person

cover image
avatar image

5.0

A wonderful day.... on Lake Garda - ALL INCLUSIVE

Duration:

1 day - 0 nights

Italy:

Lake Garda

avatar image
avatar placeholder
avatar placeholder

+86 travellers

have booked

Starting from

€99

Per person

cover image
avatar image

4.4

Sailing Excursion Alghero ( Skipper + Hostess )

Duration:

1 day - 0 nights

Italy:

Northern Sardinia

Give this experience a try!

€90

Per person

cover image
avatar image

4.6

Premium

PRASLIN Dream Premium 8 days - Catamaran ALL INCLUSIVE with hostess/cook

Duration:

7 days - 7 nights

Indian Ocean:

Seychelles

avatar image
avatar placeholder
avatar placeholder

+8 travellers

have booked

Starting from

€1,540

Per person

cover image
avatar image

5.0

A fantastic day on a boat in the blue sea of Tuscany

Duration:

1 day - 0 nights

Italy:

Tuscany

Give this experience a try!

€130

Per person

cover image
avatar image

5.0

Sailing, swimming and aperitif at sunset ... What else?

Duration:

1 day - 0 nights

Italy:

Lake Garda

avatar image
avatar placeholder
avatar placeholder

+10 travellers

have booked

Starting from

€69

Per person

cover image
avatar image

5.0

Aperitif on a Sailing Boat and - All inclusive!

Duration:

1 day - 0 nights

Italy:

Liguria

Give this experience a try!

€90

Per person

cover image
avatar image
7 Day Greek Sailing Adventure - Dodecanese Islands

Duration:

7 days - 6 nights

Greece:

Dodecanese

Give this experience a try!

€1,653

Per person

cover image
avatar image

4.8

Let's sail in relaxation on Lake Garda - All Inclusive

Duration:

1 day - 0 nights

Italy:

Lake Garda

Give this experience a try!

€150

Per person

cover image
avatar image

5.0

All inclusive day trip sailing around the Golfo Paradiso - flex dates

Duration:

1 day - 0 nights

Italy:

Liguria

avatar image
avatar image
avatar image

+24 travellers

have booked

Starting from

€126

€140

Per person

cover image
avatar image

5.0

A day sailing in the fantastic Gulf of Trieste

Duration:

1 day - 0 nights

Italy:

Venice and the Gulf of Trieste

avatar image
avatar placeholder
avatar placeholder

+4 travellers

have booked

Starting from

€66

€69

Per person

cover image
avatar image
Fine Settimana in Liguria - All inclusive

Duration:

2 days - 2 nights

Italy:

Liguria

avatar placeholder
avatar placeholder
avatar placeholder

+21 travellers

have booked

€380

Per person

Why book a holiday with Sailsquare?

The world's largest marketplace for sailing holidays

The world's largest marketplace for sailing holidays

80,000 travellers have already chosen their holiday from a catalogue of 12,000 proposals in 120 destinations, worldwide.

Get onboard solo, with your family or your friends

Get onboard solo, with your family or your friends

Book a single spot, a cabin or the whole boat just for yourself, or for your friends or family.

Find out before you book who's waiting for you on board

Find out before you book who's waiting for you on board

Find out more about the skipper and travellers who have already booked the holiday, to find out more about the

Sailing holidays that suit all budgets

Sailing holidays that suit all budgets

On Sailsquare, sailing holidays are within everyone's reach. Thousands of proposals to choose from, at affordable prices.

Reviews - All Inclusive Sailing Holidays & skippered cruises

618 reviews

avatar image

A day sailing in the fantastic Gulf of Trieste

05/12/2024

tiziana c.

Paolo è stato semplicemente fantastico! Accogliente, disponibile e molto preparato. La sua passione è davvero contagiosa e nonostante l'amore per la sua barca, ha permesso a noi di fare manovre, timonare e sentirci parte dell'equipaggio (persino io che non so fare nulla!). Abbiamo trascorso una giornata davvero indimenticabile in sua compagnia. Grazie!!!
avatar image

Sailing, early sun and aperitif at sunset ... What else?

05/3/2024

Cristiana L.

-

Italy

Giornata stupenda! lo skipper Emanuele molto simpatico, alla mano e soprattutto molto preparato e affidabile. Abbiamo veleggiato con un bel vento, io sono interessata alla vela ed Emanuele mi ha spiegato tante cose, fatto fare delle manovre e riposto pazientemente a tutte le mie tante domande. Abbiamo anche fatto un bellissimo aperitivo all'ancora. Non posso che consigliare vivamente questa esperienza!
avatar image

PHUKET Dream Premium - 8 Days Catamaran ALL INCLUSIVE with Hostess/Cook

03/12/2024

Giancarlo A.

😍😍
avatar placeholder

PRASLIN Dream Premium 8 days - Catamaran ALL INCLUSIVE with hostess/cook

02/19/2024

Klaembt R.

Boot ist ok, missing in the Night AC, during the day it works but in the Night??

Customer Support

nightLifeGeneralInfo

Do you need support on using the platform or for an online payment? Do you need information or is there something you don't understand? For (almost) any question, we got an answer!

search

Can't find the perfect holiday for you?

Tell us what you are looking for and let our team find the right solution for you!

6 reasons for an all-inclusive sailing holiday:

  • If you're the kind of person who doesn't like organising trips, looking for restaurants and planning your next plans, this type of holiday is for you. Booking an all-inclusive sailing holiday will make you feel more relaxed and you won't have to worry about anything.
  • Whether family, with friends, couple or alone, you will find the skippered sailing holiday that best suits your tastes and needs.
  • You'll discover a multitude of secret corners that are difficult to reach by land, so you can explore incredible places without the presence of tourists.
  • You will have a unique experience on board a sailing boat or catamaran, discovering dream places from a different perspective
  • You will have no time for boredom, you can enjoy activities all day long, from excursions by sea and land, sailing courses to learn how to sail, leisure or sports activities such as surfing, diving, etc. and, of course, time to relax by sunbathing on the deck of your boat.
  • You'll be travelling in the company of a local skipper, who knows every corner of the region, to help you discover the secret gems of each place you visit - a sailing holiday that won't leave you indifferent!

The best destinations for sailing trips in the Mediterranean:

All-inclusive sailing holidays in the Balearic Islands

The leading sailing destination in Spain. On each of its islands you can breathe a different air, because they all have something different to offer. However, they are all beautiful islands with turquoise, almost paradise-like waters. Enjoy the Mediterranean landscape and its dream islands close to home.

All-inclusive trip to the Greek islands

Trace the history of this magnificent country on board a sailing boat or catamaran, discovering its past through its fascinating and almost endless islands, as there are some 3,054 islands of which only 80 are inhabited, so you won't be bored for a minute! Try their delicious traditional food: tzatziki, tarama, moussaka and their famous Gyros.

All-inclusive travel to Sardinia

Have you ever seen such crystal-clear waters as those of Sardinia? Its coasts have absolutely nothing to envy to those of the Caribbean. You will discover its most heavenly beaches so that you can take a swim and enjoy the sun at the same time. Don't forget to visit some beaches such as Playa Rosa, Playa del Cavaliere or the beaches of Cala Coticcio, famous for their enormous rocks of different shapes.

All-inclusive trip to the Maldives

One of the most desirable tropical countries in the world, located in the Indian Ocean. This idyllic destination will leave you speechless with its breathtaking wild landscapes and totally unspoilt turquoise waters. You won't want to wait a second to dive in. You can also enjoy extraordinary moments under the sea during a snorkelling or scuba diving session to explore the underwater flora and fauna.

Why go on an all-inclusive sailing holiday?

Goodbye worries

Accommodation, transport, skipper, hostess, meals... all this and more will be included in your trip, so you won't have to worry about a thing. You'll have a trip with all the comforts and your holiday skipper will organise everything exclusively for you, so you can relax and let go.

Ideal for families

Travelling with children can often be stressful when it comes to organising holidays because you have to plan activities, food etc. and look after the children at the same time. However, if you book an all-inclusive holiday, you can be sure that peace and quiet and relaxation are also included.

Price without surprises

We generally think that all-inclusive plans are expensive, but nothing could be further from the truth, we spend much more when we improvise and often have surprises when we check our bank account when we get home. On an all-inclusive holiday you'll have everything under control, you won't spend more than you set out to spend at the start of the experience.

Let's talk Sailsquare!

HuffpostSailing todayYahoo!

Secure payments

MastercardVisaAmerican ExpressApple pay

© 2023 Sailsquare Srl SB • All rights reserved - VAT IT07860990964