518

experiences

4.8

Super!

7 days between Capri, Amalfi and Sorrento: dream sailing cruise

Italy: Naples & Amalfi Coast

7 days - 7 nights

4 departures available

August

€990

Per person

4.8

An unforgettable week between Capri, Positano, Amalfi, Ischia, Procida...

Italy: Naples & Amalfi Coast

7 days - 7 nights

One departure available

August

€977

€879

Per person

New

Week end in Costa Azzurra

Italy: Liguria

2 days - 2 nights

2 departures available

July

€300

€270

Per person

5.0

Super!

Tuscany and North Corsica on a sailing boat

Italy: Tuscany

7 days - 7 nights

One departure available

August

€1,060

Per person

5.0

Super!

Sailing cruise between the Maddalena archipelago and Corsica

Italy: Northern Sardinia

7 days - 7 nights

4 departures available

July - August

Starting from

€950

Per person

5.0

Super!

A sailing holiday: discovering the Pontine Islands

Italy: Pontine Islands

7 days - 7 nights

3 departures available

August

€650

Per person

5.0

Super!

Ogliastra to go crazy, mini-cruise among the wonders of Sardinia

Italy: Southern Sardinia

4 days - 3 nights

One departure available

September

€740

Per person

4.8

Super!

Weekend on Elba, sea, colors and scents.

Italy: Tuscany

2 days - 2 nights

One departure available

September

€200

Per person

4.9

Super!

Gulf of Poets and Cinque Terre

Italy: Liguria

2 days - 2 nights

2 departures available

July - September

€400

Per person

4.8

Super!

A sailing trip through history and food and wine to the Pontine Islands

Italy: Pontine Islands

7 days - 7 nights

3 departures available

July - August

Starting from

€900

Per person

5.0

Super!

Luxury routes among the wonders of Northern Sardinia with hostess

Italy: Northern Sardinia

6 days - 6 nights

8 departures available

July - September

€1,600

Per person

5.0

Summer 2026 - Catamaran week in the Pontine Islands

Italy: Pontine Islands

7 days - 7 nights

2 departures available

August - September

€1,020

Per person

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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

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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 - Sailboat holidays & skippered tours

17923 reviews

Four days in the Pontine Islands, just a stone's throw from Rome

06/30/2026

Simone L.

Let's talk about Antonio ... professional, helpful, nice and with many sea stories to tell. Not to mention how deliciously she cooks for her guests! And then he makes you discover all the caves of the islands by tender. You can't expect more. Book, leave and enjoy this experience 😊

Weekend on a Sailing Boat in the Magical Gulf of Poets

06/30/2026

Margherita M.

Nice weekend with pleasant crew and a prepared and nice skipper

Weekend of approach to sailing in the setting of the Gulf of Poets

06/30/2026

Lucia S.

Beautiful experience, everything according to expectations

Aeolian Islands under the Stars: 5 Nights of Volcanoes, Sea and Magic

06/30/2026

Iole D.

Magnificent experience, the Aeolian Islands are magical and exploring them on a sailboat was beautiful, between sunrises, sunsets and nights under the stars to leave you breathless. Not to mention Stromboli and its roars and trekking on the smoking crater of Vulcano. Antonio is an experienced skipper, attentive, kind and very nice (and then also a surfer 🤙🏼) and with the rest of the group we had a great time. You never got bored between swimming, diving, SUP and snorkeling in places with beautiful cobalt blue water and lots of laughter. Ah! And the dolphins! Everything really 🔝🐬🩵🌊⛵️

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