header cover
logo

Log in

Holidays and cruises by sailboat and catamaran in Pantelleria and Lampedusa

Sailing with a sailboat between Pantelleria and Lampedusa offers breathtaking views of cliffs and paradisiacal beaches, such as the Bay of Rabbits. The crystal-clear sea and gentle breezes make this experience an ode to the serenity and beauty of the Mediterranean. A journey that satisfies all the senses, including taste, with traditional dishes like fish couscous and delicacies made with capers and sun-dried tomatoes.

Why book a holiday with Sailsquare?

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

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

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 - Holidays and cruises by sailboat and catamaran in Pantelleria and Lampedusa

60 reviews

avatar image

Lampedusa, Linosa and Lampione, islands on the high seas

09/5/2026

Jacopo V.

-

IT

Beautiful experience, super experienced skipper! The islands of Lampedusa and Linosa are enchanting and the skipper Lorenzo is 10 out of 10: he has a great deal of experience and knows the place perfectly. It made us experience a beautiful and different holiday than usual, despite the weather was not totally on our side (very hot week and incessant sirocco). The only constructive criticism goes to the [hidden] boat: it is rather dated and the spaces on board are a bit tight. There were 9 of us in total (7 guests + skipper and assistant skipper), perhaps a little too high for the type of boat. Reducing the number of participants would greatly improve comfort. Apart from that, the holiday remains absolutely recommended and promoted with flying colors for the itinerary and management!
avatar image

Lampedusa, Linosa and Lampione, islands on the high seas

09/3/2026

Alberto N.

-

IT

Not just a sailing holiday, but an idea of a holiday. Lorenzo is an experienced skipper and above all he knows everyone a bit. More than Lampedusa, I was surprised by Linosa, an island of strong contrasts and less touristy, decidedly beautiful.

Lampedusa, Lampione and Linosa among magical colors

08/26/2026

cristina m.

-

IT

"Twenty years from now, you'll be more disappointed by the things you didn't do than by the things you did. And so he lets go of the moorings. Leave safe harbors. Catch the wind in your sails. Explore. Dream. Find out." If you are looking for an authentic adventure, this experience is absolutely recommended, especially with an exceptional guide like Riccardo. Lampedusa is already a magical place in itself, but experiencing it on a sailing boat with him made this holiday truly unforgettable. A trained skipper, an excellent cook and a person of great sensitivity, he managed to make us feel like friends and not just customers. He pampered us throughout the week, always available, attentive and caring. He was able to interpret our every need, making us discover spectacular bays, hidden coves and wonderful corners of the island that we would hardly have known alone. The boat is cozy and the space is not abundant, but the small sacrifice in terms of comfort is amply repaid by the beauty of the places visited, the atmosphere that is created on board and the possibility of experiencing the sea in an authentic and privileged way. Thank you, Riccardo, for letting us explore, dream and discover. An experience that we will carry in our hearts and that I recommend without hesitation to those who want to experience a special holiday, made up of wind, sea, nature and extraordinary people. ⛵☀️🌊
avatar image

Lampedusa, Lampione and Linosa among magical colors

08/17/2026

Alessandro B.

-

IT

We had a spectacular holiday and much of the credit goes to our skipper Riccardo. We had already tried sailing holidays, also here through sailsquare, but nothing comes close to the experience we had this week with Riccardo, unique in terms of preparation, availability, ability to meet the interests and needs of the crew, kindness and fishing skills :) Among the thousands of activities and adventures that we appreciated, we emphasize that we were able to visit spectacular places unknown to most, which we were able to enjoy in peace and tranquility surrounded by peace and nature.

Customer Support

customer support

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!

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!

Pantelleria and Lampedusa: the best travel ideas

Other travel ideas

Let's talk Sailsquare!

HuffpostSailing todayYahoo!

Secure payments

MastercardVisaGoogle PayApple Pay

© 2025 Sailsquare Srl SB • All rights reserved - VAT IT07860990964