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Totano's cup 2027 weekend of sailing and party on the island

Italy:

Tuscany

Duration:

3 days - 2 nights

Max number of spots:

10

Available:

October

Suitable for travellers:

18 - 70 years

Boarding from:

Rosignano Marittimo

What's included

Cancellation policy

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Organised by:

Nicola D.

Member since 2016 -

Organisation

Italian

English

This experience, in a nutshell

Experience a weekend different from the usual: a real sailing experience, the crossing to Capraia in a regatta and the unique atmosphere of the Squid Festival.

We will embark on Friday evening at Marina di Cala de' Medici, where we will meet the crew, arrange the galley and have a briefing dedicated to navigation and the regatta the next day.


On Saturday morning we will cast off to take part in the regatta from Marina di Cala de' Medici to Capraia.

During the crossing you will be able to actively participate in the management of the boat: setting the sails, rudder, tactics, maneuvers and organizing the crew. No previous experience is necessary: those who want to learn will be involved in the activities on board, while those who prefer can simply enjoy the navigation and the atmosphere of the day.

The arrival in Capraia will only be the beginning of the second part of the weekend.

We will moor directly in the port — overnight stay included in the experience — and we will have the evening at our disposal to experience the Squid Festival, one of the most characteristic events on the island, including food stands, squid-based dishes, music and the atmosphere of the village animated by crews and visitors.


On Sunday morning there will be time to relax, walk on the island, have breakfast in the port and, conditions permitting, take a swim or a short stop in the roadstead before starting the return navigation to the Tuscan coast.

The return to Marina di Cala de' Medici is scheduled for Sunday afternoon.

€350

3 days - 2 nights

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17+

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Boat & Classes of Service

Dehler Varianta 44 - 2016

Type

Sailboat

Length

13.3 m.

Toilets

2

Cabins

4

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9+

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Our itinerary

Our trip starts here:

Rosignano Marittimo.

Check-in: 4:00 PM

Our trip ends here:

Rosignano Marittimo.

Check-out: 6:00 PM

Our itinerary

A weekend of real sailing from Marina di Cala de' Medici to Capraia on the occasion of the Totano's cup. Boarding and briefing on Friday evening, regatta on Saturday morning with participation in the manoeuvres, night in the Port of Capraia included and evening at the island festival. Sunday relaxation, navigation and return in the afternoon.

The itinerary may be subject to changes due to weather conditions and/or technical or logistical reasons, in order to ensure safety and a pleasant sailing experience for all participants.

What's included in the price

Boat equipment and facilities

    Final cleaning

    Bedding kit

Onboard staff

    Skipper

Taxes, fees and moorings

    Embarkation and disembarkation mooring fees

What you'll have to pay during the experience

Below are the additional expenses you will incur during the experience.

Common Fund

€50 - €100 Per person

It depends only on the galley, fuel cost is negligible and the port is included in the price

    Galley

    Food for the skipper

    Alcoholic drinks

    Mooring fees

    Fuel (boat/tender)

What's NOT included in the price

Below are the services that are not included in the price of the experience, including any available optional services that you may pay directly to the organiser (we advise you to inform the organiser prior to departure in case you wish to purchase such services and arrange the payment terms directly with him).

Excluded

    Towels kit

    Meals/drinks consumed ashore

Frequent questions

The organiser reviews

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Organised by:

Nicola D.

Member since 2016 -

Organisation

Italian

English

4.1/5

out of

39

reviews

Skipper

Boat

Destination

Weekend Elba o Capraia

09/16/2026

Mauro G.

-

IT

Fun boat in sailing. Too bad for the weather conditions of the previous days that made the sea not optimal. Still pleasant experience throughout. I recommend, for the optimal training of the guest crew, to plan the mood of the experience in advance. Thanks again to skipper Nicola who made us experience the thrill of upwind ⛵😊👍🏻

Weekend Elba o Capraia

09/7/2026

FRANCESCA F.

-

IT

Unfortunately, the weather was not on our side in this very hot summer. Claudio top skipper!!!
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Weekend Elba o Capraia

09/1/2026

Alice R.

-

IT

It was our first time on a sailing boat and, although the weather allowed us to do only a day tour staying on the coast, it was still a new and interesting experience. I understand the fact that weather and wave conditions are not easy to predict well in advance and that no one has the power of arbitrariness of them, but we would have appreciated a more proactive attitude on the part of the skipper in managing the starts. And above all, we would have preferred more clarity from the outset on the fact that, in the event of rough seas, the journey could have been reduced to a stay in the port of Rosignano or a simple day trip along the coast, without reaching the islands. Being 9 plus the skipper, the spaces were sometimes a bit tight, especially during meals. I believe that greater attention to the organization of the kitchen, common areas and lockers could make the holiday even more comfortable for everyone. Overall it was a good experience, with some organizational aspects that, with small tricks, could be improved.
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Weekend Elba o Capraia

08/22/2026

Sara S.

-

IT

Perfect weekend, Sebastiano skipper super helpful. Beautiful experience!

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