Cruising & Charters

Cruising & Charters

Have you always wanted to sail away into crystal clear waters? What about sitting at anchor on a boat, gently rocked by the breeze after a refreshing swim?
You will have the opportunity to experience this, living on board with ease during one of our cruising events. 

You could also have the thrill of helming when the winds grow stronger, or simply catch up to the boat in front of you. All this while visiting both secluded locations and popular bays, living on board in harmony with nature according to our Sustainability at Sea principles, both in the Tuscan Archipelago or the Caribbean Islands.

Our programs span from daysails to weekends on board, to week-long cruises among the islands, or you can design your own trip with our bespoke options, including:

– Chartering a boat with our skipper and crew, who will allow you to relax completely and just enjoy being aboard

– Chartering a boat with our skipper, and if you have previous sailing experience, crewing and participating in the full sailing adventure

– At Second Star Sailing don’t provide bare boat charters


Easy Caribbean Cruising

In Antigua we offer special experiences for those visiting the island who would like to get off the beaten path (or their cruiseship) to experience the island’s lovely beaches up close. Antigua Day Sailing – a relaxed day of sailing along the western side of the island , from Deep Bay in the north to Carlisle Bay in the south – with many different options:

Antigua Circumnavigation – the best way to take in the variety of coastlines, beaches, bays and harbours that make Antigua famous.
The cruise can take between 5 to7 days, depending on how long you choose to linger in each individually stunning island location, including Deep Bay, Great Bird Island, Green Bay, Nelson’s Dockyard, Falmouth, Carlisle Bay and Five Islands Bay.
Discover Barbuda – This lovely cruise takes you to the secluded island of Barbuda, its 5 mile long white beach, frigate bird sanctuary and stunning reefs. Sailing from our base in Antigua, we spend 4-5 days relaxing at anchor, enjoying the beauty of the island.

Caribbean Mileage & Experience Builders

Enhance your experience by sailing with us in different locations on a variety of boats, gaining mileage and skills along the way.
We offer a variety of options to add to your nautical background:

  • Mileage builders along the entire Caribbean island chain from Grenada up to St. Maarten
  • Yacht deliveries
  • RYA courses such as RYA Coastal Skipper that sail to our neighboring islands
  • Offshore regattas such as the RORC 600 Caribbean or the Rolex Middle Sea Race

Basically we offer options for you all the way from 100 mile trips to Transatlantic Crossings.  Join us for one of these exciting opportunities!



Mediterranean Cruising

Our base in Pisa allows us to offer a variety of destinations with trips that range from a weekend to 5-7 days of cruising – the choice is yours! The Tuscan Archipelago is the largest protected marine area in Italy, so as sailors we have the opportunity to interact with zero impact with the sea environment that surrounds us.

• Tuscany Coastline– experience the Tuscany coastline and the lovely towns that are found along it while sailing down to Punta Ala, with stops in Etruscan ruins and the option to visit world-famous vineyards.

• Portovenere & Cinqueterre – sail north to Portovenere and the gulf of Poets, stay at anchor in the bay and see the sunset behind the steeple of the town – then you can choose to hike the Cinqueterre Via dell’Amore or sail along the coast up to the towns nearby.

 Elba Island Circumnavigation – Sail south to Elba and visit famous Porto Azzurro, Marciana Marina and Capoliveri. Soak in the sun by day and italian nightlife in the evenings.

• Corsica and Capraia Islands – visit two of our favourites, the wilder Capraia island and its Cala Rossa, then on to Corsica and its French croissants and beaches for a few days of relaxation before heading back to Italy.

• The Tuscan Archipelago – this extended tour (7-10 days) combines many of the highlights from the other trips, and will bring you to Capraia, Elba, Giglio and Giannutri islands, experiencing a variety of landscapes and both the history and the Bella Vita that we love to share in Italy.

Atlantic Crossing 2024: from the Mediterranean to the Caribbean, aka East to West

There are three sailboat delivery legs for this crossing and the Atlantic Crossing itself. You may choose to participate in one delivery leg, several delivery legs or get a full experience from preparation to the final docking!

The Atlantic Crossing and the delivery passages are an exciting and unique experience. They will involve a period of preparation prior to the crossing during which we will ready the boat for the crossing, have some sail training together, plan the provisioning and learn about safety while building our team spirit before heading out.

  • LEG 1: October 20th – 25th: Pisa – Palma de Mallorca
  • LEG 2: October 27th – November 1st: Palma de Mallorca – La Linea (Spain, Bay of Gibraltar)
  • LEG 3: November 3rd – 10th: La Linea – Las Palmas (Gran Canaria)
  • ATLANTIC CROSSING: November 17th – December 8th (roughly): Las Palmas – Jolly Harbour (Antigua and Barbuda)

If you are an experienced sailor in need of gaining mileage or a beginner looking to do a RYA Sailing Course – let’s get in touch and we will find the best solution for you!
For more information about passage plan and prices – email us at
or WhatsApp us at +1 268 723 9343