Early Booking: 2017/18 The 2017/18 season is easily our most exciting yet as our second yacht, 'Oriole' comes on line. With only 7 berths on each expedition, you need to get in early and reserve your place. You can reserve a berth on any of these routes by clicking on the reserve now button and selecting the expedition of your choice. Reservation fees range from £400-£800 and remember these trips run back to back so you can join two together for the trip of a lifetime


Christmas & New Year's Eve: Caribbean

Start: 23 Dec 2017 Pointe a Pitre, Guadeloupe

End: 2 Jan 2018  St Maarten


See in the new year Caribbean style with your friends and family. Ten days of island hopping to iconic destinations such as Guadeloupe, Antigua, St Kitts and Nevis, St Barthes and St Maarten. With an open itinerary there’s time to accommodate everyone’s wishes: exploring ashore, snorkelling amongst the coral reefs and some awesome trade wind sailing.


Anguilla and the Virgin Islands

Start: 5 Jan 2018 St Maarten

End:  18 Jan 2018 Ponce, Puerto Rico


The Virgin Islands are one of the Caribbean’s most iconic sailing destinations: anchor in a different bay each night, head ashore to a beach bar for a rum punch in the evening and sail on to the next pristine beach in the morning. Add an international voyage or two, a good dose of top quality instruction and some amazing opportunities for exploring inland in Puerto Rico, and you’ve got the perfect combination of sail, train, explore.


Leeward Islands & Jamaica

Start: 21 Jan 2018 Ponce (Puerto Rico)

End: 3 Feb 2018  Port Antonio (Jamaica)


For those with a thirst for adventure and desire to see those hard-to-reach parts of Caribbean, this has to be it. Two 48 hour passages give great opportunities for developing seamanship and sailing skills. The destinations themselves are beautiful with authentic, charming towns and lush, mountainous interiors.


Central American Adventure

Start: 6 Feb Port Antonio, Jamaica

End: 26 Feb Cancun, Mexico


A true adventure as we set sail from Jamaica, heading west for a 3 days sail in the trade winds bound for the Bay Islands off Honduras. We'll have a couple of days to explore these stunning islands, before further west to Belize City and the 175nm long coral reef north of it. This is reputedly the second longest reef in the world and the opportunities for diving, anchoring off deserted islands and exploration are almost unsurpassed in the world. We continue to head north exploring the coastline of Mexico before finishing in Cancun.


Mexico to Cuba

Start: 1 March Cancun, Mexico

End: 14 March Santiago de Cuba, Cuba


Set sail from Jamaica’s gorgeous Port Antonio, set beneath the John Crow mountians. Great trade wind sailing across the Caribbean Sea to Cuba. Explore Cuba’s south coast including Fidel Castro’s home town of Santiago de Cuba, hone pilotage skills as we weave through miles of deserted coral islands in the Jardines de la Reine and end the trip in the UNESCO city of Cienfuegos. Unmissable.


Cuba Uncovered

Start: 17 March 2018 Santiago de Cuba

End: 30 March 2018 Havana

14 days   Trip rating: Intrepid


See Cuba from a totally unique angle as we continue the cruise along the south and western shores of this unique country. Idyllic sandy islands lie along the start of the route, with some of the clearest waters in the Caribbean. As we head west we reach Cuba’s ‘bread basket’: rich agricultural lands peppered with traditional farming communities. Sail into Havana to end the trip: enough said!


Cuba – Miami

Start: April 2 2018 Havana

End: April 11 April 2018 Miami


Start off in Havana and learn the ropes whilst island hopping behind the second longest coral barrier reef in the world: the Jardines del Rey. An overnight sail to the Florida Keys gives a taste of watch systems and offshore sailing, and another dose of sun, sea and sandy white beaches. Celebrate the end of the trip in Miami style. An enormously fun trip with two totally different places.


East Coast of America: Leg 1 Miami – Charleston

Start: April 16 2018 Miami

End: April 29 2018 Charleston

14 days


Sail along the Florida coast, past the famous Cape Canaveral and Daytona Beach, before heading up in to the beautiful wilds of Georgia’s inland waterways. Explore the historic towns of Savannah and Charleston. A great mixture of offshore passage-making and intricate inshore navigation allows you to make huge gains in your seamanship on this really special route.


East Coast of America: Leg 2 Charleston – New York

Start: May 2 2018 Charleston

Ends: May 15 2018 New York


Explore the lovely inland waterways of Carolina, take on the infamous Cape Hatteras in an epic 3-day voyage around to Chesapeake Bay where we spend some time exploring and training. Fantastic offshore sailing, great opportunities for inshore navigation, and arriving in New York, New York under sail – this route pretty much has it all.


New York – Rhode Island, Passage Making Masterclass

Start: May 19 2018 New York

End: May 27 2018 Newport, Rhode Island


Build valuable skippering skills as we voyage towards the home of American sailing: Newport, Rhode Island. Training in passage planning, pilotage, weather routing and more from two highly qualified instructors.


New England, Marthas Vineyard, Nantucket to Boston

Start: June 4 2018 Newport

End: June 13 2018 Boston


Setting off from the home of American sailing, the places between here and Boston are legendary: Martha’s Vineyard, Nantucket, Cape Cod. Beautiful cruising, incredible seafaring heritage, amazing seafood, and sail into one of America’s best-loved cities to end the trip. What better place to develop your sailing skills?


Boston to Nova Scotia

Start: June 16 2018 Boston

End: June 29 2018 Halifax



Halifax to St John, Newfoundland

Start: July 3 2018 Halifax

End: July 15 2018 St John



St John, Newfoundland to Nuuk, Greenland

Start: July 18 2018 St John

End: August 07 2018 Nuuk, Greenland



Nuuk, Greenland to UK

Starts: August 11 Nuuk Greenland

Ends : August 31 stornoway hebrides



Stornoway to Oban

Starts September 5

Ends September 14



Oban to Dublin

september 15 - 23



Dublin to Portsmouth milebuilder

Septmber 25 - October 2









Make this the sailing holiday or adventiure of a lifetime by joining two trips together
No previous experience required - we'll give you the training you need
Choose your next sailing holiday carefully - only sail with the best to make sur eyour adventure goes as well as it should

The Rubicon 3 Yachts

These yachts are large, powerful and have amazing ocean-crossing pedigrees. They're also incredibly safe, fun and accessible by anyone. Oriole is new to our fleet in 2017 and will soon be branded with a stunning Rubicon 3 design. Click on the pictures to find out more about each yacht.

Sailing yacht Hummingbird, perfect for you sailing holiday, expeditions and adventures
Sailing yacht Longbow is a wonderful yacht on which to have a sailing holiday or head off on a sailing expedition or adventure

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- John Sunyer, Financial Times


  1. No previous sailing experience is needed
  2. Maximum of 8 crew on most trips
  3. Over half the crew join the boat alone
  4. Age range anywhere from early 20s to late 60s
  5. Most crews are evenly split male & female
  6. We head ashore most days
  7. Everything is included - you just need to get to & from the start / finish