Tropic Breeze Caribbean & Maldives Holidays

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Sailing Holidays

Sailing Holidays

Sailing holidays in the Caribbean

A Caribbean sailing holiday is a fantastic experience that allows you to island hop and discover a variety of unique destinations. The Caribbean is one of the most popular yacht charter destinations in the world, with crystal clear waters and thousands of picturesque islands to explore as well as secluded sandy cays and magnificent coral reefs.

Whatever your sailing experience, there is an option to suit you. Guests can choose to charter a yacht and sail it themselves (known as bareboat) while those who are less confident or who simply wish to spend their time relaxing can charter a skippered or fully crewed yacht. Yachts available include everything from a small monohull which is perfect for a couple to a spacious catamaran with plenty of space for a large group.

Another alternative is to book a cabin on a Dream Yacht Charters cruise, an intimate and affordable sailing experience on board a small luxury catamaran– you will share the crewed yacht with other passengers, following a well-planned itinerary sailing between stunning Caribbean islands.

We offer sailing holidays with Sunsail and The Moorings and can also book many of the leading independent yacht charter companies. Antigua, the British Virgin Islands and the Grenadines are particularly popular destinations for a sailing holiday but it is also possible to visit other islands.

Tropic Breeze founder Jo is an experienced sailor and has sailed throughout the Caribbean, so is always happy to discuss your holiday options. We can offer tailor-made holiday packages with or without flights – just call us on 01752 880 880 or email and we will put together an option that is perfect for you.

Tropic Breeze holidays are fully bonded and protected, whether booked with flights via our ATOL 5615 or for accommodation only holidays with our ABTA Y5401.

Bareboat & Crewed Yacht Charters

Bareboat charters are suitable for those who have sailed previously and who have an understanding of basic seamanship, boat handling and navigation. A crewed charter allows you to sail with a professional captain and a private chef, with all meals, snacks and drinks included in the cost of your holiday.

Yacht charter packages usually include a fully equipped yacht for the duration of your holiday, as well as a dinghy with outboard engine, one tank of outboard fuel, cooking gas, all linen, towels and snorkelling equipment. Yacht fuel is usually not included, nor are mooring and marina fees, cruising and national park taxes, yacht security insurance or food and drink (for bareboat yacht charters).

Charter yachts are fitted out with the necessary safety and navigation equipment, as well as a number of additional amenities to make you feel at home including air-conditioning, an AM/FM stereo and CD player, a TV and DVD player, a barbeque grill and all kitchen equipment. Inclusions vary depending on the specific yacht and charter type – full specifications are available upon request.


Come Sail with Us at East Winds, St Lucia

Package includes:

  • 7 nights on an all inclusive basis
  • 4 half day sailing lessons with Jus' Sail
  • Return transportation from East Winds on each sailing day
  • 1 sunset cruise during stay per couple or family

Valid on stays between 1 July - 31 August 2019. 


Feeling Inspired?

14 nights from £3890pp including 3 nights at South Point, Antigua, 7 nights aboard yacht charter and 4 nights at The Inn at English Harbour, Antigua. 


Dates for the Diary

Barbados Sailing Week: 16 Jan - 22 Jan 2019

Pineapple Cup, Jamaica: 27 Jan 2019

Grenada Sailing Week: 28 Jan - 03 Feb 2019

Super Yacht Challenge, Antigua: 31 Jan - 03 Feb 2019

Jolly Harbour Valentine's Regatta, Antigua: 08 Feb - 11 Feb 2019

Loro Piana Caribbean Superyacht Regatta: 15 Mar - 18 Mar 2019

St Barts Bucket Regatta: 21 Mar - 24 Mar 2019

St Thomas International Regatta: 22 Mar - 24 Mar 2019

BVI Spring Regatta and Sailing Festival: 25 Mar - 31 Mar 2019

Bequia Easter Regatta: 11 Apr - 15 Apr 2019

Les Voiles de Saint Barth: 14 Apr - 20 Apr 2019

Antigua Classic Yacht Regatta: 17 Apr - 23 Apr 2019

Antigua Sailing Week: 27 Apr - 03 May 2019


2020 dates TBC.

Dream Yacht Charters -  1

Dream Yacht Charters

  • Rent a cabin on a crewed catamaran
  • Well-planned itineraries
  • British Virgin Islands or Grenada & The Grenadines
Sunsail In The British Virgin Islands - Caribbean- Tropic Breeze -  0


  • Charter a yacht with or without a skipper
  • Monohulls and catamarans
  • Beginners or professionals
The Moorings -  1

The Moorings

  • Great choice of catamarans and monohulls
  • Easy access to marinas
  • Bareboat or crewed yacht charters
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·Tropic Breeze · The Old Coach House, Yealmbury Hill · Yealmpton · PL8 2JH ·
ATOL 5616 ABTA number Y5401