Caribbean Sailing Holidays
Starting from: £1749 - 7 or 10 day Trips
Safe & Secure Checkout
Ditch the winter blues for the crystal clear blues of the Caribbean sea & sky. Sun, Sand & Sailing; interested? Then please see below what we have on offer in 2026 / 2027.
- Sail in the gorgeous Caribbean waters
- Visit multiple islands along the way
- 72ft yacht with highly experienced Skipper & Mate
Safe & Secure Checkout
Great Trip
Yet another great trip with First Class Sailing..... We had plenty of input into where we went.... This is my 7th trip with First Class Sailing, and I would recommend them without hesitation.
Nick S
Verified Customer
Cruise, explore and sail in the beautiful Caribbean with our hands on sailing holiday in December 2026 & January 2027. Sail in the turquoise waters, anchor off pristine white sandy beaches. Swim or take the dinghy ashore. Sip cocktails in beach bars, eat freshly caught grilled tuna, wahoo, and dorado and breath in the exotic aromas of Caribbean spices. Absorb the local cultures and European heritage of many Caribbean Islands throughout your time on board. Enjoy lush volcanic peaks tumbling down to palm lined beaches and sparkling waters create a lovely setting for a sailing adventure.
Our 7 and 10 day Caribbean trips are designed to allow you to couple your fondness for sailing with a want for exploration and relaxing. Generally sailing shorter distances between islands will allow plenty of time to get ashore to the beach or the local town. For those who are so minded there may even be time for the odd hike up some of the islands mountainous topography.
5.0 based on 496 Happy Customers on Tripadvisor
RYA-certified sailing courses
5.0 based on 220 Happy Customers on Google Reviews
More Info on our Caribbean Holidays
Sail the Caribbean in Style: Cruise turquoise waters aboard the legendary Challenger 72, a sleek ocean-racing yacht built for adventure and comfort.
Unforgettable Island-Hopping: Explore hidden coves, vibrant coral reefs, and sun-drenched beaches from St. Lucia to Grenada, with plenty of time to swim, snorkel, and unwind.
Hands-On Sailing Experience: Whether you're a seasoned sailor or a curious beginner, take the helm, trim the sails, or simply sit back, relax and watch the world go by. You will be expected to get involved with the domestic chores and in helping to sail the yacht - it is very much an immersive sailing holiday.
Friendships That Last Beyond the Horizon: Share unforgettable moments with fellow adventurers, forging bonds over sunsets, shared stories, and the thrill of the open sea - you may depart with life long friends.
Key Trip Details
Here’s a breakdown of the most important information about these Caribbean Sailing Holidays
Required Experience
- Start Yachting or equivalent recommended
- Chat to one of the team to find out more
Voyage Duration
- 7 Days: 16 - 22 December 2026
- 10 Days: 3 - 12 Jan 2027
- Between 200 - 400nm
Why This Holiday?
- Peak season Caribbean Sailing
- Sun, Sea, Sand & Sailing, what's not to like
- Share you're experience with like minded individuals
- Large & safe yacht, a Challenger 72
The Yacht
- Challenger 72 Sloop
- 72ft long, spacious saloon
- Highly experienced Skipper & Mate
3 Easy Steps to your Caribbean Adventure
Get started now!
Enquire
If you have any queries about our Caribbean sailing holidays please email or call our friendly team who will be ready to answer your questions.
Book
Book and pay online or over the phone. Payment plan on request. Fill out your booking form and you're all set.
Cruise the Caribbean
Pack your summer wear, sun cream and pick up a tipple at the airport, you are ready for the Sun, Sea, Sand and Sailing in the Caribbean.
Caribbean Sailing Holidays
The Islands
The Caribbean chain of islands can be split into the Windward and Leeward Islands. South of Dominica are the Windwards which embrace the warm easterly trade winds. They are more mountainous and vary greatly in size. Both trips will transit through and visit the Windward Islands visiting idyllic archipelagos such as Tobago Cays.
The Leeward islands round away from the Atlantic to the northwest. Some of these islands are mountainous like the Windward Islands however many are flatter and there are many beaches to enjoy. Antigua, a Caribbean hub of yachting and a destination on the latter trip, is included in the Leeward Islands.
Which Islands you visit on your trip will depend precisely on weather an timings but you can expect to visit a new island almost every day!
The Yacht
The Yacht is a Challenger 72, built to sail around the world. A feat it has achieved twice in the BT Global Challenge Race. She is a very safe and solid yacht, spacious and comfy; well suited to sailing in the Caribbean. She meets all MCA (Maritime and Coastguard Agency) safety Category 0 (the highest level) Coding requirements.
There will be a professional skipper and mate aboard who will ensure your safety, give as much instruction/training/coaching as needed to enable the crew all come together to sail the boat as a team and for you to achieve your goals. You will take an active role in helping sail and run the boat.
The accommodation is arranged towards the stern of the boat in 2 areas comfy bunks. There is good refrigeration on board and a water maker so plenty of showers will be available.
Prices & Travel
Prices
- 7 Day Trip: £1749
- 10 Day Trip: £2499
This can be paid in full or in three instalments. To discuss payment plans please contact the office
- Deposit of 25% at time of booking
- Interim payment of 50%
- Balance: 25%
Included within the price...
- All food on board
- Mooring fees
- Custom entry fees and insurance*
- Foul weather gear
Not included
- Travel to and from the yacht
7 Day Itinerary: St Lucia to Grenada
Following on for a First Class Atlantic Crossing the yacht will have a rest in St Lucia before departing on a fantastic trip, south, through the Windward Islands to Grenada.
Day 1: Join the Yacht in the morning to meet your fellow Caribbean adventurous, familiarise with the vessel and set out on a short training sail/passage. Perhaps spend the first night anchored under the Pitons.
Day 2-5: Depart St Lucia and head into St Vincent & the Grenadines. This incredible stretch of the Caribbean has over 10 different islands to choose from. Work your way gently through some of them experiencing nature at its fullest. Carriacou, Union, Tabago Cays, Canouan, Mustique, Bequia & St Vincent are all options for this part of the trip.
Day 6: Depart St Vincent & the Grenadines to head for Grenada for your final port of call. Enjoy your final meal either at anchor under the setting Carribean sun or at a local beach bar
Day 7: Sort outs and farewells. You will be able to depart the Yacht from early afternoon in time to make it home for Christmas or to further extend your Caribbean holiday in Grenada.
*This is an example itinerary based on the expected seasonal weather. Actual destination or timings may vary.
10 Day Itinerary: Grenada - Antigua
Start your new year off with some sailing in the Caribbean peak season. Stable winds, warm temperatures and plenty to explore.
Day 1: Join the Yacht in the morning to meet your fellow Caribbean adventurous, familiarise with the vessel and set out on a short training sail/passage. Perhaps spend the first night anchored under the Caribbean starts ready to push off into St Vincent and the Grenadines. Carriacou, Union, Tabago Cays, Canouan, Mustique, Bequia & St Vincent are all options for this part of the trip.
Day 2 - 5: Set of from Grenada to explore St Vincent & the Grenadines. This incredible stretch of the Caribbean has over 10 different islands to choose from. Work your way gently through some of them experiencing nature at its fullest.
Day 6 - 9: Depart the Grenadines and begin your trip up to Antigua and the leeward Islands. Martinique, Dominica, Ils des Saints, Guadeloupe and Monserrat are all options for this segment of the cruise. The passages will be a little longer but there will still be plenty of opportunity to visit a few islands on route, get ashore and explore. Arrive in Antigua in the afternoon or evening of day 9 ready to enjoy a final evening meal at anchor or at a local restaurant.
Day 10: Sort outs and farewells. You will be able to depart the Yacht from early afternoon in time to fly that afternoon, extend your Caribbean holiday in Antigua or perhaps even have a couple of quiet days before joining the trip back to the UK!
*This is an example itinerary based on the expected seasonal weather. Actual destination or timings may vary.
What Sailors Say About Us
5.0 based on 577 Happy Customers On Tripadvisor 
5.0 based on 337 Happy Customers On Google ReviewsNot Sure Where to Start?
Use our guides to determine your level and find suitable courses.
See how internationally recognised RYA courses progress alongside your sailing skills.
You may be interested in...
Whatever your experience, we help you navigate your entire sailing journey. Here's more of what's on offer.
The Atlantic Ocean: Sail from Antigua to Portsmouth
Sail across the Atlantic Ocean from Antigua to the UK. January/February 2027.
Learn MoreThe Atlantic Ocean: Sail from Antigua to PortsmouthNorway Sailing Adventures
Sailing in Norway. Explore the Norwegian Fjords on a 72ft yacht. Includes a sail from or to Portsmouth in the UK depending on which leg you choose
Learn MoreNorway Sailing AdventuresSailing Holidays to the Isles of Scilly
Sailing Holiday to the Isles of Scilly. Sail from Falmouth and cruise this archepelagic jewel
Learn MoreSailing Holidays to the Isles of Scilly