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Caribbean adventure sailing holiday: Antigua Explorer

Caribbean adventure sailing holiday: Antigua Explorer

Coastal Sailing

No previous experience required

Steeped in its unmistakable Caribbean beauty, Antigua is one of the world's great sailing destinations. Situated in the middle of the Leeward Islands, the island has over 50 miles of picture perfect coastline with its 365 (one for each day of the year) white sand beaches. On this sailing adventure, we explore this Eastern Caribbean wonderland with a very relaxed schedule, discovering endless shades of turquoise-blue water along the way. Around sunset, we can immerse ourselves in Antigua’s wonderful nightlife, with friendly locals, wonderful cocktails, cold beer and live music guaranteed This is a sailing holiday where you can join solo or as a group, and just soak up every ounce of natural beauty, peace and quiet Antigua has. Wonderful sailing each day, but with short distances, so it's short hops between anchorages and a holiday you will never forget.  
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Route Map Image

These are the available dates and routes. To book your place, please select the dates from the drop-down above the ‘Add to Cart’ button.


  • Start date / place: March 07 2022. Antigua
  • End date / place: March 12 2022. Antigua
  • Full price: £899
  • Deposit: £400


  • Start date / place: March 14 2022. Antigua
  • End date / place: March 19 2022. Antigua
  • Full price: £899
  • Deposit: £400


  • Start date / place: March 21 2022. Antigua
  • End date / place: March 26 2022. Antigua
  • Full price: £899
  • Deposit: £400


Please see ‘TRAVEL – GETTING TO & FROM YOUR TRIP’ tab for advice on start and end points.



All crew must produce a negative Covid-19 test result within 72 hours before the start date.

This is non-refundable. On making payment, your berth is guaranteed.

Paying the balance
The balance of the invoice can be paid at any time. It must be received by Rubicon 3 90 days before the trip start date or your place will automatically be cancelled. We will remind you of the date nearer the time.

Cancellations and moving trips
Our expedition sailing yachts only have between 7 and 10 berths on them. When you book, you are committing to take one of these places. Due to these very limited numbers, we will often have turned away someone else who would have liked the berth. Unlike many other holidays, please understand this gives us little if any flexibility to make changes or to move trips. We will always endeavour to assist you (& the earlier you tell us the better), but unless we can find someone else to take your place, we usually cannot move your booking.

Initial training and getting out sailing

Today is all about getting up to speed with the boat. Whether you are a complete novice and learning to sail for the first time or a more experienced sailor, everyone benefits from detailed introductions, safety briefings and training sessions. You will have two highly qualified instructors to guide you through every aspect that you need to know to have a great sailing holiday.

By lunchtime, we should be casting off the lines, and it’s time to learn the ropes. You’ll be hoisting the sails and working through all the critical sailing manoeuvres such as tacking and gybing, reefing and knot tying! By the end of the day, everyone on board should feel comfortable with the basics – even though there’s more to learn and practice every day. We’ll find a wonderful spot to anchor for the night and have dinner and a beer under the stars and in the warm, spice-laden Caribbean air. This holiday has most definitely started!

Falmouth Harbour

Falmouth Harbour is where we’ll drop anchor for our first evening at sea in the middle of a secluded horseshoe-shaped bay that is every bit as stunning as it is spacious. We can take the RIB (or swim!) ashore and soak up the unique history and culture of Antigua’s original British settlement.

Jolly Harbour

From its 18-hole golf course to the beautiful white sandy beach encircling the port, Jolly Harbour is a lovely spot to anchor and explore ashore. We can take a jeep and walk the trails in Greencastle Hill National Park that pass volcanic rock formations and offer sweeping island views. We can then maybe have dinner ashore with a real seaside dining experience at one of the harbour’s fine restaurants which of course, serves up some of the freshest seafood dishes you’ve ever tasted.

Great Bird Island

Often regarded as a “desert island dream”, Great Bird Island captures the true essence of a Caribbean adventure sailing holiday. The snorkelling is remarkable and the views from the hike that leads to the top of the island are spectacular. The most peaceful of settings, Great Bird Island is an offshore sanctuary and naturally safe haven for a variety of endangered wildlife species, including red-billed tropic birds and West Indian whistling ducks.

Great Bird Island is actually part of the group of small islands known as the North Sound National Park. Adjacent Rabbit Island is home to the exotic brown pelican, and the largest island of the group, Long Island, has been the site of a successful Hawksbill sea turtle monitoring project.

Dickenson Bay

Situated at the northernmost tip of Antigua, Dickenson Bay is one of the most popular areas on the island. The vast white sand beaches extend right across the bay and are an idyllic place for swimming, relaxing in the sun and having a cold beer or two. Just off the coast of the bay, we can also head to a few uninhabited islands that are home to a mile-long coral reef, which makes for a superb snorkelling site.

Green Island

Uninhabited and unspoilt Green Island is a delightful little hideaway just off the eastern coast of Antigua. Another really popular snorkelling destination, we have a choice of anchorages, and can expect exotic bird sightings, and unrivalled relaxation. Green Island’s neighbour to the left – Nonsuch Bay – is also worth exploring, with its tranquil waters, pleasant sea breezes, and barrier-reef protection.

English Harbour

English Harbour is a Caribbean sanctuary rich in maritime significance and naval history. The main entrance to the protected harbour features two fortresses standing tall on both sides, transporting you back in time to the 18th century when the Royal Navy’s Caribbean fleet was first established there.

Not far from Nelson’s Dockyard, English Harbour has plenty to offer, with an array of bars and restaurants, an English pub that serves British fare with a Caribbean twist and “jump up” steel band sessions that are too much fun not to join in!

Diepp Freeman Bay

Home to top-rated Galleon Beach, Freeman’s Bay is an uncrowded sanctuary and the perfect place to spend our last day of uninterrupted bliss aboard the yacht. A breathtaking haven with lush tropical foliage and splendid snorkelling conditions, Freeman’s Bay is a hidden gem that is just a short distance away from Nelson’s Dockyard.

Pack up and goodbyes

That’s it. The holiday is at an end, and all that remains is to pack away our holidays, fill our bags with any momentoes we have picked up along the way, sign logbooks and exchange details with the rest of the crew. Many crew members join these adventures solo, but with the friends you meet and share the experiences with, time and time again we see everyone heading off on new adventures together and that is all part of the magic.


  • You should join the boat in Falmouth Harbour, Antigua at 0900 hrs on the first day.
  • You will disembark the boat in Falmouth Harbour, Antigua  at 1200hrs on the last day.


  • Antigua Airport (IATA code ANU) is well served by many airlines



These adventure sailing holidays are open to everyone aged 18 years and over. If you are aged 70 or over, or have any concerns about your health, we ask that you get a doctor’s note before booking. This is just to make as certain as possible that you will be okay out on the water.


We provide the foul weather clothing, life-jackets and all other technical equipment you will need. You need to bring a sleeping bag and some waterproof boots.

See more information and the full kit list here


We believe that as many people as possible should be able to head out to sea and have a great adventure. However, it is essential for everyone’s safety that you are in a fit enough state to be on board. Ability to complete the five exercises below is a pre-requisite for joining as a crew member. They are not designed to be physically taxing and almost everyone should be able to complete them. Rather they are in place to check that you have the stability and basic physical condition to be on-board. If when you join the vessel the skipper believes you are not capable of completing these exercises, you will probably not be allowed to embark. If you have any doubts at all about your ability to complete these exercises safely, you must contact your doctor before attempting them.

Fitness to sail


Four weeks before your trip start date, you will be sent final joining instructions. At this time you will be asked to complete our medical declaration. At the time of booking, it is your responsibility to be sure that you will be able to pass all the criteria at the start date of your trip. If you cannot pass the criteria you will probably be refused permission to board.

See the Medical Declaration here


  • All crew must have adequate travel insurance in place for your sailing holiday.
  • We strongly recommend that you arrange insurance as soon as you book. This ideally will cover you for any mishaps, medical or otherwise, in the build-up to your holiday so that should you have to cancel, you can reclaim your fees.
  • Please note we will not refund your money or cancel your invoice due to medical issues that disqualify you from joining your trip.
  • For our latest guidance on travel insurance, please read here.


For a full explanation of what to expect with the various trip ratings please click here.


  • Foul weather clothing to keep you dry in any conditions.
  • Fladen immersion suits. These will keep you warm in even the coldest, windiest conditions.
  • Ocean-spec lifejackets. These are the best on the market.
  • All on-board food and snacks.
  • Daily sailing lessons and tuition from two highly experienced instructors.
  • RYA sailing qualifications where applicable.


  • Your travel to and from the start and end points.
  • Travel insurance (see our travel insurance page here)
  • Any alcohol – but feel free to bring your own or buy some along the route
  • Any meals you eat ashore


Everything’s included except for flights, travel insurance, a sleeping bag and some waterproof boots. There are no hidden extras.

  • These expeditions have small numbers of people on board. When you book, you are committing to being a part of the crew.
  • These are genuine adventure sailing holidays and you will be helping sail the boat, planning where we go, navigating, cooking and keeping the boat clean and tidy.
  • When you book, the deposit is non refundable. It is possible to cancel subsequently, however you may still be liable for the balance of the invoice, depending on how close you are to the start date when you cancel.
  • Please ensure you  have read and agreed to the T&Cs and read the Trip Notes before booking.

    Terms & Conditions