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Sail from the Caribbean to New York

Sail from the Caribbean to New York

Offshore & ocean sailing

Day Skipper, ASA 104 or above


Join the crew for this spectacular offshore adventure, as we sail from the jungles, coral reefs and wildlife of the Caribbean to the bustling metropolis of New York, USA.

Sailing location 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.

TRIP CODE: ATN19032022

  • Start date / place: March 19 2022. Antigua
  • End date / place: April 08 2022. New York City
  • Full price: £4,199
  • Deposit: £1,680


This is an entirely optional day prior to the start of the trip in New York City or Newfoundland where we train you in the navigational and passage planning skills needed for an ocean passage.

Find out more about the day here.

If you wish to attend the Ocean Theory Training Day (please ensure you add the module to your basket), you will need to join the boat at 1000hrs the day before the main start date. You will be allowed to stay on the boat that night


  • This trip meets the RYA Yachtmaster Ocean for a qualifying passage, so long as you are a watch leader.
  • If you wish to join as a watch leader, you must meet the criteria as detailed on our ‘Watch Leader‘  page.
  • It is also compulsory to attend the ‘Ocean Training Day’ which gives you in depth training on how to run an ocean passage.
  • You must book the watch leader place at the same time as you make your main booking. Please ensure you have added a ‘watch leader’ module to your cart.
  • There are only three watch leaders spaces per yacht.




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

This is 40% of the trip price and 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.

This is a typical itinerary for sailing from Antigua to New York City. What makes this type of adventure holiday so special, however, is that there can be no fixed itinerary and no timings within this can be guaranteed. The wind and the weather ultimately shape what’s possible and the exact route we take.

Training and pre-departure briefings around Antigua

Staying safe is obviously always at the top of the list and the first few days are an intensive sailing course to get everyone up to speed, both with their individual skills and with our abilities as a crew. These first few days are all about getting up to speed with the boat.

Your skipper and mate are two highly experienced instructors who will guide you through everything that you need to know to have a great sailing holiday. We’ll be working through all the key sailing manoeuvres such as MOB recovery, tacking and gybing, reefing and knot tying! It’s drills, drills, drills to ensure everyone is ready. We’ll likely spend a couple of days sailing and training around Antigua and by the end of the period, everyone on board should feel comfortable on the boat.

Sail north to Anguilla

We’ll start with a short sail either to Barbuda or Anguilla. This will help us start to get a feel for the open ocean and consolidate our skills. It’s around 90nm north west to Anguilla, so we’ll start midday and sail through the night, arriving late morning. This will be invaluable experience, as sailing in the dark also takes some getting used to.

Fringed by white-sand beaches shaded by coconut palms and sea-grape trees, Anguilla is a spectacular island. Back from the seafront, colorfully painted, open-sided bars serve sizzling barbecues, feisty rum punches and play live reggae tunes. It is also famous for its crystal-clear waters and reefs offering spectacular snorkeling and kayaking. Since we’d going to be at sea for a while, we’d be crazy to miss it!

Ocean passage to the USA

The exact route we take to get to NYC will depend on the weather conditions at the time. We may head directly there or we may make landfall further south, in the Delaware region. It will simply depend on timings and weather.


Prior to departure we’ll spend a full day going over the yacht and systems, checking everything is in working order. With the guidance of two seasoned ocean instructors you’ll try out the storm sails and learning how to rig the drogue and emergency steering. There’s a lot to cover, but the secret to ocean sailing is that if you put in the work to prepare the boat, then the sailing bit is easy!

It is some 1500nm north to New York, so we can expect to be at sea for around 10 days. Far out to sea, we’ll sail past Puerto Rico, Turks & Caicos and the Bahamas. Around 500 to our starboard side is Bermuda.

Sailing under the stars

It may be a cliché but the experience of sailing at night under a carpet of stars really is magical. Far from the light pollution of land you’ll find the Milky Way comes to life and shooting stars often zip across the sky.

Celestial navigation

As we settle into the rhythm of the watch system to keep the boat moving around the clock we’ll also learn how to navigate traditionally. Navigating without GPS means keeping our dead reckoning by estimating our course and distance travelled, and using the sextant to give us accurate position fixes. For those looking to complete the RYA Yachtmaster Ocean qualification this is an excellent passage for taking those all important astro-fixes.

Arrival into New York City

There can be few more iconic landfills in sailing than edging past the Statue of Liberty. Coney Island to our right, Staten island to our left. The vast skyscrapers of Manhattan gleaming in the sun – it is a magical, exciting place to arrive to in a yacht and one you will never forget. We will likely dock in Liberty Landing Marina, Newark, just across the Judson River from the excitement of Manhattan.

Clean up and disembark

It’s the final day and it can be emotional to say goodbye to each other and goodbye to the boat. As a group, we will have been on a huge adventure together and have made friends for life. It’s time to go though and today we clean the boat, sign logbooks, trade contact information and then it’s off home.

We can often find long haul flights at cheap prices. Ask us!

  • You should join the boat in Antigua at 0900 hrs on the start date. We will ask you closer to the time to let us know your travel details.
  • You will disembark the boat in New York City at 1200 hrs on the last date



New York is well served by many airlines. You have various choices of airport from:

  • John F. Kennedy International Airport (JFK)
  • LaGuardia Airport (LGA)
  • Newark International Airport (EWR)


  • V. C. Bird International Airport (IATA code: ANU)

Rubicon 3 runs expedition yachts to remote locations and on serious ocean passages. They are tremendous fun to sail and the skipper and mate are real experts from whom you will learn a huge amount. The routes themselves are adventurous, unusual and, for the most part, far from the beaten track. You will be joining the yacht for a couple of weeks at some point on its 11-month long voyage. It is important that you understand that this is true ocean and expedition adventure sailing, not a sanitised charter sailing holiday. You will be a full part of the crew, helming, navigating, trimming sails and more. You will also be fully involved in cooking and keep the boat clean as we go. If the weather is strong you will be living life at an angle and may have waves landing on you while you work on deck. (Our foulies will keep you dry as much as possible and the boat is always warm down below.) Conversely in hot regions, you may be trying to keep cool and wishing for that wave! Adventure sailing and life at sea is far more basic than life at home. It is amazing, extraordinary and life-affirming but you will be living in close quarters with the rest of the crew, need to be able to deal with the occasional discomfort or mishaps that inevitably come with being on the sea or in remote regions and should come with a ‘can-do’ attitude. The boat itself is on a long voyage far from home and will always have certain jobs, maintenance and repairs being done on it. This is the reality of adventure sailing. The rewards though are beyond what you can imagine and you will have experiences, memories and new friendships that will last a lifetime.


These adventure sailing holidays are open to anyone aged 18 – 70 years. Although this trip is open to beginners, we recommend that you have some sailing experience before, even if it is just an introductory weekend. This will enable you to be confident that a prolonged passage at sea is something that you will enjoy.


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.


  • Oilskins
  • 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 can be earned 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 Trip Notes before booking.


  • To be a watch leader on a Rubicon 3 ocean passage, we require you to have sufficient skills and experience to be able to approach the role meaningfully. This means you should have a minimum of RYA Coastal Skipper practical and theory. We accept international equivalents. After booking, you will be asked to provide evidence of your qualifications.
  • On arrival, we will ask you to complete a short theory test to ensure that you are at the required level. If you are able to complete RYA Yachtmaster Coastal theory questions, you will be fine. If you are not at the required standard, we will downgrade you to a standard crew member.


  • On booking, you will receive a copy of the Rubicon 3 Watch Leader’s training manual. This is an invaluable resource and you should try to read as much of it as you can before joining.
  • You should arrive at the boat the day before the advertised start time, being ready to start studying at 1000 hrs. You will spend a full day learning about passage planning, the yacht and helping prepare the yacht. You will be able to stay on the boat that night
  • There is an additional fee of £150 to cover these extra training costs.


If you are planning to proceed to Yachtmaster Ocean, there are various requirements. Please read this guide carefully before boarding: Rubicon 3 Yachtmaster Ocean overview


Yes. as this is a serious, long-distance voyage you must have a minimum of RYA Day Skipper or ASA 104.


Almost everyone comes alone. Couples and groups are very welcome and we do get them. On the whole, however, most crew join solo and so if you are coming alone, you will be one of the crowd!


Except in exceptional circumstances, we limit the crew size to 9 (except for Atlantic crossings) plus two instructors. This means that there are enough people to sale the boat safely, but you will still have lots of time helming, navigating, trimming sails and such like.


Absolutely. First and foremost, we are here to ensure everyone has an amazing time. Sailing is about having fun, experiencing nature at its most majestic and gently pushing yourself to try and learn new things. Rubicon 3 voyages are a unique mix of sailing and training, and you will get far more involvement and training than on any other sailing holiday you may try!


We have a remarkably similar group of people who join all our trips. They come from all around the world, are an even mix of men and women and with an average age of 35-65. As we said above, most come alone and experience varies from none at all to Yachtmaster. Most of the crew would describe themselves as having a rusty Day Skipper.


Go the ‘BOOK NOW’ button near the top of the page. This will take you through to our booking system, and it will ask you for a deposit of £400. As soon as this is paid, your place is reserved. The balance of the trip must be paid by 60 days before departure.