The Caribbean Yachting Season: Ultimate Guide

Whether you’re an experienced crew member or a newbie eager to set sail, this complete guide will help you chart your course through the Caribbean Yachting Season.

Here I delve deeper into the Yachting Season in the Caribbean, looking at where to go and when, crew agencies, marinas, visa requirements, and big events.

When is the Caribbean Yachting Season?

The Caribbean Yachting season occurs between November and May. This is also known as the Winter Season in Yachting, referring to winter in the Northern Hemisphere.

The timing of this season occurs during these months as this timeframe is outside of the hurricane season.

During the winter months, you can expect to feel slightly cooler temperatures of about 28°C, as well as windy conditions, ideal for sailing enthusiasts.

View from a hilltop of a busy marina during the Caribbean Yachting Season with a cruise ship and lots of sailboats anchored in the bay.
Views over Yacht Haven Grand, St Thomas, USVI

Main Events to look out for during the Caribbean Yachting Season

If you are hoping to secure a job on a Yacht in the Caribbean, then you are going to want to head over a few weeks before the season starts. This is the time that Yachts are getting ready for the season. Leading up to the season, Yachts may be hiring new crew members or simply needing extra assistance as they get ready.

Another great job opportunity is to position yourself in a location leading up to main events that will attract many yachts to one location:

  • The Fort Lauderdale Boat Show (End of October) is an ideal time to find a job on a yacht. After the show, boats start getting ready to head to the Bahamas and the Caribbean.
  • The Antigua Boat Show is a 6-day event in the 1st week of December.
  • The St Maarten Heineken Regatta is held in March.
  • Christmas and New Year’s Eve. Now these may seem like obvious events to mention, but this is the Caribbean’s busiest time of year. Job seekers should attempt to find work before December, but equally as important is being available in January as many yachts make crew changes for those that didn’t make the cut during the busiest month.

Key Destinations in the Caribbean

The Caribbean consists of thousands of islands, however, there are a few key islands you would want to situate yourself in order to increase your chances of finding a job.


Antigua is a popular destination for yachting activities and a common starting point for most Yacht charters.

The Antigua Boat Show

The Antigua Charter Yacht Show in early December is a popular event for industry professionals and newcomers alike.

The show marks the start of the Caribbean yachting season and attracts impressive luxury yachts in the region. The main purpose of the show is for yacht brokers, vendors, Captains, and the Press to network.

It is an opportunity for yachts to be showcased before the season kicks off, in the hopes of booking charters and impressing charter brokers.

A man and a woman dressed in colourful t-shirts, standing on a hill with a background view of boats and yachts anchored in bays surrounded by mountains
Shirley Heights – Antigua

Marinas in Antigua

The 3 most popular marinas in Antigua are conveniently located within walking distance of each other.

  • Nelsons Dockyard
  • Falmouth Harbour
  • Antigua Yacht Club

Crew Housing in Antigua

Crew housing is limited in Antigua so depending on your budget you would need to look into staying at hostels or an Airbnb.

Pineapple House

This Crew House accommodates a maximum of eight guests, dormitory style. Very basic but lovely accommodation located just above the Antigua Yacht Club.

St. Maarten/St. Martin

This island is a hub for Yacht Crew and a strategic location to look for job opportunities during the Caribbean Yachting Season. Its dual nationality means you have access to both the Dutch and French sides.

St. Maartens Key Event

Heineken Regatta (March): Although the St. Maarten Heineken Regatta is mainly a sailing event, it also draws a significant number of Superyachts and luxury sailboats. Many crew members go to St. Maarten during this period in search of job opportunities.

St Maarten Crew Houses

Smilers Crew House is located in the central area of Cole Bay, making it easily accessible to all marinas. Some are within walking distance, while others are only a few minutes away by bus.

Shrimpy’s Crew Quarters is very basic accommodation ideally located in Marigot. Bookings are through Airbnb.

Marinas in St Maarten

Some of the top marinas to check out in St Maarten are:

  • Yacht Club Port de Plaisance
  • Isle de Sol Marina
  • Palapa Marina
  • Simpson Bay Yacht Club Marina
woman standing on a perfect white sand beach with crystal clear blue water in the Bahamas
A moment to enjoy the perfect Bahamas beaches

The Bahamas

While the Bahamas may not be officially considered a Caribbean destination, it remains a highly sought-after location during the Caribbean Yachting Season.

Most yachts will travel back and forth between Fort Lauderdale and The Bahamas in between charters. If you are hoping to land a job in the Bahamas, then it would be a good idea to position yourself in Fort Lauderdale or West Palm Beach.

For crew housing options in Fort Lauderdale check out my post on The Top Crew Houses in Fort Lauderdale.

Visa and Passport Requirements for the Caribbean Yachting Season

Many islands offer you a visa upon entry such as the Bahamas, Antigua, and the BVI’s.

If you are planning on starting your search from the USA, then you will need a B1/B2 visa. Even if a vessel flew you into the Caribbean from outside of the USA, that vessel will always make its way back at some point, so it is advisable to have your B1/B2 visa.

If you plan on heading to St Maarten you will need a Schengen visa. The island is split between the French side and the Dutch side. If you are not able to get a multi-entry visa, then your preference would be for the Dutch side of the island.

Crew Agencies in the Caribbean

Most crew agencies will have connections or clients in the Caribbean but their offices are in America or Europe.  

If you have chosen to start your journey into yachting from Florida or West Palm Beach, the top crew agencies you want to sign up for and meet with are:

  • Luxury Yacht Placement
  • Elite Crew
  • Northrop and Johnson
  • The Crew Network
  • Hill Robinson
  • Meridian
  • Cotton Crews

For more detailed information on these agencies check out my post on the Top Fort Lauderdale Crew Agencies.

super yachts docked in a busy marina during the Caribbean yachting season
Yachts arriving for the Antigua Boat Show

My Favourite islands to visit during the Caribbean Yachting Season

Whether you are on a Motor Yacht or Sail Boat, these are some of the top islands worth visiting in the Caribbean.

  • Antigua
  • British Virgin Islands
  • US Virgin Islands
  • Martinique
  • St Kitts and Nevis
  • Turks and Caicos
  • Bahamas
  • Guadeloupe

Hi, my name is Lisa, a Chief Stewardess in the yachting industry with 10 years of experience, as well as 8 years of hospitality experience prior to that. Being in the yachting industry has been a whirlwind of adventure, growth, challenges and some of the best experiences of my life, and I am excited to share my knowledge and experiences with all of you.