The Caribbean season overview
The Caribbean charter season begins in November and reaches its peak around Christmas and New Year. From December through March, the eastern Caribbean — Antigua, St Maarten, the BVI, St Barths, Grenada — is packed with charter yachts and their crews running back-to-back charters for guests who are escaping northern hemisphere winters. April marks the end of the season for most operators, and by May, the fleet has largely departed for summer bases or entered hurricane storage.
The Caribbean is a charter-dominated market, which means crew income includes not just salary but tips. On a high-end Caribbean charter, guests typically tip 15–20% of the charter fee at the end of the week. On a $12,000/week charter, that's $1,800–2,400 divided between crew. Tips can add $500–1,000/month to a crew member's effective income during the peak season — a significant boost over the base salary alone.
The ARC — Atlantic Rally for Cruisers
The ARC (Atlantic Rally for Cruisers) is one of the most significant annual events in the sailing calendar. Hundreds of sailing yachts — primarily privately owned cruising boats but with some crewed charter vessels — congregate in Las Palmas, Gran Canaria in November and cross the Atlantic Ocean together, arriving in Rodney Bay, St Lucia approximately 3 weeks later.
For crew, the ARC represents two distinct opportunities. First, many ARC yachts need additional passage crew for the Atlantic crossing itself — the ocean passage requires watch-keeping crew who can handle the boat in open ocean conditions for 2–3 weeks. Second, ARC arrivals in St Lucia in late November mark the unofficial beginning of the Caribbean charter season. Crew who position in St Lucia for the ARC arrivals are in the right place at the right time as the season begins.
The main Caribbean hubs for crew
Antigua — English Harbour
One of the most famous yachting destinations in the world. English Harbour and Nelson's Dockyard host hundreds of yachts throughout the season. Primarily sailing-focused. Antigua Sailing Week in late April/early May is the Caribbean's premier sailing regatta. See our full Antigua dock walking guide.
St Maarten — Simpson Bay
The largest protected lagoon in the Caribbean hosts hundreds of yachts throughout the season. A mix of charter vessels, private superyachts, and cruising boats. Lively social scene. See our St Maarten dock walking guide.
British Virgin Islands
The charter capital of the Caribbean. Bareboat and crewed sailing charter dominates. The Sir Francis Drake Channel provides some of the most beautiful sailing grounds in the world. Best for crew who want genuine sailing experience. See our BVI dock walking guide.
St Barths — ultra-luxury
St Barths (Saint-Barthélemy) is the most exclusive and least accessible of the Caribbean's main yachting destinations. The anchorage at Gustavia is filled with some of the world's most expensive superyachts at Christmas and New Year. Public dock access is extremely limited — most crew contact happens through crew agencies or established personal connections rather than dock walking. It's worth understanding St Barths exists as a market even if direct dock walking is difficult.
Fort Lauderdale — the gateway
While technically US rather than Caribbean, Fort Lauderdale serves as the operational hub for vessels heading into the Caribbean season and returning from it. Many Caribbean-bound superyachts are based in Fort Lauderdale. FLIBS in late October is the best opportunity to connect with Caribbean-bound captains before the season begins.
Grenada — the southern Caribbean
Grenada and the Grenadines are increasingly popular with superyachts at the southern end of the island chain. Port Louis Marina in Grenada has grown significantly. Grenada is below the main hurricane belt, making it a year-round option for some vessels. Worth knowing as the market continues to grow.
Hurricane season — the annual reset
The Atlantic hurricane season officially runs from June 1 through November 30, with peak activity from August through October. Most charter operators and superyacht owners take their Caribbean-based vessels out of the hurricane belt during this period — either heading north to the US eastern seaboard, making the Atlantic crossing back to the Med, entering hurricane storage in Grenada or Trinidad (which are largely below the main hurricane tracks), or hauling out in a certified hurricane-rated boatyard.
For crew, the end of the Caribbean season (April/May) is therefore also the end of their employment on Caribbean-based vessels — unless the vessel is making a transatlantic crossing or has a summer US program. Planning your next move before the Caribbean season ends in April is important.
What Caribbean crew positions pay
Caribbean base salaries are broadly comparable to Med positions for equivalent roles, but the tip income in the Caribbean can be significantly higher due to the charter-intensive nature of the market. Caribbean charter guests are typically American and tip generously by global standards. A stewardess earning $3,500/month base salary might earn an additional $500–1,000/month in tips during peak charter season — a meaningful supplement.