Crossing the Atlantic: best windows for delivery captains

The transatlantic delivery isn't a year-round job. The trade winds, hurricane seasons, and high-latitude lows all conspire to make some months excellent and others unworkable. Here's what the seasons actually look like.

Eastbound (Caribbean → Europe): May through July

The classic Caribbean-to-Europe delivery leaves Antigua, Saint Lucia, or the BVI in late April through June, follows the higher latitudes via Bermuda or the Azores, and lands in Lagos, Gibraltar, or the Solent four to six weeks later.

Latest realistic departure: Mid-July. After that, North Atlantic low-pressure systems pick up and the southern route becomes uncomfortable.
Hurricane risk: Starts to build in June for the western Atlantic. By mid-July, most deliveries should be north of 30°N.
Typical stops: Bermuda for fuel and rest, the Azores (Horta or Ponta Delgada) for the second jump.

Westbound (Europe → Caribbean): November through early December

The trade-wind crossing leaves Las Palmas, Mindelo (Cape Verde), or southern Portugal in mid to late November and follows the trades west to the Eastern Caribbean. Two to three weeks of downwind sailing if the weather plays.

ARC departure: Typically the third Sunday of November. ARC+ leaves a week earlier from Mindelo.
Commercial window: Mid-November through early January. Earlier than that and you risk autumn lows; later and the boats are already booked for charter.
Routing decision: The classic "south until the butter melts, then west" remains the safe choice. Boats that try to shortcut by going west first often hit headwinds and break gear.

Northbound (Caribbean → US East Coast): April through May

Boats moving from Caribbean charter season back to summer in New England or the Chesapeake leave in April or May, often via Bermuda. Wind angles are tight — expect close-hauled work — but the route is short (10-14 days typical).

Southbound (US East Coast → Caribbean): October through November

Reverse of the above. Leave Newport or Annapolis after the boat shows, harbor-hop down the US coast, then jump from Bermuda or directly from Fort Lauderdale to the Eastern Caribbean.

What the windows mean for your gig pipeline

If you're a delivery captain or crew on Boat Gigs, you should expect to see:

September–October: Heavy posting for autumn westbound deliveries
March–April: Posting for eastbound transatlantics and northbound coastal runs
January–February: Quiet for ocean work; lots of Caribbean inter-island deliveries
June–August: Quiet for transatlantics, busy for Med inter-port and Northern Europe deliveries

Set up email alerts on Boat Gigs (coming soon) for the seasons that match your availability and you'll see the gigs land in your inbox.

A note on insurance

Most yacht insurance policies prohibit ocean crossings outside specific windows — often "north of 35°N before July 1" or "no Caribbean voyages between June 1 and November 30". Always verify the policy before accepting a gig; an uninsured delivery is your problem if something goes wrong.