Every October, the docks at Shelter Island in San Diego fill with cruising boats from Alaska to Florida, all pointing south. In late October or early November, 150 to 200 of them leave together on the Baja Ha-Ha — the world’s largest amateur offshore sailing rally, run by Latitude 38 magazine since 1994.
The rally covers roughly 750 nautical miles from San Diego to Cabo San Lucas in three legs, with stopovers at Bahia Tortugas and Bahia Santa Maria. It is not a race. It is a buddy-boat system that makes the offshore jump to Mexico approachable for boats that have never been outside coastal waters, while still being a working trip for seasoned bluewater sailors.
This guide covers the route, the working stops, the weather windows, the paperwork, and the preparation — for the Ha-Ha itself or for an independent passage on the same timing.
The route at a glance
The classic southbound coastal route follows the Pacific side of the Baja peninsula:
- Leg 1. San Diego → Bahia de Tortugas — about 390 nm, typically 3–5 days
- Leg 2. Bahia de Tortugas → Bahia Santa Maria — about 225 nm, 2–3 days
- Leg 3. Bahia Santa Maria → Cabo San Lucas — about 140 nm, 1–2 days
Total: about 750 nm. Most boats complete it in 7–12 days of sailing. The Ha-Ha officially starts the last Monday of October and typically arrives in Cabo about two weeks later including stopover time.
Why the Ha-Ha
The Baja peninsula is a long, mostly uninhabited coastline with few bail-out options between stops. Cell service disappears south of Ensenada. Weather forecasts become less reliable beyond the reach of NWS coastal zones. For a first offshore passage, that is a working pile of unknowns.
The Ha-Ha solves several at once:
Safety in numbers. With 150+ boats in loose company, someone is always within VHF range. Fleet communications run on SSB net morning and evening. Mechanical problem or medical emergency: help is 20 miles away rather than 200.
Pre-vetted timing. The Ha-Ha departure date is chosen to coincide with the seasonal shift in Pacific weather — the NW swell dies down, Santa Ana conditions are possible but manageable, and the Pacific hurricane season has effectively ended. Independent cruisers often try to mirror the timing even outside the rally.
Camaraderie. The beach parties at Tortugas and Santa Maria are the working social calendar of the trip. Boats meet the community of cruisers who winter in Mexico, and many Ha-Ha friendships last years.
Entry preparation. The rally organisers work with Mexican port captains to pre-arrange group check-in. The customer still needs all their own paperwork, but the process is streamlined when arriving as part of the fleet.
Leg 1: San Diego to Bahia de Tortugas (390 nm)
The first and longest leg sets the tone. Leave San Diego on the evening tide and the boat is past Point Loma by dark, past Ensenada by dawn, picking up the Pacific swells by mid-morning of day two.
What to expect offshore. South of Ensenada the coastline turns barren — desert down to the water. The Baja Current runs NW at 0.5–1.5 knots most of the time; the boat is bucking it the whole way south. Typical conditions in late October are NW 10–20 knots with 4–8 ft NW swell. Reaching or running most of the way if the trades have filled in early; on bad years, motor-sailing sections.
Bahia de Tortugas. A small fishing village 390 nm south of San Diego, the first real anchorage on the Pacific side. The bay is deep (50–80 ft in most of the anchorage), open to the NW — uncomfortable in NW swell, fine in settled conditions. Fuel by panga (small-boat delivery), basics at the Pemex (when it has diesel), and the working order: cold beer at Enriqueta’s restaurant on the beach. Most boats anchor for 2–3 nights.
No official customs at Tortugas. Boats that have already cleared into Mexico at Ensenada (recommended for independent passages) can use the bay as a working anchorage. Ha-Ha boats typically have not cleared and proceed directly to Cabo.
Leg 2: Bahia de Tortugas to Bahia Santa Maria (225 nm)
The hardest leg. The coastline gets more exposed, and Punta Eugenia — the westernmost point of Baja — creates its own wind acceleration zone. Boats often see 25–30 knots around the point regardless of the forecast. Once past Eugenia the wind typically settles.
Bahia Santa Maria. A nearly circular bay at the foot of the Magdalena Bay complex, 350 nm north of Cabo. Nothing here — no town, no fuel, no supplies — just a stunning anchorage with good holding in 20–30 ft over sand, ringed by dunes and mangroves. Fishing is excellent. Whale sharks and manta rays are common from October onward. The Ha-Ha throws a beach party here; independent boats anchor quietly. Plan a day at minimum.
Leg 3: Bahia Santa Maria to Cabo San Lucas (140 nm)
The reward leg. The Pacific swells round Cabo Falso and the boat ride smooths out as the boat enters the lee of the cape. Cabo Falso lighthouse appears around dawn on a two-day run from Santa Maria. Round the point, enter the famous arch — El Arco — on the port hand, and the boat is in the Pacific-to-Sea-of-Cortez transition zone. The marina and anchorage are a few miles east. See the Cabo San Lucas guide for the working harbour detail.
Independent passage timing
For boats not doing the Ha-Ha, the same weather window applies. Late October to mid-November is the working optimum. Earlier risks late-season hurricanes (the eastern Pacific hurricane season officially runs June 1 through November 30). Later means stiffer NW swells and shorter days.
For a solo southbound passage:
- Clear out of the US (CBP eAPIS required for international departures)
- Clear into Mexico at Ensenada — the closest official port of entry, with a well-practised system for cruising boats. See the Mexico clearance guide.
- Or clear directly into Cabo San Lucas for a non-stop passage
Weather routing. GRIB files from Passage Weather, PredictWind, or Weather4D are reliable south to about 24°N. Beyond that, the NHC and Mexican weather service (SMN) are the working resources. Download enough data before departing — internet disappears past Ensenada. See Reading Marine Weather for the working framework.
Safety gear for the Baja passage
This is an offshore passage, not coastal sailing. The working minimum kit:
- EPIRB (registered, battery current)
- Life raft rated for the crew
- SSB radio or satellite communicator (Iridium GO, Garmin inReach) — VHF is useless 50 miles offshore
- Sea anchor or drogue for heavy-weather management
- Paper charts or downloaded charts on a backup device (iPad with Navionics works)
- 5+ days of food and water independent of any landfall
The Pacific coast of Baja is big-ship traffic. Run AIS Class B (transmit and receive) and keep a working watch schedule. See Marine Safety Equipment for the offshore equipment list.
After Cabo: where the fleet goes
Most Ha-Ha boats spend 2–4 weeks in Cabo, then split:
Up the Sea of Cortez. La Paz (80 nm east via the southern cape) becomes the cruiser hub for winter. From La Paz, boats fan out through the Sea to Loreto, the Midriff Islands, and eventually Puerto Peñasco (Rocky Point) near the US border. The Sea of Cortez is one of the world’s working great cruising grounds — calm seas, dramatic desert mountains, abundant fishing, and relatively few boats outside March–April. See the La Paz & Sea of Cortez guide.
Mainland Mexico. Some boats cross from Cabo or La Paz to Puerto Vallarta or further south to the Gold Coast — Manzanillo, Zihuatanejo, Huatulco — and beyond into Central America.
The Coconut Milk Run. A few adventurous boats continue from Cabo through the Panama Canal and into the South Pacific, though most of those boats have committed to that voyage long before the Ha-Ha.
Registering for the Ha-Ha
The rally is organised by Latitude 38 magazine and typically opens registration in July for the October departure. Entry fees are modest (under $500 in recent editions) and include insurance paperwork assistance, the party packages at Tortugas and Santa Maria, and the VHF/SSB net coordination. Full details and registration at latitude38.com.
The same route is workable on an independent schedule — the Ha-Ha is a rally, not a requirement. Independent boats make the passage every week throughout October and November.
Closing notes
The Baja Ha-Ha is the working introduction to Mexican cruising for hundreds of US sailors every year. The combination of working buddy-boat safety, pre-vetted weather timing, and the beach parties at Tortugas and Santa Maria makes the rally the most accessible offshore passage on the Pacific Coast.
For boats that have summered in the Pacific Northwest and worked the West Coast down to San Diego, the Ha-Ha start is the working transition into the next phase of the cruise. The boat that has crossed the Columbia bar, sailed the Oregon coast, rounded Conception, and arrived at Shelter Island in October is exactly the boat the Ha-Ha was designed for.
The arch at Cabo is the photograph the trip is remembered by.
Related: Cabo San Lucas Cruising Guide · La Paz & Sea of Cortez Cruising Guide · Ensenada & Northern Baja · Mexico Cruising Clearance Paperwork · San Diego Bay Cruising Guide · Marine Safety Equipment · Reading Marine Weather