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The best time to cross is in advance of a cold front where the wind shifts to the south or southwest. But better make damn sure you're in Bimini before the wind clocks to the North/Northeast, as the Gulfstream can turn hellacious in the actual front itself. In fact, your timing of this question is ideal...there's a front arriving tomorrow night. Just look at this forecast, remember that leaving from SE Florida, you're generally going to have to make southing to counter the effect of the 2-3 knot current pushing you north.

Before the front...when I would cross. Start as far south as possible but by all means BE OUT OF THE GULFSTREAM BEFORE THE FRONT ARRIVES. Motor sail or just motor!!!
THURSDAY
SOUTH SOUTHWEST WINDS 5 TO 10 KNOTS BECOMING WEST
SOUTHWEST IN THE AFTERNOON. SEAS LESS THAN 2 FEET. DOMINANT PERIOD
8 SECONDS. INTRACOASTAL WATERS A LIGHT CHOP.
Now the front arrives...notice how things are starting to get dangerous. West wind is good *nearshore* as it lays the seas down...however offshore, westerlies tend to be strong and GUSTY, causing steeper seas.
THURSDAY NIGHT
WEST WINDS 10 TO 15 KNOTS BECOMING NORTH
NORTHWEST 15 TO 20 KNOTS AFTER MIDNIGHT. SEAS AROUND 2 FEET
BUILDING TO 2 TO 4 FEET WITH OCCASIONAL SEAS TO 5 FEET AFTER
MIDNIGHT.
DOMINANT PERIOD 5 SECONDS. INTRACOASTAL WATERS A MODERATE CHOP.
ISOLATED SHOWERS AFTER MIDNIGHT.
All hell breaking loose as the front arrives...better pray you're in safe harbor (not even anchoring...a marina) when this slop arrives.
FRIDAY
NORTH WINDS 20 TO 25 KNOTS. SEAS 9 TO 11 FEET WITH
OCCASIONAL SEAS TO 14 FEET.
DOMINANT PERIOD 7 SECONDS. NORTH NORTHEAST
SWELL 3 FEET IN THE AFTERNOON. INTRACOASTAL WATERS A MODERATE
CHOP. A SLIGHT CHANCE OF SHOWERS.

FRIDAY NIGHT
NORTHEAST WINDS 15 TO 20 KNOTS. SEAS 9 TO
11 FEET WITH OCCASIONAL SEAS TO 14 FEET SUBSIDING TO 7 TO 9 FEET
WITH OCCASIONAL SEAS TO 11 FEET AFTER MIDNIGHT. NORTH SWELL
3 FEET IN THE EVENING. INTRACOASTAL WATERS CHOPPY IN EXPOSED
AREAS.
My usual path was to leave port everglades and motor as far south...usually to about Baker's Haulover Inlet. To avoid the stream, we would hug the shore in about 15-20 feet of water trying to stay inside the dive buoys lining the coast. Go as close to shore as you're willing to. THen make a sharp left and sail *HARD* east...motoring as fast as you can. This would generally cause us to land about 4-5 miles north of Bimini due to current. We'd leave at night and hope to arrive 10 hours later at the banks. Then we'd sail or motor back south, casting lines to try and catch a mahi. Its an "s" shaped route. When we arrive, into the marina, clear customs....then pass out from lack of sleep as the front arrives and wind howls. Wake up, clean the fish we caught earlier, then drinks at the bar as the front moves off and we plan our next passage further east. Not much to do or see in Bimini beyond a long weekend. Waters are too shark infested to dive nowadays.
 

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Good post by NightOwl.

My method is essentially the same but I prefer to leave from Angelfish Creek (Pumpkin Key) at near the southern end of Biscayne Bay (or Rodriquez Key further south on the Hawk Channel) to get a boost from the Gulf Stream AND I can still sail with a S-SE wind. From the Miami area, I will add 20°M to compensate for GS flow if Im going 'straight across' in calm winds (37ft boat).
You do NOT want to approach N.Bimini in a strong SW-NW 'blow' as if there is a peak ebb flow out of the harbor (Alicetown) the 'cut' into the harbor can easily be 'at rage' conditions.

Bimini a nice place; but as others have stated - beyond a week or a few days stay its not going to be 'good', you're going to need a marina or the Bimini Bay Resort (expensive) at the north end of N.Bimini for any convenience, and you'll soon find that your not going to be wandering around after dark. The harbor isn't 'really all that good for anchoring due to the small ships and a lot of traffic going to/from Bimini Bay. Best time for Bimini is "Homecoming" .. first week of April.

Good advice about the sharks. Lemon sharks (winter through spring) and Bull sharks abound, especially in/near the harbor where they clean a lot of fish and simply dump the 'scraps' into the water. Winter-early spring time can bring quite a few Tiger Sharks along the Bimini shores.
 

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June or July. But I don't know what you'd do in Bimini for several months.
This advise puts you in Bimini in the middle of the hurricane season. Check your insurance and make sure you have a plan if a storm threatens.
 

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Crossing to the Bahamas vs. 'weather'.

MAY-JUNE & Sept-October (sans tropical cyclones) are generally best.

Equinoctial (change of season due to jet stream shift) N-NW gales blow from late Oct through Nov., and again from late Feb to end of March.

The enhanced (NE at a steady 20-30kts) trade winds are found from mid Dec through March.

Summertime when the humidity is high will usually produce 'serious' thunderstorms .. which for some reason usually begin at ~4PM

*** NightOwl has already stated the 'best' time to cross the Gulf Stream - 2-3days 'before' a cold front (with an approaching high pressure zone 'behind' the cold front), and with the S-W winds that will 'retard' or 'stop' the trade winds ... typically about every 10-15 days during wintertime and about every 15-20 days in summer (and there aren't many T'storms).
Typically a slow moving high pressure cell, from the west & moving 'over' Florida will bring 'benign' conditions ... and that can happen 'anytime' during the year.

El Niño/La Niña can 'change' all the above.
Fall/Winter/Spring of 2015-2016 (El Niño) had only 3-4 brief 'weather windows' of moderate to 'benign' sailing 'across' the GS from Early Nov. through the end of April.
 

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Other than avoiding hurricane season and bad weather for the passage window, I'm not sure there is a particularly right month. Bimini is not all that far, so you can pick a safe window.

That said, I truly like the Bahamas in the summer. They are warmer, less populated and the water is generally calmer (sans that forecast for 9-11ft with occasional 14ft and 7 sec period, which would be horrific!). I highly prefer the out islands, which is why I say less populated, not less crowded. They are never crowded. In fact, I refuse to ever return to Nassau or Freeport. I've been to Abaco, Andros, Long Island, Cat Island and Exuma. Each had it's own charm and lifetime memory.

The only issue is being able to get back to FL, in time, to be hauled for a hurricane. I've taken my chances in June/July and won a few times. I would not push it later, unless I really knew how I was going to secure the boat and get out.
 
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