Bahamas, Part 1: Gulf Stream Crossing, Clearing In, and the Berry Islands
We didn't let a lack of sleep get in the way of finding adventure!
It’s been a little over a week since we crossed from Fort Pierce, FL to the Bahamas—making it high time to share an update on the most memorable portion of our journey so far. Over the past week, we’ve experienced a number of firsts: an overnight passage, bringing our boat to a foreign country, exploring the remote Berry Islands, and so much more. Before jumping in, here’s a quick recap.
Route Overview
Saturday, 12/27: Final preparations in Fort Pierce, FL
Sunday, 12/28 into Monday, 12/29: Fort Pierce, FL → West End, Grand Bahama Island
Monday, 12/29 into Tuesday, 12/30: West End, Grand Bahama Island → Ambergris Cay, Berry Islands
Tuesday, 12/30 – Wednesday, 12/31: Ambergris Cay, Berry Islands
Thursday, 1/1: Ambergris Cay, Berry Islands → Soldier Cay, Berry Islands
Friday, 1/2: Soldier Cay, Berry Islands → Hoffman Cay, Berry Islands
Saturday, 1/3: Hoffman Cay, Berry Islands
Crossing the Gulf Stream
The Bahamas consist of a chain of more than 3,000 islands spread over 500 miles. At its closest point, the Bahamas lie about 50 miles off the coast of Florida. A 50-mile passage is not excessively long, even for a slow-moving sailboat like Osprey. Distance isn’t the challenge—navigating the Gulf Stream is.
The Gulf Stream is a warm ocean current that runs north from the Gulf of Mexico along the East Coast of the United States before turning east and becoming the North Atlantic Current, carrying warm tropical water toward both the eastern U.S. and Western Europe.
You can think of the Gulf Stream as a “river” in the ocean. It is one of the fastest ocean currents in the world, averaging between 2.5 and 4 knots. For context, Osprey’s average speed is somewhere between 5.5 and 6.5 knots. Just as you wouldn’t want to paddle a canoe against the flow of a river, a sailor doesn’t want to sail against the Gulf Stream.
In addition to current direction, wind speed and direction are critical factors when crossing. Ideal conditions include very light wind (less than 10 knots) or wind coming from the same direction as the Gulf Stream (from the south). Even moderate winds opposing the current can create ocean chop and standing waves that are uncomfortable at best and dangerous at worst.
Considering these factors, Michael and I patiently waited for an acceptable weather window to cross the Gulf Stream. We also remained flexible about which Florida port we would depart from. Leaving farther south, such as Miami, allows sailors to ride the Gulf Stream north toward the Bahamas—almost like floating down a lazy river. Departing farther north lengthens the passage, as the current pushes you northward and requires you to double back south after crossing.
If you read our previous post, you’re familiar with the time we spent in Fort Pierce completing final projects to prepare for 4–5 months largely off-grid in the Bahamas. We didn’t expect to leave directly from Fort Pierce, since it’s farther north than most typical crossing points. Instead, we imagined heading farther south after finishing our work. However, the weather window we were tracking looked like it would allow a rare safe and comfortable crossing directly from Fort Pierce.
The winds the weekend after Christmas were incredibly light, with no northerly component to kick up waves in the Gulf Stream. Additionally, the south-flowing current that typically spins off the western edge of the Gulf Stream was unusually calm—making a Fort Pierce crossing possible.
Our plan was to leave Fort Pierce and head toward West End, Grand Bahama, about 80 nautical miles to the southeast. Knowing the Gulf Stream would push Osprey north, we planned to make as much southing as possible before crossing, staying close to the Florida coast in case of mechanical issues. Near Jupiter, FL, where the Gulf Stream brushes the coast, we would turn east and begin the crossing. After clearing the Stream, we expected to be 20–30 miles northwest of Grand Bahama and would then turn southeast for the remainder of the passage.

After confirming the plan with our sailing coaches, we chose the Sunday after Christmas as our departure day.
That morning, after stopping at a nearby marina to fill water tanks and take out the trash, we left the Fort Pierce Inlet around 11 a.m. As we headed toward the inlet, we were delighted to see our friends on S/V Water Wings off our starboard stern. They escorted us toward the inlet, wished us well, and snapped a few lovely photos of Osprey. We’re incredibly grateful to have met Water Wings in Brunswick and spent more time together in Fort Pierce. As more experienced cruisers, they’ve offered invaluable advice and support—and we look forward to reconnecting when they make their crossing later this season.
We timed our exit close to slack current, resulting in a calm and beautiful entrance into the Atlantic. We were able to sail for the first 30 minutes before the wind died completely, requiring us to motor the rest of the way. Just north of Jupiter, we turned east. I made a quick dinner, which we enjoyed while watching the sunset over the Florida coast, and around 6:30 p.m. we entered the Gulf Stream.

Even with light wind, the Gulf Stream brought noticeable swell, causing Osprey to buck and roll. While not the most comfortable motion, we felt safe throughout.
Around 8:30 p.m., we began our watch schedule to allow each of us some rest during the ~18-hour passage. Michael took first watch while I napped below. Just after midnight, we switched, and by then we were out of the Gulf Stream. The seas calmed significantly, and we were making such good time that we had to slow down to avoid arriving in West End in the middle of the night.
We saw dozens of cruise ships overnight—and even a small fishing boat in the middle of the Gulf Stream! Using our navigation instruments, we were able to track each vessel’s course and safely maneuver around one another.

Around 4:30 a.m. on Monday, land was in sight. Since we arrived earlier than expected, we shut down the engine and bobbed in calm water until sunrise. While waiting, I cooked breakfast and we eagerly anticipated our next step: clearing into the Bahamas.
Clearing into the Bahamas
After sunrise, Michael expertly navigated us into the marina at West End to clear customs and immigration. We tied up around 8 a.m. and waited for the office to open. While waiting, we raised our yellow quarantine flag, signaling that we hadn’t yet cleared into the country. Until officially checked in, we weren’t allowed to leave the boat—even to take Maisie ashore.
Several other sailboats arrived while we waited, and we chatted cockpit-to-cockpit about crossings and plans. A little after 9 a.m., Michael and the captain of S/V Synergy headed into the office to complete the process.
Clearing into the Bahamas is fairly straightforward. Much of the paperwork had been completed online while we were still in Fort Pierce, including uploads of our passports, vessel registration, and Maisie’s pet permit. The immigration official reviewed everything and determined how long we were allowed to stay.
The length of stay can feel somewhat arbitrary—some cruisers receive 180 days, others as few as 30. We requested 180 days and were granted 100. After that, we can apply for an extension (for a fee). Maisie’s permit, however, is valid for six months—so technically, she could stay longer than we can!
Once the paperwork was complete, Michael returned to Osprey and we raised the Bahamian courtesy flag, officially signaling that we were legally in the country. After a much-needed shore break for Maisie and saying hello to friends from our home marina who happened to be there, we began planning our next move.
With excellent wind forecast for Monday night into Tuesday, we decided to continue south rather than linger in Grand Bahama. After a quick nap, a late-afternoon walk for Maisie, and an oil change in the protected anchorage of Ginn Sur Mer, we set off on our second overnight passage.
Back-to-Back Overnight Passages
Riding the high of a smooth crossing and official arrival in the Bahamas, we lifted anchor as the sun set and headed 90 miles southeast to Ambergris, Berry Islands.
With only 3–4 hours of sleep the day before, fatigue was the biggest challenge. Fortunately, the conditions were ideal: calm seas and steady wind at a beam or broad reach the entire way. We shortened our watch rotations to ensure neither of us became overtired.
The parade of cruise ships continued as we passed Freeport and Great Stirrup Cay, Norwegian Cruise Line’s private island. We even saw a massive cargo ship maneuvering offshore, with its pilot boat hailing nearby sailboats to ensure safe distances.
We chose Ambergris Cay for its protection from predicted westerly winds. We arrived around 9:30 a.m. Tuesday, dropped anchor, took Maisie ashore, and spent the rest of the day resting and recovering after nearly 200 miles of sailing.

Exploring the Berry Islands
The Berry Islands are a mostly uninhabited chain of about 30 islands located roughly 120 nautical miles east of Miami. Known for pristine beaches and excellent snorkeling and diving, they’re slightly off the beaten path and less crowded than other cruising destinations.
In Ambergris, we shared the anchorage with S/V Anjuna, S/V Synergy, and later reunited with S/V Silver Lining. We gathered for a New Year’s Eve beach bonfire, met cruisers from around the world (many from France), and even sampled fresh-caught rock lobster and conch—fueling our excitement to catch our own.
Michael, Maisie, and I attempted to explore Shark Creek by dinghy but quickly learned just how shallow Bahamian waters can be. Even the dinghy couldn’t make it through. Wildlife sightings would have to wait.
On New Year’s Day, we followed Silver Lining to Soldier Cay to test our snorkeling and spearfishing gear. While we didn’t catch dinner, we became more comfortable in the water and began to appreciate the underwater beauty of the Bahamas.
With west winds continuing, we moved on to Hoffman Cay. Before leaving, we were delighted to reconnect with S/V Eleanor, whom we hadn’t seen in nearly a month. Reunions like these are one of the joys of this life—crossing paths again after traveling separate routes. We hope to meet up again somewhere in the Exumas.
Hoffman Cay was stunning. Over two days, we explored above and below the surface: diving on a wrecked sailboat, jumping into a blue hole, and spotting sea turtles. Without an underwater camera, we recommend following Silver Lining on Instagram or YouTube for visuals we simply can’t capture.
We could easily spend weeks exploring the Berry Islands, but our journey south continues.
Continuing Our Southward Journey
There are 14 island groups in the Bahamas. So far, we’ve visited just two: Grand Bahama and the Berry Islands. Each group offers something unique, and all are breathtaking.
We’re hoping to explore more remote island groups like Long Island, Ragged Island, and Conception Island. To get there, we’ll first make our way south through the Exumas, using George Town as a hub for exploring the “outer islands.”
There are several routes from the Berries to the Exumas—via New Providence or Eleuthera—and weather will ultimately decide both our route and pace. As always, our plans are written in sand, ready to be reshaped by wind and tide.
We’ll keep you posted on where we head next and what adventures await.
Until then, cheers!
– Jen, Michael, and Maisie












First, Glad you made it safely!!! Second, the waters have definitely changed to the most gorgeous azure!!! Happy new year and your grand adventure. Great post! Keep them coming. I stop whatever I am doing to read them immediately. We love you.
You guys are amazing 👏 I love reading the experience through your perspective. Very well written, I feel like I am reliving the experience on Osprey! Loved it. Thank you for the shout out🙈❤️