The Keys to Having Fun in Paradise
Well, not everything goes as planned but despite cool weather, strong winds, and a flexible itinerary, the crews of Southern Cross and Pretender still had fun on this January 2026 cruise.
Moonlight on Newfound Harbor.
Photo by Jan Cornelius
The fun started even before we arrived at the boats. Gary (Trip Leader) received a call from the charter company, Sail Away Key West, that one of our chartered boats, Sugar Magnolia, had been damaged during the previous charter and would have to be swapped for a seaworthy replacement. Our choices were to take a 4-cabin boat and then swap the boat mid-cruise for a different 4-cabin boat, or to take a newer, 3 cabin boat for the entire cruise. Rather than deal with the logistics of switching boats mid-cruise, the crew chose to take the 3-cabin boat.
The crews met up at The Perry Hotel and Marina on Stock Island (the first island east of Key West) on Saturday, January 17th. The crew of Southern Cross checked out and boarded their boat. But the crew of Pretender, the substitute for Sugar Magnolia, found out their boat was at a different marina. For some that meant their clever plan of staying at the pricey Perry Resort to be right at the marina had fallen apart. Pretender’s crew made their way to the more remote Stock Island Marina. Or was it Stock Island Yacht Club? Depended on who you asked. On top of that, Pretender’s non-perishibles provision order failed to be delivered.
So while Mia and some of the crew of both boats did the boat checkout with the Sail Away technician and a boat handling session with a Sail Away Captain, several crew members went to the grocery store.
After a long day, it was time for Southern Cross’s crew to enjoy some seafood and libations at the Hogfish Grill. Pretender’s crew entertained friends of two crew members and ordered Cuban food from a local restaurant. The provisioning shoppers finally returned from their second run for perishables just as dinner arrived and we enjoyed our delicious food with Cuban music.
Saturday evening the skippers reviewed the plan for Sunday and the weather forecast. Winds on Sunday were forecasted to be 20 to 30 knots with gusts to 40+ and waves outside the reef to be 3 to 5 feet. Additionally, temperatures were predicted to be in the mid-60s. Another major consideration was that we would be anchored in an unfamiliar and shallow harbor. After discussion with the crews, the decision was made to not sail to the reef for snorkeling or to proceed and anchor in Newfound Harbor.
Karen, Cherie, Dave, and Hallie — Pretender crew at Hogfish Bar and Grill.
Photo by Mia McCroskey
On Sunday morning the crew of Southern Cross decided to take a short “shakedown” sail before the winds piped up too much. The main was raised to the second reef point and the jib unfurled for a bit of sailing before returning to the marina and successfully docking the 48 foot catamaran back in her assigned slip. Pretender’s crew declined to go out, as their slip was barely wider than the boat, and the charter skipper had said someone from Sail Away Key West would dock her when we returned at the end of the week. Instead, some crew went to the marina pool and some lounged on the boat. They gathered early in the evening and hailed a ride to Hogfish Grill for dinner.
The winds on Monday were still stiff and, while the waters in Hawk Channel were reasonably calm as they were protected by the reef, the waves outside the reef were still 3 to 5 feet, so we decided to proceed directly to Safe Harbor Marathon Marina at the entrance to Boot Key Harbor rather than stopping at the reef to snorkel. The Southern Cross crew hoisted sails as soon as they were safely out of the harbor and sailed nearly all of the 37 mile trip to Safe Harbor Marathon on a beam reach.
Pretender’s crew was more conservative – or maybe just too cold. Nobody was willing to climb up on top of the solid bimini to unzip the main sailcover. So they motored into the driving wind. They were relieved to see their assigned spot in the marina at the end of a T dock.
Ann, Karen, Gary, Hallie, John at Safe Harbor Marina, Marathon.
Safe Harbor Marathon was a welcoming marina resort with a number of amenities. We made use of one of their pavilions to socialize and enjoy the appetizer dinner that we had planned for the previous evening.
Tuesday morning was still a bit windy and chilly so the crew proceeded directly to Hawks Cay Resort and Marina. With winds on our nose, both crews motor sailed east along the Keys to Duck Key where the Marina was located. Shortly after lunch, we motored around the Duck Key outside channel.
Southern Cross tied alongside.
Photo by Hallie Lee
After a couple attempts to back into our slip while fighting a cross wind and current, Southern Cross opted to dock alongside a spot further in the marina.
When the harbor master offered that same slip to Pretender, having been warned, we declined and opted for a slip over near the fuel dock. Or was it on the fuel dock? Confusing directions came from the harbor master, heard by both the harbor master and the dock attendant, which ultimately had Pretender stuck in the sand a few feet from the fuel dock. Both Mia and Josh, the dock attendant, were not pleased to hear the harbor master on the radio say “No, not over there, it’s too shallow,” after having sent us there. We managed to pull into deeper water and come around a short finger pier to back into the next slip over, but the wind and current still knocked us against a piling on that finger pier before we were secure.
In the afternoon, we explored the resort a bit and then both Crews dined at the Angler & Ale Restaurant at the marina.
Mia, unknown new friend, Bobby, Sally, Ann, John in the hot tub at Hawk’s Cay Resort.
Photo by Gary Brubaker
Wednesday was a planned layover day and the crews took advantage of the amenities offered by the resort. The resort was also preparing for a sailboat show and some of the crews strolled around the Duck Key Inner Harbor to view the multihulls that would be on display.
Back home in the northeast the weather reports were starting to get scary. A major winter storm was coming on the weekend. When many of us were supposed to fly home. Those with Saturday flights were likely fine, but those with Sunday travel plans started looking at their options.
Kathy walks on water.
Photo by Jan Cornelius
On Thursday the temperature had warmed a bit and the winds had also subsided. Our original plan was to visit Bahia Honda State Park and anchor out for the evening but rather than visit a sometimes crowded anchorage between two bridges, we decided to proceed to Newfound Harbor, where we were supposed to anchor on the first night of our cruise. We were also considering a snorkel stop at one of the reefs, but as we neared it the sky clouded over. Enthusiasm aboard Pretender waned and we headed directly for our anchorage. Naturally the sky cleared by the time we got there.
Southern Cross followed Pretender into the harbor and both boats found the holding good for the night. Once anchored and after the obligatory “victory beer” many of the crew decided to test the water and go for a swim. Dinner was aboard the boats and after the clean-up, there was a rousing game of Farkle on board Southern Cross. Pretender’s game of the trip was “Oh Shit,” a deceptively not so simple card game.
Southern Cross crew in Newfound Harbor.
Photo by Ann Pollack
On the final day of our cruise, Pretender led the way out of the anchorage but Southern Cross had one more challenge for the crew: the windlass refused to work. Despite several attempts to cycle the windlass breaker and also attempting to move the windlass by hand, the 70 foot of anchor chain that had been deployed was raised by cranking the windlass manually. Pretender, being out of the anchorage early, proceeded to Western Sambo for some snorkeling while Southern Cross, departing a bit later, proceeded directly to her berth at Perry Marina.
Lisa snorkels Western Sambo reef.
Photo by Mia McCroskey
After a fun snorkel and lunch, Pretender started in toward Stock Island Marina – ah, Yacht Club. Mia texted Sail Away Key West to arrange to be met at the fuel dock as instructed. They got to the fuel dock and were told by the attendant there that they had “done it wrong” and had to move around a smaller boat that was already tied up there, into a spot behind it. Okay, could have shouted to us as we came in, you were standing right there… We moved and took on fuel.
Our driver was due. Mia texted again and got an ETA for fifteen minutes later. We waited, watching fishermen cleaning enormous game fish at the adjacent fish cleaning table. Pelicans and one pushy white ibis also watched. Time passed. Boaters circling, waiting for the fuel dock, started complaining. But the fuel dock folks didn’t, so we stayed put. Finally our contact texted they were parking. Finally – almost a half hour later than promised, our driver arrived. Once at the helm he said “I’ve never driven this boat. And I’ve never docked in this slip.” Mia wondered why they hadn’t sent someone with a bit more experience. And indeed, it took him several tries to line up the boat, accounting for the current, and back straight into the slip, all the while being instructed and encouraged by his partner who was on the dock.
Pretender’s last night on board was a must go dinner that satisfied everyone. Plus we had to finish the liquor.
On Saturday we off-loaded and cleaned up, then met with the technician again for a checkout discussion. And then we scattered, some to hotels, some to the airport. Those with Sunday travel plans had changed them to Monday, which meant another day in paradise, even if it was unseasonably cold.
