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Smooth Sailing

a short story and discussion by Ted Boretti

Jim spends his vacation time sailing his family's boat through the tropical islands of the Caribbean. When he takes his girlfriend, Vivian, with him, his romantic getaway suddenly becomes a test of their compatibility.

Props, Preparations, and Tips

  • Print a copy of the story with the Discussion Starters below for the facilitator. Read the story and then use the Discussion Starters at the end of the story to start a conversation.
  • Print a large-print copy of the story. Ask individuals if they would like to read a section.
  • Also, if you want, download this PDF slide presentation to go along with the discussion. Show it on your widescreen TV. If this slideshow is useful and you would like to see more in the future, let us know.

Jim’s parents owned a 35-foot sailboat, and while it’s home port was Miami, Florida, it wasn’t found there very often. Jim’s parents weren’t millionaires, but they had budgeted wisely and now spent most of their retirement sailing around the Caribbean. For three weeks out of every year, though, the sailboat was Jim’s for the taking. So he worked through the holidays and notified his boss months in advance that he was taking three weeks off in the middle of the summer. Those three weeks of sailing were more precious than gold to Jim. Sailing, he thought, was as close as he could get to flying.

This year, Jim’s sailing trip was special. He was taking his girlfriend, Vivian. Vivian did not even know that Jim was a sailor. They had met in the dead of winter, trapped with hundreds of other hapless commuters in Washington, D.C., in a train station during a sudden snowstorm. At first, Jim and Vivian shared complaints. Then they shared coffee. That one cup turned into seven hours of conversation. By the time they boarded the train, their heads were spinning. They were in love.

Winter gave way to spring. Spring turned into summer. Jim felt a familiar tug. It was nearly time for his sailing trip in the Caribbean. And he was planning on taking Vivian with him.

Jim wanted to surprise Vivian, so they flew to Miami. She thought they were going to a hotel. They had planned a few weeks of rest and relaxation on Miami’s sandy white beaches. But instead of going to a hotel, Jim told the taxi cab driver to take them to the marina. Vivian smiled a cautious smile.

“I’ve never seen this side of you,” she said. “So mysterious and shrewd.”

“Shrewd?” Jim asked. “That makes me sound like a con artist. I’m trying to be romantic.”

“Is that what you’re being?” asked Vivian. “Well, now that I know that, I can stop thinking that you’re kidnapping me.” Vivian laughed. Jim saw his own smile reflected in her dark sunglasses. They were both happy and free.

Vivian’s smile again turned cautious when she saw the sailboat bobbing up and down in the water. The dock swayed beneath her feet and she lost her footing. Jim caught her.

“Welcome aboard,” he said. He put on a silly captain’s hat that he had stashed in his suitcase just for this moment and hopped on board the sailboat.

“Welcome aboard what?” Vivian asked. “Aboard this boat?”

“It’s my boat,” Jim said.

“It’s your boat?” Vivian couldn’t believe it.

“Well, it’s my parents’ boat, but they let me take it out sailing for a few weeks every summer. I sail,” Jim explained.

Vivian was speechless.

“I’m a sailor,” Jim repeated.

Vivian bit her lip and removed her sunglasses to get a better look.

“We’re going sailing,” Jim said. “Surprise ...”

Vivian didn’t say a word the entire time Jim stowed their luggage down in the cabin. She had no questions when he showed her the galley and the head. They had dinner at a restaurant in Miami. With some food in her stomach, Vivian finally spoke to Jim. She said, “I’ve never been on a boat before, Jim. I’m nervous. Really nervous. And, especially, I don’t want to disappoint you.” Tears welled up in Vivian’s eyes.

Jim took her hand in his.

“I’m not disappointed,” Jim said. “I’m just stupid. I never should have surprised you with such a big trip. I wasn’t thinking. Sailing is so second nature to me. I forgot how intimidating it can be.”

So Jim and Vivian stayed put in Miami. They slept on the sailboat but spent their days in town and on the beaches. On the third day, though, Vivian began to get her sea legs.

They were having coffee out on the deck of the boat when she asked, “Where were we going to sail, anyway?”

For two days Jim had struggled to not say a word to Vivian about his plans. He had, after all, painstakingly planned their cruise. Each day he watched jealously as other sailboats departed from and returned to the marina. So, when Vivian asked him this question, he went below deck and brought up his collection of maps, guide books, and brochures. Jim turned into a travel agent.

“It was nothing too ambitious,” he said. “Just a tour of the Bahamas. I hope you don’t mind, but I took the liberty of packing your passport.”

Vivian’s eyes grew big. Jim laid out before her pictures of sandy beaches lined with palm trees, picturesque waterfalls, hidden coves, deep sea fishing, swimming adventures with dolphins, fine restaurants, romantic lighthouses, and quaint avenues for shopping.

“How far away are the Bahamas?” Vivian asked.

“Bimini is only fifty miles,” Jim said. “I’ve made the passage dozens of times. And once we’re in the Bahamas, there are plenty of islands we could visit and spots we could anchor in.” Jim was on the edge of his seat.

“But how many hours would it take to sail fifty miles?” Vivian asked.

“Just a couple of hours. Not even,” Jim said, “depending on how fast we go.”

Vivian looked again at the brochures spread out before her. She looked at the other sailboats entering and leaving the marina, the capable men and women standing at the wheels, effortlessly guiding the boats through the calm water, the happy faces of the passengers on board with their hair blowing in the breeze or their bodies stretched out upon towels on the decks. It all looked too good to be true.

“Okay,” Vivian said. “I think I can do this.”

“Of course you can do this,” Jim said. “We’ll take it slow.” He leapt onto the dock and began to unmoor the boat.

“What are you doing?” Vivian asked.

“Getting ready to leave,” Jim said.

“Just like that?” Vivian said.

“Just like that,” Jim said. He looked eastward over his shoulder, up at the sky. It was clear and blue, scattered with clouds that looked like soft wisps of cotton. It was a perfect day for sailing. He started the motor.

At first, Vivian wore a life vest and didn’t dare venture far from Jim’s side. But Jim kept the boat moving slowly, and the rise and fall of the boat in the waves gained a natural rhythm. Soon Vivian was lounging on her towel on the deck. Miami shrank into the distance behind them, and they were surrounded by blue water. Vivian gazed out at the ocean. She felt both scared and yet completely free. Then she spied a few other sailboats. They weren’t alone after all. Then she saw the dolphins. They broke the surface and raced away in graceful arcs.

“Jim, look! Dolphins!” But when she turned around, Jim was gone from his place at the helm.

She called out, “Jim? Jim! Where are you?” She fell to her knees. The boat suddenly seemed to have lost its rhythm and was lurching from side to side. She sank lower onto her belly and clung to whatever handholds she could find. “Jim,” she cried. “Jim!”

Jim skipped back up the stairs to the deck, whistling. When he saw Vivian spread out across the deck, he ran to her.

“What’s the matter?” he asked.

Vivian trembled. “I thought you had fallen overboard,” she said. “I saw the dolphins and then I turned to find you and you were gone.”

“I just went below to get this,” he said, and held up a small flag of the Bahamas. “Come sit with me while I run it up the mast.”

They sat together for the rest of the passage. When Vivian saw Bimini on the horizon, she hugged Jim close. She breathed easy at last.

Bimini was only 50 miles from Miami but a world away. It was a tiny island paradise. Jim did not dock at the marina but anchored in shallow water just off the beach. While Jim took the dinghy ashore to clear customs and immigration, Vivian watched fishing boats return to port with anglers proudly displaying large marlins, tuna, and swordfish. Nearby, Vivian saw scuba divers and snorkelers swimming around the vast, rusted-out hull of a wrecked ship. Seaplanes flew in from the mainland and landed in the surf, sending up a burst of spray and foam. Vivian thought of her life, and, for the first time, of the possibility of being married to Jim. She loved him. Marriage was a certainty. But could sailing around the Caribbean on this very boat really be a part of the rest of her life?

Jim had thought about their future together long before Vivian had. Indeed, he had stowed more than a corny captain’s hat in his luggage. He had a diamond engagement ring. Jim had planned all along to ask Vivian to marry him on this cruise, but after Vivian’s jitters on the short passage from Miami to Bimini, he wasn’t sure. Jim was a sailor, after all. Any wife of his would have to be a sailor, too. Suddenly, his sailing trip had turned from a romantic engagement cruise into a litmus test of Vivian and their compatibility.

Happily, upon Jim’s return from customs, he found Vivian snorkeling in the water around the sailboat.

“I couldn’t resist,” Vivian said. “The water is so clear and so warm. I practically ransacked the cabin looking for the snorkeling equipment.”

“Couldn’t resist, huh?” Jim said. He liked the sound of that. Maybe sailing was in Vivian’s blood after all.

Jim spent much of the afternoon fishing for their dinner while Vivian enjoyed the water. She proved an incredibly strong swimmer. After a late afternoon visit to the island and a magical sunset, they had a dinner of fresh-caught snapper under a darkening sky full of stars. The next day offered more of the same: a different anchorage off the Bimini beaches and zero worries. Vivian even enjoyed her first lesson in reading nautical maps.

Their next stop was the Berry Islands, another small island chain 50 miles to the east of Bimini. Where Bimini put Jim and Vivian’s sailboat within sight of dozens of other boats, the Berry Islands offered them stretches of beach all to themselves without another boat in sight. Day after day, paradise and unparalleled freedom to roam by sailboat awaited them. Vivian and Jim, like all other visitors to the Bahamas, did not tire of it.

After the Berry Islands they sailed to the Abacos Islands. From there they ventured south to Eleuthera Island, with its pink sand beaches and pineapple plantations. Each day, Jim marveled at Vivian’s growing prowess with the sailboat; her eagerness to learn; and her excitement, enthusiasm, and charm. When they docked at the marina in Nassau, which seemed a busy metropolis compared to the outer islands, Jim and Vivian both knew they could forevermore make a happy couple.

Jim proposed at dinner. Vivian said yes. They ordered oysters on the half shell and champagne to celebrate.

“I didn’t take you on this cruise to trick you into marrying me,” Jim said.

“I’m not going to lie to you, Jim,” Vivian said with a laugh. “This trip has made it pretty hard to say no. I just hope I haven’t disappointed you.”

“Disappointed me? Are you crazy?” Jim said. “You’ve learned more during this past week or so than I learned in my first five years of sailing. You’re practically a pro. I’m considering asking you to sail us all the way back to Miami.”

Vivian’s face went white. “Oh, Jim, I’ll marry you, but if you’re asking me to sail us back home, I swear to you I’m never going to leave this island.”

The truth was they were both eager to leave Nassau behind for the more relaxed pace of the outer islands. It was hard to believe they were already making their return trip, once again through the Berry Islands, one last stop on Bimini, and then on to Miami.

It wasn’t long after they had set out for the Berry Islands that the sky turned dark—the first bad weather of their trip. The seas turned choppy, and the wind howled. Vivian tried to read Jim’s face, and she did not like what she saw. Jim looked green. Was the weather really that bad?

“Jim, what is it? Lightning? A hurricane?” Vivian asked.

Jim laughed, despite his pallor. “It’s not the weather, Viv,” he said. “It’s my stomach. Here, take the wheel and keep her steady.” Vivian grabbed the wheel as Jim leaned over the side of the boat and was sick. Vivian was worried about Jim, but she was far more worried about the wheel in her hands. She felt the heavy pull of the boat. She felt the wind blowing them off to the southwest. She struggled to keep her line straight while she heard Jim get sick again. He finally appeared next to her to retake control of the wheel.

“Those oysters,” he muttered. “It must have been those oysters. Viv, it’s only thirty miles or so to Chubb Cay. Stick to this heading and get me in an hour or so. This bad weather isn’t going to last. We’re only on the edge of it. The winds seem to be dying already. Viv? Vivian?”

Vivian could barely speak. She gripped the steering wheel so tight that her knuckles were white.

“Vivian?” Jim said.

“It’s alright,” she said through gritted teeth. “I’m okay. ‘In sickness and in health,’ right, Jim? In sickness and in health. Get some rest.”

“Thanks,” Jim murmured. He put the captain’s hat on Vivian’s head and went down below to the cabin.

When Jim woke up, he knew that far more than an hour had passed. Despite the nausea in his stomach, he jumped out of bed and leapt up the stairs. He was amazed at what he saw. The skies had cleared. The sails were down, and the boat was anchored off a sandy white beach. Vivian was nowhere to be seen. Then Jim saw her in the dinghy, returning from the island.

“Hey there, Sleeping Beauty,” Vivian said. “Feel any better?”

“I don’t know yet,” Jim said. “This isn’t Chubb Cay.”

“Nope,” replied Vivian. “It’s Cat Cay.”

“Cat Cay? You sailed us all the way back to Bimini?” Jim was incredulous. “That’s 80 miles.” He beamed at his fiancée. He loved her more than ever.

“Well, after the weather cleared, I just kind of got the hang of it,” Vivian said. “I figured another 50 miles wasn’t all that different from 30. You taught me how to read the maps. Anyway, I got you some antacid from shore. Did I do a good job, Jim?”

“You did great, Viv,” Jim said. “And to answer your question, I do feel better. I feel better than ever.”


Discussion Starters

  • Have you ever sailed a boat, large or small? What kind of boat have you been on? How is boating different from other means of travel?
  • In this story, Jim decides to surprise Vivian with a sailing trip to the Bahamas. Do you think that such a surprise was a good idea? How do you feel about surprises? Do you like them or not?
  • Two weeks of sailing to tropical islands is certainly a dream vacation for some people. What is your idea of a dream vacation? Where would you go?
  • When Jim gets sick, he asks Vivian to steer the boat. Do you think this is too much for Jim to ask of Vivian? If you were Vivian, how would you have responded to such a request?

Additional Activity

The Bahamas consist of more than one hundred islands. Explore these diverse islands by doing some research. Visit to learn more.