This reading group guide for The Summer Sail includes an introduction, discussion questions, ideas for enhancing your book club, and a Q&A with author Wendy Francis. The suggested questions are intended to help your reading group find new and interesting angles and topics for your discussion. We hope that these ideas will enrich your conversation and increase your enjoyment of the book.

Introduction

Three college roommates reunite for a twentieth wedding anniversary celebration on board a cruise ship. Abby, the proverbial mother hen of the group, is hoping to enjoy the occasion despite the secret that she and her husband, Sam, are keeping from their friends. Caroline, an ambitious and independent career woman, is hoping for a proposal from her boyfriend, Javier. And Lee, a single mom, is most looking forward to having some bonding time with her daughter, Lacey, as their relationship took a turn for the worse during Lacey’s first year in college. As the ship sets sail and tensions rise, Abby, Caroline, and Lee soon realize that their secrets won’t just disappear in a sunset cocktail or an ocean breeze.

Topics & Questions for Discussion

1. Describe Abby, Caroline, and Lee. How do their differences complement each other? What do they teach you about female friendship?

2. Lee admittedly sacrifices her own happiness for the sake of Lacey’s. But rather than feel appreciative, her daughter considers this cruel. To what extent has being a mother affected Lee’s relationship and career choices? Are Lee’s sacrifices unusual or all part of being a good mother?

3. Caroline decides that if Javier does not propose by the end of the cruise, their relationship is over. But she does not actually tell him this. Do you understand Caroline’s rationale, or do you find her decision unreasonable? Should she be more up front with Javier? When, if ever, is it fair to deliver an ultimatum in a relationship?

4. While writing her article for Glossy, Caroline observes the passengers. What does she learn? Do you think the excessive eating, drinking, and partying offers a “larger commentary on American society in general”? Have you ever been on a cruise? What was your experience like?

5. Lee thinks her daughter is more preoccupied with her boyfriend than she is with her future career, and this often causes friction in their relationship. But Lacey is frustrated by her mom’s expectations and resents the notion that she must “single-handedly carry the torch for all women.” She thinks, “Women were already equal. If Hillary Clinton could run for president, then what was left?” And despite how grateful she is for her privileges, Lacey thinks: “sometimes it seemed like her mom’s generation had gotten it all wrong. In their race to shatter glass ceilings, many of them had put their own families on hold.” Do you think Lacey’s convictions about women are outdated? Is Lee’s concern for her daughter’s priorities warranted, or is Lacey’s behavior a prime example of a young woman blinded by love?

6. When first arriving on the Bermuda beach, Abby instantly feels her mood lighten and her stress subside. She thinks, “It was hard not to be grateful for every little thing.” Do you believe in the healing power of nature? Is there a place that makes you feel at peace?

7. Despite having written an article for Glossy suggesting that women should feel free to propose if their partner is taking too long to do so, Caroline doesn’t want to propose to Javier. Now that she’s in this predicament, she realizes that it’s “different in practice,” and that she’s still old-fashioned. What do you think of women proposing? Is there a stigma in society that shames women for taking the initiative? Do you think it’s time this changes?

8. Abby hasn’t yet told her boys about her health to “protect them for as long as she could.” Do you think Abby is right to wait? What would you do? Are there some situations when it’s necessary to withhold information from loved ones?

9. Thomas tells Lee that now that his daughters are grown up, he’s going to try to worry less and let them make their own decisions. Lee considers this: “Maybe it was different for fathers. They couldn’t wait for their kids to turn into miniature adults, even friends, while most moms Lee knew wished that the snuggling pockets of childhood would last a few years longer.” Do you think men and women differ when it comes to parenting and wanting to protect their children for as long as possible?

10. As Abby prepares to renew her marriage vows, she admits that she loves Sam more now than she did on their wedding day—but that it’s a different kind of love, describing it as “one that had mellowed over time, one that swam a smoother line.” Do you think love evolves and changes over time?

11. Discuss how secrets are a major theme in the novel. Why do each of the women conceal parts of themselves to those closest to them? How do they ultimately grow as characters once their truths are revealed?

12. Lee believes that the essence of being a mother is “to be able to show your children love even during the times when your instincts told you to scream, when it was the hardest of all to love them.” Do you agree? Discuss how Lee exemplifies motherhood by book’s end. Do you think Lacey relates to her mother better?

13. How did each of the women evolve over the course of the trip? What did they learn about themselves? Are there any challenges that they still must overcome in their personal relationships?

14. When the ship docks, Abby promises herself: “If nothing else, remember to be amazed.” What do you think of her new mantra? How can you incorporate it into your daily life?

Enhance Your Book Club

1. Friendship is at the heart of the novel and unfortunately, many of us don’t take enough time to express our appreciation to our friends. Show your friends how you care about them. Consider writing cards, inviting them over for dinner, or, better yet, organize a trip.

2. Something’s Gotta Give is one of Lee’s favorite movies. Consider watching it at your next group meeting. Why did Lee admire Diane Keaton’s character? Discuss with your group.

3. Have you ever celebrated a milestone event with a girls’ trip? If so, share your experience with your book club and bring in some of your favorite pictures or videos.

4. Consider these other summer reads for your book club: Beach House for Rent by Mary Alice Monroe, Mystic Summer by Hannah McKinnon, or Wendy Francis’s own The Summer of Good Intentions.

A Conversation with Wendy Francis

Why did you set this novel on a cruise? What was particularly appealing about having the women interact on shipboard? And, most important, did you take any research trips in order to write this book?

To my mind, a cruise immediately says vacation and summer—two of my favorite words in the English language. A cruise ship also seemed the ideal setting for exploring the bonds of friendship among three women in need of a relaxing holiday. And where better to make tensions come to a head than on a boat hundreds of miles out to sea? So much can happen!

As for research, I’ve been on three cruises now. The first cruise I took was several years ago with my extended family, all eighteen of us, including cousins, aunts, uncles, and grandparents. Initially, I was a tad skeptical, worried that despite the beautiful setting, I might get seasick. But thankfully, you can barely tell you’re moving on such large ships, and our cruise to a tropical island ended up being a wonderful time. It’s easy to see why roughly twelve million Americans set sail on these luxury liners each year. With tons to do for the kids, adults can truly relax poolside; and once you dock, the beaches are pristine—a slice of heaven.

Sisterhood and strong female friendships are key elements to your novels. Is there a character or relationship in this novel that you can most identify with? Why?

Indeed. There are elements in all of these women that speak to me. I share Abby’s maternal, nesting instincts along with her aptitude for worrying about everyone and everything. I can appreciate Caroline’s wanting Javier to propose already! Not that my husband dragged his feet, but up until my mid-thirties, I was fairly career driven. When I finally found the guy I wanted to marry, I was more than ready to tie the knot. And while I can’t imagine the complexities of being a single parent, there is something about Lee that I find irresistible. I admire her no-nonsense attitude and her uncontainable love for her daughter. I imagine I’d share her frustration with Lacey’s infatuation with her boyfriend, but I’d be equally relentless in making sure that Lacey finished college and pursued her passions, whatever those might turn out to be.

Each chapter is told from the point of view of one of the three friends, with a few sections told from Lacey’s perspective. Why did you feel that it was important for Lacey to tell her own story?

If only we could all know what goes on in the teenage mind! I didn’t set out to include Lacey’s point of view, but she seemed to demand it the further I wrote into the story. It was that persistent, nagging feeling I sometimes get when my youngest accuses me of not listening (and he’s usually right). So I tried to let Lacey whisper in my ear from time to time, to remind me what it’s like to be a teenager so wrapped up in her own world. She’s really a good kid at heart but has a lot to learn. By the end of the cruise, I hope she’s a little wiser.

Your book comes out on the heels of an interesting political year. When Lee pitches the importance of women getting ahead in the world to Lacey, however, she doesn’t mention the #MeToo movement or the various women’s marches across the country. Why?

The easy answer to that is deadlines. Most of the novel had already been written before we knew just how crazy things would get in this country. Politics is a tricky thing to delve into in fiction—everything changes so quickly, and it’s hard to know how relevant today’s news will be a year from now, let alone next week. Though I didn’t explore the current political scene, I trusted it was already pretty clear where Lee and her roommates stood on such matters.

Abby joked that traveling with separate suitcases was one of the secrets to a happy marriage. Is this one of your own secrets? Care to divulge any other tips to your readers?

Ha! My husband and I do travel with separate suitcases, but we usually end up sharing a suitcase with one of the kids anyway. A better way to ensure a happy marriage is to let Mom sit by herself on the airplane (preferably with a glass of wine) while her spouse entertains the kids en route. To that, I’d add one piece of advice a friend offered: If you find yourself in an argument with your spouse, sometimes it’s best to say, “You’re probably right,” rather than roll up your sleeves for a full-out battle. That way, your partner thinks he or she has won, but you haven’t completely ceded your point. My husband and I use this line every so often—at the very least, it lightens the mood. Just sometimes I put more emphasis on the word probably.

What was your inspiration for this story?

I’d been wanting to write a novel about college roommates—and the strong friendships that form during those years—but couldn’t figure out the setting. Then one day it dawned on me that an anniversary cruise might be the perfect way to bring the roommates together again.

Abby struggles to conceal her illness from her friends, oftentimes experiencing anxiety, fear, and shame. How important was it to you to show your readers the emotional distress an ill person battles when trying to be open with their loved ones?

This question is unfortunately personal for me: my mother was sick with the same rare kind of leukemia that Abby has in the book. For more than a year and a half, my brother and I watched our mom struggle with the constant anxiety of wondering if—and when—her condition would worsen. My mom was such a graceful and accomplished person that I can only imagine how difficult it was for her to weather this particular storm. She was reluctant to ask for help beyond her immediate family—I suspect she didn’t want to be a burden to anyone, nor did she want to worry her friends, much less invoke their pity. Beautiful, smart as a whip, and funny as hell, my mom possessed a certain midwestern toughness up until the very end. Having Abby reveal her illness to her roommates was almost cathartic for me—I wanted Abby to have the support system that my own mother often refrained from seeking out. Writing Abby’s story also helped me revisit my mom’s illness with a more hopeful ending.

Your novels are perfect for summer reading. What books do you like to take with you to the beach? Are there any authors or stories that encourage your own writing?

Thank you! I pretty much love anything by Elin Hilderbrand, Mary Alice Munroe, Karen White, Patti Callahan Henry, Jane Green, and Nancy Thayer. Summer is my favorite season, and those are all great authors of books to take to the beach. I’m also a fan of books that explore female friendships or family relationships, so other favorite authors include Liane Moriarty, Jennifer Weiner, Emily Giffin, Emma Straub, Ann Patchett, Ann Hood, and Lynda Cohen Loigman. I could go on and on, but I’d better stop.

Have you ever vacationed with girlfriends? Is there a particular destination you would recommend for a fun girls’ trip?

Yes, it’s essential to maintaining our sanity! Every year or so my college girlfriends and I reunite to share stories and recharge. Our getaways are typically short and sweet (a long weekend), but we pack a lot into those seventy-two hours. Our trips have included D.C., Cleveland, Boston, Chicago, New York, San Francisco, Charleston, and Austin. I highly recommend all these cities for their wonderful restaurants, museums, and walking trails. Such travels may sound indulgent, but off-season airfares can be reasonable—and sharing a hotel room with friends helps defray costs. After our getaways, I always feel as if I’ve returned from the spa, restored and slightly more at peace with the world. After all, no one knows you better than your college roommates/girlhood friends—well, except for maybe your spouse or partner.

What would you like readers of The Summer Sail to take away from the book?

There’s so much that I hope will resonate with readers—the powerful, evergreen friendships women have; the challenges—and rewards—of being a parent; the solace and peace that the natural world can offer even in our darkest moments. In the end, though, I hope each reader will take away a little something different, whether it’s nodding her head in recognition of Lacey’s perplexing adolescent behavior or identifying with the humor and love that sustain longtime friendships like those shared by Abby, Lee, and Caroline.

Would you consider writing a sequel to The Summer Sail? What would each of the women be up to?

It’s funny—I often get asked the same question about The Summer of Good Intentions, but I find that once I’ve written a book, I’m usually ready to let those characters go. If Abby, Caroline, and Lee continued on, I’d hope Abby would be living life to its fullest many years later; that Caroline and Javier would be happily married, maybe with a couple of kids, and residing somewhere other than New York. Perhaps Paris? Or Hawaii? As for Lee, I’d love for her to finally find true love and to see Lacey graduate and then go on to become a CEO of a Fortune 500 company while raising her own family—a modern-day feminist despite her teenage rebellions.

And, of course, the roommates would still be getting together every year. Maybe in their golden years, they could all live in one of those tiny-house communities.

Are there any relationship dynamics or familial stories that you haven’t yet explored, but are interested in developing for future novels?

Yes, but I don’t dare breathe a word of them so early—so please stay tuned!