Claire Kingsley writes contemporary romance across several connected small-town series, a few romcom series, and some collaborative projects. Most books should be read within their own series. If you want to avoid spoilers, don’t jump into the middle of the Miles, Bailey, or Haven books.
The shortcut: pick one shelf
If you only want one clean plan, choose the shelf that matches your mood:
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- Small-town family saga with the most crossovers: start with Broken Miles (Miles Family #1)
- Small-town pranks + feuding towns: start with Protecting You (Bailey Brothers #1), but it lands best after Miles Family
- Small-town romantic suspense (later timeline): start with Obsession Falls (Haven Brothers #1), but it’s set after Bailey Brothers
- Romcom quartet with a friend group: start with Faking Ms. Right (Dirty Martini Running Club #1)
- Beach-town contemporaries: start with Behind His Eyes (Jetty Beach #1)
- Collaborative small-town mystery series: start with Whiskey Chaser (Bootleg Springs #1)
What connects to what (so you don’t spoil yourself)
The Tilikum timeline (read in this order for maximum clarity):
- Miles Family
- Bailey Brothers
- How the Grump Saved Christmas (timeline overlap; flexible)
- Haven Brothers (set years later)
Everything else below can be read without that timeline.
The Tilikum timeline
Miles Family (publication order)
A small-town family series that feeds directly into Bailey Brothers via shared characters.
- Broken Miles: A messy small-town romance where a family feud and old history keep getting in the way of what feels right.
- Forbidden Miles: A “brother’s best friend” setup where chemistry becomes a problem the moment it’s noticed.
- Reckless Miles: A big-feelings, big-chaos romance where commitment means choosing one life and letting another go.
- Hidden Miles: A protective romance that digs into secrets, vulnerability, and the cost of staying quiet.
- Gaining Miles: A later-series love story where the family circle closes ranks and the final couple gets their shot.
Bailey Brothers (publication order)
This series follows the Miles timeline and is meant to be read in order for maximum cameo payoff.
- Protecting You: A childhood-friends romance where one night changes everything and the “easy” friendship stops being enough.
- Fighting For Us: A second chance for the same couple where love has to survive consequences, not just chemistry.
- Unraveling Him: A grumpy/sunshine romance where the stoic brother falls hard and tries to pretend he didn’t.
- Rushing In: A forbidden-leaning romance where wanting her is simple and being allowed to is not.
- Chasing Her Fire: A high-tension romance where attraction burns hotter because it’s inconvenient.
- Rewriting the Stars: A later-series payoff where the final brother’s story ties the wider arc together.
Tilikum holiday bridge
This standalone sits in the same town and can be read on its own, though it overlaps Bailey-era timing.
- How the Grump Saved Christmas: A grumpy/sunshine holiday romance where the season forces proximity and the walls don’t hold.
Haven Brothers (publication order)
A small-town romantic suspense series set in the same town years after Bailey Brothers. These are designed as interconnected standalones, but reading in order preserves cameos and town-history reveals.
- Obsession Falls: A protective small-town suspense romance where a threat forces the hero too close to stay “just helpful.”
- Storms and Secrets: A danger-forward romance where secrets in a small town turn intimacy into risk.
- Temptation Trails: A suspense-tinged romance where attraction is the easy part and trust is the hard part.
- Whispers and Wildfire: A rescue-and-recovery romance where the past won’t stay buried and the town notices everything.
- Captivation Creek: A friends-to-more romance with a mystery thread, where solving the problem might cost them the friendship. (Listed as forthcoming in some catalogs.)
- Peaks and Promises: A single-mom protection romance where the hero’s instincts go all-in long before she’s ready. (Availability varies by edition/listing.)
Romcom and contemporary series that do not require the Tilikum timeline
Dirty Martini Running Club (publication order)
A friend-group romcom set where earlier couples pop up later, but each book can stand alone.
- Everly Dalton’s Dating Disasters: A prequel-style intro where dating chaos sets the tone and the friend group clicks into place.
- Faking Ms. Right: A fake-relationship romance where “just for show” turns real when they stop performing.
- Falling For My Enemy: An enemies-to-lovers romance where rivalry turns into the kind of tension you can’t ignore.
- Marrying Mr. Wrong: A marriage-of-convenience romance where commitment starts as strategy and ends as the point.
- Flirting With Forever: A romance about choosing the real thing when the timing finally stops being awful.
Book Boyfriends (publication order)
Interconnected romcom standalones with recurring characters.
- Book Boyfriend: A fun, flirty romance where the fantasy “perfect guy” collides with real-life complications.
- Cocky Roommate: A roommate romance where boundaries evaporate and sarcasm becomes foreplay.
- Hot Single Dad: A nanny/single-dad romance where caretaking turns into attraction nobody planned for.
3.5. Her Best Friend: A short, bonus-style entry that expands the circle with a friends-to-lovers lean. (Listed in some bibliographies; treat as optional.)
Always (publication order)
A compact, angst-leaning contemporary set with an “after” novella.
- Always Have: A friends-to-lovers romance where years of closeness finally turn romantic, and messy.
- Always Will: An office romance where competence, attraction, and pride collide until someone folds.
2.5. Always Ever After: A novella epilogue that revisits both couples and closes the door softly.
Jetty Beach (publication order)
Beach-town contemporaries with light crossover; reading in order keeps friend-group references clean.
- Behind His Eyes: A small-town-adjacent romance where a guarded hero can’t hide what he feels forever.
- One Crazy Week: A week-long proximity romance where a “temporary” situation becomes emotionally permanent.
- Messy Perfect Love: Opposites-attract chaos where the mess is the reason it works.
- Operation Get Her Back: A second-chance style pursuit where “winning her back” requires real change.
- Weekend Fling: A fling-that-isn’t-a-fling romance where feelings show up early and refuse to leave.
- Good Girl Next Door: A “teach me” chemistry-heavy romance where the good girl stops playing safe.
- The Path To You: A protective love story where commitment means stepping into danger with her.
Collaborative shared-world projects
Bootleg Springs (with Lucy Score)
A six-book collaborative series meant to be read in order. It is not required for any Claire Kingsley-only series.
- Whiskey Chaser: A small-town mystery-romance opener where trouble arrives with a smile and a past.
- Sidecar Crush: A slow-burn tension romance where the town chaos keeps forcing them together.
- Moonshine Kiss: A romance where secrets and chemistry mix like a strong drink, hard to put down.
- Bourbon Bliss: A high-heat romance where comfort turns into craving and the stakes get personal.
- Gin Fling: A romantic shake-up where the town’s mystery thread tightens around the couple.
- Highball Rush: A finale romance that pays off the town’s long con and the series-wide mystery.
Bluewater Billionaires (CK’s entry)
A collaborative series where each author writes one interconnected standalone. Claire Kingsley’s book is:
- The Mogul and the Muscle: A billionaire romance where power and protection collide with attraction that won’t stay professional.
Standalones
These can be read anytime.
- His Heart: A heartfelt standalone where emotional healing is the real plot, and love is the risk.
- Finding Ivy: A standalone romance built around choosing yourself while still choosing someone else.
- Sleigh Bells and Snowstorms: A small-town winter romance where a storm locks them into honesty faster than planned.
Recommended reading routes
If you want a decisive plan without browsing:
Route 1: The full small-town experience (most connected)
Broken Miles → (finish Miles Family) → Protecting You → (finish Bailey Brothers) → How the Grump Saved Christmas → Obsession Falls → (finish Haven Brothers)
Route 2: The romcom sampler (lowest commitment)
Faking Ms. Right → Falling For My Enemy → Marrying Mr. Wrong → Flirting With Forever
Route 3: Collaborative small-town mystery binge
Whiskey Chaser → Sidecar Crush → Moonshine Kiss → Bourbon Bliss → Gin Fling → Highball Rush
Notes on “latest / upcoming”
The Haven Brothers series has entries that appear in some catalogs as forthcoming or edition-dependent. If a title above shows as unavailable in your preferred store, treat it as not widely released yet and keep to the earlier books that are live.
Bottom line
If you want the safest, least confusing start: Broken Miles. It opens the most connected continuity and sets you up to enjoy the Bailey and Haven crossovers without spoilers.
Frank is the editor of BookSeries.blog, focusing on publication order, chronological timelines, and spoiler-free reading guides for book series and fictional universes.