Fall Events at Sundial

DATE: October 2, 2026

Fall is HERE and we are ready for it! Whether you’re looking for sun-soaked pool days, unforgettable wine-pairing dinners, or vibrant live music under the palms, we’ve stacked our calendar with can’t-miss events all season long. Grab your calendar, invite your friends, and get ready to celebrate!

Live Music at Turtle’s Tiki Bar

Sip, celebrate, and soak in the coastal breeze with live beats right by the water at Turtle’s Tiki Bar! Catch these incredible artists:

October 1: John McLane | 4:00 – 7:00 pm

October 3: Chris Casdia | 12:00 – 3:00 pm

October 31: Mark Dupuy | 5:00 – 8:00 pm

November 1: Chris Casdia | 12:00 – 3:00 pm

November 7: Mark Dupuy | 4:00 – 7:00 pm

November 26: John McLane | 12:00 – 3:00 pm

November 27: Mark Dupuy | 12:00 – 3:00 pm

Sundial Pool Parties

Oct 3, Nov 1, Dec 5, & Jan 30 | 10:00 am – 6:00 pm

Admission: Adults $50 | Kids $30 (Includes a $30 dining credit for adults & $15 for kids!)

Make a splash at our signature resort pool parties! Your pass unlocks beach and pool access, beach chair and umbrella service, mid-day entertainment, poolside bingo, themed rec activities, and delicious cocktail specials. Parking is included, and luxurious private cabanas are available at an additional cost.

Open to the public! No advanced reservations needed—first-come, first-served.

Little Pink Dress Night

October 7 & the First Wednesday of Every Month | 5:00 – 8:00 pm at Captain’s Catch Bar

Put on your favorite pink dress and join us for an evening of networking, live tunes, interactive fun, drink specials, and small-bite delights! Held in partnership with the San-Cap Pink Project, each monthly gathering supports local cancer-related needs in our community.

October 7 Kickoff: Live painting and art auction by local artist Rachel Pierce, live music by Douglas Coventry, and a bespoke “Bloom Bar” hosted by Blue Door Flower Company—Sanibel’s luxury floral design studio!

The Prisoner Wine Pairing Dinner

Wednesday, October 21 | 5:30 PM – 8:30 PM

Get ready for an extraordinary culinary journey! Treat your palate to an evening of multi-course gourmet bites expertly paired with the bold, iconic flavors of The Prisoner Wine Company. It’s the ultimate night to relax, chat, and savor exceptional sips and bites with friends old and new.

Reservations required. View the menu and reserve now!

Live Jazz Fridays with John McLane

Every Friday starting October 23 | 6:30 – 9:30 pm at Captain’s Catch

Unwind from the week with smooth jazz riffs and fresh seafood. Join us in Captain’s Catch every Friday night to hear John McLane live from the bar or dining room while indulging in our irresistible Shrimp Night Dinner Specials.

Trick or Tiki Party

Saturday, October 31 | 5:00 – 8:00 pm at Turtle’s Tiki Bar

Admission: FREE & Open to the Public!

You’d be ghoulish to go anywhere else this Halloween! Join us poolside for a spooktacular evening packed with a costume contest, themed games, trivia, free entertainment, and a cash bar with festive cocktail sips.

Plan your visit today and make memories with us at Sundial! See you poolside!

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