The season around Bay Colony doesn't start all at once this year. It comes in three waves, each a different distance from the gate. Artis–Naples on Pelican Bay Boulevard goes first, with new exhibitions opening October 17. The Pelican Bay Foundation's beaches follow with Welcome Back Weekend, November 13 through 15. Waterside Shops comes last. Its largest new tenants are scheduled for late 2026 and early 2027.
So your arrival date matters more than it used to. An owner who lands in early November will see a different neighborhood than one who comes after New Year's. A few of the first events have already filled.
The Calendar, in Order
Here are the dates that are already fixed, as of early October 2026:
- October 17: The Surrealist International: Fifty Years of Dreams and Florida Contemporary 2026–27 open at The Baker Museum.
- October 20, 7:30 p.m.: Miami City Ballet performs with the Naples Philharmonic in Hayes Hall.
- November 13 to 15: Pelican Bay's Welcome Back Weekend, ending with the first Sunday Brunch at Marker 36.
- November 24 to 29: Hamilton plays Hayes Hall.
- December 5: Baron Wolman: Capturing the Sound of an Era opens at The Baker Museum.
- Holiday 2026 into early 2027: LoveShackFancy, Peter Millar, RH, TWP and Buck & Rider open at Waterside Shops.
That list runs from the arts to the beach to the shopping center. Each wave has its own pace, so each section below picks up where the one before leaves off.
October Belongs to Pelican Bay Boulevard
Artis–Naples sits at 5833 Pelican Bay Boulevard, so Bay Colony's nearest major cultural venue is inside the same master-planned community. The 2026–27 season, announced in July, is called "To Light: The Art of Hope." Its backbone is Alexander Shelley leading the Naples Philharmonic through all nine Beethoven symphonies. Guest artists include Yo-Yo Ma, Audra McDonald, Itzhak Perlman, Sutton Foster and Kelli O'Hara.
The Baker Museum opens two shows on the same day, and they run on very different timelines. The Surrealist International: Fifty Years of Dreams runs October 17 through February 14, 2027. Florida Contemporary 2026–27 stays up until June 27, 2027. It features Dustin Harewood, Nicario Jiménez-Quispe, Savannah Magnolia and Anastasia Samoylova. The Surrealist show closes in mid-February. Owners who come down only for the peak months of March and April will miss it, while the Florida artists will still be on the walls.
Baron Wolman: Capturing the Sound of an Era opens December 5 and runs through June 13, 2027. It's the one exhibition timed for holiday arrivals.
The Baker Museum Store also carries a book written about Pelican Bay itself. Pelican Bay: A History of Our Home in Paradise won a 2026 Silver Medal from the Independent Book Publishers Association, in the Best Regional eBook, Nonfiction category of its IPPY Awards. The Pelican Bay Foundation commissioned the 144-page hardbound history. A team of residents, Nancy Bicket, Tim Corcoran, Elizabeth Flaherty and Kris Turner Sinnenberg, worked with author Harriet Howard Heithaus to produce it. The book covers the community's early fights, including being denied water connections by both the city and the county. Copies are also sold at The Commons, the Community Center and both Racquets Centers.
Artis says programming, performers and dates can change, so confirm specific nights before you plan around them.
Mid-November Moves to the Sand
Bay Colony owners have two sets of beach privileges. The Bay Colony association lists membership at the private Bay Colony Beach Club, with Gulf-front dining, a pool, the Sunset Terrace and the Chickee Bar. It also lists "additional amenities through the Pelican Bay Property Owners Association." Pelican Bay's rules say all natural persons who own residential plots are members. The Foundation's tram links its beaches and restaurants through eight stations and boardwalks that cross the mangroves.
The Foundation's two beach restaurants sit at opposite ends. Marker 36 is on North Beach, and Sandbar is on South Beach. Bay Colony is in Pelican Bay's northwest corner, which makes Marker 36 the nearer of the two. That matters this year, because the biggest change on the Foundation's fall calendar is happening at Marker 36.
According to the October 2026 Pelican Bay Post, Welcome Back Weekend runs like this:
| Day | Event | Where | Status in the October issue |
|---|---|---|---|
| Friday, Nov. 13, 5–9 p.m. | Welcome Back Beach Bash with DJ Bam and the tribute act Never Stop Believin' | South Beach | Registration required |
| Saturday, Nov. 14, 9:30 a.m.–noon | Tennis and Pickleball Kickoff | Racquets | Sold out |
| Saturday, Nov. 14, 3:30 p.m. | Polynesian Show with Tuika's Polynesian Island Magic | Sandbar, South Beach | Reservations closed, open to watch |
| Sunday, Nov. 15, 9–11 a.m. | Sunday Brunch debut | Marker 36, North Beach | Sold out |
| Sunday, Nov. 15, afternoon | Beach Bocce | Beach | No registration required |
Two of the five events, the racquets kickoff and the brunch debut, had already sold out by the October issue, about six weeks ahead. Lifestyle Manager Arlene Harper wrote that Sunday morning "marks the beginning of something new at Pelican Bay." Foundation leadership and management will join the Marker 36 team for a special opening-weekend buffet.
"From a Friday night beach bash to the debut of Sunday Brunch, Welcome Back Weekend offers plenty of ways to reconnect and celebrate the start of another season in Pelican Bay."
The Polynesian show is still open to anyone who wants to watch. Its program includes island music and drumming, dances representing Hawaii, Tahiti, Samoa and New Zealand, and a Samoan Fire Knife Dance at the end.
After the opening weekend, the beach settles into its weekly rhythm. The Foundation lists live music at Sandbar on Mondays and Wednesdays and at Marker 36 on Tuesdays and Thursdays, from 5 to 8 p.m. during the season. Add Sunday Brunch, and Marker 36 now has something on the schedule three days a week.
Waterside Finishes Last
Waterside Shops, at 5415 Tamiami Trail North, sits on the U.S. 41 side of the Pelican Bay boundary. Its redevelopment is the loudest story of the three, and it has the longest timeline. In July, the Naples Daily News reported that three new restaurants and six retail stores would open there over 2026 and early 2027.
Some of it is already open. Eddie V's Prime Seafood opened June 7 at 765 Seagate Drive, and Dior opened June 11. Vuori was open by September, and Piranesi was listed as open by October 2. OMEGA is running a temporary boutique at 5375 Tamiami Trail North, Suite 11, and plans to move to Suite 15 at 5555 Tamiami Trail North once construction is done. No completion date has been given.
The rest, including two of the three new restaurants, is still on the way:
- LoveShackFancy, 5455-1 Tamiami Trail N, listed for Holiday 2026
- Peter Millar, 5485-9 Tamiami Trail N, late 2026
- RH, 5489 Tamiami Trail N, late 2026, with a restaurant as part of the gallery
- TWP, 5455-7 Tamiami Trail N, early 2027
- Buck & Rider, in the former Brio Italian Grille space, early 2027
Buck & Rider's date has already slipped once. Its April announcement said late 2026, and the center's current listing says early 2027. Piranesi went the other way. It was announced in June for fall and is already open. Either way, the restaurant openings are the dates most likely to move. An owner who arrives in November will find Eddie V's open and RH and Buck & Rider still to come.
Matching the Return Date to the Season
Taken together, the calendar sorts itself by arrival date. An October return catches both Baker Museum openings and the Miami City Ballet night. A return before November 13 puts you on the sand for the Beach Bash and on North Beach the morning Marker 36 starts brunch, though the opening buffet is full. Arriving Thanksgiving week still gets you to Hamilton, which closes November 29. A December or January arrival trades all of those for the Baron Wolman opening and a Waterside that is closer to finished. Owners who come for February alone have until the 14th to see the Surrealist exhibition.
Hosting guests during one of these windows, or deciding which weekend to fly down? Blake Owen keeps this calendar close and is happy to share what's opening near Bay Colony and when. Request a private tour, and we'll plan it around the dates that fit your season.
This article is general information, not legal, tax or financial advice. Consult a qualified professional about your situation.
