Downtown St. Pete has the last week of September largely to itself. The Rays finish the regular season on the road, the Rowdies do not return to Al Lang until October 3, and the Saturday Morning Market comes back that same morning, so the nine days from September 24 to October 2 belong to the museums, the courtyard at Jannus, and the Mahaffey. Four picks below, from a one hour wine tasting at the Dali to the Florida Orchestra's opening night, and nearly all of them are easier to park for than they will be a week from now.
South of the Equator Wine Tasting at The Dali
Why It Stands Out
Thursday, September 24, from five until six in the evening, The Dali Museum at One Dali Boulevard hosts a guided tasting of six wines from Chile and Argentina in its Raymond James Community Room, timed to Hispanic Heritage Month. The hour covers how geography, altitude, climate, and Andean snowmelt shape what ends up in the glass, with Mendoza Malbec on the list. Tickets are twenty dollars for members and twenty five for non members through the museum's site, and gallery access is not included, so treat it as its own event rather than a museum visit with wine.
Best For
Couples and friends who want a reason to be on the waterfront at five on a weeknight, and relocation clients who have walked past the Dali and not yet found a reason to go in after hours. An hour is short enough to fit in front of dinner and structured enough to learn something.
Insider Tip
The Mahaffey next door has Little Big Town at 7:30 that night, so the lots around the museum will be filling by six. Arrive at 4:30 and you will be leaving as that crowd arrives. From there it is a fifteen minute walk north along the water to the Museum of Fine Arts, where Art After Dark runs until eight with Classical Revolution St. Pete playing in the conservatory, and Beach Drive handles dinner.
Art and Nature Sunset Tour with the Museum of Fine Arts and Tampa Bay Watch
Why It Stands Out
Sunday, September 27, from 3:30 until 7:30, the Museum of Fine Arts at 255 Beach Drive Northeast and the Tampa Bay Watch Discovery Center on the Pier split an afternoon between them. It opens with an hour long docent led tour on nature in art that features the New African Masquerades exhibition, and it closes with a sunset cruise from the Pier from 6:30 to 7:30, with Tampa Bay Watch marine scientists pointing out wildlife, the bird sanctuary, and the skyline, plus art making on board with materials provided. Forty five dollars, forty for MFA members, free under three, and the ticket includes admission to both the museum and the Discovery Center.
What to Expect
A two hour gap between the tour and the boat, which is the point. You can stay in the galleries, walk the half mile out to the Pier through the waterfront parks, and eat before boarding. Sunset that evening falls at about 7:23, so the boat is on the water for it.
Timing and Planning
Book through the link on the MFA's event page. Park once near Beach Drive or in the Pier's Dolphin and Pelican lots, which run two dollars and fifty cents an hour on weekends, and leave the car for the whole afternoon. This is the one event on the list that shows a newcomer the museum, the parks, the Pier, and the bay in a single ticket.
The Format with The Get Up Kids at Jannus Live
Why It Stands Out
Tuesday, September 29, doors at 6:30 and the show at 7:30, The Format bring their Boycott Heaven tour to Jannus Live at 200 1st Avenue North, with The Get Up Kids opening. The show is all ages, presented with 97X, and the band donates a dollar from every ticket to food insecurity programs, marginalized communities, and local animal shelters. Jannus is an open air courtyard walled in by the brick backs of Central Avenue buildings, and late September is when an outdoor show there starts to feel comfortable again.
Best For
Friend groups, and anyone who had this band on repeat twenty years ago. It is standing room, so it is a night out rather than a sit down evening.
Timing and Planning
Tickets are mobile only through AXS. With no home games anywhere downtown, the Sundial and South Core garages will be quiet on a Tuesday. If a courtyard concert is not your evening, the same night offers two seated alternatives within a ten minute walk: the James Museum at 150 Central Avenue screens the documentary Our Mr. Matsura at six for ten dollars, and the Dali stages Moving Surreal, a roving performance by four emerging choreographers, at 7:30 for twenty.
The Florida Orchestra Opening Night: Tchaikovsky's 1812 Overture
Why It Stands Out
Friday, October 2 at 7:30 in the evening, The Florida Orchestra opens its season at the Mahaffey Theater, 400 1st Street South, with Michael Francis conducting and the Master Chorale of Tampa Bay on stage. The program runs from Rossini's William Tell Overture and Christopher Theofanidis's The Gift to Beethoven's Wellington's Victory and the 1812 Overture after intermission. A free pre concert conversation begins an hour before for ticket holders, and the orchestra's Classical Kids program admits ages five to eighteen free with a paying adult.
Best For
Couples first, and families with older children second, because a program this recognizable is the easiest possible introduction to the hall. For anyone new to St. Pete, opening night is also where a good share of the city's arts patrons will be in one room.
Timing and Planning
Buy through the orchestra at 727-892-3337 or its site. This is the busiest night of the window downtown: First Friday takes over Central Avenue between 2nd and 3rd Streets from six to ten, and Streetlight Manifesto plays Jannus at eight. Dine on Beach Drive by 5:30, walk south along the waterfront, and be in your seat for the 6:30 talk. The Mahaffey garage is the last place to look for a space after seven.
Event Q&A
Which event is best for families?
The Art and Nature Sunset Tour on September 27, where children under three are free and the boat does the entertaining. For something that costs nothing, Movement Mondays at the Pier on September 28 from seven to nine is a free, sober, family friendly evening of DJs, dance, and flow arts on the North View Edge.
Which event feels most on-brand for a date night?
Opening night with The Florida Orchestra on October 2, with dinner on Beach Drive first. The Dali wine tasting on September 24 is the shorter, lighter version.
Which event is worth planning ahead for?
The Sunset Tour, since it can only be booked in advance and the cruise is part of the ticket, and opening night, which draws the orchestra's subscribers. The Format is a nostalgia tour in a small courtyard, so do not count on the door.
Which option is the most relaxed and low-commitment?
Art After Dark at the Museum of Fine Arts. The Thursday, October 1 edition adds a trivia night with Max Blowers at six, built around a clue hunt through the galleries, at twenty one dollars for non members and five for members and anyone seventeen and under.
How is parking downtown this week?
As easy as it gets until Friday, October 2. The Pier has more than five hundred spaces of its own, with the Sundial garage as overflow, and the Looper and the SunRunner both reach the waterfront. Saturday, October 3 is another story, with the Saturday Morning Market back at Al Lang, Piertoberfest on the Pier, and the Rowdies at home that night.
