72nd Annual Labor Day RegattaSeptember 1-2, 10 am – 4 pm – Free to Spectators

  • Hosted by the Sarasota Sailing Squadron, this annual event draws hundreds of competitive sailors ages 8-80 from across the U.S. and Canada. Featuring five race courses, live music, barbeque, refreshments and an awards ceremony. 1717 Ken Thompson Parkway Sarasota, FL 34230 – Call: (941) 388-2355

10th annual Downtown Venice Craft Festival: September 1-2, 10 am – 4 pm – Free Admission, Free Parking

  • Vendor fair featuring Art, Crafts, Gifts, Plants. Miami Avenue, downtown Venice, Florida

Reggae Pon Di Lake Pre-Labor Day Party & Music Festival at Nathan Benderson ParkSeptember 2, 2 pm – 9 pm – Admission $30All Ages, VIP $70

  • A host of local and regional live Reggae bands and DJs, Food Trucks of all food types and a kids play area. Swimming, Paddleboard rentals (12 years or older), Pontoon Pedal Boat rentals and Kayaks allow listening to the live music from the water. 5851 Nathan Benderson Park, Sarasota, FL 34235

Monday Night Kids’ Jam Session at the Music CompoundSeptember 3, 6 pm – 7 pm, Free and Open To Public – Ages 6 and Up

  • Bring the kids and jam to build music skills, enhance confidence, communication and social interaction abilities. 1751 Cattlemen Rd, Sarasota, FL 34232 – Call: (941) 379-9100

Florida Studio Theatre presents “Gilbert & Sullivan Unplugged”: September 4 (and nightly), 7:30 pm, 90 minutes w/ intermission – Balcony Admission: $34

  • Description Courtesy FST: Gilbert & Sullivan Unplugged has delighted audiences across the US with lovingly loopy renditions and joyfully irreverent excerpts from HMS Pinafore, The Mikado, and The Pirates of Penzance. Last seen at New York’s 54 Below, this isn’t your grandmother’s Gilbert & Sullivan. Dining available 1 hr. prior to show in Cabaret (no reservation required). 1241 North Palm Avenue, Sarasota, FL 34236 – Call: (941) 366-9000

Ringling Underground: September 6, 8 pm – 11 pm – Admission: $15

  • Local and regional emerging artists perform live music and showcase artwork in the museum courtyard. Ringling Museum of Art, 5401 Bay Shore Road in Sarasota – Call: (941) 359-5700.

Lakewood Ranch Presents Music on MainSeptember 7, 6 pm – 9 pm (First Friday of Every Month) – Free Admission

  • Featuring live music, food, beer and wine. Bring: outdoor chairs, dogs/Don’t Bring: coolers. Located east of I-75 on University Parkway

Sunshine and Show Jumping $25,000 Grand Prix September 8, 9 AM – Admission $5, Free Parking

  • Fox Lea Farm hosts the first $25,000 Grand Prix of the fall season, featuring the Olympic sport of Grand Prix Show Jumping. 800 N. Auburn Road, Venice, FL 34292 – Call: 941-786-8028

38th Annual Juried Photographic Exhibition at Marie Selby Botanical GardensSeptember 9, 10 AM – Entry: $10 – $20

  • View photography entries and watch the judging during the 38th Annual Juried Photographic Exhibition. There are five categories of photographs depicting the scenery of Selby Gardens which will be awarded cash prizes : Favorite Selby Scene, Plant Life at Selby, Selby Gardens’ Geometry, Selby’s Birds, Bugs & Critters, Selby in Black & White. “Best in Show” winner will also be named. 811 S Palm Ave, Sarasota, FL 34236-7726 – Call: (941) 366-5731

Yoga in the Gardens (Session 1) with Instructor Michelle Roy at Marie Selby Botanical Gardens: September 10, 9 AM – Class Fee: $75

  • Start your week off right by treating yourself to a peaceful mind/body Yoga experience in a beautiful Garden or indoor setting. Focus is on alignment, breathing techniques and relaxation. For beginners as well as advanced students. September 10 thru October 1, 2018. 811 S Palm Ave, Sarasota, FL 34236-7726 – Call: (941) 366-5731

Salute to the Queen of Soul: A Tribute to Aretha FranklinSeptember 11-15, 8 pm – Admission: $39 Adults, $20 Students and Active Military

  • Westcoast Black Theatre, 1646 10th Way (Off Orange, N of 10th St), Sarasota, FL 34236 – Call: (941) 366-1505

17th annual Friday Fest at the Van Wezel with the Dr. Dave Band: September 14, 5 pm- 9 pm – Free Admission, Rain or Shine

  • A popular high-energy house band known for their blend of southern rock, bluegrass banjo and fiddle. Food and beverage available from local vendors. Bring: Lawn chairs, blanket. Prohibited: eating and drinking outside. Located on the Bayfront Lawn, Van Wezel Performing Arts Hall, 777 N Tamiami Trail, Sarasota, FL – Call: (941) 953-3368

5th Annual A Taste of Downtown Sarasota: September 15, 1 pm – Tickets: $75

  • Located at the historic Sarasota Opera House; features fine menu samplings, wine pairings and assorted beer selections from downtown. Sarasota Opera House, 61 N Pineapple Ave, Sarasota, FL 34236 – Call: (941) 328-1300

Monday Night Kids’ Jam Session at the Music CompoundSeptember 17, 6 pm – 7 pm, Free and Open To Public – Ages 6 and Up

  • Bring the kids and jam to build music skills, enhance confidence, communication and social interaction abilities. 1751 Cattlemen Rd, Sarasota, FL 34232 – Call: (941) 379-9100

Jerry Seinfeld at the Van Wezel Performing Arts HallSeptember 20, 7 pm and 9:30 pm – Tickets: $88.25-$164.22

  • 777 N Tamiami Trail, Sarasota, FL 34236 – Call: (941) 953-3368

The Flying Carrs Circus at the Sarasota Fairgrounds and Robarts Arena: September 21, 11 am – 9 pm – Tickets: $8 – $50 – All Ages

  • 3000 Ringling Blvd, Sarasota, FL 34237

Oktoberfest at JDub’sSeptember 23, 11 am – Midnight – Admission: Free

  • Features German-style beer and in-house recipes and food provided by the Schnitzel Trailer. Music, Stein Games, Best Dressed Contest Awards at 3:30 p.m. JDub’s Brewing Company, 1215 Mango Ave, Sarasota, FL – Call: (941) 955-2739

Monday Night Kids’ Jam Session at the Music CompoundSeptember 24, 6 pm – 7 pm, Free and Open To Public – Ages 6 and Up

  • Bring the kids and jam to build music skills, enhance confidence, communication and social interaction abilities. 1751 Cattlemen Rd, Sarasota, FL 34232 – Call: (941) 379-9100

Stelliferous Live at The South Florida Museum’s Bishop PlanetariumSeptember 26, 7 pm – Tickets: $5 Non-Members (reservation required)

  • A monthly discussion of stars, planets, constellations and current events in astronomy including Q&A at end of presentation. 201 10th Street W., Bradenton, FL 34205 – Call: (941) 746-4131

Other Excursions & Tours


Tour an Award-Winning Rum Distillery


See every step of the process as hand-crafted spirits are locally made in small batches utilizing premium ingredients in a copper pot still. Tours are very popular, so arrive early. Tuesday, Wednesdays and Saturdays. (50-60 Minutes)

Drum Circle Distilling, 2212 Industrial Blvd, Sarasota, FL 34234-3120 – Call: (941) 702-8143

Explore a Botanical Garden


This tropical wonder on Sarasota Bay features stunning horticulture displays and a variety of gardens to explore and enjoy, such as the Rainforest Garden, Fragrance Garden, Butterfly Garden, Edible Garden and many more. Also offers botanical photo tours, group tours, classes and volunteer opportunities.

Marie Selby Botanical Gardens, Hours: 10 am – 5 pm, 811 S Palm Ave, Sarasota, FL 34236-7726 – Call: (941) 366-5731

Visit a Big Cat Habitat and Sanctuary


This big cat rescue advertises 3 large indoor/outdoor housing complexes with adjoining exercise habitats that mimic native environments with swimming pools, toys and palm trees. It is home to dozens of exotic large-animals in need of rehabilitation, placement or sanctuary, and relies on volunteers and the admissions proceeds from daily tours, demonstrations and tours. Petting Zoo, Big Cats, Alligators, Bears, Bison, Monkeys, llamas, Turkeys, and so much more…

Big Cat Habitat and Gulf Coast Sanctuary, Hours: Wed – Sun, 12 – 4 pm, 7101 Palmer Blvd, Sarasota, FL 34240-9407 – Call: (941) 371-6377