Seasonal · West Palm Beach / Palm Beach Gardens / Delray Beach / Boca Raton / Wellington / Miami Beach / Winter Park / Orlando
January 2027: fresh starts and lovely days for two
Art afternoons, coastal picnics, live shows, and a gentle start to a new year.
Make room for time together after the holiday rush. These January ideas mix published Florida outings with simple plans you can make your own.
Choose one January art outing
Spend an hour browsing art, then each choose a favorite and explain what caught your eye over a café stop. The dated listings below cover Palm Beach County, Miami Beach, and Winter Park. Check the actual event date and admission details before setting out.
A winter picnic, Florida style
Pack a substantial snack, water, and a windproof layer for a daylight waterfront picnic. Pick a legal public picnic area and check park hours. Allow two hours and $15–30 for groceries, plus any parking. If wind or rain arrives, move the same menu indoors.
Make it a theater date in Orlando
Choose a published performance of Wicked in January and book seats together through the official presenter. Reserve dinner with enough time for parking and the venue’s arrival guidance. Pick a matinee if a late night would make the outing feel rushed.
Try a no-spend adventure jar
Write six free ideas on slips: a neighborhood photo walk, a library browse, a home film night, a playlist exchange, a picnic with pantry food, and a shared puzzle. Draw one each week, keeping either person free to veto and redraw.
A future-us café hour
Bring a notebook and agree to dream rather than audit each other. Each choose one affordable outing, one skill to try together, and one way to help someone this year. Put only the first date on the calendar; leave room for life to change.
The dates to know
Published dates are shown with their year and source-review date. Confirm programs and availability with the organizer.
Downtown Palm Beach Gardens Fine Art Festival
· Saturday 11 a.m.–8 p.m.; Sunday 10 a.m.–5 p.m.
Browse outdoor art displays and meet the artists behind paintings, sculpture, jewelry and photography. Free admission; purchases extra
Downtown Palm Beach Gardens
Good to know
An art-browsing outing; no dedicated children’s workshop is promised.
Downtown Delray Beach Festival of the Arts
· 10 a.m.–5 p.m.
See an outdoor collection of glass, paintings, photographs, jewelry and other handmade artwork. Free admission; purchases extra
West Atlantic Avenue · downtown Delray Beach
Good to know
Booths run west from Swinton Avenue toward NW 5th Avenue; check downtown parking before arrival.
Boca Fest at the Town Center at Boca Raton
· 10 a.m.–5 p.m.
Take a relaxed walk through outdoor displays of fine art and handmade work. Free admission; purchases extra
Town Center at Boca Raton · outdoor festival
Good to know
Festival area is near Glades Road and St. Andrews Boulevard, close to Chase Bank.
Saturday Night Lights at the Winter Equestrian Festival
· Gates 6 p.m.; competition 7 p.m.
Watch show jumping with food, music and family entertainment during the Winter Equestrian Festival. Free general admission; general parking $25 per car
Wellington International
Good to know
Each date comes from a published January competition week naming its Saturday evening event. Jan 9 features Battle of the Sexes; later January Saturdays feature Grand Prix events. Food and optional experiences cost extra.
Art Deco Weekend
· Street festival: Fri noon–6 p.m.; Sat–Sun 10 a.m.–6 p.m.
Celebrate Miami Beach architecture and culture along Ocean Drive during the festival’s 50th edition. Free community festival; some tours and special programs may cost extra
Ocean Drive and Lummus Park
Good to know
Confirm individual 2027 activities before going; the website also displays highlights from the previous edition. Artist and vendor tents are advertised for Jan 16–17.
Free Friday Nights at the Morse
· 4-8 p.m.
Enjoy a relaxed evening exploring the museum's art and Tiffany collection; selected holiday Fridays include music. Free admission during Friday evening hours.
Charles Hosmer Morse Museum of American Art
Good to know
Published 2026-27 season. Christmas Day and New Year's Day are omitted because the museum FAQ lists holiday closures; confirm before visiting.
Wicked at Dr. Phillips Center
· Performance times vary; choose a listed matinee or evening show
Follow the unlikely friendship behind the witches of Oz in the touring Broadway musical. Paid reserved-seat tickets; prices vary by performance and seat.
Walt Disney Theater, Dr. Phillips Center
Good to know
Recommended ages 8+. Running time 2 hours 45 minutes. See the organizer for accessible-performance dates and current availability.
Art Palm Beach — Public Show Days
· 11 a.m.–6 p.m.
Explore contemporary and modern art from international galleries, with time to compare favorites over a conversation afterward. $40 one-day general admission; check booking fees
Palm Beach County Convention Center
Good to know
These are the public show days. The Jan 27 opening-night premiere is a separate $150 ticket, 5–9 p.m. Art purchases and parking are extra; check ticket conditions and availability with the organizer.
Good to know
Are these bookable packages?
No. These are original planning suggestions. Confirm opening hours, prices, accessibility, reservations, and any special arrangements directly. Budget ranges are planning estimates for two, not quoted venue prices.
Can we adapt these ideas to another city?
Yes. At-home ideas travel easily; for an outing, substitute a local public venue and check its current details.
Sources & editorial notes
Official venue, operator and local destination pages support the practical details. The combinations and personal touches are our editorial suggestions, not claimed firsthand reviews or bookable packages. See the source-check dates on event cards. This guide was updated Oct 17, 2026; current terms can change.
- Downtown Palm Beach Gardens Fine Art Festival ↗ (opens a new tab)
- Downtown Delray Beach Festival of the Arts ↗ (opens a new tab)
- Boca Fest at the Town Center at Boca Raton ↗ (opens a new tab)
- Saturday Night Lights at the Winter Equestrian Festival ↗ (opens a new tab)
- Art Deco Weekend ↗ (opens a new tab)
- Free Friday Nights at the Morse ↗ (opens a new tab)
- Wicked at Dr. Phillips Center ↗ (opens a new tab)
- Art Palm Beach — Public Show Days ↗ (opens a new tab)
For full admission, accessibility, dietary, weather and cancellation requirements, check directly before booking. No paid placements or affiliate booking links are included.
