Nearly 2.5 miles of car-free oceanfront means you can talk for an hour without once deciding where to go — beach bandshell, public art and café patios pass by in sequence. Rent bikes or a surrey from the shops on the promenade if you want the playful version; on foot at golden hour is the romantic one.
📍 101 S Broadwalk, Hollywood, FL 33019 (promenade runs the length of Hollywood Beach)Free — Public oceanfront promenade. Optional bike and surrey rentals are priced in the rental shops, not online.
City parks on the beach run sunrise to sunset; the promenade itself is the evening stroll.
Free live music under the stars, five nights a week, with the ocean behind the stage. The Margaritaville resort programs the Hollywood Beach Theatre — rock, R&B, blues and Latin bands, roughly 7–9 PM Wednesday through Sunday — and the crowd is locals in flip-flops, dancing on the plaza. Dinner before, concert after, Broadwalk stroll to finish: a whole date for the price of parking.
📍 200 Johnson St at the Broadwalk, Hollywood Beach (next to Margaritaville Hollywood Beach Resort, 1111 N Ocean Dr)Free — Concerts are free and open to the public per the resort's entertainment calendar; schedule is weather-dependent — check the calendar before you go.
A funky Intracoastal institution famous for its 13 oz burger, decorated with salvaged beach finds and toilet-seat art, with boats passing the dock. No reservations — the restaurant says so proudly — just show up hungry. It is the dinner that feels like a beach day that kept going.
📍 1100 N Ocean Dr, Hollywood, FL 33019$18 per person — The Original 13 oz burger on Le Tub's official menu (add $1.50 for cheese); the Key Lime Pie to share is $11. Beer $6, cocktails $13–$16 on the same menu.
No reservations. Open until 1 AM (2 AM Fri–Sat) per the venue.
Downtown's front lawn: a full-block park with an amphitheater that runs free Friday movie nights (8 PM, bring a blanket or chairs) plus concerts and festivals through the year. It is the rare date that starts on a picnic blanket and ends at a Harrison Street table two blocks away.
📍 1 N Young Circle, Hollywood, FL 33020 (Hollywood Blvd at US-1)Free — Movie nights are free per the City of Hollywood; festival pricing varies by event — check the city calendar.
City parks are plastic- and foam-free; single-use containers are not allowed inside the park.
The inland half of the date: two walkable blocks of restaurants and bars around Young Circle — Harrison Street's dining run (including the Social Room at 1916 Harrison St and the Block 40 Food Hall at 1820 Hollywood Blvd, per the downtown directory) lets you park once and graze. Pick dinner by mood when you get there instead of by reservation a week out.
📍 Hollywood Blvd & Harrison St, downtown Hollywood, around Young Circle
Directory listing — individual restaurant hours and menus are on each venue's own page.
The quiet morning date: a maze of mangrove trails in West Lake Park, on Hollywood's Intracoastal side. Rent a kayak and paddle in near-total stillness — herons, jumping mullet, the occasional manatee — then let the beach be the afternoon. Weekday mornings might be just you two and the birds.
📍 West Lake Park, Sheridan St, HollywoodAbout $20–$30 — Kayak rental range for a couple of hours, as recorded in the repo's verified Fort Lauderdale guides; confirm current rental prices at the park before you go.
Listed here as Hollywood's nature option — the park sits inside Hollywood, west of the beach.
The Guitar Hotel is Hollywood's big-night-out machine: a concert at Hard Rock Live, dinner at a celebrity-chef restaurant, the casino floor after, and the light show over the water as the finale. It is a whole evening at one address when you want the date to feel like an event.
📍 1 Seminole Way, Hollywood, FL 33314
Casino open 24 hours; concert and restaurant times vary — check the resort calendar.
Hollywood is on the Water Taxi map: the southern route stops at Margaritaville on the Broadwalk, so you can ride the Intracoastal up to Fort Lauderdale's Las Olas and beach stops on the same all-day pass. A beach afternoon in Hollywood, dinner in Fort Lauderdale, boat home — two cities, one date.
📍 Margaritaville Hollywood Beach Resort dock, 1111 N Ocean Dr, Hollywood$38 per person — All-day hop-on, hop-off pass at the operator's listed price on 2026-11-09, covering the Fort Lauderdale, Hollywood and Pompano Beach routes.
