An Evening Itinerary in Englewood

Englewood's charm comes alive in the evening, offering a perfect blend of coastal beauty and downtown charm.

South of Sarasota, Englewood, Florida offers an outlying, laid-back locale blending Old Florida charm with coastal hotspots – making it an ideal destination for a memorable night out. Whether you're savoring a sunset on the beach, dining at waterfront eateries, exploring the vibrant local scene or checking out cultural experiences, here's an hour-by-hour itinerary for an enchanting evening in Englewood. 

4:00 PM - Stroll Historic Dearborn Street:

historic dearborn street

Begin your evening taking a leisurely stroll down Historic Dearborn Street in Olde Englewood Village, where charming shops, boutiques, wine shops and galleries await. Explore the local art scene, discover unique finds and soak in the "Old Florida" ambiance of this quaint district.

5:30 PM - Catch the Sunset on Englewood Beach:

englewood beach

Before the evening grows dark, catch golden hour on Englewood Beach and stroll the sands a bit to watch the sunset show cast its colors on the night sky. The breathtaking hues of a Gulf Coast sunset are unlike any other. Sink your toes into the warm water, watch the sun dip below the horizon and savor the tranquility of this lesser crowded public beach.

6:30 PM - Be Seated for a Waterfront Dinner:

farlow's on the water

Head to Landy's Restaurant for a culinary journey that fuses flavors from the Mediterranean and Gulf Coast. This waterfront eatery, just minutes from Englewood Beach, offers a diverse menu of surf-and-turf options, classic Mediterranean favorites and creative specials, opt for seating on the beautiful garden patio to enjoy your meal in the Florida night air. Don't miss the delightful sparkling wine and sangria selection.

For another exotic meal waterside, Farlow's on the Water specializes in Caribbean cuisine with a delicious southern twist. From fresh local seafood to hand-cut steaks, your evening will begin with a laid-back, open-air patio atmosphere, a variety of craft beers and tropical cocktails and a beautiful view of Ainger Creek.

7:30 PM - Catch Live Music or See a Show:

Immerse yourself in the lively atmosphere during your evening out in Englewood. There are a handful of local gems and bars dishing out live entertainment at night—including White Elephant Pub, SandBar Tiki & Grille, Calico Jack's, Englewoods On Dearborn, Shipwreck Pub, Lighthouse Grill and Tiki Bar and more. Indulge in some local beers, or maybe a frozen drink, and enjoy the tunes from the local cover bands and artists on stage that particular evening. 

If you're more in the mood for live theater and some laughs, check out Lemon Bay Playhouse for an entertaining performance. This local theater often features a variety of shows – usually comedies with mysteries and dramas interwoven in the story. Be sure to plan your outing during the playhouse's production season, which stretches from early September to the end of June. 

9:00 PM - Ice Cream Sundae Nightcap:

Conclude your evening with a sweet treat nightcap. Savor the last moments of your night out at Ice Cream at Swirls N Curls for a delightful array of ice cream flavors and toppings. The award-winning ice cream shop is open till 10pm, so grab your favorite flavor and head out to the outfitted yard and gazebo seating area – complete with checker game tables, PutterBall Golf, bean bag toss and other games to enjoy! Sundaes and late-night mini golf seem like a pretty solid way to top off a night on the town in Englewood.

10:00 PM – Head Back "Home"

Whether Englewood for you is a staycation or vacation, Conch Out Vacation Rentals offers waterfront and island homes located just a 1/2 mile off the Englewood mainland on Manasota Key. From the quaint beach cottages and beach villas to larger waterfront and multi-family mainland houses and condominiums, these coastal-chic rental properties provide a relaxing, worry-free stay – especially when you're ready to "conch out" after a long night!