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Date Ideas near me in Maitland, FL

Looking for date ideas in Maitland? This small city just north of Orlando is easy to plan a whole evening around. Start with dinner under the oaks at Eden Bar, catch an independent film at the Enzian Theater, then end with live jazz at Jazz Tastings or a nightcap at Packwoods.

6 picks · Updated October 2026

The ranked list

  1. Enzian Theater

    Venue

    A nonprofit single-screen cinema since 1985 showing independent and international films with food and drinks served at your seat. It is also home to the Florida Film Festival.

    • Date idea
    • Indoor
    • Rainy day
    • Local favorite
    Call Enzian TheaterWebsite for Enzian Theater (opens in a new tab)Directions to Enzian Theater (opens maps)

  2. Eden Bar at Enzian

    Restaurant

    Garden seating under centuries-old oaks, house-made food and a late-night menu make this the natural before-or-after stop for a movie next door at the Enzian.

    • Date idea
    • American
    • Cocktails
    • Lunch
    Call Eden Bar at EnzianWebsite for Eden Bar at Enzian (opens in a new tab)Directions to Eden Bar at Enzian (opens maps)

  3. Jazz Tastings

    Venue

    Dinner and a show in one booking, with live jazz and bossa nova and a seasonal menu. Open Tuesday through Saturday evenings.

    • Date idea
    • Live music
    • Adults
    • Nightlife
    Call Jazz TastingsWebsite for Jazz Tastings (opens in a new tab)Directions to Jazz Tastings (opens maps)

  4. Packwoods

    Bar

    An upscale cocktail bar for a nightcap, with Tiki Tuesday, $10 martinis and margaritas on Wednesdays, and tastings or workshops that work as a shared activity.

    • Date idea
    • Cocktails
    • Happy hour
    • Adults
    Call PackwoodsWebsite for Packwoods (opens in a new tab)Directions to Packwoods (opens maps)

  5. Maitland Art & History Museums

    Museum

    A daytime or rainy-day date at the Maitland Art Center and three small sister museums, which are quiet enough for real conversation.

    • Date idea
    • Indoor
    • Rainy day
    Call Maitland Art & History MuseumsWebsite for Maitland Art & History Museums (opens in a new tab)Directions to Maitland Art & History Museums (opens maps)

  6. Florida Film Festival

    Event, $$

    Enzian's 10-day festival screens more than 160 independent features and shorts each April and is Oscar-qualifying. Screenings are paired with parties and food and drink at the theater's Eden Bar.

    • Date idea
    • Film
    • Festival
    • Spring
    Call Florida Film FestivalWebsite for Florida Film Festival (opens in a new tab)Directions to Florida Film Festival (opens maps)

Planning a date night in Maitland

The classic Maitland date is a film at the Enzian Theater with a drink or dinner at Eden Bar first, both on the same property off South Orlando Avenue. Check the Enzian schedule and buy tickets ahead for popular screenings, and arrive early to get a garden table at Eden Bar. Jazz Tastings is a good alternative when you would rather listen to music than watch a film, and Packwoods works for a final drink either way.

For a daytime date, the Maitland Art Center's courtyards and the nearby historical museums are an easy, low-key visit, and Lake Maitland and Lake Lily are close for a walk when the weather cools. In summer, save outdoor plans for after sunset and keep an umbrella handy for afternoon storms.

To choose, match the plan to your date. Film lovers should build the night around the Enzian, music fans around Jazz Tastings, and cocktail fans can make Packwoods the main event with a tasting or workshop. For an early or first date, the museums and a walk by the lake are relaxed and inexpensive.

About this list

Every place here is a locally run business in Orange County with its own website, which we checked for hours, menus and contact details. We leave national chains off our best-of lists and favor places with a clear specialty.

This page covers 6 date ideas in Maitland.

About Maitland

Maitland lies between Winter Park and Altamonte Springs along Lake Maitland. Its office parks near I-4 house many law firms, medical and dental practices, and other professional services.

Frequently asked questions

What is the Enzian Theater in Maitland?

The Enzian is a nonprofit single-screen cinema cafe founded in 1985 that focuses on independent and international films. Food and drinks are served during screenings, and it runs the outdoor Eden Bar and hosts the Florida Film Festival each year.

Where can I hear live jazz in Maitland?

Jazz Tastings is a small jazz club and restaurant in Maitland that pairs live jazz and bossa nova with a seasonal dinner menu. It is open Tuesday through Saturday evenings, so plan a weeknight or Saturday date there. Reserve a table for weekend nights.

What is a good rainy-day date in Maitland?

Catch a film at the Enzian Theater, where you can eat and drink during the movie, or visit the Maitland Art & History Museums, which include the Maitland Art Center, a historical museum, a telephone museum and a restored 19th-century residence.

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