The world is your oyster when it comes to date night in Key West. Start the evening with a sunset gaze, enjoy fine dining, go for a nocturnal paddle in surrounding mangroves, or catch a show at the local theater.

Not quite sure what to do? Let’s explore your options.

Start with the sunset

There are three different ways to approach sunsets in Key West, which we just so happen to have a guide for. Go for a communal viewing at Mallory Square, complete with street musicians and performers; get to Fort Zach before sunset to watch the sun go down without all the noise and crowds, or, take a relaxing sunset cruise with Fury Water Adventures. You can’t go wrong with any option – it just depends what you’re in the mood for.

Key West Theater or live music

This local theater brings some big acts to the island, and with its intimate setting, great acoustics and recent renovations, it’s the perfect venue to see a show. See upcoming acts on the theater calendar that coincide with your visit. Just steps away from The Gates Hotel is the Sunset Green Event Lawn, which sees its fair share of concerts and events. See what’s coming to the Sunset Green ahead of time.

An active kind of outing

For something out of the box and totally memorable, night kayak trips and paddleboard adventures are offered through Ibis Bay Paddle Sports. Picture this: a nighttime paddle with colorful LED lights illuminating the active sea life below. Not your cup of tea? Opt for a daytime trip in the company’s clear bottom kayaks for a sunnier glimpse of the ocean world below.

Tapas, cocktails, dinner, dessert

It’s so easy to find good food in Key West, this is the obvious option. What are you in the mood for? For a few rounds of tapas and drinks, the cozy Santiago’s Bodega in Bahama Village is perfect for an early-evening starter. If you’re looking for fine dining in an intimate setting, Azur in Old Town is sure to please, which focuses on Mediterranean cuisine, masterfully prepared.
Want to lounge after dinner with a cocktail or glass of wine? For a fancy martini and live music, make sure to stop by Virgilio’s. For a speakeasy vibe complete with cigar privileges, Berlin’s Cigar and Cocktail Bar is another favorite, located upstairs from A&B Lobster Restaurant.
Finally, don’t forget dessert. Key West makes this painless. Make reservations at the Better Than Sex dessert restaurant, which is exactly as it sounds. Feast on sinful desserts and sweet cocktails in an all-too-cozy atmosphere.

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Traveling to Key West? Check out rates at The Gates Hotel.