Key West Valentine’s Day 2024

Well, the sweetest day of the year is almost here. Yes, I am talking about Valentine’s Day. If you are going to be visiting our island city for this lovers holiday, be prepared to wow your significant other. Or, maybe just go ahead and treat yourself instead. You deserve it! You can always get the usual candy and flowers, which are much appreciated any time. But, here are some ideas from your friendly Key West Island concierge to kick the holiday up a notch.

Top 10 Ways to Celebrate Valentine’s Day in Key West

  1. Charter a custom private charter with Dream Catcher Charters! You can have a romantic day on the water snorkeling, sightseeing, dolphin watching, or even fishing! Bring along some Prosecco and make it even more special. Call us at 305-292-7212 to make your reservation.
  2. Toon Time Charters offers a host of options for a private charter. Enjoy a sandbar charter in the secluded backcountry. Go birdwatching, take an eco-tour, or enjoy a sunset cruise. All aboard the most comfortable boat on the water in Key West, a new 27′ Barletta tritoon with a ton of shade. Call us at 305-292-7212 to make your reservation.
  3. Pamper yourself or someone else at one of the many spas that dot the island of Key West. A romantic couples massage sounds like just the thing!
  4. Take in a romantic movie at the Tropic Cinema. You can even get a glass of wine and some gourmet snacks to enjoy from their concessions area.
  5. You cannot go wrong with a romantic dinner out at one of Key West’s fine dining restaurants. Here are our top choices:
  6. Spend the day strolling hand in hand around the island. There are so many gardens and beaches to enjoy in Key West. Some that immediately come to mind would be the Oldest House Gardens and the Audubon House.
  7. Sail with your sweetheart on the highly rated Danger Charters Wind and Wine Sunset Sail. From 5 pm – 7 pm enjoy hors d’oeuvres, chocolates, wines, beers, soft drinks and water for $109 plus tax per person. Call us at 305-292-7212 to make your reservation.
  8. Enjoy dessert at the most romantic desserts only bar in Key West, Better Than Sex.
  9. Wander down to Mallory Square to enjoy the nightly Sunset Celebration. But be sure to get a drink and maybe join in some salsa dancing at El Meson de Pepe’s while there to make it a really memorable night.
  10. Order Uber Eats and spend the night in your hotel room with your significant other.

More About Key West

Our busy season is here, so be sure that you make advanced reservations for whatever special thing you decide to do! If you don’t you will be sitting alone in your hotel room wishing you had planned ahead.

For more information about things to do and see in our island city, go to our Key West Web Site. You can also visit our Key West Events Calendar to see more details on upcoming special events.

And for more restaurant reviews check out our restaurant review section of this blog as well as our restaurant reviews at

Island Genn – Your Key West Concierge

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