Valentine's Day In Key West - 9 Date Ideas To Celebrate In Style!

Valentine's Day In Key West

Make this the year you spend Valentine’s Day in Key West with your sweetheart! Couples seeking shelter from winter’s reach can enjoy warm sand, shade-giving palm trees, and tons of attractions catering to love birds.

As the country’s southernmost point, Key West offers a perfect way to enjoy a tropical getaway without a passport! That means that you can easily plan a surprise getaway without raising suspicions.

Valentine’s Day in any city can include dinner at a great restaurant, decadent desserts, champagne, and live music. While Key West has all of those things, it also offers unmatched opportunities for adventure!

With average daily temperatures hovering near 75 degrees Fahrenheit on the island in February, Key West is the perfect place to soak up the sun, spend the day on the water, or stay up late under the pale moonlight on the most romantic day of the year.

Here’s what you need to know to plan a Key West Valentine’s Day adventure with your special someone!


1) Book A Night Kayaking Excursion To Celebrate Valentine’s Day

Experience the magical, crystal-clear waters of Florida under the moon’s bewitching glow on a guided nighttime kayak tour! This adventure is both relaxing and exhilarating because of the way gentle tides help kayakers glide along into moonlit “parts unknown.”

As your headlamps cut through enchanted mangrove tunnels cloaked in the misty darkness, the following nocturnal marine creatures will be revealed:

  • Lobsters

  • Jellyfish

  • Nurse sharks

  • Squid

There’s no need to try to plan an after-dark kayaking adventure for your special someone on your own. Your romantic evening adventure on the island can be fully planned for you with help from Key West Paddle.

As Key West’s top night kayaking tour company, we at Key West Paddle offer guided tours from local experts who will lead you safely through the water while making sure you know exactly where to look to spot the magical creatures that call the waters of Key West home. Our guests never miss a thing because we make the journey in LED-illuminated glass-bottom kayaks.

Book your spot today and get ready for an enchanting evening adventure with your loved one!

Night Kayaking In Key West For Valentine's Day


2) Pencil In Some Pampering At Pier House Resort & Spa

The iconic Pier House Resort & Spa on Duval Street in Key West is situated on a private white-sand beach. This retreat on the water’s edge offers terrific restaurants and bars. However, it’s the luxurious in-house spa that makes Pier House a perfect addition to a Key West Valentine’s Day itinerary.

After enjoying a couple’s massage, branch off to be pampered with skin treatments, facials, or manicures and pedicures to enjoy a little more time out of the sun. Pier House also has an amazing outdoor hot tub with a waterfall.

Enjoy Massage And Spa Services


3) See A Key West Sunset With Your Sweetie

Are you looking for a free activity to add to a perfect Valentine’s Day in Key West? Simply find a gorgeous place to watch the Key West sunset on the island with some sparkling wine, cheeses, crackers, and chocolates. Here’s a list of the best spots to watch a sunset in Key West:

  • Mallory Square Dock

  • The docks at Key West Harbor

  • Fort Zachary Taylor State Park (Fort Zach)

  • Truman Waterfront Park

If you don’t mind paying to see a Key West sunset, you can book a spot to set sail on a sunset cruise. Additionally, some hotels in the area with decks and verandas overlooking the ocean offer special sunset dinner experiences for guests.

Sunset in February in Key West takes place at around 6:30 p.m. You’ll want to be in place at least an hour in advance in order to take in the full glory of moody streaks of orange, red, and pink closing in on the horizon.

Pro tip: Key West sunsets are best when you’re in a spot where you can see the colors reflecting on the water!

Atlantic Ocean Sunset Sails For Valentine's Day In Key West


4) Share A Decadent Dessert To Celebrate Valentine’s Day

With Valentine’s Day being the ultimate day to indulge your passions, no Valentine’s Day in Key West is complete without some decadent desserts. Fortunately, it’s easy to find great chocolate and sweets on the island! Here’s a list of the best dessert shops to hit on Valentine’s Day:

  • Mattheessen’s

  • Chimney Cakes

  • Kermit’s Key West Key Lime Shoppe

  • Key Lime Pie Bakery

  • Better Than Sex – A Dessert Restaurant

The menus at these acclaimed sweet shops feature pastries, pies, fudge, ice cream, café Cubana, and much more!

Celebrate Valentine's Day With A Dessert


5) Book A Key West Hotel With A Private Beach For Valentine’s Day

Many people choose the Florida Keys for romantic getaways because they love the privacy and seclusion offered here. One way to enjoy an ultra-private Valentine’s Day in Key West is to book a stay at a hotel with its own private beach. Consider booking a room at any of these spots:

  • Hyatt Centric Key West Resort and Spa

  • Sunset Key Cottages

  • Courtyard by Marriott Key West Waterfront

  • Casa Marina Key West

  • Coconut Beach Resort

  • Pier House Resort & Spa

  • Southernmost Beach Resort

In addition to offering private beach access, a high-end hotel provides the perfect way to unwind in the lap of luxury while enjoying the Florida Keys on Valentine’s Day. Chairs and towels are typically provided for hotel guests. Concierge services will generally cover everything from meals on the beach to transportation to attractions around Key West.

Stay In A Private Beach Resort This Valentine's Day


6) Celebrate Valentine’s Day In Key West With Live Music

There’s nothing more romantic than listening to some island beats in Key West. Many bars and restaurants near Key West’s Old Town and Duval Street regularly host live music. Here’s a list of the best spots to check out:

  • Schooner Wharf

  • Smokin’ Tuna

  • The Green Parrot

  • Sloppy Joe’s

  • RockHouse Live

If you prefer to book tickets at a venue, check out the list of acts coming to the Key West Amphitheater around Valentine’s Day. Willie Nelson, Aaron Lewis, Foreigner, Marshall Tucker Band, the Black Crowes, and Jelly Roll are just some of the big acts that roll in regularly.

Celebrate Valentine’s Day In Key West With Live Music


7) Plan A Valentine’s Day Wine Date In Key West

Make a toast to the perfect Valentine’s Day over wine or champagne at one of the relaxing wine bars in Key West. Here are some spots for Valentine’s Day reservations:

  • Wine-O

  • Vinos on Duval

  • D’vine Wine Bar

  • Viv Wine Bistro

With most of Key West’s wine bars located in the vicinity of Petronia Street and Duval Street, you can even plan a romantic bar crawl for two!

Valentine's Day Wine Date In Key West


8) Celebrate Valentine’s Day In Key West With Dinner

Romance in the Florida Keys is easily found in a simple waterside dinner that includes golden, bubbly champagne. Fortunately, there’s no shortage of amazing places on the island where you can enjoy an unforgettable evening. Here’s a list of popular restaurants where couples can celebrate Valentine’s Day with dinner by water in Key West:

  • Half Shell Raw Bar

  • Latitudes

  • Four Flamingos

  • Salute! On the Beach

  • A&B Lobster House

  • Bagatelle

While people who like to play it safe can enjoy burgers and steaks, true seafood lovers will adore the menus full of oysters, whole snapper, spiny lobster, conch chowder, and scallops that dominate the menus at these romantic Key West restaurants!

Celebrate Valentine’s Day In Key West - Dining Experience


9) Plan A Valentine’s Day Walk Along Key West’s Historic Seaport

While you may want to pull out all the stops by booking fancy dinners and fun extrusions during your romantic getaway, be sure to leave some room in the schedule for an arm-in-arm stroll along the harbor walk at Key West Historic Seaport.

Covering a mile-long stretch along the water from Whiting Street to Front Street, the harbor walk is the historic epicenter of Florida’s fishing industry. It’s also one of the best spots to see tarpon and manatees bobbing up from the water. You can also dip into one of the great seaport bars or restaurants.

Walk Along Key West's Historic Seaport


Planning Your Romantic Valentine’s Day Getaway In Key West

You don’t have to look very far to find romance when you celebrate Valentine’s Day in Key West. However, people who have spent time soaking up the sun and warm breezes here know that the real magic happens nightly after each Key West sunset!

That’s why a moonlit guided kayaking tour among the mangroves is the best way to celebrate a Valentine’s Day that your sweetheart will never forget! We take care of every detail by offering guided tours in LED-lit, glass-bottom kayaks. Book a Valentine’s Day reservation for two with Key West Paddle today!

1 hour 30 minutes
Group Size
Up to 18

Night Kayak Guided Tour

Get a single or double glass-bottom kayak illuminated with lights and follow our tour guide on this one of a kind, unforgettable and simply magical adventure.

This slow paced, immersive, and very relaxing experience will allow you to see some cool, active at night marine life as you are gliding through crystal clear waters of Key West.

Guests will experience going through narrow mangrove tunnels at night, floating around shallow and calm waters as the tour guide will look for interesting critters for everyone to see.

3 hours
Group Size
1 to 6

Key West Sandbar Trip

Key West sandbars are our local well kept secret. This is where we take our families to hang out and relax on our days off. This is the perk of our island lifestyle. Now we want to share this experience with you.

Turquoise shallow waters, epic picture worthy sights all around you that look like a postcard - that is what you're signing up for!