Valentine’s Day Weekend in Key West

Tropical Key WestWhat’s better than spending a romantic weekend in a sun-drenched, tropical paradise with swaying palm trees, spectacular sunsets, water sports aplenty and restaurants that will make any celebration a memorable one.

Well, nothing actually! Head on down to Key West and spoil your sweetheart with a weekend of fun and delicious food.

Traveling from South Florida, meander on down Overseas Highway, past the blue-green sparkling waters and  decide where you want to spend a few hours. Take a dive into those crystal clear waters with Florida Keys Dive Center in Islamorada for a special price of $59 with tanks and weights( if you mention their web ad) or just take a seat overlooking the sea and sip on a drink at Loreleis.

If you have some extra time, stop in at Bahia Honda State Park, one of Dr. Beach’s top 10 beaches in the U.S., and relax on the sand for a few hours.

Adirondack Key West Sunset SailUpon reaching Key West, make plans to take a romantic Valentine’s Day sail aboard the Schooner Adirondack III to watch the sun sink below the horizon as it colors the warm tropical waters. This 2-hour cruise features complimentary beer, wine, champagne, sodas and water and is served with cheese and fruit platters and chocolate covered strawberries ($60) or hook up with a Fury snorkel or champagne sunset trip and receive 10% off from this Key’s coupon site –  (Just an FYI – the Keys coupon site also offers discounts at Hogfish Bar & Grill, Smokin Tuna Saloon, Trails & Tales of Key West Walking Tour and Two Friends Restaurant among others.)

Of course you can always enjoy the sunset at the famous Mallory Square Sunset Celebration and sip on a few cocktails from the nearby Westin bar. Try their frozen green cocktail and let me know what you think.

Here are a few top restaurant suggestions for that special occasion:

Latitudes RestaurantLatitudes (4/5) –  An upscale but casual restaurant with both indoor dining & alfresco beachfront dining (and I mean literally on the beach). Great for a romantic dinner with tables placed under the palm trees, in the sand and surrounded by tiki torches.  You are treated to a spectacular view day or night but especially at sunset. There is a short ferry ride to the island (ferry leaves dock every :15 & :45 past the hour – check with the Westin concierge, which is behind the naked sculptures, for your ferry pass) There are also two bars, one inside & one out, which offer a tapas menu and a great selection of wine. You will enjoy the wonderful service and fantastic food at both establishments. Best Bets –  – sweet potato encrusted grouper and the sunset shrimp.

Azur (Rated 4.5/5) – A quaint upscale gem located off the beaten track and well worth the effort to find. Delivering a romantic atmosphere with both indoor and outdoor seating (request the shaded terrace by the waterfall for that special occasion) along with beautifully presented & delicious dishes, you will want to come back again and again. Best Bets – their fresh gnocchi and zuppa di pesce!

Blackfin Bistro (4/5) – A small upscale, contemporary restaurant with a casual relaxed feel. They feature a large outdoor patio in back, shaded by palms and lit with tiki torches (my favorite) and an inside dining room with a romantic softly lit atmosphere.  Their staff is attentive and knowledgeable and the reprieve from the noise on Duval Street is perfect. Offering a bistro-style menu specializing in local catches. Best Bets – Shrimp Provencal or Hogfish and Mediterranean Mussels.

Harbour View CafeHarbour View Cafe (5/5) – Located in the Pier House resort is a classic restaurant in a beautiful beach front setting. Dine inside or out on the deck while watching the sunset over the Gulf and listening to the background piano music from the Wine Galley Piano Bar. Best Bets – creamy White Conch Chowder and  “Floribbean” style fish.

Hot Tin Roof (4/5) –  Swanky white table cloth look but with a friendly, casual atmosphere. Offering beautiful ocean views, incredible service, and music that drifts up from Sunset Pier. Sit inside or out and enjoy the best seat in the house for the Key West sunset. Best Bets – tapas for appetizers  and their local seafood special.

La Trattoria (4/5) – “Italian food done right” A small upscale restaurant using the freshest herbs, seasonings and local catches. Request a window seat and people watch. Best Bets – hands down their bread with olive oil & vinegar (ask for seconds) as well as their bruschetta and the homemade pasta and clams (Linguine e Vongole).  Visit Virgilios, in back, after dinner for some entertainment and after dinner drinks.

Michaels (4.5/5) – On a quiet street in Key West  sits a quiet pretty & romantic restaurant.  Tables are set nicely with white linen cloths while soft jazz music plays in the background. They serve both inside and outside but I suggest outside in their little garden under the umbrellas. They also have an inside bar with a great fondue menu. Best Bets –   crab cakes, seared duck & the veal chop stuffed with mozzarella & prosciutto. Leave room for dessert as their lava cake served with homemade ice cream and raspberry sauce is fantastic!

Rooftop CafeRooftop Cafe (4/5) – A casually elegant restaurant, located on the second floor overlooking the crowds on Front St. & Mallory Square. Dine inside or outside on their tree shaded deck. Great atmosphere, great service  and wonderful food. Best Bet – Surf, Surf, Surf & Turf Pasta.

Santiagos BodegaSantiago’s Bodega (4/5) – Located in a charming corner house filled with dark mahogany woods and Spanish inspired décor, this tapas style restaurant is sure to please. Seating is available inside, outside on the wrap-around porch or at the bar.  Portions are appetizer size (although the salad is huge) so order your own as you will not want to share. Finding this gem can be difficult, and not in the best of neighborhoods, but it will be worth the trek –  just walk down Petronia, past Blue Heaven, and keep going (located on the backside of Bohemian Village). Best Bets – dates stuffed with goat cheese, tuna ceviche, lamb chops and tenderloin with blue cheese.

Little Palm IslandOn your way home Sunday morning, make some reservations to have brunch on Little Palm Island, off Little Torch Key.  A casually elegant ocean front/beachfront dining experience on a private 6-acre island paradise, accessible only by boat or seaplane. Join in the experience and be motored to the island aboard their private yacht (make sure to confirm yacht transfer at time of booking) As you come upon this picturesque island you will think you have journeyed to the Caribbean. Dine amidst the palms with the soothing sound of  piano music in the background making this one of the most romantic spots in the keys. Brunch isn’t cheap but well worth the price. Word of advice, go easy on the table laden treats and the egg breakfast and order the smaller single serving sized portions from the entree menu on the table. Take your time and eat your way through the morning. Everything you try will be delicious! Reservations a must. Upscale casual attire required and no one under 16 admitted.

Curry Mansion Key WestIf you will be in Key West on the actual day, make reservations to the 29th Annual Wesley House Party held  at the Curry Mansion on Caroline Street. The gala features a world-class dinner buffet, open bar, music, dancing and a silent auction all benefiting Wesley House Family Services.

Valentines Day


Happy Valentine’s Day!





About Vacationplanit

Linda Warren is a former marketing director and now owns her own vacation planning website, She has traveled extensively throughout the United States, the Caribbean and Asia and is sharing her experiences and love of new places with her fellow travelers. Very curious and organized, she researches each trip and plans itineraries with the intent of getting the most out of each exciting destination. Join Linda on her website,, and take advantage of her vast knowledge and research to make your vacation planning simple and fun.
This entry was posted in Florida, Florida Keys, Holidays, Islamorada, Key West, travel & leisure, Valentine's Day and tagged , , , , , , , , , , , , , , , , , . Bookmark the permalink.

Leave a Reply

Your email address will not be published. Required fields are marked *