Love on Longboat Key: Finding the most romantic spots on the island

How do you go about upping your game on the most romantic day of the year when you already live in paradise? We’ve got a few ideas, but if we missed your favorite Valentine’s Day activity that’s just “so Longboat Key,” let us know. 

On meeting someone new

According to U.S. Census Bureau, 78% of couples on Longboat Key are married. If you’re part of the 22% of the population still looking for someone to share paradise with, look no further than the next traffic jam. Who knows, maybe the person whose car is nearly kissing your bumper is your unexpected soulmate. If you’ve made it to St. Armands Circle and ditched the car to wait out the traffic with a drink, maybe the cutie at the other end of the bar is worth chatting up. Sample conversation starter: The red of your brake lights really sets off your blue eyes. Too much?

On taking the next step

Looking to make things more official? You don’t have to step off the key to have a magical wedding. The Longboat Key Club Resort marries dozens of couples a year, with 60-80 weddings taking place around the property, said Ayla Goggin, director of events and catering at the resort. Just be prepared for your family and friends protesting against your “destination wedding” — but hey, this is just where we live. Not everyone can be so lucky.

On perfect dates

The best beach spot on the Key might never be settled; there might not be just one. Every clear night, Longboaters take to the beaches to watch the sun sink into the Gulf. The Garden Club of Longboat Key celebrates with Love on the Beach at the Bay Isles Beach Club.

Club President Susan Phillips married Steve Branham on the beaches of Longboat, so they hold the beach close to their hearts. However, residents Carol and Bob Erker prefer the beach near Mar Vista because that’s where Bob proposed.

Test your compatibility by renting a tandem bike or two-person kayak from Longboat Key’s Backyard Bike Shop. Add a fun layer of concentration to cycling the length of the Key among the dozens of avid riders. For a first date, figuring out the balance and teamwork required to stay atop a tandem bike could prove a quick test to go forth with the relationship or go back to the single bike. John Schneider at the bike shop recommends having a good relationship at the foundation of any tandem adventure.

On celebrating a lifetime of love

Of course, Longboat Key has a smorgasbord of fine dining restaurants to choose from, and like the best sunset spot, the best romantic dining spot is much debated. Do you go to Dry Dock with its award-winning views? Lazy Lobster or Harry’s Continental Kitchens for the amazing food? Hit up the Haye Loft for dessert and drinks? If you and your sweetheart have been together for a while now, you’ve probably got your routine down pat. Pick your favorite, then head to your tried-and-true sunset spot.