The holidays are hectic, but they still offer many of us time to connect with family and friends, especially here in the Florida Keys, where the winter weather is beautiful and our friends are family. What better way to connect than over food and cocktails ó with short bike rides between each dinner course?

A progressive dinner is simply a roving party with each course served at a different hostís home. Think potluck, but extended across three, maybe four, locations. (Bonus: a progressive dinner party brings your group together, while spreading the work and expense among all.)

The progressive style switches up a basic dinner party and allows hosts to showcase their particular cooking skills as well as their holiday decor. Some planning and logistics are involved, so find your most organized friends to put together a plan.

For a successful flow, the locations should be close enough to walk, bike or hop on a golf cart. (Note: Walking and biking allow for portable cocktails.)

The first home opens the evening with hors díoeuvres or an appetizer. The second house does the entrÈe, the third does a decadent dessert and after-dinner drink. If you have four homes, add a soup/salad course in the middle. 


Each host should plan to provide a beverage that pairs well with the course theyíre serving. Make it easy with a pre-made cocktail like Rosemary Pear Sangria. Slice some oranges and in a small saucepan, bring º cup sugar, 1 rosemary sprig, orange zest, and º cup water to a simmer. Remove from heat and set aside for 5 minutes, strain and discard solids. Add the rosemary simple syrup to your pitcher along with a bottle of dry white wine, Ω cup elderflower liqueur, sliced pear, and rosemary sprigs. Stir and top with club soda before serving.

Pro tip: A clear pitcher shows off the fruit slices. 

Garnish each glass with a sprig of rosemary for a festive touch.


Keep it simple with tasty finger foods served on a platter. You canít go wrong with a crowd-pleasing bruschetta (thick slices of bread grilled or toasted, rubbed with garlic, drizzled with olive oil, often topped with tomatoes, balsamic and fresh basil). Feel free to mix things up with a non-traditional bruschetta combination like gorgonzola, fig and honey or add some goat cheese or pesto to the traditional tomato and basil recipe.


This course need not require the most planning. Dust off that Crock Pot or Instant Pot for that ìset it and forget itî simplicity. I have a go-to Italian Herbed Chicken that cooks perfectly within 10 minutes in the pressure cooker and allows you to enjoy the appetizer stop while the Instant Pot does all the work. Pair your protein with a premade salad and voila, dinner is served! If you prefer a more elegant approach, try a Beef Wellington or a one-pan lasagna that can rest while you start the night at the previous homes. 


Make the last stop memorable with something to end the night on a sweet note. Bake your favorite cake or ask a local bakery to curate a holiday cookie platter to please all palettes. Make it merry and pair with an easy dessert cocktail or mocktail. Something like this three-ingredient Peppermint Chocolate Martini is simple and satisfying. For one serving: Add 1 cup chocolate almond milk, 1 shot chocolate liqueur and a Ω shot peppermint liqueur. Shake it all up and garnish the rim with crushed candy canes.

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Annie Briening moved to Key West 15 years ago from Philly and hasn’t looked back. She is a foodie at heart, always down to dive into a new dish with a great view… oh and don’t forget the wine! You can find her biking around town, on a boat, or hanging with her hubby and her sweet pup.