Key West Food & Wine Festival: A Foodie’s Weekend Guide

Key West already knows how to eat well. Add visiting chefs, curated wines and special culinary experiences, and the entire island becomes one long, delicious reason to stay for the weekend.

The 18th Key West Food & Wine Festival is scheduled for January 27–31, 2027. Its “Connected by the Oceans” theme explores the food, wine and culinary stories of five continents, reflecting Key West’s place between the Atlantic and the Gulf.

Tickets are scheduled to go on sale September 30, 2026. Here is how to plan your festival weekend without missing the flavors—or the pool time.

Before You Arrive

Festival events can be individually ticketed and may take place at different locations around Key West. Review the official Food & Wine Festival schedule before booking your itinerary.

Prioritize the experiences you care about most, then purchase those tickets early. Avoid filling every hour. A little room between tastings makes the weekend more enjoyable.

FOODIE TIP

Confirm each event’s location, start time, dress code and transportation plan. “Key West casual” can mean very different things depending on the venue.

Friday: Check In and Ease Into the Weekend

Check into Blue Flamingo Resort, drop your bags and begin with something easy.

Head to Rum Row for a tropical cocktail and island-inspired bites, or settle beside the pool for a relaxed start before your first festival event.

If your ticketed schedule begins Saturday, use Friday evening for dinner in Old Town. Choose somewhere with shareable plates or fresh local seafood, but resist the urge to order everything. This weekend is a marathon, not a tasting-menu sprint.

Saturday Morning: Start Slowly

Begin with coffee and breakfast at Toasted Coconut. Keep the morning meal light if your festival itinerary includes multiple tastings.

Review your tickets, confirm transportation and carry the essentials:

• Water
• Sunscreen
• Photo identification
• Comfortable shoes
• A portable phone charger
• Your ticket confirmations

Saturday Afternoon: Taste Your Way Around the Festival

Let the official schedule guide the afternoon. Festival programming may include chef-led meals, wine experiences, cultural storytelling and intimate culinary events.

Taste thoughtfully rather than rushing. Ask questions, try something unfamiliar and make notes about wines or dishes you want to revisit later.

Drink water between events and build in time for a proper break. Returning to Blue Flamingo for a swim or cabana hour is an entirely respectable festival strategy.

Saturday Night: Make Dinner Count

If your evening does not include a ticketed dinner, reserve one of Key West’s standout restaurants.

For a Romantic Splurge

Latitudes on Sunset Key combines a ferry ride, waterfront atmosphere and refined island dining.

For Shareable Plates

Santiago’s Bodega offers tapas in a warm, intimate Bahama Village setting.

For Key West Character

Blue Heaven delivers tropical gardens, island history and a setting unlike anywhere else.

RESERVATION TIP

Festival weekend is a busy time for dining. Make restaurant reservations well before arriving.

Sunday: Brunch, Pool and One Last Bite

Sunday should be uncomplicated.

Choose a festival brunch if one appears on the official schedule, or keep the morning relaxed at Blue Flamingo. Revisit the weekend’s favorites over coffee, take one final swim and order lunch beside the pool.

Before leaving, pick up an edible souvenir: Key lime treats, Cuban coffee, hot sauce or something from a local gourmet shop.

Book your Key West Food & Wine Festival stay at Blue Flamingo.

Frequently Asked Questions

When is the 2027 Key West Food & Wine Festival?

The festival is scheduled for January 27–31, 2027.

When do festival tickets go on sale?

The official festival website states that tickets are scheduled to go on sale September 30, 2026.

Do you need tickets for every event?

Festival experiences may be separately ticketed. Review each listing carefully and purchase your preferred events in advance.

Where should you stay during the festival?

Choose a resort with convenient access to Old Town and enough amenities for downtime. Blue Flamingo provides pools, cabanas and on-property dining between events.

What should you wear?

Dress codes vary. Comfortable resort attire works for casual events, while special dinners may call for polished island wear.