Best 2027 Wedding Dates in Florida (Key Largo & Florida Keys Guide)

Imagine exchanging vows on a private waterfront estate, with the sun melting into the calm waters of the Florida Bay. This is the magic of getting married at Dream Bay Resort in Key Largo. As one of the most sought-after wedding venues in the Florida Keys, we offer an exclusive setting that combines the laid-back island vibe with polished, professional service. Our palm-studded shoreline, private boat dock for stunning photos, and flexible indoor-outdoor spaces create a canvas for your perfect day. With on-site lodging for your wedding party and the convenience of being just a short drive from Miami International Airport, Dream Bay provides a seamless and breathtaking destination wedding experience. Every day in Key Largo is one of Best 2027 Wedding Dates in Florida!

We specialize in turning your wedding day into a weekend-long celebration. Our exclusive buyout model allows you to reserve the entire property for a truly private event, from a Friday welcome party to a Sunday farewell brunch. We proudly offer Friday, Saturday, and Sunday wedding dates throughout 2027, giving you the flexibility to craft an unforgettable experience. Whether you envision a grand Saturday affair or a more intimate Sunday gathering under the stars, our team is ready to help you find the perfect date and bring your vision to life on our slice of paradise.

Before we get to our topic on wedding dates to consider for 2027, we hope to share a little information about what makes Dream Bay Resort the perfect beach front resort for diving enthusiast. Stunning sunsets, sandy beaches, tiki huts, and swaying palms come together to create a serene, peaceful experience. If you’re searching for the ideal Key Largo resort experience and Dream Bay seems like the perfect fit, we’d be delighted to assist you. Feel free to contact us to arrange a virtual or in-person tour. Explore our resort accommodations and cabins, wedding packages, cozy cottages, and availability calendar for all the details you need to begin planning your adventure. We look forward to welcoming you.

Your Guide to 2027 Florida Keys Wedding Dates

Choosing a wedding date is one of the first big decisions you'll make. In the Florida Keys, timing is everything. It influences weather, crowds, pricing, and the overall atmosphere of your celebration. This guide breaks down every Friday, Saturday, and Sunday in 2027, alongside unique dates and seasonal tips to help you select the ideal day to say "I do."

2027 Fridays, Saturdays & Sundays by Month

January 2027

Fridays: 1, 8, 15, 22, 29
Saturdays: 2, 9, 16, 23, 30
Sundays: 3, 10, 17, 24, 31
Notes: Cooler, drier weather with gorgeous sunsets. High season for tourism, so book accommodations early.

February 2027

Fridays: 5, 12, 19, 26
Saturdays: 6, 13, 20, 27
Sundays: 7, 14, 21, 28
Notes: Prime wedding season. Beautiful weather continues. Valentine's Day weekend (Feb 14) is a popular choice.

March 2027

Fridays: 5, 12, 19, 26
Saturdays: 6, 13, 20, 27
Sundays: 7, 14, 21, 28
Notes: Still peak season with Spring Break crowds appearing. Expect warm days and pleasant evenings.

April 2027

Fridays: 2, 9, 16, 23, 30
Saturdays: 3, 10, 17, 24
Sundays: 4, 11, 18, 25
Notes: One of the best months. The weather is spectacular, and the winter crowds start to thin.

May 2027

Fridays: 7, 14, 21, 28
Saturdays: 1, 8, 15, 22, 29
Sundays: 2, 9, 16, 23, 30
Notes: Temperatures rise. A great shoulder-season month with fewer crowds. Memorial Day weekend (May 29-31) offers a three-day celebration opportunity.

June 2027

Fridays: 4, 11, 18, 25
Saturdays: 5, 12, 19, 26
Sundays: 6, 13, 20, 27
Notes: The official start of hurricane season, though early June is typically calm. Expect heat, humidity, and afternoon showers.

July 2027

Fridays: 2, 9, 16, 23, 30
Saturdays: 3, 10, 17, 24, 31
Sundays: 4, 11, 18, 25
Notes: Hot and humid. The 4th of July weekend is a festive but busy time in the Keys.

August 2027

Fridays: 6, 13, 20, 27
Saturdays: 7, 14, 21, 28
Sundays: 1, 8, 15, 22, 29
Notes: Peak hurricane season. Hot and humid, but venues may offer value. Lobster mini-season draws crowds.

September 2027

Fridays: 3, 10, 17, 24
Saturdays: 4, 11, 18, 25
Sundays: 5, 12, 19, 26
Notes: Historically the most active month for hurricanes. Labor Day weekend (Sept 4-6) is a popular holiday.

October 2027

Fridays: 1, 8, 15, 22, 29
Saturdays: 2, 9, 16, 23, 30
Sundays: 3, 10, 17, 24, 31
Notes: Humidity and rain chances decrease. The weather becomes beautiful again, marking the start of the shoulder season.

November 2027

Fridays: 5, 12, 19, 26
Saturdays: 6, 13, 20, 27
Sundays: 7, 14, 21, 28
Notes: Fantastic weather and the official end of hurricane season. A very popular wedding month.

December 2027

Fridays: 3, 10, 17, 24, 31
Saturdays: 4, 11, 18, 25
Sundays: 5, 12, 19, 26
Notes: Festive and dry. Christmas and New Year's Eve dates offer a magical holiday wedding feel but expect premium pricing and high demand.

Special Dates in 2027

Full Moon Dates
A full moon wedding reception over the bay is unforgettable.

Jan 2 (Sat), Feb 1 (Mon), Mar 2 (Tues), Apr 1 (Thurs), Apr 30 (Fri), May 30 (Sun), Jun 28 (Mon), Jul 28 (Wed), Aug 26 (Thurs), Sep 25 (Sat), Oct 25 (Mon), Nov 23 (Tues), Dec 23 (Thurs)

Holiday Weekends
Perfect for multi-day events when guests have extra time off.

Martin Luther King Jr. Day: Weekend of Jan 16-18
Presidents' Day: Weekend of Feb 13-15
Memorial Day: Weekend of May 29-31
Independence Day: Weekend of Jul 3-5
Labor Day: Weekend of Sep 4-6
Columbus Day / Indigenous Peoples' Day: Weekend of Oct 9-11
Veterans Day: Thursday, Nov 11
Thanksgiving: Thursday, Nov 25

Unique & Fun Dates
Choose a date that's easy to remember and fun to say.

Seven-Twenty-Seven: Tuesday, 7/27/27
February Repeats: Thursday, 2/27/27 & Sunday, 2/7/27
Lucky Elevens: Thursday, 11/11/27
End-of-Year Repeats: Monday, 12/27/27 & Tuesday, 12/7/27
Other Patterns: Saturday, 10/27/27

15 Things to Know About Choosing a Wedding Date in Key Largo

Hurricane Season: It runs from June 1 to November 30. Peaks are August through early October. Always have a backup plan and consider wedding insurance.
Sunset Windows: Dream Bay is a bayfront venue, perfect for sunsets. In winter, the sun sets earlier (around 5:30 PM), while in summer it can be as late as 8:15 PM. Plan your ceremony time accordingly.
Tide Tables: For photos on sandbars or near the water's edge, check the tide charts. Low tide reveals more beach, while high tide brings the water right up to the seawall.
Sargassum Season: This seaweed can sometimes wash ashore, primarily in the warmer months (spring/summer). Bayfront venues like Dream Bay are generally less affected than oceanfront ones.
Group Room Blocks: High season (Dec-May) means hotels book up fast. Secure your room blocks as soon as you have your date.
Keys Traffic on US-1: Friday afternoons heading south and Sunday afternoons heading north can be very congested. Advise guests to travel during off-peak hours.
Vendor Availability: The best photographers, planners, and florists book 12-18 months in advance, especially for popular Saturday dates.
Noise Ordinances: Key Largo has noise regulations. Music typically must be lowered or moved indoors by 10:00 or 11:00 PM, depending on the location.
Daylight Saving Shifts: Remember the time "springs forward" in March and "falls back" in November. This affects your available daylight for photos and your ceremony.
Local Festivals: Check for major fishing tournaments, seafood festivals, or boat races that can cause traffic and book up accommodations.
Sea Breeze & Heat: Even on a hot day, a bayside breeze can make it feel pleasant. However, plan for the heat from May to October with fans, water stations, and shaded areas.
Backup Weather Plans: Florida weather is unpredictable. Ensure your venue has a solid "Plan B" for rain that is just as beautiful as your "Plan A."
Transportation: If planning boat outings or group transport, book charters and buses well in advance.
Golden Hour: The hour before sunset provides the most magical light for photos. On the bay side, this is the main event.
Permits: If you plan any activities outside your private venue (like a public beach photoshoot or drone photography), check if local permits are required. At a private estate like Dream Bay, this is not an issue.

5 Reasons Couples Book Dream Bay Resort (Key Largo)

Private Waterfront Campus: With cottages and suites on-site, your closest friends and family can stay with you, creating a relaxed, communal atmosphere all weekend long.
Epic Sunset Ceremony & Reception: Our iconic pier is the perfect aisle leading to a stunning ceremony over the water. Afterward, dine and dance under a canopy of string lights on the beach.
Flexible BYO Vendor-Friendly Policies: We believe your wedding should reflect you. We offer the flexibility to bring in your own licensed and insured vendors, giving you control over your budget and style.
The Weekend-Long Experience: Why limit the joy to one day? Our buyout model allows for a welcome party, rehearsal dinner, wedding day festivities, and a farewell brunch, all in one seamless location.
Stress-Free Planning Support: While we offer flexibility, we aren't hands-off. We provide a curated list of trusted local professionals who know our property inside and out, ensuring your planning process is smooth and enjoyable.

Book Your Tour at Dream Bay Resort

Reading about dates and details is a great start, but nothing compares to experiencing the magic of Dream Bay in person. We invite you to schedule a tour to walk the property, see the sunset views from the pier, and envision your perfect wedding weekend. Our 2027 calendar for Friday, Saturday, and Sunday dates is open, and popular weekends are already being reserved. Acting early ensures you can secure your first-choice date.

We offer both in-person and virtual tours to accommodate your schedule. To get started, reach out to our team with your ideal guest count, the vibe you're dreaming of, and your top three preferred dates. We’ll walk you through our availability and packages, and show you why so many couples choose to begin their forever at Dream Bay. Let's start planning your unforgettable Key Largo wedding.

Book your stay at Dream Bay Resort today! The tropical views (and your adventure of a lifetime) are waiting. Looking for inspiration or advice? Explore Dream Bay Resort as your ultimate proposal and wedding venue, and start planning this incredible chapter of your story. Contact Dream Bay Resort for more information. Featuring breathtaking sunsets, private accommodations, and personalized touches, we are here to help make your destination wedding truly unique.

From proposing at the water’s edge to enjoying the beauty of Key Largo, your wedding will be one to remember when you choose our Florida Keys Resort wedding venue. We invite you and your fiancé to visit Dream Bay Resort for a wedding venue tour or call us to inquire about pricing and availability.

Whether you’re planning a grand wedding, intimate ceremony, micro wedding, elopement, weekday celebration, or a full resort buyout for the ultimate private experience, we are here to accommodate your vision. For additional wedding inspiration, follow us on Facebook and Instagram. We look forward to helping you plan the wedding of your dreams. Fill out our contact form to learn more. Here’s to a beautiful celebration and a lifetime of love and happiness! 🌴💍