Planning a Key West Sunset Sailboat Wedding
11/05/2025 | Southernmost Weddings
Affordable Private Destination Sunset Sailboat Wedding Packages with Beautiful Wedding Photography for Key West & the Florida Keys.
Key West Sunset Sailboat Wedding Packages
Scroll Down for Wedding Packages for up to 60 Guests
Scroll to the bottom of the page to see real wedding photos from these Sailboats.
Imagine sailing into the sunset as you say your vows or raise a glass of champagne in a toast to your new life. A wedding cruise on a sailing yacht, spacious catamaran or schooner is a great way to get married in Key West. Feel the warm tropical breezes and the gentle rocking of the ocean as you say your wedding vows. What could be more romantic, more ideal, that a sunset wedding in Key West.
SUNSET SAIL WEDDINGS IN KEY WEST FOR THE WEDDING COUPLE & A FEW FRIENDS
| Key West Beach Wedding followed by a Private Sunset Sail |
| • Afternoon Ceremony in Key West Florida followed by a Private Sunset Sail for the Wedding Couple and 4 Guests |
| • Professional Wedding Officiant, Custom Ceremony & Wedding Vows of your Choice. |
| • Filing of your marriage license with the State of Florida after the wedding ceremony by the officiant. |
| • 30 Minutes of Incredibly Beautiful Professional Wedding Photography before, during & after the ceremony. |
| • Approximately 80 Professionally Edited Full Size Images, delivered by E-mail & downloaded directly to your computer. |
| • Photo Release form allowing you to make prints. |
| • Add a Tropical Boutonniere for a Fresh Hand Tied Tropical Bouquet |
| • Wedding Planning & Consultations Included (305) 900 8500 |
| • Bring your own Beer, Wine or Champagne |
| • Due to the delicate nature of the Island of Key West and the beautiful oceans around us. We only use Hand Tied Fresh Tropical Flowers by a dedicated local florist or we provide you with silk flowers. We do not allow the use of additional Silk Flowers, Streamers, Confetti, Rice, Balloons, or anything else that could harm or damage our delicate environment during our weddings. |
| • Two Hour Private Sunset Sail |
| Private Sunset Sailboat Wedding Ceremony for up to 6 People |
| • Private Sunset Sailboat Wedding for the Wedding Couple & 4 Guests |
| • Wedding before Sunset performed by the Captain, Custom Ceremony & your Choice of Wedding Vows. |
| • Filing of the marriage license with the State of Florida after the ceremony by the Captain. |
| • Includes champagne, beer, wine, and soft drinks. |
| • Wedding Planning & Consultations Included (305) 900 8500 |
| • Add a Tropical Boutonniere for a Fresh Hand Tied Tropical Bouquet |
| • Due to the delicate nature of the Island of Key West and the beautiful oceans around us. We only use Hand Tied Fresh Tropical Flowers. Designed by a dedicated local florist. We do not allow the use of Silk Flowers, Streamers, Confetti, Rice, Balloons, or anything else that could harm or damage the environment during our weddings. |
| • Two Hour Private Sunset Sail |
| Private Sunset Sailboat Wedding Package for up to 4 People |
| • Private Sunset Sailboat Wedding for the Wedding Couple & 2 Guests. |
| • Wedding before Sunset performed by the Captain, Custom Ceremony & your Choice of Wedding Vows. |
| • Filing of the marriage license with the State of Florida after the ceremony by the Captain. |
| • Includes champagne, beer, wine and a Cheese & Fruit Appetizer Tray. |
| • Also includes a Handmade Wedding Cake. With your choice of Style and Flavors. |
| • Includes Incredibly Beautiful Professional Wedding Photography during the Sail. |
| • Approximately 100 Professionally Edited Full Size Images delivered by E-mail & downloaded directly to your computer. |
| • Photo Release form allowing you to make prints. |
| • Wedding Planning & Consultations Included (305) 900 8500 |
| • Add a Tropical Boutonniere or a Fresh Hand Tied Tropical Bouquet |
| • Two Hour Private Sunset Sail |
PRIVATE CATAMARAN SUNSET SAIL WEDDINGS
Catamaran Wedding Packages for up to 12 People
| E-12 Catamaran Sunset Wedding Package for 12 People |
| • Private Sunset Wedding on the Water for the wedding couple and 10 guests |
| • Ceremony at Sunset, Wedding Officiant, Choice of Wedding Vows & the Filing of the marriage license after the ceremony by the officiant. |
| • Includes champagne, beer, wine, soft drinks and a fruit & cheese appetizer tray. |
| • Includes Incredibly Beautiful Professional Wedding Photography during the Sail. |
| • Approximately 120 Professionally Edited Full Size Images, delivered by E-mail & downloaded directly to your computer. |
| • Photo Release form allowing you to make prints. |
| • Two Hour Private Sunset Wedding Sail on a catamaran. |
| • Wedding Planning & Consultations Included (305) 900 8500 |
PRIVATE CATAMARAN SUNSET SAIL WEDDINGS
Catamaran Wedding Package for up to 16 People
| P-16 Catamaran Sunset Wedding Package for 16 People |
| • Private Sunset Wedding on the Water for the wedding couple and 14 guests |
| • Ceremony at Sunset, Wedding Officiant, Choice of Wedding Vows & the Filing of the marriage license after the ceremony by the officiant. |
| • Includes champagne, beer, wine, sangria, soft drinks and chef' selection of appetizers. |
| • Includes Incredibly Beautiful Professional Wedding Photography during the Sail. |
| • Approximately 120 Professionally Edited Full Size Images, delivered by E-mail & downloaded directly to your computer. |
| • Photo Release form allowing you to make prints. |
| • Two Hour Private Sunset Wedding Sail on a sailing catamaran yacht. |
| • Wedding Planning & Consultations Included (305) 900 8500 |
PRIVATE SCHOONER SUNSET SAILBOAT WEDDINGS
Sailboat Wedding Packages for up to 20 People
| A-20 Schooner Sunset Wedding Package for 20 People |
| • Private Sunset Wedding on the Water for the wedding couple and 18 guests |
| • Ceremony at Sunset, Wedding Officiant, Choice of Wedding Vows & the Filing of the marriage license after the ceremony by the officiant. |
| • Includes champagne, beer, wine, sangria, soft drinks and chef' selection of appetizers. |
| • Includes Incredibly Beautiful Professional Wedding Photography during the Sail. |
| • Approximately 120 Professionally Edited Full Size Images, delivered by E-mail & downloaded directly to your computer. |
| • Photo Release form allowing you to make prints. |
| • Two Hour Private Sunset Wedding Sail on a wooden two-masted bugeye schooner. |
| • Wedding Planning & Consultations Included (305) 900 8500 |
PRIVATE SCHOONER SUNSET SAIL WEDDINGS
Wedding Parties with up to 22 People
| F-22 Schooner Sunset Wedding Package for 22 People |
| • Private Sunset Wedding on the Water for the wedding couple and 20 guests |
| • Ceremony at Sunset, Wedding Officiant, Choice of Wedding Vows & the Filing of the marriage license after the ceremony by the officiant. |
| • Includes champagne, margaritas, beer, wine, soft drinks. |
| • Includes Incredibly Beautiful Professional Wedding Photography during the Sail. |
| • Approximately 120 Professionally Edited Full Size Images, delivered by E-mail & downloaded directly to your computer. |
| • Photo Release form allowing you to make prints. |
| • Two Hour Private Sunset Wedding Sail on a 54' sailing vessel. |
| • Wedding Planning & Consultations Included (305) 900 8500 |
PRIVATE SCHOONER SUNSET SAIL WEDDINGS
Wedding Parties with up to 28 People
| D-28 Schooner Sunset Wedding Package for 28 People |
| • Private Sunset Wedding on the Water for the wedding couple and 26 guests |
| • Ceremony at Sunset, Wedding Officiant, Choice of Wedding Vows & the Filing of the marriage license after the ceremony by the officiant. |
| • Includes champagne, beer, wine, soft drinks and fruit, caprese salad skewers, summer sausage & cheese platter. |
| • Includes Incredibly Beautiful Professional Wedding Photography during the Sail. |
| • Approximately 120 Professionally Edited Full Size Images, delivered by E-mail & downloaded directly to your computer. |
| • Photo Release form allowing you to make prints. |
| • Two Hour Private Sunset Wedding Sail on a 65' Schooner . |
| • Wedding Planning & Consultations Included (305) 900 8500 |
PRIVATE SCHOONER SUNSET SAIL WEDDINGS
Wedding Parties with up to 39 People
| J-39 Schooner Sunset Pirate Wedding Package for 39 People |
| • Pirate Themed Wedding on the Water for the wedding couple and 37 guest |
| • Ceremony at Sunset, Wedding Officiant, Choice of Wedding Vows & the Filing of the marriage license after the ceremony by the officiant. |
| • Includes water, soft drinks and fruit & cheese platter. Bring your own Liquor. |
| • Includes Incredibly Beautiful Professional Wedding Photography during the Sail. |
| • Approximately 120 Professionally Edited Full Size Images, delivered by E-mail & downloaded directly to your computer. |
| • Photo Release form allowing you to make prints anywhere. |
| • Two Hour Private Sunset Wedding Sail on a classic 80’ coastal topsail, fashioned after the schooners of old. |
| • Wedding Planning & Consultations Included (305) 900 8500 |
PRIVATE SCHOONER SUNSET SAIL WEDDINGS
Wedding Parties with up to 47 People
| A-47 Schooner Sunset Wedding Package for 47 People |
| • Private Sunset Wedding on the Water for the wedding couple and 45 guests |
| • Ceremony at Sunset, Wedding Officiant, Choice of Wedding Vows & the Filing of the marriage license after the ceremony by the officiant. |
| • Includes champagne, beer, wine, sangria, soft drinks and fruit & cheese platter |
| • Includes Incredibly Beautiful Professional Wedding Photography during the Sail. |
| • Approximately 120 Professionally Edited Full Size Images, delivered by E-mail & downloaded directly to your computer. |
| • Photo Release form allowing you to make prints anywhere. |
| • Two Hour Private Sunset Wedding Sail on a majestic 86’ windjammer, fashioned after the schooners of old |
| • Wedding Planning & Consultations Included (305) 900 8500 |
PRIVATE CATAMARAN SUNSET SAIL WEDDINGS
Wedding Parties with up to 60 People
| S-62 Catamaran Sunset Wedding Package for 62 People |
| • Private Sunset Wedding on the Water for the wedding couple and 60 guests |
| • Ceremony at Sunset, Wedding Officiant, Choice of Wedding Vows & the Filing of the marriage license after the ceremony by the officiant. |
| • Includes mixed drinks, champagne, beer, wine, soft drinks and chef' selection of appetizers. |
| • Includes Incredibly Beautiful Professional Wedding Photography during the Sail. |
| • Approximately 120 Professionally Edited Full Size Images, delivered by E-mail & downloaded directly to your computer. |
| • Photo Release form allowing you to make prints. |
| • Two Hour Private Sunset Wedding Sail on a brand-new state of the art Custom Sailing Catamaran. |
| • Wedding Planning & Consultations Included (305) 900 8500 |
SOUTHERNMOST WEDDINGS (305) 900 8500
All Inclusive Wedding Packages and Affordable Wedding Photography for Key West, Florida & the Florida Keys.
Specializing in Private Sunset Sailboat Weddings, Sandy Beach Weddings & Intimate Tropical Garden Weddings.
Southernmost Weddings is your affordable Wedding Planning and Photography Company in Key West, Florida. Our wedding planning department has a variety of All-Inclusive Sandy Beach Wedding Packages, Intimate Tropical Garden Wedding Packages & Private Sunset Sailboat Wedding Packages that will fit any budget. We also have Wedding Packages for Cruise Ship Passengers, Weddings at Historic Key West Venues, Beach Weddings followed by a Sunset Sailboat Reception. Several Romantic Elopement - Wedding Packages. Southernmost Weddings gladly welcomes couples from all walks of life and orientations and we are proud to assist any gay or lesbian couple that wishes to get married in Key West or the Florida Keys. All of our wedding packages can be hand crafted to make you your own special Key West or Florida Keys destination wedding, vow renewal, or commitment ceremony. Southernmost Weddings Key West is the best Wedding Planning and Photography Company in the Southernmost City of the United States!
We are a group of local wedding planners dedicated to creating the destination wedding of your dreams, and wedding photographers who will capture beautiful photographic images of your wedding. Years from now when the memories fade, our images will still be there a timeless reminder of your special event.
All the images below were shot by Southernmost Weddings Key West
Wedding couple enjoys their sunset sail off the coast of Key West, Florida
Wedding couple celebrate their wedding with a champagne toast at sunset
Wedding couple relax on the bow of their private catamaran sunset sail
Barefoot Beach Wedding and a Private Sunset Sail for 18 guests
Barefoot Beach Wedding and a Private Sunset Sail for 18 guests
Barefoot Beach Wedding and a Private Sunset Sail for 18 guests
Barefoot Beach Wedding and a Private Sunset Sail for 14 guests
Barefoot Beach Wedding and a Private Sunset Sail for 14 guests
Barefoot Beach Wedding and a Private Sunset Sail for 14 guests