Key West Beach Weddings with Sunset Sailboat Reception Packages

Barefoot Beach Weddings followed by a Sunset Sail Receptions on the Water

Wedding Couple poses for photos after the wedding on a spacious catamaran

If you can get to Key West, or the Florida Keys, we can Marry the Two of You.
No Deposit, Booking Fees, or Initial Payment need to hold your date & time on most new contracts.

Scroll Down to view All Inclusive Sandy Beach Wedding Packages with Sunset Sailboat & Catamaran Receptions for up to 100 guests

Beach Weddings in Key West or the Florida Keys are often what brides-to-be dream of. Exchanging vows with wind-tousled hair and sandy toes, while the rhythmic sounds of ocean waves and seagulls fill your ears. Or maybe you are thinking a wedding cruise on a sailing yacht, spacious catamaran or historic schooner would be a great way to get married. So, what if you can't decide between a Beach Wedding or a Sailboat Wedding on the Water. Well Southernmost Weddings Key West has you covered with our beach wedding and sunset sail reception packages designed for every wedding size and budget. 

Choose from one of our all-inclusive beach wedding packages along with a Sunset Sail Reception.

Barefoot Beach Wedding and a Private Sunset Sail

For up to 6 People - Only $1045.00 includes tax, fees & crew gratuity
For up to 14 People - Only $2035.00 includes tax, fees, & crew gratuity
For up to 18 People - Only $2695.00 includes tax, fees, & crew gratuity

Includes a Beach Wedding followed by a Private Sunset Sail

Professional Wedding Officiant, Custom Ceremony, Choice of Wedding Vows
Filing of the Marriage License after the wedding by the officiant.
30 Minutes of Creative Wedding Photography before, during , & after the Ceremony
Approximately 75 edited images, delivered by E-Mail & downloaded directly to your computer.
Photo Release Form allowing you to make prints anywhere.
Wedding Planning & Consultations

Wedding Add-on's Design your own Special Beach Wedding

2 Post Bamboo Arch, draped with Shear White Fabric, accented with Lanterns, Conch Shells, & Starfish
$234.00

Aisle Way lined with Lanterns, Conch Shells, & Starfish
$129.00

White Ceremony Table - For use with Sand Blending, Unity Candles, Flower Tying, or Cake Cutting
$39.00

Portable Bluetooth Speaker
 $50.00

Fresh Hand Tied Tropical Bridal Bouquet
$100.00

Fresh Tropical Boutonniere
$32.00

Aisle Way sprinkled with Rose Petals
$79.00

2 Fresh Tropical Floral Pieces for the Sides of the Bamboo Arch
$179.00

6 Copper Lamp Stands
(Tiki-Torches)
$79.00

Extra half hour of photography
$129.00

Champagne Toast with Keepsake Starfish Champagne Glasses 
$99.00

Add White Padded or Dark Bamboo Chairs for the comfort of your guest
$10.00 EACH

Luxury Limousine Transportation with a complementary bottle of Champagne
$$$$$$$


EVERYTHING YOU NEED TO KNOW ABOUT YOUR PRIVATE SUNSET SAIL RECEPTION

PRIVATE SUNSET SAIL FOR UP TO 6 PASSENGERS AFTER THE WEDDING

Includes soft drinks & water 

Bring your own champagne, beer or wine

Two Hour Private Sunset Sail on a 41′ Island Trader, blue water cruising ketch

PRIVATE SUNSET SAIL FOR UP TO 14 PASSENGERS AFTER THE WEDDING

Includes champagne, beer, wine, soft drinks and a fruit & cheese appetizer tray.

Two Hour Private Sunset Sail on a Catamaran

PRIVATE SUNSET SAIL FOR UP TO 18 PASSENGERS AFTER THE WEDDING

Includes champagne, beer, wine, sangria, soft drinks and chef' selection of appetizers.

Two Hour Private Sunset Sail on a 41’ Maine Cat sailing catamaran yacht

ADD WEDDING TRANSPORTATION FOR YOUR WEDDING GUEST

Air-Conditioned Luxury Limo for you and your guest.
for 2 hours 

Call for special pricing

Air-Conditioned Luxury Bus for you and your guest.
(Up to 15 people)
From your hotel to the beach and then to the reception.

Only $300.00 dollars

Old Fashion Trolley for you and your guest 
(Up to 20 people)
From your hotel to the beach and then to the reception.

Only $375.00 dollars

Wedding Planning & Consultations
(305) 900 8500

  • Due to the delicate nature of the Island of Key West and the beautiful oceans around us.
    We only use Fresh Tropical Flowers, for our Bridal Bouquets, Boutonnieres, & other floral decor.
    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.
  • We strongly suggest you purchase "wedding insurance” to cover any expenses relating to the postponement of your wedding.

Sea Shell Wedding Package and a Private Sunset Sail

For up to 22 People - Only $4295.00 - Includes tax, fees & crew gratuity
For up to 24 People - Only $4149.00 - Includes tax, fees & crew gratuity
For up to 30 People - Only $4499.00 - Includes tax, fees & crew gratuity

All Packages Include an Afternoon Beach Wedding followed by a Private Sunset Sail
PLUS Transportation from the Hotel, to the Wedding & to the Sailboat for the reception.

Professional Wedding Officiant, Custom Ceremony, Choice of Wedding Vows
Filing of the Marriage License after the wedding by the officiant.
2 Post Bamboo Arch, with Shear White Fabric, accented with Lanterns, Starfish & 4 Copper Lamp Stands.
Aisle Way lined with Lanterns, Conch Shells, Starfish & Sprinkled with Rose Petals.
On-site Wedding Coordinator.
White Padded Chairs or Dark Bamboo Chairs for the comfort of your wedding guest.
One Hour of Creative Wedding Photography before, during & after the Ceremony
Approximately 125 edited images, delivered by E-Mail & downloaded directly to your computer.
Photo Release Form allowing you to make prints anywhere.
Wedding Planning & Consultations

Wedding Add-on's Design your own Special Beach Wedding

Add a Second Photographer
$129.00

Hire a Steel Drummer or Solo Guitarist
$300.00

Portable Bluetooth Speaker
$50.00


Fresh Hand Tied Tropical Bridal Bouquet
$100.00

Fresh Tropical Boutonniere
$32.00

2 Fresh Tropical Floral Pieces for the Sides of the Bamboo Arch
$179.00

White Ceremony Table
For use with Sand Blending, Unity Candles, Flower Tying, or Cake Cutting
$39.00

Switch to a 4 Post Bamboo Arch with Shear White Fabric
$234.00

EVERYTHING YOU NEED TO KNOW ABOUT YOUR PRIVATE SUNSET SAIL RECEPTION

PRIVATE SUNSET SAIL FOR UP TO 22 PASSENGERS AFTER THE WEDDING

Includes champagne, beer, wine, sangria, soft drinks and chef' selection of appetizers.

Two Hour Private Sunset Wedding Sail on a wooden two-masted bugeye schooner.

PRIVATE SUNSET SAIL FOR UP TO 24 PASSENGERS AFTER THE WEDDING

Includes champagne, margaritas, beer, wine, soft drinks

Two Hour Private Sunset Wedding Sail on a 54' sailing vessel

PRIVATE SUNSET SAIL FOR UP TO 30 PASSENGERS AFTER THE WEDDING

Includes champagne, beer, wine, soft drinks and fruit, caprese salad skewers, summer sausage & cheese platter.

Two Hour Private Sunset Wedding Sail on a 65' Classic Skipjack


This Package Includes Transportation for up to 30 guests on an Old-Fashioned Trolley

Wedding Planning & Consultations
(305) 900 8500

  • Due to the delicate nature of the Island of Key West and the beautiful oceans around us. 
    We only use Fresh Tropical Flowers, for our Bridal Bouquets, Boutonnieres, & other floral decor.
    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.
  • We strongly suggest you purchase "wedding insurance” to cover any expenses relating to the postponement of your wedding.

Conch Shell Beach Wedding and a Private Sunset Sail

For up to 35 People - Only $4375.00 - Includes tax, fees & crew gratuity
For up to 39 People - Only $4825.00 - Includes tax, fees & crew gratuity

For up to 47 People - Only $5625.00 - Includes tax, fees & crew gratuity

All Packages Include an Afternoon Beach Wedding followed by a Private Sunset Sail

Professional Wedding Officiant, Custom Ceremony, Choice of Wedding Vows
Filing of the Marriage License after the wedding by the officiant.
2 Post Bamboo Arch, with Shear White Fabric, accented with Lanterns, Starfish & 4 Copper Lamp Stands.
Aisle Way lined with Lanterns, Conch Shells, Starfish & Sprinkled with Rose Petals.
On-site Wedding Coordinator.
White Padded Chairs or Dark Bamboo Chairs for the comfort of your wedding guest.
One Hour of Creative Wedding Photography before, during & after the Ceremony
Approximately 100 edited images, delivered by E-Mail & downloaded directly to your computer.
Photo Release Form allowing you to make prints anywhere.
Wedding Planning & Consultations


WEDDING ADD-ON'S DESIGN YOUR OWN SPECIAL BEACH WEDDING

Add a Second Photographer
$149.00

Hire a Steel Drummer or Solo Guitarist
$300.00

Portable Bluetooth Speaker
$50.00

Fresh Hand Tied Tropical Bridal Bouquet
$100.00

Fresh Tropical Boutonniere
$32.00

2 Fresh Tropical Floral Pieces for the Sides of the Bamboo Arch
$179.00

White Ceremony Table 
For use with Sand Blending, Unity Candles, Flower Tying, or Cake Cutting
$39.00

Switch to a 4 Post Bamboo Arch with Shear White Fabric
$234.00

EVERYTHING YOU NEED TO KNOW ABOUT YOUR PRIVATE SUNSET SAIL RECEPTION

PRIVATE SUNSET SAIL FOR UP TO 35 PASSENGERS AFTER THE WEDDING

Includes champagne, beer, wine, soft drinks, sandwiches, fresh fruit, and a cheese & cracker platter.

Two Hour Private Sunset Sail on an 80' William Garden design Schooner. Largest & Roomiest decks of any Schooner.

PRIVATE SUNSET SAIL FOR UP TO 39 PASSENGERS AFTER THE WEDDING

Includes water, soft drinks and fruit & cheese platter. Bring your own Liquor

Two Hour Private Sunset Sail on a classic 80’ coastal topsail, fashioned after the Old-Historic Schooners of Yesterday

PRIVATE SUNSET SAIL FOR UP TO 47 PASSENGERS AFTER THE WEDDING

Includes champagne, beer, wine, sangria, soft drinks and fruit & cheese platter

Two Hour Private Sunset Sail on a majestic 86’ windjammer, fashioned after the Old-Historic Schooners of Yesterday


SWITCH TO A STATE OF THE ART, 3 DECK (PARTLY COVERED), LARGE STABLE CATAMARAN FOR YOUR WEDDING RECEPTION INCLUDING APPETIZERS, MIXED DRINKS & A DJ FOR ONLY
$5945.00

Add transportation for the comfort of your wedding guests

Transportation for the wedding party & guest from your Hotel to Smathers Beach for the wedding. 
Then we will take you and your guest to the Historic Seaport for your Sunset Sailboat Reception on waters of the Gulf of Mexico off the coast of Florida.

Your wedding guest will enjoy premium transportation in Two Air-conditioned 
30 Passenger Minibus

ADD $575.00 DOLLARS FOR (2) MINIBUSES and 30 Passengers 
Plus $18.00 for each additional Passengers

Your wedding guest will enjoy premium transportation in one of our 40 Passenger Old-Fashioned Trolleys

ADD $375.00 DOLLARS For 20 Passengers 
Plus $18.00 for each additional Passengers

Your wedding guest will enjoy premium transportation in one of our 56 Passenger Old-Fashioned Trains.

ADD $550.00 DOLLARS For 30 Passengers 
Plus $18.00 for each additional Passengers

Wedding Planning & Consultations
(305) 900 8500

  • Due to the delicate nature of the Island of Key West and the beautiful oceans around us.
    We only use Fresh Tropical Flowers, for our Bridal Bouquets, Boutonnieres, & other floral decor.
    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.
  • We strongly suggest you purchase "wedding insurance” to cover any expenses relating to the postponement of your wedding.

Wedding Ceremony on Smathers Beach in Key West, Florida
followed by a Sunset Sail Reception on the Water

SAND DOLLAR BEACH WEDDING & SUNSET CATAMARAN SAIL RECEPTION

$6245.00 Includes tax, fees, & crew gratuity

Professional Wedding Officiant, Custom Ceremony, Choice of Wedding Vows
Filing of the Marriage License after the wedding by the officiant.
4 Post Bamboo Arch, draped with Shear White Fabric, accented with Lanterns, Starfish & 4 Copper Lamp Stands.
Aisle Way lined with Lanterns, Conch Shells, Starfish & Sprinkled with Rose Petals.
On-site Wedding Coordinator.

Up to 50 White Padded Chairs or Dark Bamboo Chairs for the comfort of your wedding guest.

One Hour of Creative Wedding Photography before, during & after the Ceremony

Approximately 100 edited images.
Delivered by E-Mail & downloaded directly to your computer.
Photo Release Form allowing you to make prints anywhere.


WEDDING ADD-ON'S DESIGN YOUR OWN SPECIAL BEACH WEDDING

Add a Second Photographer
$149.00

Hire a Steel Drummer or Solo Guitarist
$300.00

Hand Tied Tropical Bridal Bouquet
$100.00

Fresh Tropical Boutonniere
$32.00

2 Fresh Tropical Floral Pieces for the Sides of the Bamboo Arch
$179.00

White Ceremony Table - For use with Sand Blending, Unity Candles, Flower Tying, or Cake Cutting
$39.00

Portable Bluetooth Speaker
$50.00


EVERYTHING YOU NEED TO KNOW ABOUT YOUR PRIVATE SUNSET SAIL RECEPTION

You will have the best wedding reception in Key West on a state of the art 65-foot catamaran. Key West's newest catamaran is one amazing boat to have your reception on. This boat is Key West's only true triple deck sailing catamaran. Offering three different decks for your special occasion. This large stable vessel is an excellent choice if there are children or elderly guest. The catamarans flat deck surface is also perfect for those wishing to dance the night away.

Private Sunset Sail Reception for 2 Hours

Include open bar with mixed well drinks, rum runners, margaritas, champagne, draft beer, wine and soft drinks, appetizers, DJ, sales tax and crew gratuity

Appetizers Include 
Swedish Meatballs • Cheese & Crackers Veggies with Ranch Dip • Pita Bread & Hummus • Pin Wheel Ham & Cream Cheese • Pin Wheels with Broccoli, Carrots & Cream Cheese 

Add transportation for the comfort of your wedding guests

Transportation for the wedding party & guest from your Hotel to Smathers Beach for the wedding. 
Then we will take you and your guest to the Historic Seaport for your Sunset Catamaran Reception on the Gulf of Mexico off the coast of Florida.

Your wedding guest will enjoy premium transportation in an Air-conditioned 
30 Passenger Minibus

ADD $550.00 DOLLARS FOR UP TO 30 PASSENGERS

Your wedding guest will enjoy premium transportation in one of our 40 Passenger Old-Fashioned Trolleys

ADD $750.00 DOLLARS FOR UP TO 40 PASSENGERS

Your wedding guest will enjoy premium transportation in one of our 56 Passenger Old-Fashioned Trains.

ADD $1010.00 DOLLARS FOR UP TO 56 PASSENGERS

Wedding Planning & Consultations
(305) 900 8500

  • Due to the delicate nature of the Island of Key West and the beautiful oceans around us.
    We only use Fresh Tropical Flowers, for our Bridal Bouquets, Boutonnieres, & other floral decor.
    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.
  • We strongly suggest you purchase "wedding insurance” to cover any expenses relating to the postponement of your wedding.

NEED MORE INFORMATION CONTACT US