Now Open: Cayo Caicos Mermaid Outfitter
⋆ cayocaicos.com ⋆
Now Open: Cayo Caicos Mermaid Outfitter ⋆ cayocaicos.com ⋆
SEA GYPSY - KEY WEST
Sailing Adventures & Events
Private Classic Sailboat Events & Adventures
Let us create a professionally planned, one-of-a-kind, private event aboard a beautiful, classic sailing yacht or luxury catamaran.
Here are just some of the magical sailboat adventures and events, boarding in Key West, Florida:
- Private Sailboat Events
- Corporate Sailboat Events
- Sailing Retreats
- Sailboat Photo & Video Shoots
Our custom sailing packages will always be tailored completely around your needs.
Professional Sailboat Photo & Video Shoots
Our classic sailboats have been the location for numerous private and commercial photoshoots.
Sail into your shared future with the love of your life and capture lasting impressions from your intimate wedding aboard a sailing yacht.
From engagement photos to Flying Dress photoshoots - you will be thrilled by the amazing results!
Add a Classic Twist to Your Sailing Adventure
Experience the charm of a classic sailing yacht! Our custom sailing event packages will be tailored around the needs of our group.
Are you looking for an adventure, a classy catered event, or would you like to relax and unwind?
From an intimate sunset cruise for 2 to a private sailboat event for up to 100 people - we have the perfect boat and crew for your needs.
Relax on a Day Trip aboard a Luxury Sailing Yacht
Enjoy the most luxurious private day trips to snorkel at the most beautiful reefs of the Florida Keys, or simply enjoy the view of Key West from the boat.
Our private catamaran, powerboat, and sailboat charters all come with qualified captains and crew.
Discover Tropical Destinations
Experience the joy of “discovering” tiny Florida Keys, tropical reefs, and crystal clear water from aboard our sailing catamarans and sailboats.
Connect with Friends & Family
Enjoy your company and create lasting memories on the water.
Build Your Custom Sailing Experience
We’ll help you create an unforgettable experience on the water that’s customised for your requirements.
“Our sailing event was amazing! The Captain and crew were so knowledgeable and fun. Don’t miss out on the awesome catering and beverage choices!”
— Crystal F.