Do I need a scuba certification to join the expedition?

Scuba certification is recommended for diving portions, but snorkeling and sailing activities are accessible to all skill levels.

What meals are included during the dinner boat experience?

Guests enjoy freshly prepared local dishes paired with a selection of fine wines, focusing on seafood and regional flavors.

Is transportation provided from Key West to the embarkation point?

Transportation to and from the boat is typically the guest’s responsibility, but Restless Native Charters can offer recommendations for local shuttles and taxis.

What should I bring for the overnight stay on the boat?

Pack comfortable clothing, toiletries, a swimsuit, and any personal medications; sleeping accommodations and bedding are provided onboard.

Can I customize the activities during the expedition?

Yes, the private nature of this trip allows guests to tailor activities like skydiving, scuba, or wine tasting to fit their preferences.

How is safety managed during adventurous activities like skydiving and scuba diving?

Restless Native Charters partners with certified professionals and follows strict safety protocols for all activities, ensuring guest safety at all times.

Overnight Expedition Adventure in Key West, Florida | Boat Tour | Dinner Boat

Experience the ultimate overnight expedition with Restless Native Charters in Key West, Florida. This private, multi-activity adventure combines sailing, snorkeling, scuba diving, skydiving, and a unique dinner boat experience that showcases the vibrant marine life and stunning sunsets of the Florida Keys. Spend your night on the water, drifting under starry skies after an exhilarating day exploring coral reefs and hidden coves. Enjoy freshly prepared meals and local wines aboard your private vessel, creating a perfect blend of relaxation and excitement. Whether you're an adrenaline seeker or a nature lover, this trip covers it all—from thrilling skydiving jumps to calm snorkeling sessions in crystal-clear waters. Knowledgeable guides ensure your safety and share insider tips on the best underwater spots and local history. This expedition is not just a tour but an immersive experience offering unmatched privacy, personalized service, and unforgettable views. Discover Key West’s coastal treasures in comfort and style while creating memories that will last a lifetime.

About Restless Native Charters

Restless Native Charters is a Key West, Florida-based charter operator offering private sailing experiences aboard a luxurious 42' catamaran yacht. The company specializes in customizable private charters including weddings, memorial services, full-day sailing adventures, 3/4‑day sails, and tailored custom sailing trips for up to six guests.

For weddings, Restless Native Charters provides indoor accommodations, customizable vows, and an all-inclusive onboard event option that turns a ceremony into a seamless celebration at sea. Memorial services take place in the waters of the Florida Keys National Marine Sanctuary, where ashes are respectfully scattered during a guided remembrance ceremony.

Recreational day trips include an eight-hour Full Day Sail and a six-hour 3/4 Day Sail. Both itineraries feature snorkeling, SCUBA diving, guided reef tours, and supplied gear so guests can explore coral formations and local marine life. Custom Sailing Adventures offer private itineraries guided by an expert captain who adapts the route and activities to guest preferences.

All charters depart from Key West and focus on safety, comfort, and personalized service. The vessel’s size and layout accommodate intimate groups while delivering stability for water activities. Booking options are private and tailored to the occasion, with clear descriptions of trip length, included activities, and guest capacity.

Restless Native Charters positions itself as a trusted provider for memorable maritime events and adventure-focused sails in the Florida Keys, combining a premium catamaran, guided service, and destination-specific itineraries designed for meaningful experiences. Reservations, availability, and detailed safety information are provided when confirming each charter booking by phone directly.