Are meals provided on sailing trips?

Many trips offer freshly prepared meals onboard featuring local seafood, with options for custom menus depending on the trip length and group preferences.

Can beginners sail with Restless Native Charters?

Absolutely. Their experienced captains manage the vessel, offering a safe and comfortable experience for all skill levels.

Is snorkeling available during the trips?

Yes, several itineraries include stops for snorkeling, especially around reef areas and Boca Grande Key.

What is the cancellation policy?

Policies vary depending on the trip but generally require advance notice; guests should confirm details when booking directly.

Are weddings and private events accommodated?

Restless Native Charters specializes in intimate and memorable celebrations on the water, with customizable arrangements.

How do I prepare for seasickness?

Over-the-counter seasickness medications are recommended if you’re prone to motion sickness; consult your doctor for the best option.

Sailing Adventures in Key West with Restless Native Charters

Key West, Florida, where the Gulf of Mexico meets the Atlantic Ocean, offers some of the most dynamic sailing conditions and vibrant marine life in the continental United States. Restless Native Charters operates here as a standout provider of tailored sailing adventures ranging from brief half-day sails to multi-day expeditions, including trips to the remote and pristine Dry Tortugas. This operation operates with a focus on personalized experiences aboard well-maintained catamarans like Zodiac and Aria, delivering comfort and agility on the water.

The waters around Key West boast crystal-clear visibility and warm temperatures year-round — a playground for marine wildlife such as playful dolphins frequently seen riding the bow waves, and vibrant coral reef systems just offshore. Restless Native Charters highlights these elements through varied trips like sunset sails, full-day excursions, and overnight expeditions that offer everything from beachcombing on tiny private islands to sampling fresh, local seafood served onboard. The crew, captained by Brad and Maddie, is noted for their professionalism, warmth, and deep local knowledge, transforming every outing into a blend of adventure and hospitality.

Special occasions, including weddings and memorials, find a unique setting aboard their vessels, where guests experience unobstructed horizons and quiet moments away from the usual island crowds. Their custom sailing adventures give freedom to craft itineraries that range from leisurely coastal cruises to capturing the spectacle of Fourth of July fireworks over the water.

Restless Native Charters is more than just a boat company—they are ambassadors of Key West’s marine environment and culture. Their commitment to pristine, responsible boating practices helps keep this corner of Florida as vibrant as the days when seafarers first dropped anchor here. Whether it’s a family outing, a meaningful celebration, or a spirited voyage to the Tortugas, this charter ensures an immersive maritime encounter that combines the thrill of sailing with the ease of luxury service.

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.

Sailing Adventures in Key West with Restless Native Charters

Adventure Brief

Keep the Adventure Going

Frequently Asked Questions

Key Highlights

Local Insights

Related Adventures & Guides

Operated By

About Restless Native Charters

Reserve a Private Key West Charter Today

Adventure Tips

Recommended Gear