Customizable private charters aboard a 35' Carolina Classic and a 24' Sailfish — up to 6 guests with equipment and crew provided.
Private Key West charters for fishing, snorkeling, island hopping, sunset cruises, and overnight stays.
boat-charters · Key West
Set sail on a private 24-hour boat adventure in Key West with the 35' Carolina Classic. Perfect for exploring the Gulf, fishing, or relaxing on the water—this experience offers personalized luxury in the Florida Keys. Keep reading to discover why this trip stands out.
Good Times Key West operates out of Key West, Florida, offering private charter experiences aboard a 35' Carolina Classic and a 24' Sailfish. The company provides a range of customizable trips including 2‑, 4‑, 6‑, 8‑ and 12‑hour charters plus overnight options, accommodating groups up to six people and a cabin that sleeps four. Each charter includes a licensed captain and first mate, all necessary equipment, and complimentary on‑site parking where available. One meeting location is the tiki hut at Mellow Ventures Cafe for certain departures.
Itineraries are tailored to guest interests: fishing, snorkeling, island hopping, wildlife viewing, or sunset cruises. Guests are invited to bring personal snacks and beverages while crew members manage navigation, safety, and gear. The fleet’s two vessel types allow both day adventures and overnight comfort, with the Carolina Classic offering cabin accommodations and the Sailfish optimized for shallow-water fishing and quick island access.
Good Times Key West emphasizes private, personalized service and clear, upfront inclusions. Reservations accommodate families, small groups, anglers, and visitors seeking scenic cruises or active water sports. Safety briefings, life jackets, and standard safety equipment are provided on every charter. With a focus on local waters around Key West, the business delivers guided maritime experiences that combine convenience—equipment and parking—with knowledgeable crews and flexible itineraries suited to diverse group needs.
Free parking is available nearby for many departures, and captains adjust routes for weather and guest preferences to maximize safety and comfort while delivering a tailored Key West boating experience for families.
“Every outing is organized with local river knowledge, basic safety instruction, and equipment checks before departure.”
Cabin comforts and fishing-ready hulls
Perfect for families and small groups
2–12 hour charters and overnight options
Private charters and overnight stays
Open the individual experience guide to confirm current availability, pricing, policies, conditions, and inclusions before booking.
The operator provides clear meeting points, departure times, and destination coordinates for all outings.
Personal flotation devices, emergency protocols, equipment checks, and paddling orientations are provided before departure.
Recommended layering, water shoes, sunscreen, and dry bags are detailed in each experience guide.
Guides share rich knowledge of regional flora, fauna, scenic landmarks, and river navigation.
A glimpse into the experiences, natural landscapes, and adventures waiting on your next trip.
Images supplied on the current Good Times Key West listing.
Good Times Key West offers a variety of guided outdoor excursions, scenic routes, rentals, and custom itineraries tailored for families, couples, and adventure enthusiasts.
Yes. Most trips feature comprehensive safety orientations, equipment fittings, and calm routes suited for first-time adventurers. Check the details on individual experience guides for specific age and skill requirements.
Standard safety equipment (such as certified life vests and essential gear) is supplied for each booking. Detailed checklists regarding weather-appropriate attire and personal items are provided prior to departure.
Book a 2‑hour cruise, full-day fishing trip, or overnight cabin aboard the 35' Carolina Classic — captain, mate, equipment, and free parking included on many departures.
boat-charters · Key West
Set sail on a 12-hour private adventure through the stunning waters of Key West aboard the 35' Carolina Classic. Discover hidden spots, enjoy personalized experiences, and soak up the beauty of the Florida Keys on this exclusive boat rental with Good Times Key West.
boat-charters · Key West
Set sail on a private 8-hour boat charter in Key West and discover the stunning waters of Florida’s iconic coast. Perfect for adventure seekers and relaxing travelers alike, this experience promises a day full of scenic beauty and personalized fun.
boat-charters · Key West
Experience the beauty of Key West from the water with a private 6-hour boat charter aboard a 35' Carolina Classic. Perfect for fishing, sightseeing, and relaxing, this trip offers unforgettable ocean adventures tailored just for you.
boat-charters · Key West
Set sail on a private 4-hour boat charter in Key West with Good Times Key West. Discover stunning ocean vistas, local wildlife, and customizable routes that make for an unforgettable day at sea.
boat-charters · Key West
Set sail into Key West's stunning sunset aboard a luxury boat with a glass of champagne in hand. Discover scenic views, marine wildlife, and a peaceful evening on the water with this private cruise experience.
boat-charters · Key West
Set sail on a private 2-hour charter aboard the 24' Sailfish in Key West. Perfect for relaxing, exploring, and discovering the stunning waters of the Florida Keys.
boat-charters · Key West
Discover the ultimate private sailing experience in Key West with a 6-hour charter aboard the sleek 24' Sailfish. Perfect for exploring pristine waters and hidden islands, this trip promises a day of relaxation and adventure—read on to find out more!
boat-charters · Key West
Discover the thrill of private sailing in the Florida Keys with a 4-hour boat rental aboard the 24' Sailfish. Perfect for exploring secluded spots, wildlife spotting, and enjoying the sun, this experience offers a custom day on the water you won't forget.
boat-charters · Key West
Set sail on a personalized 8-hour private charter aboard the 24' Sailfish in Key West. Discover pristine waters, encounter marine wildlife, and enjoy a flexible, luxury boating experience tailored to your needs.
boat-charters · Key West
Experience the magic of Dry Tortugas National Park with a private overnight sailing trip aboard a classic 35-foot Carolina. Swim, snorkel, and explore historic Fort Jefferson on this unforgettable 2-day adventure.
Unknown · Key West
Set sail from Key West on a private 12-hour journey to the stunning Dry Tortugas National Park. Discover history, snorkel vibrant reefs, and enjoy an unforgettable day on the water aboard the 35' Carolina Classic.
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