Is prior sailing experience required for this trip?

No prior sailing experience is needed as the crew handles navigation and sailing; guests can relax and enjoy the scenery.

What types of wildlife can I expect to see?

You might encounter colorful tropical fish, sea turtles, various seabirds, and occasionally dolphins in the surrounding waters.

Are meals included on the overnight trip?

Yes, the trip typically includes snacks, water, and light meals; you can confirm specific details with Good Times Key West when booking.

Is the Fort Jefferson accessible during the trip?

Absolutely, visiting Fort Jefferson is a key part of the experience, with ample time to explore the historic site and learn about its past.

What should I bring for the overnight stay onboard?

Bring casual clothes, swimwear, a light jacket for the evening, personal toiletries, and any preferred medicines or comfort items.

How many people does the boat accommodate?

The 35-foot Carolina Classic comfortably accommodates up to six guests, making it a perfect private group experience.

Dry Tortugas Overnight Trip: Explore Fort Jefferson by Sail | Boat Tour | Lodging

Set sail on an extraordinary 2-day adventure with Good Times Key West aboard a 35-foot Carolina Classic, offering an intimate and cozy overnight experience for up to six guests. This trip takes you to the remote Dry Tortugas National Park, home to Fort Jefferson—the largest brick structure in the western hemisphere. As you glide through the crystal-clear turquoise waters, prepare to snorkel among vibrant coral reefs, swim in serene bays, and watch for diverse wildlife including tropical birds and marine life. The overnight stay aboard this classic sailboat provides a unique blend of comfort and adventure, letting you soak in the tranquility of this isolated island environment. By day, explore the historic fort and learn about its fascinating past, from Civil War defense to prison tales. At night, enjoy star-studded skies far from city lights, the gentle rocking of the sea, and the camaraderie of a small private group. This trip is perfect for nature lovers, history enthusiasts, and those looking to escape the crowds, combining breathtaking scenery, rich heritage, and peaceful sailing into a memorable getaway off Florida’s Keys.

About Good Times Key West

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.