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Some motorcycle rides are about reaching a distant destination. Others are about finding a place that immediately makes you feel like you have escaped.
Gilbert’s Resort & Marina in Key Largo delivers both.
Located at Mile Marker 108 on the bayside, Gilbert’s is positioned near the entrance to the Florida Keys. The resort calls itself the “first and last stop in the Florida Keys,” making it an ideal turnaround point for a South Florida day ride—or the first stop on a longer trip toward Islamorada, Marathon or Key West. (Gilbert's Resort)
A Florida Keys Ride Without Going All the Way to Key West
You do not have to ride to Key West to experience the unmistakable atmosphere of the Florida Keys.
Gilbert’s Resort is approximately 82 miles from Hollywood, making it a manageable destination for riders departing from DaMonkey MotoRentals near the Hard Rock Guitar Hotel. The distance is long enough to feel like a real motorcycle adventure while remaining practical for a same-day round trip. (Travelmath)
From the Hollywood area, the ride gradually transitions from South Florida’s urban landscape into open stretches of road, mangroves, bridges and tropical scenery. By the time you reach Key Largo, it feels like you have traveled much farther than the mileage suggests.
Pick up your Harley in the morning, ride south, enjoy several hours on the waterfront and return before the end of the day.
One of the First Places to Stop in the Florida Keys
Gilbert’s is located at 107900 Overseas Highway, near the northern entrance to Key Largo and overlooking Blackwater Sound. Because of its location, riders do not have to travel deep into the Keys before reaching the waterfront. (Gilbert's Resort)
That makes Gilbert’s particularly appealing for:
- Riders visiting South Florida for only a few days;
- Couples looking for a memorable lunch destination;
- Groups planning a relaxed weekend ride;
- First-time Florida Keys visitors;
- Riders who want the Keys experience without a full-day trip to Key West; and
- Guests staying near Hollywood, Fort Lauderdale or the Hard Rock Guitar Hotel.
It is also a convenient meeting point for riders continuing farther south. After lunch, you can turn around for South Florida or continue along the Overseas Highway toward Key Largo, Islamorada and the Middle Keys.
Waterfront Dining, Tropical Views and Live Music
The destination is a major part of what makes this ride worthwhile.
Gilbert’s combines a waterfront restaurant, tiki bar, marina, sandy shoreline and resort accommodations in one laid-back location. Riders can step away from the motorcycles, find a waterfront seat and enjoy the tropical atmosphere overlooking Blackwater Sound. (Gilbert's Resort)
Live music is also central to the Gilbert’s experience. Its entertainment calendar regularly features local and regional performers playing classic rock, country, reggae and contemporary music. Performance times and bands change, so riders should check the resort’s current music calendar before planning their trip. (Gilbert's Resort)
A typical ride can become an entire Keys experience:
Ride south. Park by the water. Enjoy lunch and live music. Take in the view. Ride home with another Florida memory.
More Than a Century of Florida Keys History
Gilbert’s is not a newly created tourist attraction. The property traces its history to 1903, when it began as a fishing camp and bait shop. Over time, it developed into the waterfront resort, marina and entertainment destination riders know today. (Gilbert's Resort)
That history contributes to its character. Gilbert’s still feels connected to an older version of the Florida Keys—one centered around fishing, boating, outdoor dining, live music and time spent near the water.
It is casual, energetic and unmistakably Florida.
Turn the Ride Into a Full Key Largo Adventure
Gilbert’s can be the main destination or simply the first stop.
Riders who want to explore more of Key Largo can continue south on the Overseas Highway. Nearby attractions include John Pennekamp Coral Reef State Park, waterfront restaurants, marinas and other places to experience the northernmost island in the Florida Keys. Gilbert’s is approximately five miles from John Pennekamp Coral Reef State Park. (Google)
A longer itinerary might look like this:
Morning: Pick up your Harley-Davidson from DaMonkey MotoRentals in Hollywood.
Late morning: Ride south toward Key Largo and arrive at Gilbert’s.
Afternoon: Enjoy waterfront dining, live music and the marina atmosphere.
Optional extension: Continue farther into Key Largo before turning north.
Evening: Return to Hollywood after a full day of Florida riding.
Travel times can vary significantly with weekend, holiday and Florida Keys traffic, so allow extra time and plan your return conservatively.
The Right Harley for a Key Largo Ride
A Key Largo trip is enjoyable on several types of Harley-Davidson motorcycles, but the right choice depends on your riding style.
A Street Glide or Road Glide provides wind protection, storage and touring comfort for a longer round trip. An Ultra Limited or Road Glide Limited is a strong choice for two-up riding, while a Low Rider ST delivers a more performance-oriented experience without giving up all-day capability.
DaMonkey MotoRentals offers premium Harley-Davidson motorcycles equipped with features that may include upgraded handlebars, exhaust systems, lighting, highway pegs, backrests and premium audio.
At DaMonkey, upgrades are included.
That means you can choose a motorcycle built for the experience rather than settling for a stripped-down rental bike.
Make Gilbert’s Your First Florida Keys Ride
Gilbert’s Resort gives riders something valuable: an authentic Florida Keys destination that can be reached from South Florida without committing to a trip all the way to Key West.
It has the water, tropical setting, live entertainment and laid-back energy people imagine when they think about the Keys. More importantly, getting there gives you a reason to spend the day doing what you came to Florida to do—ride.
Pick up your Harley-Davidson near the Hard Rock Guitar Hotel, head toward Key Largo and make Gilbert’s Resort the first—or last—stop on your Florida Keys adventure.
Don’t just visit Florida. Ride it.
Fueled by adventure. Driven by friendship. Built for memories that endure.