Discover the Best Harley Davidson Rentals in Southeast Florida

Route Overview

• Start: Boynton Beach, FL

• End: Naples, FL (Downtown / 5th Ave S or Pier)

• Distance: ~125–135 miles

• Ride Time: ~3–4 hours with stops

• Ideal For: Day trips, coastal getaways, Everglades riders

  
  

Two Great Route Options

Route 1: Fast & Scenic

US-27 → I-75 West (Alligator Alley)

• Cruise west through Wellington and South Bay.

• Link onto Alligator Alley (I-75 W).

• Enjoy wide open, smooth roads. You’ll pass nothing but sky, sawgrass, and alligators.

• Stop at MM 35 Rest Area for a look over the water and possible wildlife.

  
  

Pro Tip: This route is great if you want a quicker ride with Everglades vibes. It offers easy access into Naples via Collier Blvd (SR 951).

Route 2: Classic & Rustic

US-27 → US-41 (Tamiami Trail)

• More of an old Florida cruise, this route passes through:

- South Bay

- Big Cypress Preserve

- Miccosukee Indian Village

• It’s a slower pace, but you’ll see tree islands, airboats, and untouched wetlands.

• Ends with a beautiful approach into East Naples along 41.

  
  

Best For: Riders looking for character, swamp air, and roadside gator jerky.

Scenic or Tasty Stops Along the Way

| Location | Stop | Why |

|--------------|----------|---------|

| South Bay | Café 27 (if detouring) | Biker stop, music & cold drinks |

| Big Cypress | HP Williams Roadside Park | Gator spotting zone |

| Ochopee | Smallest Post Office in the U.S. | Quick, quirky photo op |

| Naples | The Dock at Crayton Cove | Waterfront food & sunset views |

When You Arrive in Naples

Roll down 5th Avenue South and feel the shift—upscale shops, beachy breeze, and zero stress. Park the bike and explore:

• Naples Pier: Catch a Gulf sunset.

• Tin City Waterfront Shops: Souvenirs & casual eats.

• The Dock or Tommy Bahama’s Café: Beachside food with flair.

  
  

Ride Tips

• Fuel up before the Glades—stations are limited between towns.

• Sunscreen and hydration are key.

• Avoid Alligator Alley at night—poor lighting and gator crossings.

• Consider overnighting if you want to catch the sunset and ride back refreshed.

  
  

Final Thoughts

Whether you’re riding for the beaches, the swamps, or just the freedom of the road, the trip from DaMonkey MotoRentals to Naples delivers all of it in one unforgettable day. Fast or slow, direct or scenic—this ride is all Florida, all the way.

Throttle up. The Gulf is calling.

Experience the Thrill of the Ride

If you’re ready to hit the road, check out DaMonkey MotoRentals for the best Harley Davidson rentals. You’ll find everything you need for an unforgettable journey through Southeast Florida.