Island Hopping🏝

Island Hopping

Skip the crowded ferries and cattle boats—this is a small-group charter built around your style. Remote beaches, hidden bars, or family stops: every trip is flexible and personal.

Island hopping boat at sunset with dockside view

Overview

Island Hopping is about freedom and choice. We can point north toward Boca Grande or south toward Naples, or keep it local with quiet back-bay loops. Expect a mix of sightseeing, water-access-only restaurants and bars, and beaches where crowds can’t follow. Perfect for families, couples, or small groups looking to escape the usual tours.

Group size: typically 4–5 guests (occasionally 6). Typical duration: 4–6 hours. Pickup/drop-off: flexible—marinas, public docks, and select residences when feasible.

Best Time

  • Late mornings to afternoons: ideal for pairing a lunch stop with sightseeing.
  • Early evenings: golden light for photo-friendly rides and beach breaks.
  • Shoulder seasons: spring and fall mean quieter docks and easier seating at remote restaurants.

Runs are great year-round—we plan the day around tides, weather, and your goals.

Destinations

  • Boca Grande
  • Cabbage Key
  • Cayo Costa
  • North Captiva
  • Sanibel & Captiva back-bays
  • Naples waterfront (conditions)

We can cover distance or keep it close—routes flex to your appetite for water time.

Plan & Options

  • Restaurant hopping: iconic island spots like Cabbage Key or tucked-away back-bay bars.
  • Family beach day: shelling, swimming, and exploring where no ferries land.
  • Sightseeing loop: cover miles of shoreline with dolphin, osprey, and manatee sightings.
  • Custom mix: pair a lunch stop with a sandbar swim and a sunset ride home.

Every trip is custom—we’ll set the pace and stops with you before departure.

What’s Included

  • USCG-licensed local captain & safe, stable, shallow-draft boat
  • Cooler with ice & water; dry storage
  • Flex routes, restaurant/bar stops, and optional beach gear staging

What to Bring / Essentials

  • Polarized sunglasses, hat, reef-safe sunscreen
  • Swimwear and a towel if you’d like to wade or swim
  • Budget for dockside dining or drinks
  • Refillable water bottle, snacks for kids or quick energy

Request Dates

Tell me your window and goals—family beach day, bar hopping, or long-range sightseeing. We’ll match the tide and weather for the perfect custom route, from Boca Grande to Naples or a quiet back-bay loop.

Request Trip