Maine Cruising Destinations: Island Hopping on Casco Bay

From the historic shores of Great Diamond to the quiet coves of Jewell Island, every stop feels like a hidden gem. There’s no better way to soak in Maine’s summer magic than by boat!

Peaks Island

  • Just minutes from Portland
  • Restaurants, art galleries, and bike rentals for island exploring

Little Diamond Island

  • Smaller, quieter, great for anchoring off and enjoying the sunset

Great Diamond Island

  • A tranquil, upscale retreat
  • Known for it’s luxury homes, historic charm, and The Inn at Diamond Cove

Long Island

  • Laid-back, unspoiled, and community driven
  • Great spot for kayaking, sandy beaches, and classic Maine scenery

Cliff Island

  • Remote and small, perfect for a peaceful day on the hook

Chebeague Island

  • Largest island in Casco Bay
  • Protected anchorage, beaches, golf, and island hospitality

Jewell Island

  • A boater favorite with protected anchorage and WWII-era ruins to explore
  • Ideal for hiking and overnight stays
Share this: Share on Facebook Share on Twitter Share on Twitter

Thank You!

We have received your request and a Dimillo's representative will contact you shortly.