Jewell Island

Jewell Island is everything we love about boating in Casco Bay — wild, beautiful, and completely yours to explore. From its climbable WWII towers to the driftwood-covered beaches and quiet forest trails, Jewell feels like an adventure waiting to happen. It’s not polished or packaged — and that’s the point.

Whether you’re here with your kids hunting sea glass in the Punchbowl or with friends grilling lunch after a morning hike, Jewell has room for both peaceful moments and big memories. It’s just far enough off the beaten path to feel like a discovery — and close enough to make it a perfect day trip or overnight escape.

An aerial photo looking down on Cocktail Cove at Jewell Island
A photo of a campsite overlooking Cocktail Cove on Jewell Island
A photo looking up through the trees at one of the World War 2 observation towers on Jewell Island
A photo taken from the top of one of the world war two observation towers, looking out across jewell island
An aerial photo looking down on Cocktail Cove with several boats anchored for the night
A photo of several people hiking along the coast of Jewell Island. Lobster buoys that have washed ashore have been hung in trees along the path for decoration.

Jewell Island, Maine: The Crown Jewel of Casco Bay

If you’re planning to explore the Casco Bay islands by boat, Jewell Island belongs at the top of your list. Just eight miles from Portland, Jewell Island, Maine offers the perfect combination of wild beauty, historical intrigue, and accessible adventure — especially for DIY boaters and families looking for something more than a generic tour.

A Must-See in Casco Bay

Tucked between Cliff Island and the open Atlantic, Jewell Island is one of the most iconic destinations in Casco Bay. With nearly 3.5 miles of walking trails, hidden beaches, abandoned WWII ruins, and one of the best anchorages in the area, it’s a favorite stop for anyone serious about boating in Casco Bay.

Whether you’re planning a day trip or an overnight campout, Jewell offers an unforgettable off-grid experience — and it’s only reachable by private boat or charter. (There’s no ferry.)

Anchor at Cocktail Cove

Most boaters access Jewell Island via Cocktail Cove, a well-protected harbor on the island’s northwest shore. On summer weekends, it’s common to find motorboats and sailboats gently swinging at anchor, while kids splash in the shallows and dinghies buzz ashore.

The island has two main landings:

  • Main Landing (eastern shore of the cove): Offers stone steps up to the trail network and several campsites.

  • The Point (southern end of the cove): A small spit of land with easy trail access and great views of Little Jewell Island.

Top Things to Do on Jewell Island

Jewell Island is a choose-your-own-adventure destination — perfect for confident boaters and curious families. Here are some of the best places to explore:

1. The Observation Towers

These two concrete WWII-era towers are steeped in history and offer panoramic views of Casco Bay. You can climb inside (carefully!) and take in the sights from the top. They’re one of the island’s most memorable features — and a favorite photo op.

2. The Battery & Military Ruins

Bring a flashlight and a sense of adventure. The island’s southern section is home to old bunkers, gun mounts, and mossy concrete tunnels — all remnants of Jewell Island’s military reservation during WWII.

3. The Punchbowl

Located on the eastern side of the island, the Punchbowl is a crescent-shaped beach with tide pools, warm shallows, and great beachcombing. If you're visiting with kids, this is your go-to spot for hermit crabs, driftwood forts, and classic Casco Bay island fun.

4. Buoy Beach & Hidden Paths

Explore the south and western parts of the island for more secluded spots. Buoy Beach is decorated with washed-up lobster buoys and driftwood, while paths like the Peninsula Trail and Mine Trail lead through quiet forests and ridge-top meadows.

Jewell Island Camping: What to Know

Jewell Island camping is first-come, first-served, with multiple sites scattered across the island. Some are right along the shoreline; others are tucked into the trees. Most are accessible via the trail system that begins at Cocktail Cove.

Camping Details:

  • Facilities: Composting privies (outhouses) located near major trail junctions

  • Fires: Allowed in designated fire rings only

  • Trash: Pack in, pack out — leave no trace

  • Gear: Pack light — campsites are a short hike inland from shore

  • Caretaker: A seasonal steward helps maintain trails and campsites and promotes responsible recreation

Camping here isn’t glamping — it’s real island-style backcountry camping. But that’s what makes it so good.

Trail Network Overview

Jewell Island’s trails are flat, scenic, and easy to follow — great for kids and relaxed hikers. The 3.3-mile network includes:

  • Cove Trail & Interior Trail: Connect the main trailheads and most of the campsites

  • Towers Trail: Leads to the WWII observation towers and battery ruins

  • Smugglers Trail: Loops along the western shoreline, with views and ruins

  • Punchbowl Trail: Quick walk from Main Landing to the crescent beach

  • Peninsula & Mine Trails: Pass through old homesteads and quiet woods

Most trails can be explored in a few hours. Plan for about three hours total on the island, or longer if you’re spending the day swimming, grilling, or hanging out at a campsite.

What to Bring on Your Jewell Island Trip

Jewell Island feels wild — but it’s just prepared enough that a little planning goes a long way:

  • Boat gear + anchor for a safe stay in Cocktail Cove

  • Picnic supplies or grill kit (fires allowed in designated pits)

  • Sturdy shoes for uneven trails and rocky landings

  • Swim gear + towels for Punchbowl dips

  • Flashlight (especially if you’re exploring the battery)

  • Bug spray + sunscreen

  • Camera or phone — you’ll want to capture this place

  • Respect — for the land, its history, and your fellow boaters