A visit to an island — wild, urbanized or something in between — should feature on any good travel itinerary. Make your escape complete by heading to Little Diamond Island and spending some time by the water.

After you've paid a visit to Little Diamond Island, a water-surrounded land mass in Portland, you might be on the lookout for something else to do. Portland Head Light is nearby and interests many travelers.

Plan a trip to see Little Diamond Island

Price found within the past 48 hours. Click for updated prices.

Portland Harbor Hotel

Downtown Portland

$648

per person

Nov 29 - Dec 5

found 18 hours ago

Roundtrip flight included

Atlanta (ATL) to Portland (PWM)

9.2/10 Wonderful! (1,581 reviews)

The parking was easy and very secure. The attendants were the best! The room was exquisite, and the coffee, tea, pastry, etc bars on each floor were so nice. All seating areas and the restaurant offered everything we could want. Very welcoming and helpful staff.

Reviewed on Oct 12, 2025

Cliff House Maine

Save 100% on your flight

$1,146

per person

Nov 15 - Nov 19

found 2 hours ago

Roundtrip flight included

Atlanta (ATL) to Portland (PWM)

9.4/10 Exceptional! (1,007 reviews)

The views were absolutely breath taking every where on the property. Staff extremely friendly and caring. Night time entertainment was a plus.

Reviewed on Oct 8, 2025

InnSeason Resorts The Falls at Ogunquit

$741

per person

Dec 29 - Jan 2

found 1 day ago

Roundtrip non-stop flight included

Dallas (DFW) to Portland (PWM)

9.4/10 Exceptional! (347 reviews)

Nice and convenient

Reviewed on Oct 3, 2025

Browse tours and tickets to explore Little Diamond Island

Tours & day trips

See all 63 activities

Discover Portland City and Lighthouse Tour

Free cancellation available

Private & custom tours

See all 15 activities

Portland Golden Adventure Puzzle Quest and Tour

Free cancellation available

Adventure & outdoor

See all 3 activities

Maine Coastal Lighthouse:Two-hour bicycle tour

Free cancellation available

Holiday & seasonal tours

See all 3 activities

Portland: Sunset Lighthouse Cruise in Casco Bay with Drinks

Free cancellation available

Popular places to visit

Fort Preble

On the South Portland waterfront, survey the scene of the Battle of Portland Harbor, which is the only known Civil War conflict fought in Maine.

Bug Light

You can find out about the history of South Portland with a visit to Bug Light. Experience the area's acclaimed theater scene and great live music.

East End Beach

Swim in the Atlantic Ocean, stroll along the sand-and-pebble shoreline or enjoy a picnic with unbeatable views at Portland’s public beach.

East Prom Trail

Former rail beds are often turned into trails. At this one you can walk, run, bike or swim for active relaxation within the city.

Eastern Promenade

Built on an old rail corridor along the easternmost portion of Portland’s peninsula, this waterfront trail offers stunning views of the harbor and Atlantic Ocean.

Southern Maine Community College

Walk around the campus at Southern Maine Community College as part of your travels around South Portland. Amble around this family-friendly area's waterfront and enjoy its top-notch restaurants.