Sail Portland: Lighthouse Cruise on the Calista Ann
Difficulty
easy
Duration
2 hours
Fitness Level
Suitable for most ability levels; requires stepping on and off a low gangway and moving around a small deck.
Overview
Board the Calista Ann for a private two-hour cruise through Portland Harbor and Casco Bay. Get up-close views of Spring Point Ledge Light, Bug Light and Fort Gorges while Coast Guard–certified captains steer you through maritime history and working waterfront life.
Sail Portland: Lighthouse Cruise on the Calista Ann
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You step off Commercial Street onto a wooden dock that still smells faintly of bait and varnish, the harbor yawning open before you. The Calista Ann rocks gently against her mooring, varnished teak and brass catching a late-morning light while gulls quarrel over a passing scrap of seaweed. For the next two hours the city peels away—brick warehouses and cupolas shrink, islands appear like old coins, and the harbor insists you look toward the sea and the small, stubborn lights that mark it.
Adventure Photos
Adventure Tips
Arrive Early
Plan to be at the blue picnic tables on Commercial Street 15 minutes before departure so the captain can brief the group and load safely.
Dress in Layers
Wind and spray make temperatures feel cooler on the water—bring a windbreaker and a warm mid-layer even on sunny days.
Bring Motion-Sickness Precautions
Take medication or use acupressure bands before boarding if you’re susceptible—open ocean swell can appear quickly.
Protect Gear and Eyes
Use a UV filter for cameras, a neck strap, and polarized sunglasses to cut glare and steady shots from the moving deck.
Local Insights
Wildlife
- Harbor seals
- Common terns and ospreys
History
Portland’s lights and forts reflect centuries of navigation and defense—many date to the 19th century as shipping and coastal trade expanded in Casco Bay.
Conservation
Operators avoid sensitive shoreline approaches and encourage guests not to feed wildlife; support local marine conservation by staying within designated channels and following crew guidance.
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Adventure Hotspots in Portland, ME
Frequently Asked Questions
Recommended Gear
Windbreaker or Waterproof Jacket
Blocks spray and wind on the exposed deck while keeping you comfortable in changing conditions.
spring specific
Polarized Sunglasses and Sunscreen
Reduces glare and protects skin during hours of reflected, intense light on the water.
summer specific
Binoculars
Helps pick out distant island features, seals, and architectural details on lighthouses.
Non-marking Deck Shoes
Provides traction on wet surfaces and protects the boat’s finish.