If you’re staying with us anywhere near Portland, do yourself a favor and book a sunset cruise in Portland, Maine for one evening of your trip. I finally did this myself last week — first time, no excuse for waiting so long — and I’m already planning my next one.

The Plan: Drinks First, Then the Water

Start at The Porthole Restaurant & Pub on Custom House Wharf. Grab a table on their deck — it’s the biggest one in Portland, right over the water — and order a round of drinks and something to share before you head out. The lobster queso and a basket of their house-made chips is the move if you want something easy to split.

Then walk about thirty feet down the same wharf to Casablanca Cruises and board for your cruise. That’s it. No driving between stops, no scrambling for parking twice — just dinner, then straight onto the boat while the light’s still good.

I went aboard for a private BNI networking cruise, organized by my friend and fellow local business owner, Randy Forcier of CMG Home Loans. It was a business event first, but by the time the sun started dropping over Casco Bay, nobody was thinking about work anymore. Everyone was on the top deck with a drink, watching the light change over the water and the lighthouses go gold.

Bring your phone or a real camera. You will take too many sunset photos and regret none of them.

Good to Know Before You Go

• Location: Casablanca docks at 18 Custom House Wharf, Portland — literally next door to The Porthole at #20.
• The boat: An 85-foot, two-deck vessel that holds up to 149 people, with two full bars on board.
• Public cruises: Casablanca runs seasonal concert cruises (live local bands, 21+) — check their cruise calendar for current dates and tickets.
• Private charters: If you’re planning something with a group — a birthday, a work event, a family reunion — Casablanca books private charters too. That’s how I experienced mine, and it’s worth asking about timing it for sunset specifically.
• The Porthole: Open year-round for breakfast, lunch, and dinner, with a full deck for outdoor seating in season.

If You’re Staying Nearby

Coming from Paulee Suites in Old Orchard Beach, it’s about 15 miles up to the wharf — an easy evening drive. From Willow Creek Homestead and Time Of Wonder in Lyman plan on roughly 30 miles. Either way, it’s worth the trip in for a night on the water.

Our Take

Portland has no shortage of ways to spend an evening, but pairing drinks at The Porthole with a sunset cruise on the Casablanca might be the single best two-hour stretch you can put together here. It’s easy to plan, it’s not far from where you’re staying, and the photos alone are worth the trip.

Book your table at The Porthole Restaurant & Pub, check the Casablanca calendar or ask about a private charter, and go watch that sunset from the water. You’ll thank me.