Whether you’re starting your day with the crisp morning air, soaking in the golden glow of an afternoon, or watching the sun melt into the horizon, a Windjammer cruise offers a timeless way to experience Maine’s coastline. Sailing for two hours aboard one of Portland Schooner Co.’s majestic windjammers feels like stepping back into a simpler time—where the wind dictates your pace, and the world is framed by sails and sea spray. As the schooner glides through Casco Bay, you’ll be treated to views of lighthouses, wildlife, and rugged shores, all while enjoying your own food and drinks (yes, even a well-earned afternoon cocktail).
After a peaceful sunrise cruise with Casco Bay Lines, we wandered through Portland, grabbed breakfast, and on a whim, decided to continue our time on the water with a Windjammer sail. Tickets are available online or at the dock, and with no reservations in hand, we felt lucky to snag a spot.
Once the crew was ready, we followed them down the dock to board our ship. With three windjammers departing at once, I expected a bit of chaos, but the process was seamless, and soon we were stepping onto the Wendameen, the oldest of Portland Schooner Co.’s beautifully crafted vessels. Below deck, we discovered a small Windjammer museum and—surprisingly—a bathroom, an unexpected but appreciated convenience for an afternoon at sea.
With the sails raised and the city fading into the distance, we settled in, cracked open a drink, and let the ocean set the tone for the afternoon.
The sun was strong, but the salty breeze kept us comfortable as we sailed past familiar sights—Fort Gorges, Portland Breakwater (Bug) Light and, most memorably, the Portland Head Light. Seeing Maine’s most famous lighthouse from the water gave it a whole new presence. It felt quieter, more timeless, as if we were glimpsing it the way mariners had for centuries.
The crew moved effortlessly across the deck, tending to the sails while stopping to chat and share stories. Despite the buzz of other boats in the bay, the schooner carried us into a peaceful, unhurried world of its own.
As we turned back toward shore, I was shocked to realize nearly two hours had passed. Time, much like the tide, had slipped away. One of the crew members brought out a bubble machine, sending tiny iridescent orbs drifting through the sea air. It was such a simple thing, yet it made the moment feel like magic—like childhood joy bottled up and released into the wind.
With our feet back on solid ground, it felt like the perfect time for a classic Maine indulgence: a lobster roll. Luke’s Lobster in the Old Port had been on my radar, and this seemed like the perfect excuse to try it.
A busy spot, there was a waitlist, but we grabbed a drink at the upstairs bar and passed the time on the balcony overlooking the harbor. Watching the boats we had just sailed beside, reflecting on the afternoon, and soaking in the ocean air made the wait feel effortless.
Once seated, we didn’t have to wait long for our food. I went with a lobster roll and fries—a simple but perfect pairing. There’s something about a fresh lobster roll after a day on the water that just hits differently. The buttery, toasted bun, the chilled lobster, the hint of lemon—it was exactly what I needed to round out the day. If you’re ever in the Old Port and craving fresh seafood with an unbeatable view, Luke’s Lobster is a must-visit.
Adventure Reflections
There’s something about being on the water that slows time in the best way. The moment the sails lifted and the wind took over, I felt the world shift—less urgency, more presence. Drifting through Casco Bay, watching lighthouses rise from the shore, and feeling the steady rhythm of the waves, I was reminded of how small, yet connected, we are to the vastness around us.
The Windjammer sail was peaceful yet invigorating, a chance to just be—to breathe in the salty air, let my mind wander with the tide, and sink into the simplicity of the moment. There was nothing to do but enjoy the view, the breeze, and the occasional friendly conversation with the crew. The bubble machine at the end felt symbolic, little pockets of joy carried by the wind, much like this experience—a fleeting but beautiful memory.
And then there was lunch. A lobster roll always tastes better after time on the water, and this one was no exception. Sitting on the balcony at Luke’s Lobster, watching boats glide in and out of the harbor, it felt like the perfect way to close out the day. A reminder that the best adventures don’t have to be extravagant—they just have to be felt.
This day was everything I love about Maine: salty air, good food, and moments that remind me to slow down and just be. If you find yourself in Portland, take the sail, breathe in the ocean air, and let time slow down for a little while. You won’t regret it.
Do you have any must-see spots or unique experiences in Maine to share?
I’d love to hear your suggestions for my next Maine adventure! Feel free to reach out to me through my social media links below or shoot me an email at hellopeaceofmindy@gmail.com. Let’s connect and inspire each other with new adventure ideas!
All the photos featured in this blog post were taken by me, unless otherwise noted.
