5 Reasons to Book Your Casco Bay Sunset Cruise

There is nothing quite like golden hour, with the sun setting over the gentle waves of the Atlantic Ocean along Portland’s Casco Bay. If you haven’t yet experienced it for yourself, it’s a truly magical event that is best enjoyed from the water! At Sail Portland Maine, our specialty is sunsets – below, we’ve put together 5 reasons you don’t want to wait to book your Casco Bay sunset cruise with us!

group of friends on calista ann1. Intimate, Customizable Trips

We offer crowd-free two-hour trips aboard both of the boats in our fleet: our sailboat, the Eleanor Hawkes, and our newest motor vessel, the Calista Ann. The intimate feel of our Casco Bay sunset cruises is what sets us apart from the crowded sails of larger companies in the area.

The Eleanor Hawkes has room for up to 6 guests and is one of the smallest chartered cruises in Portland, Maine. If you have fewer than six people and would like to have the boat to yourself, we also offer private chartered cruises based on availability.

The Calista Ann has slightly more seating, so if you are looking for a larger party, this is the boat that will work best for you! It can accommodate up to 6 guests for a public trip and 12 for a private trip, ensuring you keep that intimate feel, even with a bigger group.

Our trips generally last for about two hours, but we are happy to accommodate longer sails (or even specific destinations!) by request if you’d like to spend more time out on the water.

2. Celebrate a Special Occasion

There are so many wonderful occasions in life to be celebrated! Bachelor and bachelorette parties, engagements, friend or family reunions, even elopements or micro-weddings – all of these events are made even more special and memorable when the venue is your very own privately chartered sunset sail. There is truly no better way to spend quality time celebrating with the people you love most!

chartered cruise | family vacation portland maine3. Experienced Captaining

Captain Ian Glass and his crew have years of experience crewing and chartering ocean-bound vessels, so you can enjoy your trip knowing you are in great hands! Not only will they help you feel totally secure aboard the Eleanor Hawkes or the Calista Ann, you are sure to hear some fascinating stories throughout your trip about adventures past and the history of Maine sailing!

4. Breathtaking Scenic Views

There is so much beauty to enjoy along the shores of Portland’s coastline! Trust us, there won’t be a single moment you’re not awestruck at the scenes unfolding as the sun dips lower into the sky. From the iconic Portland skyline to the renowned Portland Light House, a Casco Bay sunset makes everything even more magical.

oyster sail | day sailing in maine5. Bring Your Own Food & Drinks

No need to worry about purchasing nourishment on-board. We are fully BYOB, meaning you can bring along any beverages you’d like along for your sunset cruise – that goes for adult beverages, too! There is plenty of room below deck for small coolers to keep your drinks cold and refreshing, so you can simply sit back and enjoy the ride.

We also highly recommend snacks (or even takeout!) to add to your experience. If you need recommendations for delicious local restaurants, we are happy to advise on our favorites.

Let Sail Portland Maine bring you on the best Casco Bay sunset cruise offered in Portland. Whether you charter our boat for an event, an intimate date night or even just a fun evening with loved ones, relax and unwind as the sun sets fire to the calm sea behind you. It’s sure to be a memorable, unique experience that you’ll reminisce about for years to come! Our summertime cruises book up fast, so reserve your trip with us at Sail Portland Maine today!

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