Events to Host on a Harbor Cruise in Portland, Maine

There’s so much in life to celebrate – weddings and anniversaries, baby showers or bridal showers, bachelor and bachelorette parties, family reunions, birthdays, and beyond! Spending time with loved ones is at the heart of all these special events. Have you ever considered hosting an event like this somewhere a little unexpected – say, on a sailboat? There is no better way to celebrate your special event than with a chartered harbor cruise in Portland, Maine!

Our private sails hold up to six passengers, making for an intimate celebration that you will cherish for years to come. Below are some of the unique celebrations we can accommodate aboard the Eleanor Hawkes!

Engagements and Weddings

wedding on the eleanor hawkes | harbor cruise portland maine

At Sail Portland Maine, we love love and are always so excited when guests celebrate those special moments on board. Whether you’re planning a surprise proposal for your beloved on the open seas, or you are a couple looking to elope with a few close friends and family (and our ordained captain), we will make it a night to remember! Our captain can help you accommodate whatever you need in terms of decor, photography, or other details that will make the day special. Don’t forget a bottle of bubbly to pop for a champagne toast!

Bachelor and Bachelorette Parties

If you’re based in New England, don’t sleep on Portland, Maine for your pre-wedding festivities. In addition to Portland’s incredible food, tons of local bars and endless adventures up and down the coast, hosting a bachelor or bachelorette party aboard our sailing vessel is a cool, unique way to celebrate upcoming nuptials! Bring your own booze, snacks or takeout, and your phone for the most Instagrammable view of the city’s skyline you’ll find.


Does anything say “I love you” more than a romantic chartered sail through the Casco Bay? Our private charter sails are here to make your anniversary dreams a reality! Your imagination is the limit – sail to one of the Casco Bay islands for dinner, or simply cozy up to your loved one and enjoy the sunset with a crisp glass of wine. Let Sail Portland Maine make this an anniversary you won’t soon forget!


friends out on harbor cruise portland maine

A chartered sail is such a fun way to celebrate a birthday! Grab your closest friends and family, a few coolers with your favorite beverages and snacks, and hit the open seas. Is there anything more celebratory than a fancy charcuterie board in the middle of the ocean with a sunset backdrop? We don’t think so!

Sail Portland Maine

At Sail Portland Maine, we want every event to be as unique and special as those celebrating, which is why we go the extra mile to customize your sail. Our classic sail trip is approximately two hours, but we can coordinate with you to bring you out as long as you’d like. Our sails are always BYOB, accommodate any food you want to bring, and we are always happy to make suggestions for the best local spots to grab takeout for the journey. Get ready to experience the best harbor cruise Portland, Maine has to offer!

We can’t wait to celebrate with you! Our sails do book up quickly, so be sure to reserve your trip with us today.