Frequently Asked Questions
There are some common questions we are frequently asked prior to our chartered trips.
Sail Portland Maine is proud to provide the best boat tours Portland, Maine has to offer, with various types of cruises and options to ensure there is something for everyone! If you have questions that aren’t answered here, please contact us directly!
Charters typically start at 2 hours, but we offer flexible options up to 8+ hours so you can customize your cruise to your schedule. Whether you want a quick harbor tour or a longer adventure exploring Casco Bay, we can create an experience that fits your needs.
Absolutely! We offer flexible start times throughout the day, including morning, afternoon, and sunset cruises. This allows you to plan around cruise ship schedules, events in Portland, or simply the time of day that works best for your group.
Yes, our boat is equipped with a small private restroom for your convenience. You and your guests can relax and enjoy the cruise without worrying about making a stop on shore.
Yes, we offer free Starlink WiFi on board. Whether you want to post photos, stream music, or stay connected while cruising Casco Bay, our reliable onboard WiFi keeps you online.
We recommend layers, sunscreen, hats, and sunglasses to stay comfortable in changing weather. If you’re BYOB, bring your drinks and any snacks you’d like to enjoy. Comfortable shoes are ideal for moving around the deck and taking in the views.
Dress as you would for walking around town, but be sure to bring an extra sweater/sweatshirt and a windbreaker with you. If you’re “on the fence” about shorts versus long pants…go with the long pants. Also useful is a baseball type cap with visor, sunglasses (polarized are best) and sunscreen. And, of course, don’t forget your camera!
Here is a helpful packing guide to help you prepare.
If you have a great time onboard, feel free to show it. This is considered a tourism/service based industry where a 20% tip is common. Your captain and crews will greatly appreciate it!
Your captain monitors weather conditions closely. If it’s unsafe to cruise due to wind or storms, we’ll work with you to reschedule or adjust your charter. Our goal is a safe, enjoyable experience no matter the forecast.
Yes. But they count as a passenger towards our United States Coast Guard regulated passenger count and require a ticket purchased for them. If you show up without a ticket for them and the boat is sold out, you will be turned away and not refunded, or if there is room you will be required to purchase a ticket for them.
Yes! Our boats depart from Mavodones Landing in Portland, Maine, just steps from the cruise docks, making boarding easy and convenient. There is nearby parking available for you and your guests.
Our private charters are perfect for first-time boaters. The captain handles all navigation, so you can relax, enjoy the views, and feel confident throughout the cruise—even if you’ve never been on a boat before.
Safety is our top priority. Our boat is fully equipped with life jackets, safety gear, and a licensed captain who monitors conditions throughout the cruise. The boat is stable and suitable for guests of all ages.
Yes! Our charters are BYOB, so you’re welcome to bring beer, wine, cocktails, or non-alcoholic beverages. It’s a great way to customize your cruise and enjoy your favorite drinks while taking in the views of Casco Bay.
Yes! Guests are welcome to bring snacks, small platters, or light catering. For longer charters, we can provide suggestions for local restaurants or catering options that travel well on the boat.
Yes! We provide a cooler with ice to keep your refreshments cold throughout your charter. Just bring your beverages and food, and we’ll make sure they stay chilled for a refreshing experience on the water.
Our private cocktail cruiser, the Calista Ann, accommodates up to 12 guests, making it ideal for small groups, families, or corporate outings. The intimate setting ensures everyone can relax, mingle, and enjoy the scenic views of Portland Harbor and Casco Bay.
Yes! Private charters can explore Casco Bay, visit nearby islands, or sail past Portland landmarks, depending on your interests and schedule. Your captain can help design a route that maximizes sightseeing and creates a memorable outing for your group.
Our boats depart from Mavodones Landing, just a short walk from the cruise ship docks in Portland. You can easily disembark from your ship and be boarding your private charter within minutes—no shuttles or long transfers needed.
Absolutely! Our private charters are perfect for birthdays, anniversaries, proposals, or corporate events. From scenic cruising to BYOB picnics, we help make your special day unforgettable.
Canes and walkers are fine on the boat, though a foldable walker may be best if it is an option. Wheelchairs are not able to fit on the boat.
Please contact us first if you have pets you want to bring onboard. The Calista Ann typically has Huckleberry, the company dog, onboard most trips.
There is plenty of wildlife to be seen in Casco Bay! From seals and seabirds to a variety of fish (and even the occasional dolphin!) there is plenty of wildlife to keep an eye out for on our charters.
You can expect smooth sailing, since we will be staying within the calm waters of Casco Bay. Seasickness is uncommon, though if you are sensitive to it, preventative medication can be helpful. Please use at your own discretion.
There is no smoking of any kind allowed during our trips.