Casco Bay: Our most recommended tours and activities

Portland: Sunset Lighthouse Cruise in Casco Bay with Drinks

1. Portland: Sunset Lighthouse Cruise in Casco Bay with Drinks

Enjoy a 1.5-hour cruise around the islands of Portland's Casco Bay. Pass historic lighthouses, early-19th century forts, and quaint fishing piers as you explore the area at sunset. Guests over 21 can enjoy 1 craft beer or hard seltzers per person. As you cruise, keep an eye out for seabirds and the occasional seal that call Maine's coast home. When the timing's right, the boat will turn its bow towards Portland so you can enjoy the sunset and the city's skyline from the water. GROUP OF 6 OR MORE? Please reach out to us about private charter options for the best experience possible!

Portland: Maine Lighthouses Sightseeing Cruise with Drinks

2. Portland: Maine Lighthouses Sightseeing Cruise with Drinks

Uncover the beauty of the Portland Harbor and Casco Bay aboard the Elizabeth Grace on this sightseeing cruise from Portland. Sail past iconic lighthouses, historic forts, and rocky islands while sipping on 1 complimentary alcoholic beverage. Hop aboard a comfortable and spacious ship at the Custom House Wharf. Take in views of the city's charming skyline as you embark on your cruise. Unwind with a delectable craft beverage in hand as you sail. Feel the wind in your hair as you cruise by lighthouses, 200-year-old forts, and rocky and stunning islands. Cruise with confidence knowing that the ship is regularly maintained to the highest safety standards. Keep an eye out for local wildlife like loons, black ducks, and buffleheads as you sail. Return to your starting point at the Custom House Wharf at the end of your cruise. GROUP OF 6 OR MORE? Please reach out to us about private charter options for the best experience possible!

Portland, Maine: Sunset Kayak Tour with a Guide

3. Portland, Maine: Sunset Kayak Tour with a Guide

The hour just before sunset is the best time to be paddling on the waters of Casco Bay. The sky tends to explode with color and the seas often become glassy and calm. This trip involves a leisurely paddle just far enough along the waterfront or into the islands to enjoy a panoramic view of the sun setting over the city as we paddle back to the East End Beach. This two-hour tour is designed for paddlers of all experience levels -- including first-time kayakers.

Portland, Maine: Walking Tour Audio Guide

4. Portland, Maine: Walking Tour Audio Guide

Start by downloading the Action Tour Guide app, which will function as your personal tour guide, audio tour, and map all in one. Purchase one tour per car, not per person. Everyone listens together! Note: This 3+mile-long tour covers the essentials of Portland in 1-2 hours. Once downloaded, your tour begins outside the Visit Portland Center. Here, you'll get your first introduction to Portland's intriguing history, from its dual founding to its reconstruction following the Great Fire. Walking down the city streets, you'll learn about the Burning of Portland, the landmark United States Custom House, and the only newspaper published at sea! You'll delve into the fascinating tales of the Portland Rum Riot and the city's history of conflagration, then journey back to the times of the Underground Railroad and the life of Daniel Colesworthy, a key abolitionist voice in Portland. Stepping into the world of the Wabanaki people, you'll also gain insight into Portland's original inhabitants. The next stop is the beautifully preserved Victoria Mansion, a symbol of the city's architectural wealth. After that is the equally grand Cathedral Church of St. Luke. Stroll by the Augusta Hunt House, take a moment to admire the statue at One Longfellow Square, and learn about the struggle for Women's Suffrage in Maine. Then, pick up some trendy souvenirs in the vibrant Art District! At the Maine Historical Society, explore the Wadsworth-Longfellow House, a reminder of the city's literary heritage. After that, lounge in the beautiful Lincoln Park as you hear the thrilling tale of the Battle of Portland Harbor. Finally, you’ll pass by the University of Maine School of Law, a striking building with a lot of history. Your tour concludes here, back in Old Port where you began.

Portland Exploration: Self-Guided Driving & Walking Tour

5. Portland Exploration: Self-Guided Driving & Walking Tour

Start by downloading the Action Tour Guide app, which will function as your personal tour guide, audio tour, and map all in one. Purchase one tour per car, not per person. Everyone listens together! Note: This 13+ mile-long tour covers the essentials of Portland in 3-4 hours. Once downloaded, both tours begin outside the Visit Portland Center in downtown Portland. Your driving tour takes you first to the West End, packed with historical landmarks like the Danforth Inn and the Western Promenade. Then, you’ll swing through Downtown toward the city’s East End, where you’ll find an observatory, East End Beach, and much more. After that, cruise down into South Portland, home to the famous Portland Head Light, probably Maine’s most iconic lighthouse! Your walking tour offers a deeper dive into Old Port and Downtown Portland. Learn about everything from the Rum Riot to the Great Fire as you walk down cobblestone streets and admire stunning architecture like the old Custom House and the Victoria Mansion. Explore Portland’s Art District, visit Henry Wadsworth Longfellow’s former home, and hear about the fight for Women’s Suffrage in Portland! This comprehensive bundle offers an in-depth look at this beautiful coastal city… and, of course, plenty of photo ops to boot!

Portland: Private Lighthouse Sightseeing Cruise

6. Portland: Private Lighthouse Sightseeing Cruise

This two hour charter is the perfect way to see lighthouses, historic stone forts, wildlife, & Maine's picturesque coast. Bring your camera and experience authentic Maine aboard our classic wooden lobster boat! This is a private charter, so only you and your group is aboard plus a captain and tour guide. You and your private group will have up close views on Maine's most notable sights. Every private charter includes a licensed captain and an experienced charter host to attend to your every need! Purchase local Portland, ME beers and hard seltzers, important white and red wine, and bubbly aboard!

Portland: Sunset Paddleboard Guided Tour

7. Portland: Sunset Paddleboard Guided Tour

The hour just before sunset is the best time to paddle the waters of Casco Bay. The light is beautiful, the harbor is less busy and the seas tend to be calmer, often creating ideal conditions for paddle boarding. It’s also a great time to spot wildlife like seals and loons. Your tour will start off with a quick stand up paddle board lesson. Then your licensed Maine Guide will lead you on a leisurely paddle along the Portland waterfront. As you venture onto the open waters of the bay you’ll enjoy a panoramic view of the sun setting over the city as you paddle back to the beach. This roughly 2-hour trip is perfect for all skill levels — including first-time paddle boarders. The SUPs we use for our tours are suitable for paddlers weighing up to 250 pounds.

Portland, ME: Guided Harbor Paddleboard Tour

8. Portland, ME: Guided Harbor Paddleboard Tour

This tour takes a route along the scenic waterfront of Portland harbor, giving you views of rugged islands, beautiful lighthouses and historic forts. We often spot seals and we always view a variety of marine birds. Your tour will start off with a quick stand up paddle board lesson. Then your licensed Maine Guide will lead you on a leisurely paddle along the Portland waterfront, pointing out interesting sights along the way, including lighthouses, lobster boats and 19th-century forts. This is a great trip for anyone who’d like to get a taste of exploring the Maine coast by stand up paddle board. It’s also a good way to get a unique view of Portland harbor from the water. The stand up paddle boards use for our tours are suitable for paddlers weighing up to 250 pounds.

Other Sightseeing Options in Casco Bay

Want to discover all there is to do in Casco Bay? Click here for a full list.

What people are saying about Casco Bay

Overall rating

4.6 / 5

based on 45 reviews

Excellent! Very well done and informative. It was great having a local who clearly loves his city guide and share his knowledge. Highly recommend!!!

He is very knowledgeable about the history of the downtown area and goes into depth about a lot of interesting things!

Well informed and was able to answer all questions. Easy to understand and aware of all walkers and their pace.

Our guide, Dugan was great! He didn't just give us facts, he spun a story of the history of Portland.

Knowledgeable and informative presented with humor