Portland’s location on the edge of Casco Bay makes it a perfect spot for boat trips. With its scenic coastline, historic lighthouses, and vibrant maritime culture, a water-based adventure here is nearly a must. Whether you’re after a quick lighthouse tour or a romantic sunset sail, Portland’s waters offer a variety of options. We especially like the Harbor Lights and Sights Cruise for its mix of history and scenery, and the Sunset Windjammer Cruise for a relaxing end-of-day experience. Both provide a glimpse into Portland’s maritime heritage combined with stunning views. If you’re interested in capturing Portland’s history from the water, these tours are excellent choices. For a more exclusive experience, the Private Island Fort Tour offers access to hard-to-reach forts with fewer crowds. All these options promise authentic, memorable experiences on the Maine coast.
Quick Overview
Portland’s boat tours cover a wide range of experiences—public sightseeing cruises, private charters, sunset sails, and historic windjammer adventures. You can explore Casco Bay’s lighthouses on a leisurely cruise (Harbor Lights and Sights Cruise), enjoy a scenic dinner cruise (2.5-hour Dinner Cruise), or set sail on a traditional Tall Ship (Portland Tall Ship Cruise). For more personalized adventures, private options like Island Fort Tours (Private Island Fort Tour) and Sunset Private Charters (Sunset Lobster Boat) cater to small groups seeking intimacy. Whether you want scenic sightseeing, wildlife spotting, or a romantic evening, Portland’s boat tours offer something for every water lover.
1. Harbor Lights and Sights Cruise
At number 1 on our list, the Harbor Lights and Sights Cruise is a standout for its blend of maritime history, scenic views, and relaxed atmosphere. This 1 hour 45-minute tour takes you along Diamond Pass, where you’ll see civil war–era forts, historic lighthouses, and Maine’s oldest lighthouse commissioned by George Washington. It’s a great way to learn about Portland’s seafaring past while enjoying the fresh sea air. The boat features a bar, snacks, and restrooms, making it comfortable for all ages. Reviewers love the knowledgeable crew and the stunning views of Casco Bay Islands, Fort Gorges, and lobster boats bobbing in the breeze. It’s perfect for anyone interested in both history and scenery, especially families or first-time visitors.
Bottom line: This tour offers a practical, scenic, and engaging introduction to Portland’s maritime heritage with excellent reviews and a reasonable price for a memorable experience.
2. Port City Lights Cruise
Coming in at number 2, the Port City Lights Cruise is a shorter, more budget-friendly option that still packs a punch. For around $39, you get a one-hour tour that includes views of Portland’s four main lighthouses, Fort Gorges, and the historic harbor. It’s especially praised for its comfort and the enthusiasm of the narrator, as one reviewer notes, “fabulous tour guide and amazing sites.” The cruise offers onboard snacks and drinks, and the scenery is complemented by wildlife sightings like seals and seabirds. Its focus on Portland’s maritime and Civil War history makes it suitable for travelers wanting a quick, informative trip with lots of photo opportunities.
Bottom line: Great for those on a budget or short on time, this cruise combines history, wildlife, and scenic lighthouse views in a cozy, engaging ride.
3. Sunset Windjammer Cruise Along the Coast of Portland Maine
Number 3, the Sunset Windjammer Cruise, offers a more relaxed, romantic way to experience Casco Bay. For about $75, you’ll sail aboard a historic schooner for around 2 hours as the sun sets over Portland’s skyline. Bring your own snacks and drinks—wine, beer, or whatever you fancy—and enjoy wildlife spotting, including seals and seabirds. The highlight is watching the Fort Gorges silhouette at dusk, which creates a magical atmosphere. Reviewers describe it as “absolutely beautiful and peaceful,” perfect for couples or anyone wanting a quiet, scenic evening.
Bottom line: This trip suits those looking for a romantic, laid-back outing with a focus on sunset views and maritime scenery. It’s a relaxing way to end a day on the water.
4. Sunset Lighthouse Cruise Tour from Casco Bay
Ranking at number 4, this Sunset Lighthouse Cruise takes you on a 1 hour 45-minute journey to witness Casco Bay’s iconic landmarks during the golden hour. You’ll see Maine’s most photographed lighthouse, commission by George Washington, alongside WWII shipyard memorials and the historic Bug Light. The narrative covers the area’s WWII history and maritime defenses, making it educational as well as scenic. Passengers rave about the knowledgeable guide and the opportunity to see seals, dolphins, and get great photos. The cruise is ideal for those wanting a slightly longer sunset experience with a mix of history and wildlife.
Bottom line: Perfect for sunset lovers and history buffs, this cruise offers a balanced mix of story and scenery with excellent reviews.
5. 2.5-hour Dinner Cruise on Willamette River
Number 5 on our list, the Dinner Cruise combines a scenic two-and-a-half-hour journey with a gourmet meal. For $127, you’ll enjoy local ingredients and live music while cruising Portland’s skyline along the Willamette River. The route includes passes under historic bridges like the Hawthorne and Marquam, with sights of OMSI and USS Blueback submarine. The cruise is highly rated for its food quality and service, with many reviewers mentioning the “great food” and “fabulous views.” It’s ideal for a special occasion or a relaxed evening out, especially if you appreciate good cuisine paired with a scenic backdrop.
Bottom line: An elegant, relaxing option suited for couples or groups celebrating special moments, offering a fine dining experience on Portland’s waters.
6. Private Island Fort Tour in Casco Bay
At number 6, the Private Island Fort Tour provides exclusive access to Fort Scammel on House Island. This 2-hour tour offers a rare chance to explore a historic fort built in the early 19th century, with its impressive masonry, underground passages, and French influences. The tour emphasizes fascinating history and the opportunity to walk through preserved ruins. Many visitors rave about the small group size—only six people—making the experience intimate. The boat, the Elizabeth Grace, is well maintained, and guides share detailed stories about Maine’s coastal defenses.
Bottom line: Best suited for history enthusiasts and those seeking a private, in-depth look at Portland’s military past. Booking early is recommended due to limited availability.
7. 2-hour Lunch Cruise on Willamette River
Number 7 features the Lunch Cruise, a delightful way to combine sightseeing and dining. For $87, you’ll spend about two hours cruising Portland’s waterway with a freshly prepared Northwest meal. The route takes you under the Hawthorne Bridge and past landmarks like OMSI and the Portland Head Light. Live commentary enhances the experience, and the food has garnered praise, with some calling it “better than expected.” It’s a good option for those wanting a relaxing cruise with a casual meal, especially if you prefer daytime activities with scenic views.
Bottom line: A practical choice for lunch and sightseeing, ideal for visitors wanting to see Portland from the water while enjoying good food.
8. Portland Tall Ship Cruise on Casco Bay
Number 8 offers a classic sailing experience aboard the Maine-built windjammer, typically for around 2 hours. This trip is perfect for those wanting to see Casco Bay’s lighthouses, seals, and seabirds from a traditional vessel. Passengers can even help hoist the sails or steer the ship, making it interactive. The ships—like Bagheera, Wendameen, or Timberwind—are all historic Maine schooners listed on the National Register of Historic Places. Reviewers mention the “great crew” and the “peaceful, scenic” atmosphere, making it an authentic sailing adventure.
Bottom line: For maritime enthusiasts and families, this is a hands-on, scenic day out on a historic Maine schooner.
9. Private Sightseeing Charter on a Vintage Lobster Boat
This private 2-hour cruise aboard the vintage MONHEGAN is perfect for those wanting a highly personalized experience. For $380, you’ll see four lighthouses, with ample photo opportunities, all while learning about Maine’s nautical history. The captain is knowledgeable, and you can bring your own food and drinks, making it a flexible, intimate outing. The boat features a eco-friendly composting toilet and a relaxed pace ideal for small groups or romantic trips.
Bottom line: Excellent for small groups or couples seeking a private, customizable tour with lots of lighthouse views and local stories.
10. Scenic 2-Hour River Cruise to the Majestic Willamette Falls
Number 10 takes you on a private, customizable cruise focusing on Portland and the Willamette Falls. For $395, up to six people can enjoy a personalized tour with a guide narrating the scenery and history. This is ideal for special events, corporate outings, or families who want exclusivity. The falls are a major highlight, and the tour emphasizes sustainability and conservation. The boat allows for a relaxed environment with plenty of comfort and excellent views.
Bottom line: Perfect for private groups or special occasions, this tour offers a tailored experience of Portland’s river scenery and waterfalls.
11. Afternoon Windjammer Cruise Along the Coast of Portland Maine
Number 11 features a 2-hour sail on Casco Bay aboard a classic schooner. For $67, enjoy lighthouses, seals, and seabirds, with the crew ready to answer questions. It’s not a narrated trip, but the crew’s stories add charm. Reviewers describe it as “fabulous” and perfect for a laid-back afternoon. It’s especially suitable for those seeking a genuine sailing experience, with opportunities to help hoist sails or just relax and soak in the scenery.
Bottom line: A good pick for those wanting an authentic sailing adventure with friendly crew and scenic views.
12. Private Sunset Charter on a Vintage Lobster Boat
Number 12, this private 2-hour sunset cruise, offers a romantic escape. For $407, you enjoy breathtaking views of Casco Bay, lighthouses, and historic forts, with the option to purchase drinks onboard. The captain provides narration and the boat has a cozy, intimate atmosphere, making it perfect for couples celebrating a special occasion.
Bottom line: A top choice for a romantic, private sunset experience that combines scenery, history, and tranquility.
13. Morning Lighthouse Cruise Along the Coast of Portland Maine
Number 13 offers a 1 hour 30-minute cruise focusing on lighthouse spotting and seaside scenery. For $57, you’ll see Portland Head Light, Spring Point Ledge Light, and Ram Island Ledge Light, plus seals and seabirds. Reviewers mention the friendly narration and the “surprisingly smooth ride” even after hurricane remnants. It’s a practical, scenic way to start your day with plenty of opportunities to take photos and learn about Maine’s maritime sites.
Bottom line: Ideal for morning explorers wanting a quick, engaging cruise that showcases Portland’s lighthouse heritage.
14. Guided RIB Boat Adventure of Casco Bay
Number 14 provides an exciting 1 hour 30-minute adventure aboard a Rigid Inflatable Boat. For $75, it’s perfect for thrill-seekers and nature lovers who want to see seals, lighthouses, and islands at higher speeds. The tour is capped at 14 people, offering a personal experience. Many reviews praise the knowledgeable guides and the small-group intimacy. The ability to get close to wildlife and enjoy a more adrenaline-filled ride makes this stand out.
Bottom line: Best suited for active travelers looking for a quick, energetic tour with up-close wildlife encounters.
15. Sunset Lighthouse Cruise Along Casco Bay
Number 15 features a 1 hour 30-minute sunset cruise on a classic 1935 Falmouth-built boat. You’ll see four lighthouses, seals, and historic forts, with optional drinks onboard. Reviewers love the informative guides and the opportunity for beautiful sunset photos. It’s a relaxed, scenic way to conclude a day of exploring Portland’s waterfront.
Bottom line: This is perfect for travelers seeking a peaceful, picturesque cruise at the end of the day with plenty of opportunities for photos and wildlife viewing.
16. Small Group Sunset Lighthouse Boat Cruise With Local Drinks
Finally, number 16 offers an intimate experience aboard the Elizabeth Grace during sunset. For $69, small groups of six or more enjoy local craft beers, lighthouses, forts, and seals. The guide shares local stories, and the relaxed pace makes it fitting for couples or small groups wanting a cozy, authentic experience. The cruise offers beautiful views of Fort Gorges, Portland Head Light, and Peaks Island.
Bottom line: This is an ideal choice for those looking for a personalized, relaxed sunset cruise with local drinks and scenic beauty.
How to Choose Your Perfect Boat Tour in Portland
When selecting a boat tour, consider your budget, time, and interests. For a comprehensive introduction to Portland’s maritime history, the Harbor Lights and Sights Cruise offers a longer, in-depth experience. If you prefer a romantic sunset, the Sunset Windjammer Cruise or Sunset Lighthouse Cruise fit well. For families or adventure lovers, the Tall Ship or Guided RIB adventures provide fun, active options. Smaller groups seeking intimacy should explore private charters like the Island Fort Tour or Sunset Private Lobster Boat.
Booking early generally helps secure your preferred date, especially for the popular sunset and private tours. Also, check the weather forecast—sailing in Maine is delightful but can be chilly or windy, so bring layers. With this variety, Portland’s waters promise unforgettable experiences, whether you seek history, wildlife, romance, or adventure.
Portland’s boat tours showcase the city’s maritime charm with options that match every interest—from lighthouse safaris to elegant dinner cruises. For a hands-on sailing adventure, the Portland Tall Ship or Guided RIB tours are excellent. Want a cozy, intimate experience? The Private Island Fort Tour or Sunset Private Lobster Boat will satisfy. If your main goal is to see Portland’s iconic sights during sunset, the Sunset Lighthouse Cruise or Small Group Sunset Cruise are perfect choices. No matter what you pick, booking ahead is wise—these tours fill up quickly, especially in summer. Now’s the time to plan your water-based Portland adventure!