Portland, Maine, is a maritime town with a long-standing connection to the sea—fishing, shipping, and lighthouses define its character. It’s no surprise that boat tours and cruises are among the top ways to experience its rugged coastline and historic landmarks. Whether you’re after a relaxing sunset cruise, a wildlife spotting adventure, or a tall ship sail, Portland offers options for every type of boat lover. We’re partial to the Portland: Best of Maine Lighthouse Scenic Cruise because it combines spectacular views of Portland Head Light with a fully narrated tour, giving you both scenic beauty and historical insights. And if you’re into a laid-back, social experience, the Portland: Sunset Windjammer Cruise with its picnic dinner on a classic sailboat is a standout.
For those who want a quick, value-packed introduction, the Portland: Sightseeing Cruise to Portland Head Light offers a one-hour jaunt with plenty of photo opportunities. Meanwhile, the Portland: Private Charter on Vintage Lobster Boat provides a personalized experience perfect for smaller groups seeking exclusivity. Whatever your style, Portland’s waters promise unforgettable views, wildlife encounters, and a splash of maritime history.
Quick Overview
This list includes lighthouse cruises, sunset sails, schooner tall ships, wildlife spotting trips, and private charters. Prices range from $41 for a compact, narrated 1-hour cruise to $910 for a private full-day sail. Highlights include visits to Portland Head Light, Fort Gorges, the Calendar Islands, and the chance to see seals, seabirds, and historic forts. Many tours include full narration, some feature refreshing drinks or picnics, and multiple options cater to families or those seeking a romantic sunset experience. Now, let’s explore each one in detail.
1. Portland: Best of Maine Lighthouse Scenic Cruise
At number 1, this fully narrated scenic cruise explores Casco Bay’s most iconic sights. For around $56, you’ll enjoy a 105-minute trip that takes in Portland Head Light, Spring Point Ledge Lighthouse, and four other historic lighthouses. The tour also passes civil war-era forts and the Halfway Rock seal habitat, where you may spot seals and other marine wildlife. The guide shares fascinating stories about Portland’s maritime past, adding depth to your sightseeing. Reviewers praise the boat’s comfort and the expertise of the narration, especially during the lighthouse close-ups. This tour balances scenic views with education, making it ideal for history lovers and first-timers.
Bottom line: A well-rounded, moderately priced cruise with plenty of photo ops and engaging storytelling—perfect for families and history buffs alike.
2. Portland: Casco Bay Sunset and Lighthouse Cruise
This 105-minute evening cruise offers the magic of Casco Bay at sunset for $59. You’ll glide through the Calendar Islands, watching the sky turn brilliant shades of orange and pink. The onboard bar allows you to sip a drink while soaking in the views of Portland’s lighthouses and the rugged coastline. Highlights include passing through Diamond Pass, a narrow channel with stunning scenery, and capturing photos of lighthouses glowing in the evening light. Many reviews mention the peaceful atmosphere and beautiful sunset views, making it an excellent choice for romantic outings or a relaxing evening with friends.
Bottom line: Ideal for couples and sunset chasers who want a leisurely, scenic experience with drinks and great photo opportunities.
3. Portland: Sightseeing Cruise to Portland Head Light
For just $41, this one-hour sightseeing cruise provides a quick but comprehensive look at Casco Bay’s highlights. The boat features both indoor and outdoor seating, making it comfortable regardless of weather. Your guide shares stories about Portland’s waterfront, while you scan the water for seals and seabirds. The cruise offers an up-close view of Portland Head Light—one of the most photographed lighthouses in Maine—and other historic sites. Reviews note that the experience is perfect for families or visitors with limited time. The value is excellent considering the duration and sights.
Bottom line: A short, affordable cruise packed with views of Maine’s most famous lighthouse and marine wildlife—great for a quick introduction.
4. Portland, Maine: Sunset Windjammer Cruise Along the Coast
This 2-hour sunset sail costs $75 per person and eschews narration for a pure sailing experience. The crew is happy to answer questions, but the focus is on enjoying the peaceful coastal voyage. Bring a picnic dinner to enjoy on the boat as you watch the sun dip below Casco Bay’s horizon. The boat’s classic design and calm waters make it suitable for families and couples alike. Reviewers love the tranquil atmosphere and the chance to simply relax while taking in the stunning scenery.
Bottom line: A relaxed, scenic evening sail perfect for those wanting a taste of Maine’s maritime craftsmanship with minimal fuss.
5. Portland, Maine: Coastal Windjammer Sailing Cruise
At number 5, this 2-hour voyage on a traditional windjammer offers a quiet, classic sailing experience. For $67, you’ll enjoy views of the coast and wildlife while the crew answers questions about Maine’s maritime history. Like the windjammer cruise, you can bring along a picnic, wine, or beer to make the cruise even more enjoyable. The review highlight the soothing pace and the opportunity to learn about the region’s sailing traditions. It’s perfect for travelers looking for a laid-back, authentic sailing experience without narration.
Bottom line: A peaceful, family-friendly cruise that offers a taste of Maine’s sailing heritage in a relaxed setting.
6. Portland: Sunset Lighthouse Cruise in Casco Bay with Drinks
Aboard the Elizabeth Grace, this 1.5-hour sunset cruise for $69 includes local craft beers and fantastic views of Casco Bay’s iconic lighthouses. The tour offers an engaging mix of beauty, wildlife, and local lore. You’ll see Fort Gorges, Bug Light, and other landmarks up close, with ample time to appreciate the brilliant colors of the sunset. Reviewers mention the friendly crew and the quality of drinks, making it a top pick for a casual, scenic evening.
Bottom line: A great option for those wanting a relaxed cruise with drinks, scenic views, and a bit of Maine history.
7. Portland: Schooner Tall Ship Cruise on Casco Bay
This 2-hour sailing on a traditional schooner, at $108, offers a more immersive experience. You can sit back and enjoy the rugged coastline of Casco Bay, with chances to spot seals, lighthouses, and seabirds. The crew may teach you a bit about sailing, making it a hands-on experience for those interested in maritime skills. The reviews praise the authentic tall ship atmosphere and the scenic, less commercial vibe.
Bottom line: A fantastic choice for travelers who want to experience sailing aboard a historic schooner with opportunities to learn and relax.
8. Portland: Casco Bay Lighthouse Sunset Cruise
Rated 4.9/5 for its beauty, this 1.5-hour cruise at $67 focuses on sunset views of Portland’s main lighthouses, including Portland Head and Bug Light. You’ll also get a close-up look at Fort Gorges. The cruise offers a comfortable experience with excellent views, making it popular among romantics. Reviewers love the up-close lighthouse sights and the peaceful sunset atmosphere.
Bottom line: A top pick for sunset lovers seeking stunning lighthouse views and a relaxed pace.
9. Portland: Casco Bay Morning Lighthouse Cruise
Starting early at $57, this 1.5-hour morning cruise delivers views of Portland Head Light, Bug Light, and Spring Point Ledge. The trip offers a lively, engaging narration, perfect for families or travelers wanting an active start to their day. The close-up lighthouse views and marine wildlife sightings are highlights, with many noting it’s a fun, family-friendly option.
Bottom line: An energetic morning outing that combines sightseeing with a bit of education—great for families and early risers.
10. Portland: Casco Bay Afternoon Lighthouse Cruise
For a laid-back afternoon, this 1.5-hour cruise on the Ruth boat costs $62. It takes in the same iconic sights—lighthouses, Fort Gorges, and islands—and invites you to bring your own picnic and drinks. The boat’s smaller size makes for an intimate experience. Reviewers mention it’s a reliable, enjoyable option for families or couples seeking a relaxed experience.
Bottom line: Perfect for a casual, scenic afternoon with flexibility to bring your own snacks.
11. Portland: Private Charter on Vintage Lobster Boat w/ Drinks
For a truly personalized adventure, this private 2-hour charter costs $380 for up to 6 people. It’s ideal for groups wanting exclusivity, with a vintage lobster boat setting that adds charm. You can relax, enjoy views of Portland’s harbor and islands, and encounter wildlife like seals and seabirds. Reviewers love the intimacy and the chance to customize the experience.
Bottom line: Best for private groups or special occasions seeking a tailored, authentic Maine sailing experience.
12. Portland: Maine Lighthouses Sightseeing Cruise with Drinks
This 1.5-hour cruise for $69 combines lighthouse sightseeing with the fun of enjoying local drinks onboard. You’ll see rocky cliffs, historic forts, and iconic lighthouses such as Portland Head Light. The relaxed atmosphere and the opportunity to take photos make it popular among those wanting both scenery and a beverage. Reviewers mention the stunning views and the informative commentary.
Bottom line: A lively, scenic cruise that pairs stunning views with your favorite drinks.
13. Coastal Maine: Private Day Sail
The most exclusive on our list, this private day sail at $910 for up to 6 people offers 4 hours of sailing around Wood Island Lighthouse, uninhabited islands, and beyond. It’s perfect for those seeking an intimate, flexible experience with a knowledgeable crew. You’ll get a chance to hear about local history, explore remote islands, and enjoy the unspoiled beauty of Maine’s coast.
Bottom line: Best suited for travelers wanting an all-day, private sailing adventure with personalized service.
$910 per group up to 6
How to Choose the Right Boat Tour in Portland Maine
When selecting a boat tour, consider your budget, the experience you seek, and how much time you want to spend on the water. For a quick overview of Portland’s lighthouses, the Sightseeing Cruise to Portland Head Light is hard to beat. If you’re after a romantic sunset or sunset sail, options like the Sunset Lighthouse Cruise and the Sunset Windjammer Cruise shine. For an authentic sailing experience, the Schooner Tall Ship Cruise offers a hands-on adventure. Those looking for privacy or a special celebration should consider the Private Lobster Boat or the Private Day Sail.
Booking early is recommended, especially in summer, when Portland’s boat tours tend to fill up quickly. Think about what scenery or experience excites you most—wildlife, history, relaxing sails—and choose accordingly.
Final thoughts
Portland’s waters are a treasure trove of scenic views, maritime history, and wildlife. Whether you prefer a lighthouse cruise, a romantic sunset sail, or an authentic schooner experience, there’s something to fit your style. Two standout options are the Portland: Best of Maine Lighthouse Scenic Cruise for its balance of education and scenery, and the Sunset Windjammer Cruise for a relaxing evening with a picnic. For a private experience, the Vintage Lobster Boat Charter offers a personalized adventure.
No matter which you pick, early booking ensures you won’t miss out on the chance to see Portland from its beautiful waters. Happy sailing!