Portland, Maine, is a city that offers more than its scenic coastlines and charming streets. Its vibrant waterfront, historic lighthouses, and lively culinary scene make it a prime spot for a variety of tours. Whether you want to see Portland from the water, explore its neighborhoods, or learn its secrets from a local historian, there’s something for every type of traveler. We’re particularly fond of the Portland: Best of Maine Lighthouse Scenic Cruise for its comprehensive views of Casco Bay’s famous lighthouses and seals—an essential for anyone wanting a classic Maine experience. The Old Port Culinary Walking Tour also stands out for food lovers eager to sample local flavors while soaking up Portland’s historic streets.
Portland’s tours showcase its coastal charm, historic sites, and culinary delights in ways that fit different interests and schedules. From short boat rides to full-day bike adventures, you can tailor your experience to your pace and passions. Read on for a detailed look at each of the top options to help you decide which tour will make your Portland trip unforgettable.
1. Portland: Best of Maine Lighthouse Scenic Cruise
At number 1, the Portland: Best of Maine Lighthouse Scenic Cruise is a thoroughly enjoyable way to see Casco Bay. This 105-minute fully narrated cruise offers spectacular views of four iconic lighthouses, including Portland Head Light and Spring Point Ledge Lighthouse, along with a chance to glimpse local marine life such as seals near Halfway Rock. The guide shares stories about Portland’s maritime past while you sit back and admire the scenery. This tour is perfect for those who want an authentic boat experience, with the added bonus of spotting wildlife in their natural habitat. With a high rating of 4.8/5 from over 600 reviews, it’s clear that many find this cruise both entertaining and informative. The price of $56 per person offers good value, especially considering the memorable views and educational commentary.
Bottom Line: If you’re after a classic Maine lighthouse experience with wildlife, this cruise is a top pick that balances scenic beauty with storytelling.
2. Portland: Trolley City Tour with Portland Head Light Stop
At number 2, the Portland: Trolley City Tour is a great way to cover a lot of ground in a short time. This 2-hour fully narrated trolley tour takes you through downtown Portland, revealing hidden neighborhoods and local hotspots that are often missed on your own. The guide shares stories about Portland’s history, culture, and current events, making it both educational and fun. You’ll also enjoy sweeping views of Casco Bay from the Eastern Promenade and stop at the famous Portland Head Light in Fort Williams Park. Guests appreciate the laid-back vibe and the chance to explore Portland comfortably without walking miles.
The tour’s high rating of 4.8/5 from 574 reviews confirms its popularity, and at $56 per person, it offers a great value for those short on time but eager to see the city’s highlights. It’s particularly suited for first-timers or those interested in a broad overview with the convenience of a hop-on, hop-off style.
Bottom Line: Perfect for travelers who want a quick, rundown of Portland’s sights with good storytelling and scenic stops.
3. Portland, Maine: Tour in Vintage Fire Engine
Coming in at number 3, the Portland, Maine: Tour in Vintage Fire Engine offers a fun, nostalgic ride through the city’s streets. This 50-minute narrated tour takes you on top of a restored vintage fire engine, giving you sweeping views of Portland’s architecture and coast. It’s a playful alternative to traditional tours, ideal if you want to combine sightseeing with a bit of adventure. Many reviews highlight the uniqueness of the experience, with a 4.7/5 rating from nearly 250 reviews. It’s also quite affordable at $43 per person, making it accessible for most budgets.
This tour is best suited for families, history enthusiasts with a sense of humor, or anyone looking for a memorable story to tell. The open-air fire truck allows for great photo ops, and the guide shares insights about Portland’s historic sites and local brew scene. The only drawback might be its limited duration—perfect for a quick glimpse rather than an in-depth tour.
Bottom Line: If you’re seeking a unique way to see Portland with a touch of fun, this vintage fire engine ride delivers both.
4. Portland: Casco Bay Sunset and Lighthouse Cruise
Number 4 on our list, the Casco Bay Sunset and Lighthouse Cruise offers a relaxing 105-minute voyage during the magical evening hours. As the sun dips below the horizon, the sky turns into a canvas of colors, making it a perfect time for photography. This cruise passes through the Calendar Islands, with views of well-known lighthouses and Fort Gorges. Guests can sip drinks from the onboard bar while taking in the stunning scenery.
Rated 4.8/5 from 180 reviews, many mention the peaceful atmosphere and spectacular sunset views. The price of $59 makes it reasonably priced for what’s included—delicious scenery paired with a relaxed vibe. It’s ideal for couples, families, or anyone wanting a tranquil, picture-perfect experience.
Bottom Line: If you love sunsets and coastal views, this cruise offers an unforgettable end to a day in Portland.
5. Portland: Sightseeing Cruise to Portland Head Light
At number 5, the Sightseeing Cruise to Portland Head Light is a great introduction to Casco Bay’s maritime history. This 1-hour narrated cruise features views of Portland’s four main lighthouses, lobster boats, and seabirds, along with sightings of seals. The guide shares stories about Portland’s waterfront past, making the experience both scenic and educational. Many reviews praise the professionalism of the crew and the quality of the commentary.
For $41 per person, it’s an affordable way to get close to Portland’s signature lighthouse while enjoying marine wildlife activity. This tour is perfect for families or anyone interested in a short but comprehensive boat experience, with easy indoor and outdoor seating options.
Bottom Line: A solid choice for a quick, scenic tour that combines wildlife and lighthouse views in a relaxed setting.
6. Portland: Old Port Culinary Walking Tour
Number 6, the Old Port Culinary Walking Tour is a delicious way to explore Portland’s food scene over 2.5 hours. This leisurely walk takes you through downtown, sampling local Maine-inspired dishes and drinks, meeting culinary artisans, and learning about Portland’s gastronomic history. The tour includes tasting iconic Maine foods and craft beers, with insights into how the city’s culinary culture developed.
With a high rating of 4.8/5 from 118 reviews, many participants praise the quality of food and its engaging guides. At $160 per person, it’s a bit of an investment but well worth it for serious food lovers. It’s best suited for those with a relaxed pace and a curiosity about local flavors.
Bottom Line: Ideal for foodies wanting an immersive taste of Portland’s culinary offerings and history.
7. Portland, Maine: Hidden Histories Guided Walking Tour
Number 7, the Hidden Histories Guided Walking Tour uncovers lesser-known stories about Portland’s past. Led by a public historian, this 2-hour walk explores downtown, Old Port, and the waterfront, revealing stories about Indigenous diplomats, Chinese laundrymen, and women who shaped the city. The small group setting allows for personalized storytelling, and the tour highlights buildings that survived the fire of 1866.
Rated 4.9/5 from 74 reviews, many mention the engaging storytelling and surprising facts. For $49, this tour offers a meaningful, intimate experience for history buffs and curious travelers alike.
Bottom Line: If you want to go beyond the surface and discover Portland’s lesser-known stories, this tour is a must.
8. Portland, Maine: Sunset Windjammer Cruise Along the Coast
At number 8, the Sunset Windjammer Cruise offers a traditional sailing experience on a classic tall ship. Over 2 hours, you’ll enjoy a peaceful ride with the wind in your hair, watching the sunset over Casco Bay. This cruise is not narrated but encourages questions about sailing and the coastline from the crew. You’re welcome to bring a picnic along, turning the experience into a relaxed, family-friendly outing.
Rated 4.7/5 from 113 reviews, travelers love the authentic sailing vibe and sunset views. At $75 per person, it’s a slightly more premium option but delivers an atmospheric, memorable adventure.
Bottom Line: For those who want a genuine sailing experience combined with sunset magic, this cruise hits the mark.
9. Portland, Maine: Coastal Windjammer Sailing Cruise
Number 9, the Coastal Windjammer Sailing Cruise is similar to the previous but offers a shorter, 2-hour journey. It provides a tranquil ride on Casco Bay, perfect for relaxing and enjoying the coastline’s rugged beauty. The crew answers questions about the sites, making it educational without being formal. Like other windjammer cruises, it’s best if you bring your own picnic to enhance the experience.
With a 4.8/5 rating from 81 reviews and a price of $67, this tour offers good value for a peaceful sailing outing suitable for families and sailing enthusiasts.
Bottom Line: A calming, scenic cruise that’s ideal if you prefer wind-powered sailing over motorboats.
10. Portland: Sunset Lighthouse Cruise in Casco Bay with Drinks
Number 10, the Sunset Lighthouse Cruise with Drinks combines scenic views with a relaxed bar experience. Over 1.5 hours, you’ll cruise Casco Bay, pass lighthouse landmarks, and learn about the islands and forts. The onboard bar offers craft beers, wine, and soft drinks, making it a perfect sunset ritual.
Rated 4.8/5 from 79 reviews, travelers appreciate the casual vibe and beautiful evening scenery. At $69, it’s an accessible way to enjoy Portland’s coastline with a drink in hand.
Bottom Line: Best for those wanting a laid-back sunset cruise with drinks and great views.
11. Portland: Schooner Tall Ship Cruise on Casco Bay
Number 11 offers an authentic sailing adventure on the Schooner Tall Ship. This 2-hour cruise allows you to experience Maine’s rugged coastline from a traditional vessel, with opportunities to see seals, lighthouses, and coastal wildlife. The crew often invites guests to help sail, adding an interactive element that appeals to active travelers.
Rated 4.6/5 from over 100 reviews, guests praise the scenic routes and sailing ambiance. At $108 per person, it’s a slightly higher investment but worth it for sailing purists.
Bottom Line: For a hands-on sailing experience with memorable coastal scenery, this tall ship cruise is hard to beat.
12. Portland: Casco Bay Lighthouse Sunset Cruise
Number 12, the Casco Bay Lighthouse Sunset Cruise provides a shorter, 1.5-hour evening voyage. It features views of Maine’s most famous lighthouses and the historic Fort Gorges. This cruise emphasizes classic sunset beauty combined with storytelling about the islands’ history. Many reviewers highlight its intimate atmosphere and stunning scenery.
Costing $67 per person, it’s a well-priced option for a romantic or family sunset outing. It’s especially suitable if you want to combine lighthouse viewing with a relaxed evening.
Bottom Line: A great choice for sunset lovers seeking scenic lighthouse views along with a touch of history.
13. Portland, Maine: Sunset Kayak Tour with a Guide
Number 13, the Sunset Kayak Tour offers a more active experience. Over two hours, you paddle across Casco Bay, soaking in the changing colors of the sky and spotting seals, eider ducks, and osprey. The tour is suitable for novices and seasoned paddlers alike, with a focus on scenic, tranquil waters.
Rated a perfect 5/5 from 20 reviews, this tour is praised for its peacefulness and stunning views. At $228 per person, it’s a premium experience—best for those with kayaking experience or a desire to learn.
Bottom Line: Perfect for active travelers who want to combine exercise with scenic beauty and wildlife spotting.
14. Maine Coastal Lighthouse: Two-hour bicycle tour
Number 14 introduces the Maine Coastal Lighthouse Bicycle Tour. Over two hours, you’ll cycle along the rocky coast, visiting several lighthouses and learning about the area’s natural and cultural history. The tour is designed for all skill levels, with personal attention and plenty of photo stops. It’s a good option for active travelers who want to see the coast up close.
Rated 4.9/5 from 24 reviews and priced at $75, this tour balances physical activity with scenic sightseeing, making it a lively way to explore the coastline.
Bottom Line: Best for those who prefer cycling to boat rides, with the bonus of personal interaction and photo opportunities.
15. Portland, Maine: Coastal Lighthouses Guided Bicycle Tour
The Coastal Lighthouses Guided Bicycle Tour is a 3-hour guided ride that combines natural beauty with cultural stories. Riders visit Portland Head Light and other scenic spots, stopping at local food trucks like the Bite into Maine at Fort William. It’s a good pick for active travelers wanting a deeper dive into the area’s history and scenery.
Rated 4.9/5 from 20 reviews and $105 per person, this tour offers a blend of exercise, sightseeing, and local flavor, making it a well-rounded choice.
Bottom Line: If you love biking and want to learn more about Maine’s coast, this guided tour offers a complete package.
16. Portland: Casco Bay Morning Lighthouse Cruise
Finally, at number 16, the Casco Bay Morning Lighthouse Cruise is an early start for those wanting to see Portland’s lighthouses in the morning light. This 1.5-hour cruise offers views of Portland Head Light, Bug Light Park, and Ram Island Ledge Light, giving a quiet, peaceful experience before the city wakes up. Many reviews mention the good value and family-friendly atmosphere.
At $57 per person, it’s an economical way to enjoy Casco Bay’s beauty early in the day, making it ideal for morning persons or those with flexible schedules.
Bottom Line: A calm, scenic option perfect for early risers who want to start their day with ocean views.
How to Choose the Right Tour in Portland Maine
When selecting your tour, consider your budget, physical fitness, and what interests you most. If you want a relaxing sunset with drinks, the Sunset Lighthouse Cruise or the Sunset Windjammer Cruise are excellent. For a deep dive into local stories, the Hidden Histories Guided Walking Tour offers surprises. Food lovers should look at the Old Port Culinary Walking Tour, while active travelers might prefer the Coastal Bicycle Tour or the Sunset Kayak Tour.
Booking early is advisable, especially for popular cruises or special time slots, to secure your preferred date and avoid disappointment.
Final Thoughts
Portland, Maine, offers a wide range of memorable experiences—whether you prefer sailing, biking, walking, or simply soaking in the views from a boat. For those seeking classic sights, the Best of Maine Lighthouse Scenic Cruise is a standout. Foodies will love the Old Port Culinary Walking Tour, while history enthusiasts should consider the Hidden Histories Guided Walking Tour. For a romantic sunset or a relaxing sail, the Casco Bay Sunset and Lighthouse Cruise or Windjammer Cruises are excellent options.
No matter your choice, Portland’s tours promise authentic, engaging, and scenic experiences that will make your visit truly special. Be sure to book early and pick a tour that matches your interests—and most importantly—enjoy your time on Maine’s rugged, beautiful coast.