All Portland Tours &amp; Excursions in 2026

Discover Portland City and Lighthouse Tour

Sunset Lighthouse Cruise Tour from Casco Bay

(1,032)

from USD 57

(135)

from USD 56

The Real Portland Tour: City and 3 Lighthouses Historical Tour with a Real Local

(1,512)

from USD 69

Experience the breathtaking beauty of the Atlantic Ocean on our whale-watching tour departing from Portland, Maine. Set sail from the historic harbor, where you'll board a comfortable vessel equipped for a thrilling marine adventure. As we cruise along the rugged coastline, keep your eyes peeled for the majestic giants of the sea – humpback whales, fin whales, and minke whales are frequently spotted in these waters. Our experienced naturalist guides will be with you every step of the way, providing fascinating insights into the behavior and biology of these incredible creatures. The tour also offers the opportunity to observe a variety of other marine life, including seals, porpoises, and a wide range of seabirds. Don't forget to bring your camera, as you'll want to capture these unforgettable moments.

Maine Whale Watching Tour in Portland

3 hours 30 minutesFree Cancellation

4.0

(45)

from USD 129

Avoid the tourist traps and taste Portland, Maine's best donuts on a small-group walking tour. Follow your guide around the Old Port and sample several hand-picked donuts at award-winning bakeries with coffee or water included. Walk a scenic loop while hearing stories of Portland’s history and the invention of the donut. This tour offers a flavorful mix of food and local tales, perfect for food lovers and families alike.

Portland Walking Food Tour – Warm Donuts, History & Hidden Gems

(189)

from USD 70

Visit Portland’s scenic coast, historic sites and most vibrant neighborhoods with a sightseeing and shopping tour on a classic fire engine. Get great views of picture-perfect lighthouses and architecture from high up on the engine, and listen to live narration as you tour the city. Learn about Portland’s maritime past as you explore cobblestone streets with enjoy plenty of time to browse souvenir shops and sample the area’s most distinctive foods. Finish your tour in the heart of downtown, near historic wharves, restaurants and boutiques.

Vintage Fire Truck Sightseeing Tour of Portland Maine

Vintage Fire Truck Sightseeing Tour of Portland Maine

50 minutesFree Cancellation

(864)

from USD 45

Visitors to Portland can easily miss some of Maine's most stunning sights, since you really need a car to explore the scenic coastline. Avoid the headache of arranging your own transportation, or renting a car, on this guided tour of Portland's must-see sights. Stop in downtown Portland, and visit three lighthouses, including Portland Head Light—an historic lighthouse perched on the rocky coast.

Portland Explorer | Maine History, Culture, & 3 Lighthouses Tour

Portland Explorer | Maine History, Culture, & 3 Lighthouses Tour

4.9

(956)

from USD 91

Food lovers can explore Portland's historic Old Port independently, but to uncover the best places serving traditional local fare, you really need a guide to lead the way. Taste the best that Portland has to offer on this guided foodie walking tour, complete with stops at up to seven different eateries—and enough tastings to replace a meal. Along the way, your guide offers some stories about Portland's food scene, so you can get familiar with the local culinary stalwarts.

Old Port Culinary Walking Tour from Portland

Old Port Culinary Walking Tour from Portland

2 to 3 hoursFree Cancellation

(426)

from USD 160

Old Port "Seafood Lovers" Walking Lunch Tour in Portland, Maine

3 hoursFree Cancellation

Portland Tall Ship Cruise on Casco Bay

(148)

from USD 160

Looking for a romantic way to watch the sunset while in Maine? How about chartering a vintage lobster boat and heading out to Casco Bay, where you'll take in great views of the sea and coastline. Your captain and guide will be on board to point out lighthouses, historic forts, and natural features. A round of drinks is included to toast the sunset with, but more beverages are available to purchase onboard.

4.6

(236)

from USD 101

Private Sunset Charter on a Vintage Lobster Boat with Drinks

Price varies by group size

4.9

(40)

from USD 407

As we cruise the waters around Portland Harbor we will make stops at Portland Breakwater Light, Spring Point Light and Ram Island Ledge Light before stopping at Maine’s oldest and most iconic lighthouse, Portland Headlight. This historic beacon, with its striking architecture and stark coastal backdrop, is a sight to behold from the perspective of the Atlantic Ocean as seafarers have done for more than 200 years. After photos and information about this iconic lighthouse, we continue the ride along the rocky shores of Cape Elizabeth to Two Lights State Park, whose twin lighthouses perch atop dramatic cliffs. Our best chance for wildlife comes during the next leg of the ride as we cruise open waters to Halfway Rock Lighthouse, a true maritime relic. Standing proudly on a remote ledge in the open ocean, it has guided mariners through thick fog and turbulent waters for over a century. Seals are often found hanging on the rocks and feeding in the nutrient-rich waters.

Seven Portland Lighthouses Tour

Embark on a boat to a private island historic fort that’s only accessible with this tour. Leave from Portland and for a boat ride on Casco Bay, landing at the privately owned Fort Scammel on House Island. There, explore the architecture and preserved ruins of the stone fort—the only fort in the Portland harbor to see battle. Discover underground passages and learn the history of this previously inaccessible site.

4.1

(28)

from USD 109

Kid's can enjoy a scavenger hunt and lanterns on their exploration of the private island!

Private Island Fort Tour in Casco Bay: Boat Cruise & Island Tour

Private Sightseeing Charter on a Vintage Lobster Boat with Drinks

(64)

from USD 119

MONHEGAN is equipped with a finely finished wooden table in between cushioned "booth style" benches

Price varies by group size

(65)

from USD 380

Afternoon Windjammer Cruise Along the Coast of Portland Maine

Sail with us for a two-hour Windjammer Sail on Casco Bay in Portland, Maine — the perfect way to experience the beauty of the rugged coastline, complete with lighthouses, seals, and seabirds (NOTE: This is NOT a narrated tour, but our crew is happy to answer any questions you have about the sites). Pack a meal, bring your favorite wine or beer, and sit back and relax as you slip through the pristine waters of Casco Bay. All ages are welcome! Whether you are nine years old or 99, sailing aboard one of our Maine historic schooners is a unique adventure. All of our wooden windjammers were built in Maine and three are listed on the National Register of Historic Places.

Afternoon Windjammer Cruise Along the Coast of Portland Maine

Maine’s lighthouses are beautiful, but they’re even more gorgeous from the water. You’ll get those epic views and more on this scenic, intimate cruise, traveling from Portland’s Old Port to the harbor’s best sights. You’ll witness the old-school lighthouses, the islands of Casco Bay, a Civil War–era fort, and so much more. With a drink in hand, it’s a great way to start—or end—your time in Portland.

4.6

(186)

from USD 69

Small Group Afternoon Lighthouse Boat Cruise With Local Drinks

Small Group Afternoon Lighthouse Boat Cruise With Local Drinks

1 hour 30 minutesFree Cancellation

4.7

(55)

from USD 87

Set off on a refined culinary adventure through the serene waters of Casco Bay. Your journey begins at Portland Beer Hub, where you’ll gather before being escorted to the waterfront to board your boat. As you glide past the stunning coastline, savor freshly shucked oysters perfectly paired with crisp prosecco. Whether you’re toasting to a special occasion or simply indulging in a moment of pure relaxation, this experience blends Portland’s finest flavors with breathtaking coastal views—an unforgettable way to enjoy the best of land and sea.

Portland Lighthouse Boat Cruise with Oysters & Prosecco

Portland Lighthouse Boat Cruise with Oysters & Prosecco

1 hour 30 minutesFree Cancellation

(4)

from USD 137

Discover the lighthouses and coastal landmarks of Portland on a small-group biking tour. Hop on a provided bicycle and follow your guide to the Bug Light, Spring Point Ledge, and Portland Head lighthouses. Along the way, learn about their storied histories. Other highlights include the Liberty Ship Memorial, Cape Elizabeth, and Willard Beach. Set at a leisurely pace, the adventure also includes a complimentary lobster roll lunch at an award-winning food truck.

Portland Bicycle Tour with 5 Lighthouses and XL Lobster Roll

Portland Bicycle Tour with 5 Lighthouses and XL Lobster Roll

5 hoursFree Cancellation

(150)

from USD 165

With this small-group walking tour, you'll go beyond lobsters and lighthouses and get a look at the true Portland, Maine—across 400 years of history. Meander downtown and the Old Port, visiting hidden landmarks and learning about Wabanaki leaders and other people and events left out of the history books. Discover centuries of destruction, revival, underrepresented perspectives, and other elements that mainstream tours gloss over.

Portland, Maine: Hidden Histories Guided Walking Tour

Portland, Maine: Hidden Histories Guided Walking Tour

(523)

from USD 54

Experience Portland's rich history from its most impressive vantage point: the water. Adventuring along Diamond Pass, you'll glimpse a Civil War–era fort, old-school lobster boats, and all the lighthouses Portland is so famous for, including Portland Head Light, Maine’s oldest. Suitable for all ages, this excursion is both a dive into Portland's past and a sightseeing adventure, a two-fer that’s leisurely, scenic, and fun.

Port City Lights Cruise

1 hourFree Cancellation

Introducing Portland’s World of Flavors Walk highlighting hidden gems and great flavors that give Portland its cosmopolitan flair. Enjoy this walkable city with a big palate on our international journey, tasting locally sourced foods prepared with the recipes, customs and spices from other lands. On this 2.5-3 hour tasty romp through Portland’s historic Old Port and waterfront, you will enjoy the flavors while learning their food pathways and the owners journeys to Maine. Portland’s World of Flavor serves up a diversity of tastes and ethnicities in a compact area, packing a punch of flavors you will love. All tour experiences are highly educational and entertaining with trained, local guides.

(259)

from USD 39

Portland's World of Flavors Tour

3 hoursFree Cancellation

4.5

(6)

from USD 160

2-Hour Portland Old Port Ghost Walking Tour

1 hour 30 minutes to 2 hoursFree Cancellation

4.5

(37)

from USD 29

Large Group Private Wooden Boat Sightseeing & Lighthouse Charter

100% Private Charter for Groups up to 15 — Flat Rate Pricing This exclusive 2-hour boat tour is designed for private groups seeking an authentic, intimate experience on Casco Bay. Unlike crowded public cruises, your group of up to 15 guests will enjoy the full comfort and charm of one of our classic wooden vessels—all to yourselves. Cruise past iconic lighthouses, historic granite forts, and stunning stretches of Maine’s coastline, with opportunities to spot harbor seals, seabirds, and other local wildlife along the way. Whether you’re celebrating a special occasion or simply gathering with friends, this charter offers a personalized, relaxed way to experience the best of coastal Maine. Feel free to bring your own food—we provide all the glassware, plates, and utensils you’ll need. Local craft beer, wine, and other beverages are also available for purchase onboard, making it easy to sip, savor, and soak in the scenery.

Large Group Private Wooden Boat Sightseeing & Lighthouse Charter

Dive straight into Portland’s working waterfront—where the smell of the sea, the bustle of the wharves, and a warm bowl of classic New England clam chowder set the tone for an unforgettable walk through the city’s past. This immersive experience blends local history with maritime culture, offering a deeper look at how Portland grew from a rugged seaport into one of New England’s most vibrant coastal cities. As you stroll the cobblestone streets and working wharfs, your guide will share tales of shipbuilders, merchants, fires, and fishermen who shaped Portland’s story. The tour concludes with a warm bowl of classic New England clam chowder—a delicious taste of Maine’s coast and a comforting way to end your walk through history!

4.7

(3)

from USD 850

Per group

Portland Working Waterfront Walking Tour with Seafood

Portland Working Waterfront Walking Tour with Seafood

2 hours 30 minutesFree Cancellation

Portland Tall Ship Cruise on Casco Bay

(7)

from USD 79

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What are people saying about Portland

Patricia_J, May 2026

Must do

Captain and crew are first rate and just nice people! As is girl at intake. Enjoyed first time so much went on sunset sail on second round. Good for the soul and fun! Should bring a jacket though when sails are full and they are moving well. Can’t say enough. Thanks!

Portland Walking Food Tour – Warm Donuts, History & Hidden Gems

Lindsay_G, May 2026

The donuts are delicious...

The donuts are delicious and fresh. Loved walking around the waterfront - particularly the Portland history and lobster industry information. Our host also provided recommendations for other notable local foods to try. A great way to have a treat and explore!

Old Port Culinary Walking Tour from Portland

Careen_R, May 2026

Had an amazing time !

I loved every minute of this tour . Our tour guide was amazing , the food was amazing , and it was great learning so much about Portland, Maine . I highly recommend everyone who’s able to go, to go. It’s a great introduction of the area . You won’t regret it !

The Real Portland Tour: City and 3 Lighthouses Historical Tour with a Real Local

Careen_R, May 2026

Lovely Experience and Worth the Time

This was a great experience, and it made me wish I had a little more time to explore the Portland lighthouse a bit more. Our tour guide was on time, great communicating before the tour even began and during the experience, super kind , funny dad jokes lol and very knowledgeable .

Portland Explorer | Maine History, Culture, & 3 Lighthouses Tour

Kimberly_B, Apr 2026

Ask for John when you book a Portland, ME tour. He’s the best!

Four people registered for the experience. While John was driving, he shared interesting and historic information about Portland and the three lighthouses we visited. At each lighthouse, we were given time to take take pictures, explore the grounds, stretch our legs, and ask John questions. John was very knowledgeable, engaging and fun!

Discover Portland City and Lighthouse Tour

Anita_S, Nov 2025

Portland City Tour and Lighthouse

This tour was very informative and gave a nice overview of the city of Portland. It passed by several historical sites, the working waterfront, and the Old Port area. The stopover at the Portland Head Lighthouse was a nice ending to this tour. I would highly recommend it. The tour guide was excellent too and he shared so much information about the history of the area.

Small Group Sunset Lighthouse Boat Cruise With Local Drinks

Diya_G, Oct 2025

Do not pass! Great organizers and beautiful experience

The Portland beer club is a fantastic meet up spot where we met Christopher- he is such a gem that we decided to go back after the boat ride for a round of beer and cider. Denny and the captain were super warm and knowledgeable about the history. Highly reccomend this company and the tour!

Harbor Lights and Sights Cruise

Robert_L, Oct 2025

History Lesson w/ visuals

Unfortunately our day was windy cold and overcast but still a worthwhile trip. We didn’t see 2 lighthouses at Twin Lights State Park due to the conditions but still saw 4 lighthouses and passed by multiple islands. Best part of trip was our Narrator Mark ( a lifelong native) who provided great descriptions of what we were seeing as well as substantial history behind all. For the price, views and history, a VERY worthwhile expenditure of a couple of hours

Old Port "Seafood Lovers" Walking Lunch Tour in Portland, Maine

Tammie_G, Oct 2025

Friends Fall Trip

Excellent food and great information about the city of Portland! The guide was very knowledgeable about the history of the city. We loved that he picked restaurants he had great experiences from and knew about each of the items that was served. The city was very clean and perfect weather.

Vintage Fire Truck Sightseeing Tour of Portland Maine

Kim_Y, Sept 2025

Fun and insightful tour

We thoroughly enjoyed the tour. Loved the old fire truck. The driver and guide were friendly and knowledgeable. The tour hit all the high points and interesting information about the 4 fires Portland has experienced thru the years. The TV showing images provided by the Portland Historical Society added to the experience.

Private Sightseeing Charter on a Vintage Lobster Boat with Drinks

Ryan_D, Aug 2025

The Perfect Way to View Portland!

If you’re visiting Portland, whether as a first-timer or returning guest. this is a must! You’ll get a beautiful view of the harbor, surrounding islands, and maybe see some seals! The Captain and Deckhand were friendly, knowledgeable, and welcoming. Highly recommended!