All Portland Tours &amp; Excursions in 2026

Large Group Private Wooden Boat Sightseeing & Lighthouse Charter

All of our tours are done in a comfortable vehicle with a local driver guide and can be done at your pace. Tours can always be customized to your interests. This particular tour will show you all the main sites of Portland proper and then all of the South Portland lighthouses, including admission to the Portland Headlight at Fort Williams Park. After Portland, you will head on down the highway to Kennebunkport to visit this popular coastal village that former President George W. Bush and family called their summer home. We have a standard routing but being a private tour, we can tailor your experience to you interests.

6 Hours Private Lighthouses and Kennebunkport Tour in Portland

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.

Private Sunset Charter on a Vintage Lobster Boat with Drinks

Discover Maine's picturesque coastline on the South Coast Tour, featuring iconic locations like Nubble Lighthouse and the charming villages of York, Ogunquit, and Kennebunkport. Enjoy breathtaking ocean views along Marginal Way, savor the freshest New England clam chowder, and indulge in delicious Maine lobster. This private driving tour, lasting 6.5 hours, is perfect for couples, families, or groups, with flexible pick-up options along the coast. Whether you're an avid photographer or a history enthusiast, the knowledgeable guides will tailor the experience to your interests, ensuring a memorable adventure along Maine's stunning shores. Explore coastal gems including Nubble Lighthouse and Perkins Cove Enjoy lunch featuring Maine lobster along the water Private tour accommodating up to 5 passengers. We have larger vehicles at an additional cost. Guided experience with insights into local history and culture

Maine Private South Coast Tour Adventure

Maine Private South Coast Tour Adventure

⭐ Top-Rated Vacation Photoshoots 2025 We’re not just photographers, we’re storytellers capturing your holiday exactly as it feels. With over six years of experience photographing travellers around the world, our small team specialises in authentic, natural photography that truly reflects your trip. In Portland, we combine creativity with local knowledge to show you hidden gems, secret angles, and the best light. You’ll not only get beautiful, professional photos but also insider tips to make the most of your time here. We’re proud to be recognised among the top-rated photography tours of 2025, trusted by travellers worldwide for our relaxed style and stunning results.

Private Vacation Photoshoot with Photographer in Portland

1 hourFree Cancellation

As night falls on Portland’s historic waterfront, discover why this is the #1 ghost tour in Portland, ME. Operating nightly, year-round, this one-mile walking tour is led by expert local guides who know the city’s legends, history, and hidden corners firsthand. This outdoor-only experience weaves together documented history, local folklore, and chilling tales that bring Portland’s past to life. Along the route, you'll visit iconic locations including Bell Buoy Park, Andy’s Old Port Pub, the Portland Harbor Hotel, and even a section of the Berlin Wall. Each stop is connected to real events, maritime tragedies, mysterious deaths, or unexplained stories that have become part of Portland’s haunted legacy. Perfect for private groups, bachelorette parties, birthdays, and special events, this unforgettable ghost tour is proudly USMC Disabled Combat-Veteran-owned and women- and minority-led, offering an evening of haunting history, immersive storytelling, and unforgettable mystery.

Phantoms Penance and Poltergeists Portland ME Ghost Tour

Phantoms Penance and Poltergeists Portland ME Ghost Tour

1 hourFree Cancellation

US$26US$25

This two-hour sunset private sail is the perfect way to experience Maine's sunset on the coast - complete with lighthouses, seals, and seabirds. Sail aboard Heart's Desire, a 101 year old schooner, designed by famed yacht designer, John Alden. Heart's Desire measures 53' feet and features some of John Alden's trademark design elements including a long bowsprit and dramatic, raked transom. Built in 1925 by T.S. Soule in South Freeport, Maine, Heart's Desire has been used mainly for chartering along the Eastern seaboard in New York, New Jersey, Massachusetts, and Maine.

2 Hours Sunset Private Charter on Heart's Desire in Casco Bay

2 Hours Sunset Private Charter on Heart's Desire in Casco Bay

Paint Portland, Maine: Small Group Outdoor Painting Experience

3 hours 30 minutesFree Cancellation

Experience the beauty of coastal Maine on this private guided tour featuring iconic landmarks, scenic harbors, and charming coastal villages. From Portland travel along Maine’s scenic coastline to the picturesque harbor village of Boothbay Harbor. Walk across the historic Footbridge, built in 1901, and enjoy views of working lobster boats, quiet marinas, and classic New England waterfront scenery. Guests also have the option to enjoy lunch along the harbor at a unique restaurant built from a historic tugboat. With a knowledgeable local guide sharing stories and insights throughout the journey, this private coastal Maine tour offers the perfect blend of history, scenery, and authentic coastal charm.

Freeport, Boothbay Harbor, and Botantical Gardens Day Tour

7 to 8 hoursFree Cancellation

Private Portland to Acadia & Bar Harbor Experience

6 to 8 hoursFree Cancellation

Discover the beauty of Northwest Casco Bay on a 3-hour morning kayaking tour. No experience is necessary, as you get a crash course before the tour begins and your guide is on hand at all times. Double kayaks are available, if you prefer to paddle tandem. See Brunswick and its native wildlife from a unique vantage point. Then enjoy complimentary snacks and a brief land excursion, before your return.

Oyster Farm & Complimentary Tasting Sea Kayak Tour in Casco Bay

Unlike large group bus tours, this experience is designed to be personal, flexible, and immersive. You’ll walk the streets of Salem with a knowledgeable guide who doesn’t just point out landmarks but brings their stories vividly to life—from the haunting legacy of the Witch Trials to the maritime wealth that built the city, and the literary genius of Nathaniel Hawthorne. What makes this tour unique is the balance of history and atmosphere: you’ll explore centuries-old cemeteries and mansions, admire harbor views and gardens, and even encounter touches of pop culture like the Bewitched statue. With small groups and a customizable pace, you’ll have the freedom to linger where your interests lie most—whether it’s taking photos, diving deeper into Salem’s legends, or enjoying a quiet moment in a hidden garden. This isn’t just sightseeing—it’s a chance to experience Salem’s past and present through stories, scenery, and atmosphere in a way that big tours can’t match.

Private Day Tour of Salem MA, from Portland ME

7 to 9 hoursFree Cancellation

US$325US$309

This two-hour afternoon private cruise is the perfect way to experience Maine's coast, your special event, or a family get-together that will never be forgotten. Ride aboard Heart's Desire: designed by famed yacht designer - John Alden, measures 53' feet and features some of his trademark design elements including a long bowsprit and dramatic, raked transom. Built in 1925 by T.S. Soule in South Freeport, Maine, Heart's Desire has been used mainly for chartering along the Eastern seaboard in New York, New Jersey, and most recently Massachusetts.

Casco Bay: Private Afternoon Charter on Heart's Desire

Casco Bay: Private Afternoon Charter on Heart's Desire

Some cities are best seen from a car window. Portland, Maine is not one of them. On this fully private e-bike tour, it's just your group, a local guide, and five hours of spectacular coastal scenery — with a Maine lobster roll along the way. Ride through the Old Port's cobblestone waterfront and fishing piers. Climb to Fort Allen Park for sweeping Casco Bay views. Cruise the Eastern Promenade before crossing to South Portland to walk the breakwater to Bug Light, designed by the architect of the U.S. Capitol dome. Continue to Spring Point Ledge — the only lighthouse of its kind you can reach on foot — then Portland Head Light, commissioned by George Washington in 1791. Finish on the Western Promenade, a hidden hilltop park with views to the White Mountains that most visitors never find. Lunch is a fresh Maine lobster roll at a waterfront spot worthy of the occasion. No strangers, no set pace — just your group and the best of coastal Maine.

Private EBike Tour Portland Maine

5 hoursFree Cancellation

Go beyond the sights of Portland, Maine and take a day trip to Salem, Massachusetts. The town of Salem is known for its famous witch trials that took place in 1692. Learn about the history of Salem on a guided tour through the town and see several landmarks including the Salem Witch Museum, the memorial, and Phillips House. On your way to Salem, stop in Kennebunkport to explore the historic village.

Private Portland to Cape Ann, MA Castles & Coast

8 to 10 hoursFree Cancellation

This isn’t just another sightseeing trip—it’s a curated journey through Maine’s most iconic landmarks and hidden gems, woven together into one unforgettable day. From the elegance of Portland Head Light, the nation’s most photographed lighthouse, to the playful charm of Eartha, the world’s largest rotating globe, every stop reveals a different facet of Maine’s character. Guests walk a historic suspension bridge built by the engineers of the Brooklyn Bridge, explore the state’s proud maritime heritage in Bath, and visit the legendary L.L. Bean flagship store in Freeport. What sets this tour apart is the balance of scenery, history, and culture: stunning coastal views, hands-on heritage at museums and memorials, and Maine icons you won’t find grouped together anywhere else. And because it’s a shorter itinerary, it’s the perfect choice for cruise ship passengers or travelers with limited time who still want a rich, memorable Maine experience.

The Maine Experience: Coast, Culture & History

5 to 6 hoursFree Cancellation

Join us for an exciting **Private Coastal Tour from Portland to Camden**, exploring the beauty and history of Maine’s coastline! Start with Bath, home to the towering USS Wyoming sculpture and rich shipbuilding heritage. In Wiscasset, stroll through “The Most Beautiful Village in Maine” and visit the world-famous Red’s Eats lobster stand. In Rockland, enjoy a walk to the lighthouse and explore its maritime charm. In Camden, wander the charming streets, enjoy lunch, and see a unique waterfall flowing through town. The highlight of the tour is **Camden Hills State Park**, where you’ll take in the most breathtaking views of Midcoast Maine from the summit of Mt Battie. This fun and adventurous tour is perfect for exploring Maine’s hidden gems. Book now to experience the best of the coast!

Private Portland to Camden & Midcoast Lighthouse Experience

7 to 9 hoursFree Cancellation

What better way to see the delights than in the style of a private charter for you and five friends or family members? Experience the beauty and serenity of the rugged coastline as you gaze upon seabirds, sea houses, and islands. Guests are encouraged to help raise the sails with a deckhand and steer the ship for themselves. Your charter is your time to relax, celebrate, entertain, and sail, so you get to set the pace and atmosphere. Beer, wine, and other alcoholic beverages are permitted on board.

Portland Tall Ship Private Charter on Casco Bay

Castles of Cape Anne, Massachusetts - Private Day Tour

8 to 10 hoursFree Cancellation

US$350US$333

Experience the beauty of Maine’s central coast on a fully private, all-day tour designed just for you. Unlike crowded bus tours, our small-group experience offers personalized attention, comfort, and flexibility. Travel in style through autumn-kissed landscapes as your local guide leads you to handpicked highlights—like the iconic Portland Head Light, the charming harbor town of Boothbay, and the historic Fort Edgecomb. Walk the gently swaying Androscoggin Swinging Bridge, shop at the legendary L.L.Bean Flagship Store, and take in riverside views in Bath, “The City of Ships.” This is coastal Maine at its finest—tailored, immersive, and unforgettable.

Boothbay, Freeport and Maine Botanical Gardens Private Day Tour

Boothbay, Freeport and Maine Botanical Gardens Private Day Tour

6 to 8 hoursFree Cancellation

US$325US$309

Explore the charming coastal towns of Kennebunkport, York, and Portsmouth on this private day tour. Delve into the rich maritime history, enjoy stunning ocean views, and savor local flavors. With a personalized itinerary, this tour offers the flexibility to explore at your own pace, while an expert guide provides insights into each destination. Enjoy a relaxed atmosphere with included snacks, bottled water, and lunch to keep you energized throughout the day. - Private tour lasting approximately 7 to 8 hours - Customizable itinerary to suit your interests - Included lunch, snacks, and bottled water - Pickup from your location in an air-conditioned vehicle

Kennebunkport, York and Portsmouth NH Private Tour

Kennebunkport, York and Portsmouth NH Private Tour

7 to 9 hoursFree Cancellation

A half-day sailing charter offers a unique and personalized way to explore the stunning Maine coast. Departing from downtown Portland, this private experience aboard Sasa, a family-run small business charter sailboat, with a coast-guard certified captain, allows you to cruise through Casco Bay, enjoying views of iconic landmarks like Portland Head Light. With options to swim in secluded spots or simply relax, every charter is tailored to your group's preferences. Enjoy light refreshments and the chance to take the helm or trim the sails, making for an unforgettable day on the water.

Private Half Day Sailing Charter in Portland Maine

4 hoursFree Cancellation

There are a lot of ways to get out on the water in Maine, but we make every charter feel personal, relaxed, and genuinely memorable. We’re a small, family-run sailing charter, and Sasa is a thoughtfully restored and beautifully outfitted yacht designed to feel warm, welcoming, and comfortable from the moment you step aboard. A half-day sail is the easiest way to get out on the water and see the Maine coast from a completely different perspective. This small group Maine sailing charter is perfect if you want a relaxed few hours to cruise, take in the views, brush up and your sail trim, or just relax and maybe sneak in a swim on a warm day.

Casco Bay Sailing Escape: Half Day Custom Boat Charter

Casco Bay Sailing Escape: Half Day Custom Boat Charter

4 hoursFree Cancellation

US$199US$189

Enjoy a relaxing morning paddleboarding along Portland's Casco Bay. After a brief instruction, set out for a stand-up tour of the area—searching out native wildlife such as great blue herons and osprey as you slowly explore the waters. Learn about the area's fascinating history, from ways Native Americans used the land to how lobsters play a big part in the local economy. This leisurely and informative 2-hour tour includes an on-shore snack break before making your way back to Mere Point.

Stand Up Paddleboard Tour with Complimentary Oyster Tasting

Stand Up Paddleboard Tour with Complimentary Oyster Tasting

2 hours 30 minutesFree Cancellation

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Must-Dos in Portland

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What are people saying about Portland

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

Andresen_I, Oct 2026

Wow… what can I say.....

Wow… what can I say.. This tour was amazing. Derek is a gem. He was born and raised here in Portland. He is very vibrant and had so much information about Portland. Van was very comfortable and warm. Ever in Portland definitely do this tour yiu will not be disappointed.

Portland City and Lighthouse Tour

Gay_B, Oct 2026

Portland Trolley was a great choice

Great tour of Portland, ME. Our driver rode us through several residential areas and explained and shared stories and history of some homes. Love the Portland LightHouse visit. This was my 2nd visit to this beautiful sight. We walked from the Cruised Port and turned left. Our tour trolley picked us up there, which saved us about a 15 minute walk. It was a beautiful day in Portland. It's an interesting City to walk around. There were street vendors near the cruise port entrance.

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

Julianne_B, Oct 2026

Joe our Tour Guide was GREAT!

Very conveniently located meeting & check in location within a 5 minute walk from our Windstar/Star Pride ship docked in Portland, ME. Joe, our tour guide, was very nice, informative and accommodating. He offered us water during our trip and we had a Portland Beer Hub sample 3oz if their draft beer either before or after our tour. Very tasty!

Old Port Culinary Walking Tour from Portland

Cayla_B, Oct 2026

Ray was an amazing tour...

Ray was an amazing tour guide. Not only did we eat delicious food, he learned a lot about Portland’s history. He took us to restaurants that some may overlook (hidden gems of Portland) and the food was incredible. It’s not a hard walk at all either. Would definitely do this tour again

Afternoon Lighthouse Cruise Along the Coast of Portland Maine

Brian_K, Oct 2026

Great Personal Cruise of the Casco Bay

We enjoyed the smaller boat with a more personal experience. We thoroughly enjoyed our excursion and our Captain Nick and First Mate Niko made it a fun and educational experience. We took along our own wine and cheese which made the cruise extra special. We highly recommend!

Afternoon Windjammer Cruise Along the Coast of Portland Maine

Deirdre_N, Oct 2026

Wonderful sail in Portland!

Take Bonine if you are prone to sea sickness and bundle up against the wind in the cooler months. And try your hand at hoisting up the sails! Above all, simply enjoy the scenic coastline and the experience of sailing on a schooner that is over 100 years old. Talk to the Captain and the crew-- they will tell you all the history and stories.

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

Angela_L, Oct 2026

History at its finest!

Captain Pete and Olivia were wonderful. The fort is well preserved and a boat trip from the harbor. Pete told us he has always had an interest in the island and it shows in his tours. He was very friendly, informative and enthusiastic. It made a wonderful day even better. I highly recommend this tour.

Vintage Fire Truck Sightseeing Tour of Portland Maine

abishop, Oct 2026

Fun Day of Learning

It was a well run tour from taking pictures before to having blankets to keep warm on board and pictures on a screen in case you couldn’t see what we were passing well. Our tour guide, Miles, was passionate about his city’s history and stuck in funny parts throughout. Our 7 year old enjoyed the ride too. Good tip is that the check in is at kiosk not a building so no bathroom.

Sunset Lighthouse Cruise

William_B, Oct 2026

Made our day in Portland

The sunset cruise was just what we hoped for. John shared so much interesting information about the lighthouses and islands we passed, lobstering, and local history; and Howard skillfully navigated usamong the islands and then positioned us to see a beautiful sunset. He also found some rocks where seals and cormorants were resting. Sit on the right side for the best views. Arrive early to get an outside seat on the top deck and dress very warmly.

Sunset Windjammer Cruise Along the Coast of Portland Maine

Jessica_D, Oct 2026

Book this sunset cruise!

This was the best sunset cruise! The crew was so friendly. They offered an opportunity to help hoist the sails for those that wanted a full sailing experience. We had ample space. There’s a bathroom on board and you could bring your own beverage and snacks. Views were amazing in October.

Harbor Lights and Sights Cruise

Brian_S, Oct 2026

Awesome tour, wonderful crew

Excellent tour. I arrived on a cruise ship and the tour dock was very easy to find. It’s about a 10-15 minute walk from the terminal. The tour started right on time and we were back in exactly 1 hour and 45 mins. The crew were friendly and welcoming when we boarded. The captain did the introductions and safety stuff and we were in our way. Amazing views of the lighthouses and diamond islands, casco bridge etc the narration was excellent. Really intelligent guy that definitely knew his stuff. I’ve been to Portland a few times via car but never went out on the water. I learned more about Portland in this under 2 hour journey than every prior trip combined. Highly recommend this tour. Captain Kelton was the captain and Islander was the vessel.

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

Paula_S, Oct 2026

History and donuts

We love to take some kind of historical tour any time we arrive in a city - it helps us to get our bearings to the city and gives context to the stay. So when I found one that added donuts - pure bonus! The donuts were great - especially the part where we got to skip the massive line at Holy Donuts. But even better than the donuts were the fun facts we learned about Portland. Our guide was knowledgable and fun. He didn't let facts get in the way of having fun - he definitely had some embellished stories but gave us full warning they were embellished ;) We also loved that he gave a card with personal recommendations at the end of the tour - it was super useful for our trip. We'd recommend to everyone as a first stop when you arrive in Portland.