Top Portland Cruises &amp; Sailing

Sail with us for a two-hour morning Windjammer Sail on Casco Bay in Portland, Maine. This is 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). All ages are welcome, whether you are nine years old or 99, sailing aboard one of our Maine historic schooners is a unique adventure. See Fort Gorges, Bug Light Park, and the beautiful Portland coastline. 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 of our wooden windjammers were built in Maine and three are listed on the National Register of Historic Places.

(183)

from $77

Casco Bay Morning Windjammer Sail

Experience the scenic coastline of Casco Bay in Portland, aboard a traditional Maine windjammer. Sail past lighthouses, rocky islands, and wildlife while enjoying the peaceful pace of a classic schooner cruise. Bring your own picnic and drinks to enjoy on board as you take in the views. Suitable for all ages, this relaxing sailing experience offers an authentic way to discover the beauty of the coast.

(36)

from $61

Afternoon Windjammer Cruise Along the Coast of Portland Maine

Afternoon Windjammer Cruise Along the Coast of Portland Maine

Embark on an unforgettable 1.5-hour cruise along Maine's breathtaking coastline at sunset. See four of Maine's most iconic lighthouses, spot seals and seabirds, and take in the historic forts that dot the landscape. Bring your favorite wine or beer and a delicious meal, and unwind as we cruise through the serene waters of Casco Bay. Journey aboard Ruth—a charming 39-foot classic picnic-style tour boat crafted in 1935 at Handy Boat in Falmouth, Maine. Don't miss out on this unique sunset experience!

(243)

from $69

Sunset Lighthouse Cruise Along Casco Bay

Sunset Lighthouse Cruise Along Casco Bay

1 hour 30 minutesFree Cancellation

Small Group Sunset Lighthouse Boat Cruise With Local Drinks

(46)

from $69

1 hour 30 minutesFree Cancellation

Private Sightseeing Charter on a Vintage Lobster Boat with Drinks

(115)

from $89

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

Price varies by group size

(67)

from $380

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

1 hour 45 minutesFree Cancellation

Portland Tall Ship Cruise on Casco Bay

(1,622)

from $74

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 small-group 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.

4.6

(241)

from $102

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

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

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.

(988)

from $79

Vintage Fire Truck Sightseeing Tour of Portland Maine

Vintage Fire Truck Sightseeing Tour of Portland Maine

50 minutesFree Cancellation

4.8

(908)

from $45

Witness the stunning sunset over Casco Bay on this two-hour public powerboat cruise aboard the classic Maine-built vessel, Avelinda. As the sun sets, enjoy picturesque views of iconic lighthouses like Portland Head Light and serene islands such as Peaks Island. With a maximum of six guests per boat, relish an intimate experience while keeping an eye out for local wildlife like seals and seabirds. Captains with extensive local knowledge share tales of the region's rich history, making this cruise a perfect way to unwind and soak in the beauty of Maine's coast. Open to all ages, it’s a memorable outing for families and couples alike. - 2-hour scenic sunset cruise through Casco Bay - Maximum of 6 guests for an intimate experience - Spot local wildlife and iconic Portland lighthouses - Knowledgeable captains share local history and ecology

Intimate Portland Public Sunset Cruise

A Walk Through Time Tour in Portland

(1)

from $149

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.

(514)

from $49

Likely to Sell Out

Portland Bicycle Tour with 5 Lighthouses and XL Lobster Roll

5 hoursFree Cancellation

4.8

(158)

from $165

Portland Pedicab Taxi Reserve

5 to 20 minutesFree Cancellation

from $50

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

6 Hours Private Lighthouses and Kennebunkport Tour in Portland

from $735

Likely to Sell Out

Around The Peninsula Bike Tour

3 hoursFree Cancellation

4.6

(43)

from $89

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

Price varies by group size

(43)

from $407

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. Due to our liquor license, we do NOT permit outside alcoholic beverages on board.

Large Group Private Wooden Boat Sightseeing & Lighthouse Charter

(6)

from $850

Come sailing aboard Heart's Desire, designed by famed yacht designer - John Alden, measures 53' feet and features some of his trademark design elements. Built in 1925 by T.S. Soule in South Freeport, Maine, Heart's Desire is 100 years old this year and has been used mainly for chartering along the Eastern seaboard in New York, New Jersey, Massachusetts, and Maine. This two-hour private, morning sail is the perfect way to experience Maine's coastline. Whether you are interested in getting married in an intimate setting, a special way to celebrate a reunion, birthday or anniversary, or just want to enjoy sailing at its finest, step aboard and plan an event never to be forgotten!

2 Hour Private Morning Charter on Heart's Desire in Casco Bay

2 Hour Private Morning Charter on Heart's Desire in Casco Bay

4.5

from $550

This is a fully private Southern Maine coastal experience designed exclusively for your party (2–5 guests). No bus groups. No shared travelers — just your group, your pace, and a relaxed day along Maine’s scenic shoreline. Visit historic York’s colonial landmarks, walk through the Old Burying Ground, and enjoy views from John Hancock Wharf before stopping at Cape Neddick Light, one of New England’s most photographed lighthouses. Continue to Ogunquit for time at Perkins Cove, with the option for a short scenic stroll along the Marginal Way overlooking the Atlantic. In Kennebunkport, enjoy unhurried time in Dock Square to browse shops, walk the harbor, and dine at a local restaurant of your choice. A scenic stop at The Colony Hotel adds classic New England charm and sweeping coastal views. Because this tour is private, the experience remains flexible and comfortable, allowing you to explore at your own pace and focus on the scenery and stories that interest you most.

Southern Maine Private Tour: Kennebunkport & Nubble Lighthouse

Southern Maine Private Tour: Kennebunkport & Nubble Lighthouse

6 to 8 hoursFree Cancellation

Experience the beauty of coastal Maine on this private guided tour featuring iconic landmarks, scenic harbors, and charming coastal villages. Your journey begins at Portland Head Light, one of the most photographed lighthouses in the United States, where dramatic rocky cliffs and sweeping Atlantic views create unforgettable photo opportunities. From there, 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.

(3)

from $300

Private Portland Head Light & Midcoast Explorer

Private Portland Head Light & Midcoast Explorer

6 to 8 hoursFree Cancellation

4.5

(14)

from $350

Private Portland Sunset Powerboat Cruise in Casco Bay

Witness the stunning transformation of Portland Harbor and Casco Bay during a private sunset powerboat cruise. Aboard the classic Avelinda, enjoy a two-hour journey as the sun sets, painting the sky with vibrant hues. Marvel at iconic lighthouses like Portland Head Light and glide past charming islands, keeping an eye out for local wildlife such as seals and seabirds. This intimate experience is perfect for all ages, whether celebrating a special occasion or simply relishing the natural beauty of Maine's coastline. - Exclusive private cruise for up to 6 guests - Comfortable Maine-built powerboat with marine restroom - Experienced captains share local history and ecology - Flexible scheduling with multiple evening departures available - Alternative pickup available in Portland for added cost, saves 30 min of driving, contact us for availability

Private Portland Sunset Powerboat Cruise in Casco Bay

from $747

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

Private Half Day Sailing Charter in Portland Maine

4 hoursFree Cancellation

Price varies by group size

(1)

from $475

Maine Private South Coast Tour Adventure

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

6 hours

from $700

Afternoon Windjammer Cruise Along the Coast of Portland Maine

1 2

Top Attractions in Portland

1 / 2

Attractions

What are people saying about Portland

Kristen_G, Aug 2026

⛵️ The Escape We Didn’t Know We Needed

If you’re looking for an afternoon to truly slow down, breathe, and just enjoy being present, book the sail. You won’t regret it. We loved every minute of our afternoon on the water. The weather was perfect, the air was incredible, the views were peaceful, and the crew was absolutely wonderful. What I loved most was that this wasn’t one of those sails where you’re constantly being talked at with facts and information. Instead, it was simply about enjoying the experience. The crew was kind, personable, and interacted with everyone without taking away from the peacefulness of being out on the open water. They pointed out different areas and answered questions whenever someone was interested, but otherwise, they let the experience speak for itself. And honestly, that was exactly what I needed without realizing I needed it. Kind people. Open water. Peaceful views. A gentle breeze. No rushing. No distractions. Just quality time with my husband and the chance to simply enjoy being together. Sometimes the best adventures aren’t the loud, adrenaline-filled ones. Sometimes they’re the ones that leave you feeling lighter, calmer, and grateful you took the time to go. This was absolutely one of those adventures. We would do it again in a heartbeat. If you’re considering it, stop considering and book the sail. You deserve a few hours like this. ⛵️🌊❤️

Vintage Fire Truck Sightseeing Tour of Portland Maine

Darlene_M, Aug 2026

Portland by Trolley

Due to rain we were unable to take our fire truck ride . The company up graded us to a trolley ride around the city and it was still a little wet . The trolley car driver was SUPER knowledgeable about the area and share all kinds of interesting stories and tid bits that you wouldn’t normally hear .

Sunset Lighthouse Cruise Along Casco Bay

cphanes78, Jul 2026

Megan and Colter were great!

Our family of 4 enjoyed our experience on a Thursday night in July 2026. Megan and Colter did a great job of telling us some of the history of the area and kept us entertained with fun stories and suggestions of what to do in Portland. This was a very laid back, enjoyable time. Bring food and drink and some sunglasses!

Sunset Windjammer Cruise Along the Coast of Portland Maine

Michaeline_N, Jul 2026

Sailing into Sunset

What a great way to see Portland from the water! The crew was friendly, personable, and knowledgeable. They answered questions with enthusiasm when asked by guests. The ride was smooth and beautiful! We enjoyed seeing Portland Head Light from the water, as well as wildlife, such as seals and porpoises that came really close to our boat as we sailed. We had a great time and highly recommend this activity!

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

Tiffany_G, Jul 2026

Loved The Real Portland City Tour!

Derek was PHENOMENAL! He is a local with so much knowledge about Portland’s history. On this tour, you’ll see the city and explore a couple of lighthouses all while learning about the city. Other highlights included the intimate tour (only 15ish spots) versus larger, more impersonal tours, and recommendations from Derek regarding local spots to be sure not to miss!

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

David_V, Jul 2026

Ally (sp?) was a great...

Ally (sp?) was a great guide on our tour of Portland (in the city) and a few lighthouses. She was very knowledgeable of the area and the trips to the lighthouses were especially enjoyable for us. Love the rugged coastline of the area. We did the tour in a comfortable air conditioned van and got out of the van to walk around at the lighthouses. Highly recommend this tour.

Small Group Sunset Lighthouse Boat Cruise With Local Drinks

John_G, Jun 2026

Amazing sunset view with Portland Head Light!

Our pilot Pete, and deckhand Danny provided a fun and informative sunset boat cruise of the Portland harbor. The highlight was positioning the boat perfectly and slowly spinning it a bit for amazing sunset photo with the beautiful Portland Head Light lighthouse. Danny provided informative information about the sights we saw, while Pete navigated us around as the sun set. The boat has a few open air ports and windows in addition to the clear closed windows around the passenger area, so you get a nice breeze without being totally exposed to the elements. Highly recommend this tour!

Portland Bicycle Tour with 5 Lighthouses and XL Lobster Roll

Pamela_B, Oct 2025

Scenic lighthouses and bike trip

Fabulous trip. The guides Scott and Molly were the best! The weather was perfect and the 15 mile bike ride was so beautiful. It was a wonderful way to see the sights of Portland and take pictures of the lighthouses. They also were very knowledgeable and we learned a lot about Portland and the state of Maine. We also had the BEST lobster roll ever!!!! I definitely would recommend this excursion.