Portland Private & Luxury Tours

Discover premium private and luxury tours in Portland, Maine. Enjoy exclusive cruises, lighthouse visits, and cultural experiences tailored for you.

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

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

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 He

★ 5.0 (2)
From $675.00 USD
2-Hour Portland Old Port Ghost Walking Tour

2-Hour Portland Old Port Ghost Walking Tour

Step back in time to the bustling 18th Century port, where shipbuilding, trade, and whispers of strange occurrences at sea filled the air. Known for its picture

★ 4.5 (81)
From $29.00 USD
6 Hours Private Lighthouses and Kennebunkport Tour in Portland

6 Hours Private Lighthouses and Kennebunkport Tour in Portland

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. Thi

★ 4.7 (22)
From $735.00 USD
A Walk Through Time Tour in Portland

A Walk Through Time Tour in Portland

Curious about Portland's history with railroads, fires, wars, famous poets and Hollywood producers? Join us for a Walk Through Time! This tour begins on Commerc

★ 4.9 (517)
From $48.99 USD
Afternoon Lighthouse Cruise Along the Coast of Portland Maine

Afternoon Lighthouse Cruise Along the Coast of Portland Maine

Join us for 1 1/2 hours as we cruise along the rugged coastline, complete with lighthouses, seals, seabirds, and historic forts. Pack a meal, bring your favorit

★ 4.6 (121)
From $64.00 USD
Afternoon Windjammer Cruise Along the Coast of Portland Maine

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 li

★ 4.7 (271)
From $69.00 USD
Around The Peninsula Bike Tour

Around The Peninsula Bike Tour

Discover the rich history and stunning architecture of the City of Portland . Only 3.5 miles long and 3/4 miles wide, the Portland peninsula is packed full of f

★ 4.6 (44)
From $89.00 USD
Audio Guided Walking Tour from Old Port of Portland, Maine

Audio Guided Walking Tour from Old Port of Portland, Maine

On this smartphone-guided adventure, you'll see Portland’s historic streets and discover its stories. Go at your own pace, anytime. The tour never expires. Th

★ 4.2 (64)
From $7.75 USD
Boothbay, Freeport and Maine Botanical Gardens Private Day Tour

Boothbay, Freeport and Maine Botanical Gardens Private Day Tour

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 offe

From $325.00 USD
Camden, Rockland, Pemaquid, and Belfast Private Tour

Camden, Rockland, Pemaquid, and Belfast Private Tour

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 towe

From $325.00 USD
Casco Bay Morning Windjammer Sail

Casco Bay Morning Windjammer Sail

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, c

★ 4.9 (40)
From $61.00 USD
Casco Bay: Private Afternoon Charter on Heart's Desire

Casco Bay: Private Afternoon Charter on Heart's Desire

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

★ 4.0 (1)
From $650.00 USD
Castles of Cape Anne, Massachusetts - Private Day Tour

Castles of Cape Anne, Massachusetts - Private Day Tour

Experience the beauty and history of Ipswich and Cape Ann on this private tour. Wander Castle Hill’s grand estate, explore Ipswich’s heritage, and enjoy Glouces

From $350.00 USD
Experience Portland's Waterfront Public Scenic Powerboat Cruise

Experience Portland's Waterfront Public Scenic Powerboat Cruise

Experience the stunning beauty of Casco Bay on a personalized intimate (up to 6 guests per trip), public 2-hour powerboat cruise. Whether you're looking for a s

★ 5.0 (1)
From $139.00 USD
Guardians of the Harbor Trolley Tour

Guardians of the Harbor Trolley Tour

Hop on the “Guardians of the Harbor” trolley tour, a narrated journey with three lighthouse stops. Explore Portland’s maritime history and scenic beauty, disemb

★ 5.0 (9)
From $59.00 USD
Harbor Lights and Sights Cruise

Harbor Lights and Sights Cruise

Explore the bustling inner harbor, Diamond Pass, and the main shipping channel to get close up views of civil war era forts and as many as 4 lighthouses that gu

★ 4.8 (803)
From $61.00 USD
Intimate Portland Public Sunset Cruise

Intimate Portland Public Sunset Cruise

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 pict

★ 5.0 (1)
From $149.00 USD
Kennebunkport, York and Portsmouth NH Private Tour

Kennebunkport, York and Portsmouth NH Private Tour

Explore the charming coastal towns of Kennebunkport, York, and Portsmouth on this private day tour. Delve into the rich maritime history, enjoy stunning ocean v

★ 5.0 (2)
From $325.00 USD
Large Group Private Wooden Boat Sightseeing & Lighthouse Charter

Large Group Private Wooden Boat Sightseeing & Lighthouse Charter

100% Private Charter for Groups up to 16 — Flat Rate Pricing This exclusive 2-hour boat tour is designed for private groups seeking an authentic, intimate expe

★ 4.7 (7)
From $850.00 USD
Lighthouse Bicycle Tour from South Portland with 4 Lighthouses

Lighthouse Bicycle Tour from South Portland with 4 Lighthouses

Our 3-Hour tour leaves at 11:00 am and follows the scenic South Portland Greenbelt Pathway to three local lighthouses. The first stop on the tour will be Portla

★ 4.9 (131)
From $115.00 USD
Maine Fall Foliage Private Lobster Boat Cruise with Local Drinks

Maine Fall Foliage Private Lobster Boat Cruise with Local Drinks

Experience COLORFUL Maine on this 2-hour sightseeing tour, where you’ll take in the vibrant fall foliage and the best coastal sights in the Portland area. It do

★ 4.6 (11)
From $380.10 USD
Maine Private South Coast Tour Adventure

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, a

From $700.00 USD
Maine Whale Watching Tour in Portland

Maine Whale Watching Tour in Portland

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

★ 3.7 (67)
From $129.00 USD
Morning Lighthouse Cruise Along the Coast of Portland Maine

Morning Lighthouse Cruise Along the Coast of Portland Maine

Join us for 1 1/2 hours as we cruise along the rugged coastline, complete with lighthouses, seals, seabirds, and historic forts. Pack a meal, bring your favori

★ 4.8 (81)
From $59.00 USD
New Hampshire White Mountains Day Tour

New Hampshire White Mountains Day Tour

Our White Mountains Day Tour offers more than just scenic views—it’s a thoughtfully curated journey through New Hampshire’s most charming towns, historic covere

★ 5.0 (2)
From $325.00 USD
Old Port "Seafood Lovers" Walking Lunch Tour in Portland, Maine

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

Learn about Maine's most famous crustacean and the men and women who make their living from trap to table. Stroll along Portland's vital working waterfront , vi

★ 4.8 (157)
From $159.99 USD
Old Port Culinary Walking Tour from Portland

Old Port Culinary Walking Tour from Portland

- Portland's culinary culture is made up of many kinds of artisan food and beverage entrepreneurs from bakers, brewers and chefs to confectioners and more - whe

★ 4.8 (478)
From $159.99 USD
Phantoms Penance and Poltergeists Portland ME Ghost Tour

Phantoms Penance and Poltergeists Portland ME Ghost Tour

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 t

From $26.00 USD
Port City Lights Cruise

Port City Lights Cruise

A fully narrated 60-minute scenic cruise through busy Casco Bay and its innermost islands to see lighthouses, forts, lobster boats, seals, and seabirds. As many

★ 4.8 (317)
From $43.00 USD
Portland Bicycle Tour with 5 Lighthouses and XL Lobster Roll

Portland Bicycle Tour with 5 Lighthouses and XL Lobster Roll

Discover Portland Maine and the shores of Casco Bay by bicycle! Join us for the 5 lighthouse bicycle tour of Portland, Maine featuring the Maine coast, lighthou

★ 4.8 (163)
From $165.00 USD
Portland City and Lighthouse Tour

Portland City and Lighthouse Tour

The most comprehensive tour of Portland! Hop on board a trolley and relax as we show you around. The tour covers all of our most famous sights on the Portland p

★ 4.8 (1265)
From $61.00 USD
Portland Explorer | Maine History, Culture, & 3 Lighthouses Tour

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

Skip the city and head straight to the coast on this dedicated lighthouse tour of Maine’s best lighthouses. Explore three iconic beacons that have guided sailor

★ 4.9 (1004)
From $79.00 USD
Portland Explorer: Working Waterfront Walking Tour with Seafood

Portland Explorer: Working Waterfront Walking Tour with Seafood

Dive straight into Portland’s working waterfront—where the smell of the sea, and the bustle of the wharves, set the tone for an unforgettable walk through the c

★ 4.9 (23)
From $79.00 USD
Portland Maine Self-Guided Driving & Walking Audio Tour Bundle

Portland Maine Self-Guided Driving & Walking Audio Tour Bundle

Explore the beauty and history of Portland with this combo of a walking and driving tour. Dig deep into the city’s history as you stroll down cobblestone street

★ 4.0 (8)
From $24.99 USD
Portland Maine Self-Guided Walking Audio Tour

Portland Maine Self-Guided Walking Audio Tour

Explore the charm, history, and vibrant culture of Portland, Maine with this self-guided walking tour! Immerse yourself in the sights and sounds of this picture

★ 4.3 (13)
From $12.99 USD
Portland Tall Ship Cruise on Casco Bay

Portland Tall Ship Cruise on Casco Bay

What better way to see the delights of Portland than from the sea in one of the famous schooner tall ships. Join us for this mid morning cruise that will make y

★ 4.6 (243)
From $101.66 USD
Portland Underground Railroad Self Guided Audio Walking Tour

Portland Underground Railroad Self Guided Audio Walking Tour

On this walking tour, we’ll explore the city’s significant role in the Underground Railroad and the individuals who helped shape its fight for freedom. The tour

★ 3.4 (9)
From $9.99 USD
Portland's Best Craft Beverages Bus Tour

Portland's Best Craft Beverages Bus Tour

Most recognize Portland, Maine for its vast selection of local craft breweries. And while we retain the title for ‘most breweries per capita,’ we’re experiencin

★ 4.8 (46)
From $99.00 USD
Portland's World of Flavors Tour

Portland's World of Flavors Tour

Introducing Portland’s World of Flavors Walk highlighting hidden gems and great flavors that give Portland its cosmopolitan flair. Enjoy this walkable city with

★ 4.6 (10)
From $159.99 USD
Portland, Maine: Black History Guided Walking Tour

Portland, Maine: Black History Guided Walking Tour

Trace the steps of the Black Portlanders who moved our city, state, and country closer to the ideals of freedom, democracy, opportunity, and equality. Maine’s e

★ 5.0 (162)
From $54.00 USD
Portland, Maine: Hidden Histories Guided Walking Tour

Portland, Maine: Hidden Histories Guided Walking Tour

Meet Portland and the people—of all backgrounds and identities—whose wit and grit have made Maine's largest city what it is today. Your locally-raised guide wil

★ 5.0 (624)
From $54.00 USD
Private Day Tour of Salem MA, from Portland ME

Private Day Tour of Salem MA, from Portland ME

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 w

From $325.00 USD
Private EBike Tour Portland Maine

Private EBike Tour Portland Maine

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 fiv

★ 5.0 (2)
From $349.00 USD
Private Island Fort Tour in Casco Bay: Boat Cruise & Island Tour

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

Board the Elizabeth Grace for this exclusive one-of-a-kind experience. Whether you are a local or visiting from away, the stone fortresses built in the early 19

★ 4.9 (83)
From $109.00 USD
Private Portland Head Light & Midcoast Explorer

Private Portland Head Light & Midcoast Explorer

Experience the beauty of coastal Maine on this private guided tour featuring iconic landmarks, scenic harbors, and charming coastal villages. Your journey begin

★ 4.5 (14)
From $350.00 USD
Private Portland Lighthouses and Kennebunkport Tour - 12 Pax

Private Portland Lighthouses and Kennebunkport Tour - 12 Pax

All our tours take place in a comfortable vehicle with a local driver-guide and can be tailored to your pace. This private tour is done in our larger passenger

★ 5.0 (4)
From $1,508.00 USD
Private Portland Sunset Powerboat Cruise in Casco Bay

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 jou

From $747.00 USD
Private Portland to Acadia & Bar Harbor Experience

Private Portland to Acadia & Bar Harbor Experience

Experience the beauty, history, and charm of coastal Maine on this full-day adventure from Portland. Plan for 10–12 hours, with about three hours of travel each

★ 4.9 (32)
From $400.00 USD
Private Portland to Camden & Midcoast Lighthouse Experience

Private Portland to Camden & Midcoast Lighthouse Experience

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

★ 5.0 (1)
From $350.00 USD
Private Portland to Cape Ann, MA Castles & Coast

Private Portland to Cape Ann, MA Castles & Coast

Discover coastal New England on this private day tour from Portland, Maine to Massachusetts’ North Shore and Cape Ann. This thoughtfully curated experience blen

★ 5.0 (3)
From $350.00 USD
Private Sightseeing Charter on a Vintage Lobster Boat with Drinks

Private Sightseeing Charter on a Vintage Lobster Boat with Drinks

100% PRIVATE TOUR! Step aboard a vintage Maine Lobster Boat for a private, 2-hour lighthouse viewing & sightseeing charter. Leave the crowds behind as we cruise

★ 4.9 (70)
From $380.10 USD
Private Sunset Charter on a Vintage Lobster Boat with Drinks

Private Sunset Charter on a Vintage Lobster Boat with Drinks

Leave the crowds behind and step aboard a vintage Maine Lobster Boat for a private 2-hour sightseeing and lighthouse viewing charter, ending with a breathtaking

★ 5.0 (44)
From $407.40 USD
Private White Mountains Tour with Mount Washington Cog Railway

Private White Mountains Tour with Mount Washington Cog Railway

Experience the breathtaking beauty of New England’s White Mountains on this private guided tour from Portland, Maine. This full-day adventure combines spectacul

★ 5.0 (6)
From $395.00 USD
Private Yacht Tour in Portland, Maine 2hr, 4hr and 6hr Available

Private Yacht Tour in Portland, Maine 2hr, 4hr and 6hr Available

Explore the stunning scenery and rich maritime history of Casco Bay on a private 2hr, 4hr or 6hr powerboat cruise. Ideal for families, friends, or small groups,

★ 5.0 (4)
From $648.00 USD
Sea Kayak to an Island Tour in Casco Bay

Sea Kayak to an Island Tour in Casco Bay

Learn the basics of sea kayaking on land before launching at Mere Point in Brunswick for a leisurely 3 hour morning tour of Northwest Casco Bay!  Often we paddl

★ 4.9 (10)
From $89.00 USD
Self-Guided Audio Tour of Portland’s Historic Old Port District

Self-Guided Audio Tour of Portland’s Historic Old Port District

Discover the vibrant history of Portland’s Old Port on this engaging walking tour. Wander through cobblestone alleys and merchant blocks rich with stories of

★ 5.0 (1)
From $9.99 USD
Small Group Afternoon Lighthouse Boat Cruise With Local Drinks

Small Group Afternoon Lighthouse Boat Cruise With Local Drinks

Have you seen these iconic beacons from the water? Now is your chance! Board the Elizabeth Grace to cruise around Portland Harbor on this one of a kind sightsee

★ 4.7 (61)
From $87.00 USD
Small Group Sunset Lighthouse Boat Cruise With Local Drinks

Small Group Sunset Lighthouse Boat Cruise With Local Drinks

Board the Elizabeth Grace to cruise around Portland Harbor while sipping local craft beer. This 1.5-hour harbor cruise will take you out into Casco Bay. Keep yo

★ 4.7 (121)
From $89.00 USD
Southern Maine Private Tour: Kennebunkport & Nubble Lighthouse

Southern Maine Private Tour: Kennebunkport & Nubble Lighthouse

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

★ 5.0 (3)
From $350.00 USD
Stand Up Paddleboard Tour with Complimentary Oyster Tasting

Stand Up Paddleboard Tour with Complimentary Oyster Tasting

Learn the basics of stand-up paddle boarding on land before launching at Mere Point in Brunswick for a leisurely 2.5 hour morning tour of Northwest Casco Bay! W

★ 5.0 (2)
From $92.00 USD
Sunset & Scenic Private Boat Tour of Portland & Casco Bay

Sunset & Scenic Private Boat Tour of Portland & Casco Bay

Private Casco Bay Cruise – Up to 5 Guests Experience the beauty of Maine’s coast on a private 2-hour tour through the scenic Casco Bay islands. This intimate ch

★ 5.0 (27)
From $650.00 USD
Sunset Lighthouse Cruise

Sunset Lighthouse Cruise

This 105 minute cruise offers guests a chance to relax and unwind as we make our way around the inner islands and lighthouses of the bay at dusk. Enjoy evening

★ 4.8 (250)
From $71.00 USD
Sunset Lighthouse Cruise Along Casco Bay

Sunset Lighthouse Cruise Along Casco Bay

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,

★ 4.8 (59)
From $69.00 USD
Sunset Sea Kayak Tour on Casco Bay

Sunset Sea Kayak Tour on Casco Bay

The hours just before sunset offer the best time for paddling on the waters of Casco Bay. The sky tends to explode with color and the seas often become glassy a

★ 4.8 (129)
From $60.00 USD
Sunset Windjammer Cruise Along the Coast of Portland Maine

Sunset 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 ligh

★ 4.7 (201)
From $77.00 USD
The Maine Experience: Coast, Culture & History

The Maine Experience: Coast, Culture & History

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 $300.00 USD
The Real Portland Tour: City and 3 Lighthouses Historical Tour with a Real Local

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

Welcome to my hometown! Hop aboard for an authentic 1 hour and 45 minute historical sightseeing tour of Portland, Maine and 3 lighthouses with an experienced gu

★ 5.0 (1656)
From $74.00 USD
Two Hour Lighthouse Bicycle Tour from South Portland-Mellow

Two Hour Lighthouse Bicycle Tour from South Portland-Mellow

Our 2-Hour tour leaves at 9 am or 3 pm and follows the scenic South Portland Greenbelt Pathway to two local lighthouses. The first stop on the tour will be Port

★ 5.0 (61)
From $75.00 USD
Ultimate Portland Self-Guided Driving GPS Audio Tour

Ultimate Portland Self-Guided Driving GPS Audio Tour

Experience historic architecture, harbor views, and rich seaside culture with this driving tour of Portland, Maine! Cross the cobbled streets of Old Port, chock

★ 4.0 (68)
From $16.99 USD
Vintage Fire Truck Sightseeing Tour of Portland Maine

Vintage Fire Truck Sightseeing Tour of Portland Maine

This 50-minute sightseeing tour is a fun and unique way to discover Portland, Maine. Board a Vintage Fire Engine and travel back in time as your knowledgeable g

★ 4.8 (954)
From $45.00 USD
Walk With Ghosts in Portland

Walk With Ghosts in Portland

The most immersive way to see Historic Portland is on foot. Our 1 hour 15 minute walking tour takes you down the cobblestone pathways of our historic city in se

★ 4.6 (96)
From $33.00 USD

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