Portland Private Sightseeing Tours

Discover Portland with private sightseeing tours including boat charters, lighthouse visits, and walking tours. Experience personalized adventures today!

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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
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

★ 4.8 (25)
From $735.00 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

★ 4.3 (72)
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 $350.00 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
Freeport, Boothbay Harbor, and Botantical Gardens Day Tour

Freeport, Boothbay Harbor, and Botantical Gardens Day Tour

Experience the beauty of coastal Maine on this private guided tour featuring iconic landmarks, scenic harbors, and charming coastal villages. From Portland tr

★ 4.5 (14)
From $325.00 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

Crowded public cruises make it harder for groups to enjoy Casco Bay together. From Portland's Old Port, charter a classic wooden boat for up to 16 guests, wit

★ 4.8 (8)
From $850.00 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
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 (3)
From $325.00 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

Unearth the stories beneath historic downtown Portland, Maine on this self-guided walking tour! In the Old Port, colonial tales linger around the Customs House

★ 4.3 (13)
From $12.99 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

★ 3.6 (10)
From $9.99 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 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 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 (35)
From $512.87 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 (73)
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 (45)
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 (8)
From $395.00 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
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 (4)
From $325.00 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

★ 5.0 (1)
From $300.00 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 (76)
From $16.99 USD

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