Portland Seasonal

Discover Portland's seasonal tours including lighthouse visits, sailing, kayaking, and cultural experiences. Perfect for exploring Maine's coast year-round.

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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 Sailing Escape: Half Day Custom Boat Charter

Casco Bay Sailing Escape: Half Day Custom Boat Charter

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 s

From $199.00 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
Holiday Scavenger Hunt in Portland by Holly Jolly Hunt

Holiday Scavenger Hunt in Portland by Holly Jolly Hunt

Holly Jolly Hunt is a scavenger hunt that is played using an app on your smartphone, that brings your entire family and friends together for holiday cheer. Duri

★ 3.0 (1)
From $20.00 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
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 (135)
From $109.00 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
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
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 Half Day Sailing Charter in Portland Maine

Private Half Day Sailing Charter in Portland Maine

A half-day sailing charter offers a unique and personalized way to explore the stunning Maine coast. Departing from downtown Portland, this private experience a

★ 5.0 (1)
From $475.00 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 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
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
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 (1706)
From $74.00 USD

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