Portland Seasonal

Discover Portland's seasonal tours including lighthouse visits, sailing, kayaking, and cultural experiences. Book your local adventure today!

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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

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 Half-Day Sea Kayak Tour

Explore the beautiful islands of Casco Bay in this four-hour sea kayak tour. After a brief lesson on the basics of sea kayaking, you'll set out with a licensed

★ 4.9 (60)

From $85.00 USD

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 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

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

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

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

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

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

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

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

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

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 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 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

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

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

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

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

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

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

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