Portland Small Group Tours

Discover top small group tours in Portland Maine. Experience lighthouses, local cuisine, historic sites, and unique city adventures with expert guides.

No tours match these filters.

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
Casco Bay Half-Day Sea Kayak Tour

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 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
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
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
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 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
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
Oyster Farm & Complimentary Tasting Sea Kayak Tour in Casco Bay

Oyster Farm & Complimentary Tasting Sea Kayak Tour in Casco Bay

Tasting oysters harvested from the ocean where they were grown is significantly different and better than eating them at an oyster bar, especially when you just

★ 4.8 (36)
From $99.00 USD
Paint Portland, Maine: Small Group Outdoor Painting Experience

Paint Portland, Maine: Small Group Outdoor Painting Experience

Immerse in and interpret the natural beauty of Maine by capturing the moment in a painting. We will hike and paint on location. No experience necessary. This is

★ 4.9 (13)
From $150.00 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 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 ME: Casco Bay Boat Tour w/ Island Yoga + Mimosas or Wine

Portland ME: Casco Bay Boat Tour w/ Island Yoga + Mimosas or Wine

This experience combines three things you rarely get in one outing: a small-group boat tour, yoga on a Casco Bay island, and a celebratory drink on the water. C

★ 5.0 (2)
From $185.00 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 Walking Food Tour – Warm Donuts, History & Hidden Gems

Portland Walking Food Tour – Warm Donuts, History & Hidden Gems

Portland, Maine is known for its culinary scene, including amazing donuts. With this tour, you'll get to sample from the city's best donut shops, while also lea

★ 4.8 (231)
From $69.49 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
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 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
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
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

Reliable & Guaranteed Tickets

Browse trusted tours and experiences in Portland. Compare options, read ratings, and book with confidence.

Prices and availability are subject to change. Product details are provided by our partners and may be updated without notice.

You may also like

Speed Boat Rentals Category

Speed Boat Rentals

1 experiences

Sports Lessons Category

Sports Lessons

2 experiences

Spring Break Category

Spring Break

2 experiences

Stand Up Paddleboarding Category

Stand Up Paddleboarding

1 experiences