Portland City and Lighthouse Trolley Tour
A guided trolley ride that stitches the Old Port, the Western and Eastern Promenades and the lighthouses of Cape Elizabeth into one narrated loop. The best single orientation to Portland and its coast.
Maine
Portland, Maine
Portland is the rare small city that has a working waterfront, a nationally respected food scene, and a string of historic lighthouses all inside a few miles.
Brick Old Port streets rebuilt after the Great Fire of 1866 lead down to wharves where lobster boats still unload, while Casco Bay spreads out beyond with its islands, windjammers and sunset cruises. This guide books the city properly: trolley tours that tie the peninsula to the lighthouses, harbor cruises, kayaking, whale watching, walking food and history tours, and day trips to Freeport, Boothbay Harbor and Kennebunkport. It then matches you with a hotel, from the Old Port boutiques to waterfront towers, because in a city built around the harbor, where you sleep shapes the trip.
Don't miss
Portland City and Lighthouse Trolley Tour
A guided trolley ride that stitches the Old Port, the Western and Eastern Promenades and the lighthouses of Cape Elizabeth into one narrated loop. The best single orientation to Portland and its coast.
Harbor Lights and Sights Cruise
A relaxed narrated cruise around Portland Harbor and Casco Bay that passes working piers, island forts and lighthouses. The easiest, most scenic way to get on the water.
Peek at Portland Sightseeing Trolley Tour
A shorter narrated trolley loop that gives you a quick, low-commitment tour of the peninsula highlights. Ideal for a tight schedule, a cruise stop or a first-hour orientation.
Happy Hour Trolley Tour of Portland Craft Beverages
A trolley-based tour of Portland craft beer, spirits and cider that moves you between tasting rooms without a designated driver. A social, adults-only evening on wheels.
Things to do in Portland, Maine
Hand-picked: every experience here has strong traveler reviews and a verified booking link.
Peek at Portland Sightseeing Trolley Tour
A shorter narrated trolley loop that gives you a quick, low-commitment tour of the peninsula highlights. Ideal for a tight schedule, a cruise stop or a first-hour orientation.
Happy Hour Trolley Tour of Portland Craft Beverages
A trolley-based tour of Portland craft beer, spirits and cider that moves you between tasting rooms without a designated driver. A social, adults-only evening on wheels.
Harbor Lights and Sights Cruise
A relaxed narrated cruise around Portland Harbor and Casco Bay that passes working piers, island forts and lighthouses. The easiest, most scenic way to get on the water.
Sunset Lighthouse Cruise on Casco Bay
An evening sailing timed for golden light on Casco Bay, passing the lighthouses as the sun drops behind the city. The most romantic hour on the water.
Casco Bay Windjammer and Tall Ship Sailing
Raise real sails on a traditional windjammer or tall ship and glide past islands and lighthouses. The most atmospheric way to travel Casco Bay.
Casco Bay Half-Day Sea Kayak Tour
Paddle the sheltered waters of Casco Bay with a guide, weaving between islands, seals and lobster boats. Active, quiet and unforgettable.
Maine Whale Watching Tour from Portland
Head out into the Gulf of Maine to look for humpbacks, minkes and finbacks, with a naturalist narrating. A seasonal highlight for wildlife lovers.
Seven Portland Lighthouses Tour
A guided tour that links the lighthouses around Portland, from Portland Head Light to Spring Point Ledge and Bug Light. Perfect for photographers and lighthouse fans.
Old Port Seafood Lovers Walking Lunch Tour
A guided walk through the Old Port that doubles as lunch, sampling Maine lobster, oysters, chowder and more. The tastiest way to learn the waterfront.
Portland Walking Food Tour: Warm Donuts, History and Hidden Gems
A walking food tour that pairs warm donuts and local bites with Portland history and hidden corners. A lighter, sweeter way to learn the city.
Portland Maine Black History Guided Walking Tour
A guided walk that uncovers Black history in Portland, from free Black communities and abolitionists to the stories behind the buildings. A thoughtful look beneath the postcard.
Where to stay
Hotels we would book ourselves, from splurges to good-value bases.
The Westin Portland Harborview
Downtown / Arts District
A full-service downtown tower in a landmark building, with an on-site spa, restaurant and views toward the harbor. A polished base for a first visit.
Check rates →Portland Harbor Hotel
Old Port
A boutique-style hotel steps from the Old Port, set around a courtyard garden and an easy walk to restaurants, shops and the waterfront.
Check rates →Portland Regency Hotel and Spa
Old Port
A historic brick armory converted into a hotel in the heart of the Old Port, with a spa, a lounge and rooms that mix period character with modern comfort.
Check rates →The Press Hotel Autograph Collection
Old Port / Exchange Street
A stylish hotel in the former Portland Press Herald building, with newspaper-themed design, a restaurant and a prime Exchange Street address.
Check rates →Hilton Garden Inn Portland Downtown Waterfront
Old Port / Waterfront
A dependable mid-range hotel on the waterfront side of the Old Port, close to the ferry terminals and harbor tours.
Check rates →Hyatt Place Portland Downtown Old Port Square
Old Port
A modern, comfortable hotel in the middle of the Old Port, with spacious rooms and a social lobby. Great for travelers who want to be near everything.
Check rates →Canopy by Hilton Portland Waterfront
Old Port / Waterfront
A design-led lifestyle hotel on the Portland waterfront, built around local flavor with a neighborhood feel and an easy walk to the harbor.
Check rates →Residence Inn by Marriott Portland Downtown Waterfront
Old Port / Waterfront
An all-suite hotel with kitchens and extra space, close to the waterfront. A smart choice for families and longer stays.
Check rates →Cambria Hotel Portland Downtown Old Port
Downtown / Old Port
A newer upscale-style hotel at the edge of the Old Port, with modern rooms and a rooftop or lounge feel. A good value alternative to the boutiques.
Check rates →Inn at Diamond Cove
Great Diamond Island, Casco Bay
An island getaway in Casco Bay reached by a short ferry ride from Portland. Quiet roads, water views and a very different pace from the city.
Check rates →Portland, Maine guides
Portland, Maine in Three Days: Harbor, Lighthouses and the Old Port
A three-day plan that sequences a trolley orientation, a lighthouse morning, harbor time on the water and the museums, with tips on what to book ahead.
Where to Stay in Portland, Maine: Neighborhoods and Hotel Types
A guide to choosing between the Old Port, the waterfront, downtown and the islands, with advice on budgets, parking and the best time to book.
Eating and Drinking in Portland, Maine: Lobster, Oysters, Donuts and Craft Beer
A guide to the food and drink scene, from lobster rolls and chowder to oysters, donuts and craft breweries, with tips on how to eat well on any budget.
The Best Time to Visit Portland, Maine: Seasons, Weather and Crowds
What each season in Portland offers, from summer harbor days and fall foliage to quiet winters, with advice on crowds, prices and what is open.
The Lighthouses of Portland, Maine: Where to See Them and How
A guide to the lighthouses around Portland, including Portland Head Light, Spring Point Ledge, Bug Light and Nubble, with tips on tours, cruises and photography.
Day Trips from Portland, Maine: Freeport, Boothbay Harbor, Kennebunkport and More
The best day trips from Portland, with notes on distance, what to see, how to go by tour or car, and how to pair them with a city stay.
