If your cruise ship is docking in Portland, Maine, you’re in for a treat! This charming coastal city is rich in history, brimming with incredible seafood, and easily walkable, making it a perfect port for exploration. In this guide, we’ll take you on a walking tour of Portland’s historic Old Port, showcase its must-visit attractions, and highlight some fantastic restaurants to enjoy during your visit.
Why Portland, Maine is a Great Cruise Stop
One of the best things about Portland is that the cruise terminal is located right in the heart of downtown. Unlike some ports where you need a shuttle or taxi, you can simply step off the ship and start exploring. The city’s waterfront is a beautiful blend of historic charm and modern vibrancy, offering something for every type of traveler.
Portland’s Old Port is famous for its cobblestone streets, historic brick buildings, and bustling waterfront. It’s a fantastic place to experience Maine’s maritime heritage, with fishing boats, ferries, and tour vessels lining the piers. This city is also a food lover’s paradise, especially if you enjoy fresh seafood.
A Self-Guided Walking Tour of Portland’s Old Port
One of the best ways to experience Portland is by taking a walking tour through its historic streets. Here’s a suggested route that will allow you to see the highlights while soaking in the city’s atmosphere.
Start on Commercial Street
Your journey begins on Commercial Street, the main waterfront road lined with old warehouses that have been converted into shops, restaurants, and offices. It’s a lively area with stunning views of Casco Bay, where you’ll see a mix of working fishing boats and tour vessels heading out for whale watching or lobster hauls.
Highlights:
Working waterfront views
Historic brick buildings
Local shops selling Maine-made goods
Stroll Down Exchange Street
From Commercial Street, head inland via Exchange Street, one of the Old Port’s most picturesque streets. This area is known for its charming boutiques, art galleries, and bookstores.
Highlights:
Sherman’s Maine Coast Book Shop – A great place to browse books by local authors, including Stephen King.
Unique clothing boutiques and Maine-themed souvenir shops
Cobblestone streets and historic architecture
Visit Monument Square
As you continue walking up Exchange Street, you’ll reach Monument Square, home to Our Lady of Victories Monument, a tribute to the 5,000 Maine residents lost in the Civil War. It’s a great spot to pause and take in the city’s history.
Highlights:
The historic Portland Public Library
Seasonal farmer’s market (on select days)
Plenty of benches to rest and people-watch
Explore Congress Street & Longfellow’s House
Just beyond Monument Square is Congress Street, one of the city’s main thoroughfares. Here, you’ll find the Wadsworth-Longfellow House, the childhood home of poet Henry Wadsworth Longfellow.
Highlights:
Longfellow House & Maine Historical Society
Beautiful 19th-century architecture
Portland’s vibrant arts district nearby
Head Back to the Waterfront via Wharf Street
A walk down Wharf Street will take you back toward the waterfront. This charming pedestrian-only alleyway is filled with historic brick buildings, string lights, and some of the city’s best restaurants and pubs.
Best Restaurants in Portland’s Old Port
Portland is known as a foodie haven, and the Old Port has plenty of fantastic spots to grab a meal. Here are some top recommendations:
Seafood Lovers’ Picks:
Eventide Oyster Co. – Famous for its brown butter lobster rolls and fresh oysters.
J’s Oyster – A casual, waterfront spot with delicious steamers, lobster rolls, and chowder.
The Porthole – Offers outdoor dining with great views of the working waterfront.
Casual Bites & Pubs:
The Thirsty Pig – A great place for craft beer and locally made sausages.
Gilbert’s Chowder House – Known for their hearty clam chowder.
Becky’s Diner – A Portland staple serving classic Maine comfort food.
Upscale Dining:
Fore Street – One of Portland’s top restaurants, serving farm-to-table American cuisine.
Scales – A high-end seafood restaurant right on the waterfront.
Street & Co. – Specializing in Mediterranean-style seafood dishes.
Other Fun Things to Do in Portland, Maine
If you have extra time, consider these additional activities:
Visit the Portland Observatory
This historic maritime signal tower offers breathtaking views of the city and Casco Bay.
Take a Lighthouse Tour
Portland is home to several beautiful lighthouses, including Portland Head Light, which inspired one of Longfellow’s famous poems.
Ride the Narrow Gauge Railroad
This scenic train ride follows the coastline and offers a unique perspective of the city.
Final Thoughts: Why Portland is a Must-Visit Cruise Port
Portland, Maine, offers a perfect blend of history, walkability, great food, and stunning waterfront views. Whether you’re exploring the cobblestone streets of the Old Port, sampling fresh seafood, or taking in the beautiful coastal scenery, you’re sure to have an unforgettable time.
For more travel tips and cruising insights, be sure to subscribe to Cruising with Crystal and Marshall on YouTube! Stay tuned for our next video, where we’ll take you on a Portland lighthouse tour. Until then, happy cruising! 
