ITINERARY FOR THE WEEKEND OF MAY 17 - MAY 18, 2025

Portland’s May Showers: Sail, Savor, and Explore in the Rain

Experience the charm of Portland, Maine, this May with scenic sails and culinary delights, perfect for embracing the rain. Discover the city’s maritime magic and indulge in its famous lobster rolls, rain or shine.

Embrace the Rain: Portland’s Maritime Magic

Portland, Maine, is a city that thrives on its maritime heritage, and there’s no better way to experience this than by embracing the rain and setting sail on the Casco Bay Windjammer Sail. As the rain lightly taps on the deck of the historic schooner, you’ll find yourself transported back in time, gliding through the pristine waters of Casco Bay. This two-hour evening cruise, available from 6:00 PM to 8:00 PM, offers a unique opportunity to witness the rugged beauty of the coastline, complete with lighthouses, seals, and seabirds.

The windjammer, a wooden vessel listed on the National Register of Historic Places, provides a cozy and intimate setting for families to enjoy the sights and sounds of the sea. Pack a meal, bring your favorite wine or beer, and let the gentle sway of the boat lull you into a state of relaxation. As you sail past Fort Gorges, with its massive granite blocks interwoven with nature, you’ll gain a deeper appreciation for Portland’s rich history and the resilience of its people.

Whether you’re nine or ninety-nine, this sailing adventure is a must-do for anyone visiting Portland. The rain only adds to the charm, creating a misty, magical atmosphere that will leave you with memories to cherish for a lifetime.

Culinary Delights: A Taste of Portland

No visit to Portland would be complete without indulging in its culinary delights, and the Lobster Roll Tour is the perfect way to do just that. Available from 11:15 AM to 1:45 PM, this engaging tour takes you on a journey through the heart of Portland’s lobster industry. As you stroll along the cobblestone streets and bustling waterfront, you’ll have the chance to taste four different styles of lobster rolls from two of the Old Port’s premier vendors.

This VIP experience allows you to skip the lines and dive straight into the flavors of Maine. From cold to hot, picnic style to perfectly sauced, each lobster roll offers a unique taste of the sea. As you savor these delectable treats, you’ll also learn about the history of lobstering in Maine and the current state of the industry. The tour includes a local craft Maine beer or water to complement your fresh roll, making it a perfect midday activity for families looking to explore Portland’s culinary scene.

The rain may be falling, but that won’t dampen your spirits as you enjoy the sights, sounds, and tastes of Portland. With a stunning lighthouse view and the chance to observe working lobster boats and wharves, this tour is a feast for the senses.

Exploring Portland: Rain or Shine

Portland is a city that welcomes visitors with open arms, rain or shine. With its rich maritime history, vibrant culinary scene, and stunning natural beauty, there’s something for everyone to enjoy. Whether you’re sailing through Casco Bay or savoring a lobster roll, you’ll find that the rain only adds to the charm of this coastal gem.

For families looking to make the most of their time in Portland, planning is key. With the Lobster Roll Tour in the morning and the Casco Bay Windjammer Sail in the evening, you’ll have the perfect balance of indoor and outdoor activities to keep everyone entertained. And with the weather forecast predicting partly cloudy skies and a chance of rain, it’s wise to carry an umbrella or raincoat to stay dry during your city exploration.

As the sun sets over the city, casting a warm glow on the waterfront, you’ll find yourself falling in love with Portland all over again. The rain may come and go, but the memories you create here will last a lifetime. So pack your bags, grab your umbrella, and get ready to embrace the rain in Portland, Maine.

Your Journey, Curated by AI
We leverage AI technology to analyze reviews, testimonials, and key data points, ensuring every recommendation we make is based on real insights and designed to inspire your next adventure.
About the Author
Author Image
Olivia Barnes
Olivia is an AI family travel expert gathering data on family-friendly destinations worldwide. Her itineraries cover everything from safaris to theme parks, ensuring parents and kids enjoy every moment with minimal stress.
Popular in Portland
JOURNAL

Savoring Portland: A Seafood Lover’s Walking Adventure

Drawn by the promise of a delicious and informative experience, I embarked on the Old Port Seafood Walking Lunch in Portland, Maine. With a guide as entertaining as AJ, I was eager to explore the city’s rich maritime history and savor its iconic seafood offerings.

Fiona Ridgeway
Jun 22, 2025
Road Trips across the American Midwest
SEASONAL

Portland’s June Weekend: Indoor Escapes and Outdoor Adventures Await!

Experience the best of Portland, Maine, this June weekend with a mix of indoor escapes and outdoor adventures. From rainy day museum visits to sunny coastal walks and thrilling evening tours, there’s something for everyone to enjoy.

Melissa Parker
Jun 6, 2025
Family-Friendly Activities in the USA and Caribbean
SEASONAL

Portland’s Early Summer Weekend: Wine, Waves, and Local Wonders

Experience Portland, Maine’s early summer charm with a weekend of wine tours and sunset cruises. Embrace the changing weather as you explore local flavors and scenic views, making the most of the city’s vibrant culture and natural beauty.

Henry St. James
May 29, 2025
Wine and Culinary Journeys in France and Italy
JOURNAL

Unveiling Portland’s Hidden Histories: A Journey Through Time

Drawn by the allure of untold stories, I ventured to Portland, Maine, to experience the Hidden Histories Walking Tour. Led by the knowledgeable Dugan Murphy, this journey through time offered a captivating glimpse into the city’s past, revealing the narratives that have shaped its identity.

Yuto Saito
May 26, 2025
Cultural Experiences Worldwide
SEASONAL

Memorial Day Weekend in Portland: History and Scenic Cruises Await

Experience the rich history and maritime charm of Portland, Maine, this Memorial Day weekend. With a mix of historical tours and scenic cruises, discover the city’s colonial past and coastal beauty, rain or shine.

Sebastian Wells
May 23, 2025
Historical Travel through Europe
SEASONAL

Mother’s Day Thrills: Art and Adventure Await in Portland, Maine

Celebrate Mother’s Day weekend in Portland, Maine, with a thrilling blend of art and adventure. From painting stunning landscapes to axe throwing and beer tasting, this getaway promises unforgettable experiences amidst the city’s natural beauty and vibrant culture.

Max Donovan
May 9, 2025
Adventure Travel Worldwide
SEASONAL

Portland’s May Showers: Indoor Adventures and Historical Discoveries Await

Discover Portland, Maine’s rich history and vibrant culture this rainy weekend with indoor adventures and historical tours. Embrace the rain as you explore the city’s hidden stories and culinary delights.

Sebastian Wells
May 2, 2025
Historical Travel through Europe
SEASONAL

Rainy Day Escapes: Indoor Adventures in Portland, Maine

Discover Portland, Maine’s indoor gems this rainy weekend with a comprehensive city tour, culinary delights, and vibrant art scenes. Perfect for those looking to explore the city’s culture while staying dry!

Jordan Foster
Apr 25, 2025
City Experiences Worldwide
SEASONAL

Springtime Escapades in Portland, Maine: Discover Outdoor Adventures Amidst Mild Weather

Experience the best of Portland, Maine, this spring with outdoor adventures perfectly suited for the mild weather. From scenic lighthouse cruises to historical bike tours, discover the city’s vibrant culture and breathtaking landscapes.

Jordan Foster
Apr 19, 2025
City Experiences Worldwide