Overall Trip Highlights

• Explore Historic Portland – Wander through Portland’s charming and historic neighborhoods, rich in maritime history and architecture.
• Iconic Maine Lighthouses – Visit and view some of Maine’s most famous lighthouses along the scenic coastline.
• Boutiques & Unique Shops – Discover hidden gems in local boutiques and specialty shops, offering unique finds from Maine artisans.
• Farm-to-Table & Lobster Feasts – Indulge in Maine’s iconic lobster, freshly caught and served in authentic seaside settings, alongside farm-to-table dining that showcases the state’s local flavors.
• Charming Main Street Communities – Experience the quaint charm of Maine’s picturesque towns, each with its own unique character and history.
• Casco Bay Island Cruise – Take a scenic cruise around Casco Bay, offering stunning views of the islands and wildlife.
• Maine’s Maritime Legacy – Immerse yourself in Maine’s rich maritime history with visits to museums and historical sites.
• Kennebunkport Excursion – Visit the famous coastal town of Kennebunkport, known for its history, scenic beauty, and summer homes of presidents.
• Arts District of Portland – Explore Portland’s vibrant Arts District, featuring galleries, theaters, and street art that reflect Maine’s creative culture.
• Relaxing Coastal Scenery – Soak in the breathtaking views of Maine’s rugged coastline, pristine beaches, and forested landscapes.

Don’t just tour Maine, Experience Maine

Portland, Maine is one of New England’s most vibrant seaside cities: a place where lobstermen and lawyers walk the same streets, and every quintessential coastal experience you’ve imagined is either within city limits or a short drive away. Of course, that means lighthouses are a part of Portland’s fabric. One of Maine’s most photographed beacons—Portland Head Light—is a treasured symbol of the city and a romantic spot for a stroll—and four more lighthouses are within a 20-minute driving distance. Build your lighthouse-themed itinerary with these tips for finding, visiting, and photographing Portland’s lighthouses. 

Every Beatrice Bradley trip is crafted to maximize the experiences had during the trip.

The itineraries are specially made to allow time for engaging in conversation and having belly laughs with a new friend. We hope that the activities and experiences may allow you to come out of your comfort zone and to try new or unique things.
These trips are made to replicate a ‘friends get-away trip’. 

Past Trip Reviews

Small group size was great, hosts were excellent. Smaller group meant that they could meet individual needs and we were able to get to know each other quickly. I had travel delays, Jane was great in making sure I had airport pick up and able to join the activities quickly. –Catherine

Trips with Beatrice Bradley make it feel as though you’re not traveling solo. The hosts make it so comfortable getting to know each other. All of the guests are open to making friends and the small groups enhance this opportunity. On my first trip I didn’t know anyone before arriving. On my second trip I knew one of the hosts, Shayne. I never felt alone. –Rhonda

Day One: Lobsters, Lighthouses, and New Friends in Portland

As your plane lands at Portland International Airport (PWM), the crisp sea breeze instantly fills the air with excitement. You’re met by a friendly hostess who whisks you away to the enchanting Portland Harbor Hotel nestled in the historic Old Port District, where the other hostess will welcome you. The cobblestone streets and vintage charm create the perfect setting for the start of this unforgettable journey. Once settled in, the evening truly begins as you gather with fellow adventurers for a Welcome Happy Hour. Laughter fills the air, and with every clink of glasses, new friendships blossom. Dinner at the Harbor Bistro & Terrace is a time for connection, sharing stories and toasting to the adventures yet to come under the warm glow of the setting sun.

Highlights

• Convenient Airport Pickup: Arrive at Portland International Airport and be greeted by a BB hostess with warm smiles before being transported to the heart of Portland’s Old Port District.
• Check-in and Relaxation at Portland Harbor Hotel:  The other BB hostess will greet you at the hotel and you will settle into the elegant Portland Harbor Hotel, where history meets luxury in a romantic coastal setting.
• Welcome Happy Hour: Enjoy a toast at the Harbor Bistro, where the first sparks of new friendships light up the evening.
• Group Dinner at Harbor Bistro & Terrace: Dine under the soft, flickering lights at the hotel’s terrace, sharing heartfelt stories and laughter as you connect with fellow travelers.

Fun Fact: Portland’s Old Port District is home to centuries-old buildings that have witnessed the romance of many maritime love stories over the years.

Day Two: Lighthouses, Lobsters and Coastal Adventures

The day begins with a delicious breakfast at the Harbor Bistro, where you’ll sip your coffee while gazing out over the historic streets of Portland. Afterward, we will head to the port for a scenic Harbor Lights & Sights cruise. The crisp sea air carries the scent of saltwater as we glide through Casco Bay, passing iconic lighthouses like the Portland Head Light, which has been guiding ships since the days of George Washington. We’ll also spot hardworking lobster boats hauling in the fresh catch of the day. After the cruise, we head to the Lobster Pound to see the afternoon’s fresh haul, then indulge in a mouthwatering lobster lunch by the water at The Porthole Restaurant. The afternoon is yours to explore Portland’s vibrant streets, filled with charming shops and local treasures. In the evening, we gather once more for dinner at the stylish Via Vecchia, where stories of the day’s adventures flow as easily as the wine.

Highlights

• Group Breakfast at the Harbor Bistro: Start the day with a delicious breakfast together at the hotel’s charming bistro.
• Harbor Lights & Sights Cruise: Marvel at iconic lighthouses, lobster boats, and the stunning coastline of Casco Bay on this unforgettable boat tour.
• Lobster Lunch at The Porthole Restaurant: Savor a fresh lobster feast right by the water after seeing the catch of the day at the Lobster Pound.
• Explore Portland: Enjoy a free afternoon to shop, stroll, and discover the hidden gems of Portland’s historic streets.
• Group Dinner at Via Vecchia: Share stories and laughter over a delicious dinner at one of Portland’s most beloved restaurants.

Fun Fact: Portland Head Light, Maine’s oldest lighthouse, was commissioned by George Washington himself in 1791!

Day Three: Kennebunkport Excursion!

The day begins with a cozy breakfast at the Harbor Bistro before we set out for an adventure to Kennebunkport. Kennebunk’s Lower Village & Kennebunkport’s Dock Square are located along the ocean and Kennebunk River. Settled in the 1600’s and a long time ship building mecca, the river banks saw five-masted ships and schooners making their way down the river on their way to the sea. Sea captains built fine mansions, many of which are preserved today as lovely inns with antique charm. On the way to Kennebunkport, we will be stopping by the Seaside Trolley Museum to take a ride on the trolley and learn the history of trolleys in that area.  Then we will stop to see the Goat Island Lighthouse, a remarkable lighthouse on an island, viewable from the Cape Porpoise Pier.  Our next stop will be to view the Bush Compound on our way into the darling town of Kennebunkport.  We will spend a few hours in Kennebunkport shopping and having lunch before we head back to Portland!

Highlights

• Group Breakfast at the Harbor Bistro: Start your day with a delicious breakfast at the hotel before heading out on the day’s adventures.
• Stopping by the Seaside Trolley Museum: Enjoy a scenic tour on a the historic trolley and learn the history of trolleys in the area.
• Visit to Portland Head Light: Stop for photos and admiration of another beautiful lighthouse, Goat Island Lighthouse.
• Stopping by to view the Bush Compound in Kennebunkport
• Visiting the adorable town of Kennebunkport: You will be able to shop and explore in Kennebunkport and have lunch at a cute restaurant.
• Group Dinner at David’s Restaurant: End the day with a delicious group dinner at one of Portland’s top dining spots.

Fun Fact: Kennebunkport is the home to the Bush Summer home where both Presidents and their families spend time every summer.

Day Four: Trolleys, Timeless Streets and a Farewell to Remember

The morning begins at the beloved Becky’s Diner, where you’ll enjoy a hearty breakfast like a true Portlander. After breakfast, we’ll hop on a narrated trolley tour that takes us through the historic Portland Peninsula. You’ll get to hear fascinating stories of Portland’s rich history as we pass by charming streets, historic buildings, coastal views and you will stop by the Portland Headlight Lighthouse. After the tour, you’ll have some free time to explore the city at your leisure—whether that means discovering hidden shops, grabbing lunch at a local café, or simply soaking in the maritime atmosphere. As the day winds down, we’ll gather for a rooftop Happy Hour at the Luna Bar, with sweeping views of the city and ocean, before our Farewell Dinner at the Old Port Sea Grill. It’s the perfect setting to toast to new friends and the unforgettable memories we’ve shared.

Highlights

• Breakfast at Becky’s Diner: Kick off the day with a classic diner breakfast at one of Portland’s most famous local spots.
• Narrated Trolley Tour of the Historic Portland Peninsula: Sit back and relax as we explore the rich history and charming streets of Portland on a guided trolley ride.
• Free Time in Portland: Enjoy a leisurely afternoon to explore Portland’s shops, cafés, and landmarks at your own pace.
• Rooftop Happy Hour at Luna Bar: Sip cocktails with panoramic views of the city and coastline from this chic rooftop bar.
• Farewell Dinner at The Old Port Sea Grill: Share a final meal and toast to friendship, adventure, and the beauty of Maine’s coast.

Fun Fact: Becky’s Diner has been a Portland staple since 1991, serving up classic diner fare to locals and travelers alike, and was even featured on “Diners, Drive-Ins and Dives”!

Day Five: Farewells and Fond Memories

As the sun rises on your final day in Maine, we’ll gather one last time for a heartfelt farewell breakfast at the Harbor Bistro. Over a delicious meal, you’ll swap stories and laughter with the new friends you’ve made, reminiscing about the adventures shared. After breakfast, we’ll check out of the hotel and escort you to the Portland airport in time for your departure. If time allows before your flight, you can sneak in some last-minute shopping or explore a bit more of Portland’s charming streets. While the trip may be ending, the memories and friendships will last long after you’re home.

Highlights

• Farewell Breakfast at Harbor Bistro: Share a final breakfast with new friends, reminiscing about the adventures of the week.
• Last-Minute Shopping or Exploring: If time permits before your flight, enjoy a little more of Portland’s charm.
• Departures to Home: Head to the airport with new memories and friendships from your Maine adventure.

Fun Fact: Portland has over 230 miles of shoreline—perfect for one last glimpse of the ocean before you head home!

Note: This itinerary serves as a general guide to what we will be doing, seeing, and eating, with the final version provided approximately two weeks prior. The published itinerary is an example and may be adjusted to include accommodations, tours, or restaurants of comparable quality to ensure the best experience.

***The itinerary is subject to change