Romantic Honeymoon Itinerary in Portland, Maine

Day 1: Arrival and Exploration

Portland, Maine

10:00AM

Check into Hotel

Begin your honeymoon by checking into the luxurious Portland Harbor Hotel, where beautiful harbor views await.
Walk to the hotel from Portland International Jetport, approximately 10 minutes away.
USD200, 1 hour

11:30AM

Breakfast at Becky’s Diner

Savor a delicious breakfast featuring blueberry pancakes and fresh coffee at this classic spot.
Drive or take a short cab ride to Becky's Diner, 5 minutes away.
USD30, 1 hour

1:00PM

Explore Old Port District

Stroll through the cobblestone streets filled with charming shops and waterfront views.
Walk from the diner to Old Port, a 10-minute stroll.
Free, 2 hours

3:00PM

Visit the Portland Head Light

Marvel at Maine's most photographed lighthouse while taking a picturesque walk along the cliffside park.
Drive to Fort Williams Park, about 15 minutes.
Free, 1.5 hours

5:00PM

Dinner at The Lobster Shack

Indulge in fresh lobster rolls and chowder with ocean views, perfect for a romantic evening.
Drive to Cape Elizabeth, approximately 10 minutes.
USD70, 1.5 hours
View Hotel Availability

Day 2: Adventure and Culture

Portland, Maine

9:00AM

Breakfast at Tandem Coffee Roasters

Start your day with freshly brewed coffee and baked goods at this local favorite.
Drive to Tandem Coffee Roasters, about 10 minutes.
USD25, 1 hour

10:30AM

Visit the Portland Museum of Art

Explore the rich art collections, featuring works by Winslow Homer and other American masters.
Short drive, about 5 minutes.
USD18, 2 hours

1:00PM

Lunch at Eventide Oyster Co.

Savor an oyster tasting or fresh seafood dishes in a vibrant atmosphere.
Walk from the museum to Eventide, approximately 12 minutes.
USD60, 1.5 hours

3:00PM

Take a Sunset Cruise

Enjoy stunning views of the coastline as you relax together on a romantic boat ride.
Walk to the Old Port dock from Eventide, about 10 minutes.
USD80, 2 hours

5:30PM

Dinner at Fore Street

Experience a farm-to-table menu with seasonal dishes that showcase local ingredients.
Short walk from the dock to Fore Street, approximately 5 minutes.
USD120, 2 hours
View Hotel Availability

Day 3: Coastal Delights

Cape Elizabeth, Maine

8:00AM

Breakfast at The Good Table

Enjoy a hearty breakfast buffet at this cozy local eatery before heading to your next adventure.
Drive to The Good Table from Portland, 15 minutes.
USD40, 1 hour

10:00AM

Visit Fort Williams Park

Spend the morning exploring the historic buildings and gardens surrounding the lighthouse.
Drive to Fort Williams Park, about 10 minutes.
Free, 2 hours

12:30PM

Lunch at The Tides Beach Club

Dine with a view of the beach, enjoying delicious coastal cuisine.
Drive to Tides Beach Club, about 20 minutes.
USD80, 1.5 hours

2:30PM

Kayaking at Cape Elizabeth

Embark on a guided kayaking adventure in the serene waters, perfect for some couple's bonding.
Drive to the kayak rental service, approximately 10 minutes.
USD100, 2.5 hours

5:00PM

Dinner at The Sea Glass

Indulge in delectable seafood while enjoying stunning sunset views overlooking the ocean.
Drive back to The Sea Glass, roughly 10 minutes.
USD110, 2 hours
View Hotel Availability

Day 4: Island Escapade

Peaks Island, Maine

8:30AM

Breakfast at Your Hotel

Enjoy a leisurely breakfast at your hotel to fuel up for a day of adventure.
Grab breakfast on-site at Portland Harbor Hotel.
Included, 1 hour

10:00AM

Ferry to Peaks Island

Take a scenic ferry ride to Peaks Island, an idyllic getaway for exploration and relaxation.
Walk to the ferry terminal, about 10 minutes.
USD15, 30 minutes

11:00AM

Bike Rental on Peaks Island

Rent bikes or tandem bikes to explore the island’s charming coastline and unique sites.
Rent bikes at the local shop near the ferry terminal.
USD30, 1 hour

1:30PM

Lunch at The Inn on Peaks Island

Relax and refuel with a delicious island-inspired lunch at this local gem.
Bike to The Inn on Peaks Island, about 15 minutes.
USD60, 1.5 hours

3:00PM

Explore the Island

Enjoy scenic vistas and tranquil beaches as you explore Peaks Island together.
Bike around the island at your leisure.
Free, 2.5 hours

5:30PM

Return Ferry to Portland

Head back to Portland as you cherish the lovely memories created on your island escapade.
Bike back to the ferry terminal, return bikes and board the ferry.
USD15, 30 minutes

7:00PM

Dinner at The Olive Garden

Celebrate your adventures with a comforting Italian dinner as you reminisce about your day.
Drive to The Olive Garden, approximately 10 minutes.
USD70, 1.5 hours
View Hotel Availability

Day 5: Charming Kennebunkport

Kennebunkport, Maine

8:30AM

Breakfast at Your Hotel

Start your day with another lovely breakfast before your trip to Kennebunkport.
Enjoy breakfast on-site at Portland Harbor Hotel.
Included, 1 hour

10:00AM

Drive to Kennebunkport

Set off on a romantic drive along the coastal route to gorgeous Kennebunkport.
Drive to Kennebunkport, around 30 minutes.
Free, 30 minutes

10:30AM

Explore Dock Square

Stroll through the charming shops and galleries in this iconic coastal town.
Walk around Dock Square.
Free, 2 hours

1:00PM

Lunch at The Boathouse Waterfront Restaurant

Enjoy delightful local seafood or a burger by the water, soaking up the vibrant atmosphere.
Walk to The Boathouse, about 5 minutes.
USD75, 1.5 hours

3:00PM

Visit the Seashore Trolley Museum

Explore the fascinating history of trolleys with interactive exhibits and vintage cars.
Drive to the museum, around 10 minutes.
USD12, 1.5 hours

5:00PM

Dinner at Mabel’s Lobster Claw

Feast on fresh lobster and other seafood favorites in a cozy, inviting setting.
Drive back to Mabel’s, about 15 minutes.
USD90, 2 hours
View Hotel Availability

Day 6: A Relaxed Farewell

Portland, Maine

9:00AM

Final Breakfast at Palace Diner

Enjoy a nostalgic breakfast experience in this retro diner, famed for its fantastic food.
Drive back to Portland to Palace Diner, about 20 minutes.
USD45, 1 hour

10:30AM

Visit the Victoria Mansion

Discover the grandeur of this historic mansion, filled with stunning architecture and period decorations.
Drive to Victoria Mansion, approximately 10 minutes.
USD15, 1.5 hours

12:00PM

Lunch at Duckfat

Sample gourmet fries and creatively crafted sandwiches at this beloved local eatery.
Drive to Duckfat, about 5 minutes.
USD50, 1.5 hours

2:00PM

Shopping and Souvenirs

Pick up souvenirs and mementos from local shops to cherish your memories together.
Stroll through the local shops in downtown Portland.
Varies, 2 hours

4:30PM

Farewell Dinner at Streetside

Savor a delightful meal in a cozy setting as you reflect on your wonderful honeymoon.
Drive to Streetside, approximately 10 minutes.
USD70, 1.5 hours

6:00PM

Departure

Sadly, your romantic getaway comes to a close as you prepare to depart Portland.
Return to the hotel, pack up, and head to the airport.
Free, 2 hours
View Hotel Availability