The 9 Most Romantic Things To Do in Portland and Southern Maine

Why wait for Valentine's Day?

Lobster Trap Tree Hearts

Robert Dennis, courtesy of the 

Kennebunk, Kennebunkport & Arundel Chamber of Commerce


Want to plan a romantic date or celebration in Maine? Here's your guide to nine of the best things a twosome can do together in Portland and along the southern Maine coast this Valentine's Day or any day.

01 of 09

Paint the Town Red in Kennebunkport

Paint the Town Red in Kennebunkport

Heidi Kim,  courtesy of the Kennebunk, Kennebunkport & Arundel Chamber of Commerce

In Kennebunkport, Maine, Valentine's Day lasts the entire month of February. "Paint the Town Red" is an area-wide promotion featuring "red tag," "red plate" and other special deals and events during this romantic month. Downtown businesses are decked with hearts and lit up in twinkly red lights for these 28 days of special hotel packages, restaurant menus, retail sales, brewery tours, wine tastings, culinary classes and pop-up dinners. An ice bar kickoff party is the annual highlight.

02 of 09

Visit Portland Head Light

Head Light, Portland, Maine
Carol M. Highsmith/Buyenlarge/Getty Images

What is it about lighthouses that draws people? Portland Head Light is one of the most photographed lighthouses in Maine and is a favorite spot for couples to snap pics on a romantic stroll. A museum in the former keeper's house is open seasonally. High tide's the most dramatic time to visit and to watch the roaring surf. If you love lighthouses, this driving tour will take you to four more nearby.

03 of 09

Dine at the White Barn Inn

Romantic Dining in Maine at the White Barn Inn

© Kim Knox Beckius

Maine has a surprising number of unforgettable restaurants. One of the finest is the rustic yet exquisite White Barn Inn in Kennebunkport. Whether or not you spend a romantic night at the inn, make reservations to enjoy an elegant dinner in the restaurant, which was described in Boston Magazine as "achingly romantic." Multi-course, prix fixe menus are updated weekly to showcase the best of Maine's harvest from land and sea.

04 of 09

Explore Portland's Old Port District

Fresh fish shop in Old Port district
Peter Ptschelinzew / Getty Images

The Old Port is a delightful waterfront shopping district where couples can spend hours walking cobbled streets lined with Victorian buildings, ducking in and out of shops and art galleries and sipping fresh beer or feasting on sea fare. The atmosphere's especially lively in the summer and during the holiday season. Portland is one of New England's best destinations for jewelry lovers, so treat your sweetie to a blingy souvenir. Maine's official state mineral—tourmaline—is the stone to look for.

Continue to 5 of 9 below.
05 of 09

Treat Yourselves to Concert Tickets for Two

Enjoy a romantic evening of music by the Portland Symphony Orchestra, a popular music concert or a Broadway show at Merrill Auditorium: Portland's former City Hall turned 1,900-seat concert venue. There are more than a dozen restaurants a short walk away, so make reservations to enjoy a bite before the show at local favorites like David's Restaurant, UNION Restaurant or the small-plate-focused Portland Hunt & Alpine Club.

06 of 09

Get Away to Grey Havens Inn

Grey Havens Inn
Courtesy of Grey Havens Inn

Maine has many romantic inns tucked away along the coast, in the mountains and in quaint villages. One of the most romantic, and a favorite Maine wedding site, is the turreted Grey Havens Inn in Georgetown, an island accessible by a bridge and less than an hour's drive from Portland. The view of spruce-covered islands and ocean bay from the wide wraparound porch, the lawn and some of the rooms is unsurpassed.

07 of 09

Walk Along the Marginal Way

Marginal Way Ogunquit Maine

© Kim Knox Beckius

The Marginal Way, a one-mile-long footpath that meanders along the rocky shore in Ogunquit, Maine, offers the romance of crashing surf and scenic views. The wind can be brisk in cooler weather, so bundle up. This is a popular spot for engagement photos: There are dramatic backdrops galore and sunsets can be spectacular. When you reach Perkins Cove, share a lobster roll and visit all of the cute, little galleries and shops.

08 of 09

Picnic Aboard a Schooner

Pack your favorite beverages and nibbles for a romantic picnic aboard the Schooner Eleanor, which sails out of Kennebunkport on two-hour scenic cruises down the Kennebunk River and along the southern Maine coast. Built by its captain, Rich Woodman, and a team of local craftsmen, Eleanor launched in 1999, but it is modeled after traditional wooden sailing yachts of the 1930s. Trips are available two or three times daily from late May through early October. Book a private charter for the ultimate romantic experience.

Continue to 9 of 9 below.
09 of 09

Enjoy the Views from Portland's Eastern Promenade

Sunrise on Fort Gorges in Portland Harbor, Maine.
Mark Marchesi / Getty Images

Walk hand-in-hand along the Eastern Prom, a paved trail with views of Fort Gorges and the islands of Casco Bay. Stop to sit on the rocks and watch the boats come and go in Portland Harbor.

Was this page helpful?