Visit MaineToday's profile on Pinterest.

About The Author


Susan Axelrod

Susan Axelrod's food writing career began in the kitchen; she owned a restaurant and catering business for 15 years before turning to journalism. By day, she is the social media editor for Portland Press Herald. To relax, she bakes, gardens and hikes with her husband and their two dogs, preferably followed by a cocktail or a Maine beer. Susan can be contacted at 791-6310 or On Twitter: @susansaxelrod

Send an email | Read more from Susan

Posted: August 10, 2015

Dining Guide: 5 places for happy hour on a boat

Here are five different ways to enjoy a drink on a deck. And some of them even move.

Written by: Susan Axelrod

For full listings and more restaurants, see our searchable Restaurant & Bar Guide.

Happy Hour Cruise on the RiverTripper

Courtesy photo

Courtesy photo

Schooner Landing Marina, Damariscotta | 888-635-4309 | | $30 adults
The 50-foot long RiverTripper plies the tranquil (saltwater) Damariscotta River, passing by the area’s famous oyster farms, and offering the chance to sea seals, osprey and bald eagles. For the daily Happy Hour cruise, 5 – 7 p.m., Olga Oros serves up cocktails, beer, wine, appetizers and local oysters at Olga’s Boat Bar, while Capt. Chip Holmes regales guests with river stores from the cockpit. Your ticket entitles you to 1 drink and 1 oyster.

DiMillo’s on the Water

Claire Jeffers photo

Claire Jeffers photo

25 Long Wharf, Portland | 207-772-2216 | | $$$
A Portland waterfront landmark since 1982, DiMillo’s is housed in a former car ferry that still floats, but no longer leaves the marina. It’s 206 feet long and seats more than 600 guests in several dining rooms, the large bar, a cozy lounge (with fireplace) and outside decks (which is where you want to be on a glorious summer evening). The decor is distinctly nautical, with lots of polished brass and varnished dark wood recalling the brightwork on a stately yacht. Happy Hour 4 – 7 p.m. Monday-Friday; $1 off all drinks and discounted appetizers.

Cocktail Cruises on the Finestkind III

70 Perkins Cove Rd., Ogunquit | 207-646-5227 | | $18 adults plus cash bar
Finestkind Cruises runs a variety of boat tours aboard traditional wooden boats with an old-time feel. The Cocktail Cruises are offered on the Finestkind III, the largest of the fleet, which holds 66 passengers and has both open deck and inside seating. The 1 hour cruises depart at 5:45 p.m., 7 p.m., and 8:15 p.m. daily; you’ll raise a glass while heading out of Perkins Cove for views of Bald Head Cliff, Marginal Way and Ogunquit Beach.

Wine Sails on the Frances

Shannon Bryan photo

Shannon Bryan photo

Maine State Pier, Portland | 207-749-9169 | | $75
Now in her 10th season, the Frances is a gaff-rigged topsail cutter built in Portland as a replica of the work bing sailboats that were once common in New England. Capt. Megan Jones, who helped to build this gracious vessel, has partnered with sommelier Erica Archer of Wine Wise for Wine Sails on Saturdays and Sundays from 6 to 8 p.m. Taste a variety of wines, snack on cheeses, fruit and nuts, and gain some wine knowledge while Frances sails around Casco Bay. Tickets sell out quickly; reservations are a must. For reservations:

The Boat Bar at The Chowder House

Ted Axelrod photo

Ted Axelrod photo

22 Granary Way, Boothbay Harbor | 207-633-6616 | | $$
You’ve probably experienced bars made from parts of boats, but The Boat Bar is an actual sailboat, a sloop, with part of its mast still in place and the bartender standing in the cockpit. Take a seat on a stool (be prepared to sit sideways to avoid bumping your knees), order a Geary’s on draft (the Boat Bar offers the Summer and the Pale Ale) or the classic sailor’s drink — a Mount Gay rum and tonic — and watch the sunset over the harbor. If you’re hungry, there’s a small menu of sandwiches and snacks.

Key to prices

The approximate cost of two dinner entrees (not including appetizers, drinks, tax and gratuity).
$ – $15 and under
$$ – $16 to $25
$$$ – $26 to $45
$$$$ – $46 and up

Up Next: