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Itinerary for Seven Days of the Best Boothbay Harbor Activities

With so many different scenic Boat Tours available as well as the myriad of other activities Boothbay Harbor offers we have many guests choose us for extended stays for their Boothbay Harbor vacation.  Our guests love our brand new luxury sized Deluxe, Suite or Oceanfront rooms which were designed for our guests comfort with modern sized larger bathrooms & all the modern amenities today’s traveller’s expect.   Lounge in our Oceanside Hot Tub and start your day with a Farm to Table Gourmet full cook to order Breakfast.  

Let us be your personal tour guide!  During you stay with us we provide each room or suite with a walking map of Boothbay Harbor & surrounding peninsulas, as well as, detailed information according to each guest’s interests and preferences regarding restaurants, sights to see, art galleries, boating trips & sailing excursions, and much more.  Follow our 7 day itinerary and see Boothbay Harbor and the Mid Coast of Maine like a local!


  • 3pm: Arrive, sit on our waterfront lawn or pier, dock, float and unwind after a long car ride & watch the tide roll in or out slowly, begin to decompress

  • 4pm: Take a short Walk to downtown & peek in stores 

  • 5pm-7pm: Make reservations & enjoy a gourmet meal at Ports of Italy

  • 7:30pm: Ice Cream at BBH Ice Cream Factory

  • 8pm: See schedule for Opera House events located across the street

  • 8:15-9pm: Relax and unwind in our Oceanside 7 person Hot Tub as you watch the tide come and go



  • 9am: Head to the famous Coastal Maine Botanical Gardens to explore 300 acres of gorgeous plantings & Lunch there or (take a left out of the Gardens then another left onto Sawyer’s Island Road onto Samoset road then right onto Lakeside Drive) to West Boothbay Harbor & Southport where Robinson’s Wharf for lobster outside seating or Olivers for fancier fare

  • 1pm: Stop at the Maine State Aquarium 

  • 5pm: Enjoy a Sunset Sail 2 hour schooner

  • 7pm: Dinner at Thistle Inn



  • 9am-4pm: Jump on the boat to Monhegan Island and explore the sights from the 13 miles out to sea, bring a lunch or eat at one of the restaurants or brewer there

  • 5pm-7pm: Relax in ourHot Tub & lounge on decks

  • 7:30: Head downtown to enjoy tapas or entrees at Boat Houe Bistro (Lobster Thermadore is one of their signature dishes) & sit inside or up on their 3rd floor open air deck



  • 9:00am: Stop at the Railway Museum and explore the large antique car museum and the Village exhibit that is fascinating for history buffs, ride the antique steam train 

  • 10:30am: Take River Road for a scenic drive to downtown Damariscotta, then Head South down 130South to Pemaquid

  • 11:30pm: Stop at Pemaquid Beach (if you don’t have beach towels we can provide them) to walk a sugar sand beach (rare for our area)

  • 1pm: Have lunch outside at the Beach or Contented Sole Restaurant (nearby)

  • 3pm:  Venture into Fort Pemaquid to see a colonial historic site

  • 4pm: Climb to the top of Pemaquid Point Lighthouse for an wide outer ocean view

  • 6pm: Have an outside Lobster Dinner at Shaws Lobster or Pemaquid Lobster 



  • 9am-11: Head out to the Atlantic Ocean and see look for Whales or Puffins Watching or see the coastline via Scenic Harbor Tours all from Capt. Fish’s Boat Tours on Pier 1 & 7

  • 11-11:45am :Walk downtown and browse shops in more detail

  • Noon: Lunch at Shannon’s Unshelled Lobster Rolls or Red’s Eats famous lobster rolls

  • 1-4pm: Head to Wiscasset to browse stores and historical Museums

  • 4-5pm: Head to Indian Trail Antiques for 3 floors of fun antique shopping

  • 5-6pm: Walk downtown Damariscotta’s local shopping and explore the quaint village and shops

  • 6:30pm: Dinner at King Eider’s Pub or Boothbay Craft Brewery Watershed Tavern

  • Drive The River Road back to Boothbay Harbor



  • 9:30a Head to one of the many Land Preserve (Porter or Oven’s Mouth) sit on the water in the peace of the Maine woods

  • 11:30: at  Bet’s Fish Fry (½ or 1 pound per order) or Trevitt Store (Crab Roll)  or take food from East Boothbay General Store Gen Store for a picnic lunch

  • Noon: Drive South on 96 out to Ocean Point (wide beach view, not common in this part of main w/long peninsulas) walk around,  (if you don’t have beach towels we can provide them)pictures of Ram Island Lighthouse and the many fishing boats, bring jackets as it’s 10 deg cooler there

  • 1pm: Drive down King Phillips Trail for great views

  • 2pm: Come back to the Inn and walk to Tidal Transit to Rent Kayaks or take a guided tour 

  • 6pm: Dinner at Boothbay Lobster Wharf, Kaler’s Lobster, Mine Oyster or Boathouse Bistro for lobster or oysters or dinner at Harbor Side Tavern.

  • Ice Cream at Wannawaf

  • 8pm: Hot Tub to unwind and relax



  • 9am: Get an early start & head North to Camden/Rockland area

  • 9:45am: Stop at the Nobleboro Antique store or do a Winery Tour

  • 10:30am: See Marshall Point Lighthouse (feature in Forest Gump) 

  • 11:00am: Owl’s Head Lighthouse, explore the short walk up to the high bluff with great view of Penobscot Bay

  • Noon – Stop at Owl’s Head Transportation Museum or Farnsworth Museum

  • 12:30pm: Lunch in downtown Rockland — walk main street and stop and one of the many great restaurants there as well as the many shops 

  • 1:30pm: Walk the 3/4 mile on wide granite boulder/block out to the Rockland Breakwater Lighthouse

  • 2pm: Drive up Mt.Battie to oversee all of Penobscot Bay and see if you can see the 3 mountains of Acadia National Park in the horizon

  • 4:00pm: Drive up to Belfast if interested and have time to explore another town or just Walk Camden and shop

  • 5pm: Dinner at Primo’s – 2x James Beard winner, get there at 5 sharp and sit upstairs where no reservation required.  Order from the tapas menu or from the entree menu, outstanding.


Some other options that are more specialized would be:

  • Championship Golf and lunch

  • Burnt Island Lighthouse Tour & Cabbage Island Clambake (mid June-early Sept only)

  • Maine Maritime Museum & Popham Beach (1 hour drive South)

  • Freeport Shopping (1 hour drive South)



The Harborage Inn has maintained a long standing tradition and history of delivering guests a most pleasurable & relaxing vacation on the Maine Coast.  We take great pride in maintaining these high standards in our family run business of over 47 years.  Come stay at the Inn that is often imitated but can never be replicated for the ultimate Boothbay Harbor experience


We look forward to pampering you!




Let us be your personal tour guide!



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