Along the Maine Coast Discover by Land & Sea

10 nights

Explore the Maine coast on this relaxing 10 night holiday.  This unique fly drive allows you to discover the best villages and coastal areas at your own pace and then experience a 3 day Windjammer Cruise, letting someone else guide you into inlets and other coastal areas you would not otherwise see.

On this fly drive holiday you will start in the thriving city of Boston in Massachusetts and then discover the quieter Maine coast, the beautiful Maine islands, Acadia National Park and historical Portland on your way as you circle back to Boston.

Remember we can alter this itinerary to suit you and provide the perfect America fly drive holiday.

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The Breakdown

Here's a day-by-day guide to your itinerary. Feel free to ask us to add other days or ideas and excursions by adding them to your wishlist, so we can give you the best price.

Day 1


Fly to Boston for a two night stay. On arrival you will have time to settle in and have dinner in one of Boston’s excellent choice of restaurants.

2 nights in Boston

Day 2


Boston is a great walking city. This morning get rid of the jet lag and walk part of the Freedom Trail to see historic sites from Boston’s colonial and revolutionary periods. See the Massachusetts State House, the Old North Church and the USS Constitution, the oldest commissioned warship in the world.

Take some time to do a bit of shopping at Quincy Market / Faneuil Hall Marketplace. This lively and historic marketplace area is filled with souvenir shops and boutiques carrying a variety of Boston and New England themed items.

Day 3

Boston to Ogunquit

Collect your car from downtown Boston and drive to Ogunquit at the southern end of the Maine coastline. On the way you might like to stop at Salem, made famous by the witch trials of 1692 that resulted in the execution of 20 men and women; visit the Witch Museum or the Peabody Essex Museum. Another detour could be to the lesser known Cape:  Cape Ann is home to Gloucester and Rockport, both great fishing ports in times gone by and still home to many fisherman, a thriving art scene and some wonderful beaches.

1 night Ogunquit

Day 4

Ogunquit to Camden

This morning explore Ogunquit. This quaint fishing hamlet is one of the most picturesque seaside resort villages in New England. Walk the mile long Marginal Way over rocky ocean cliffs to Perkins Cove. Enjoy a mouth-watering lobster lunch before departing along the coastal road to Camden. You will sleep tonight aboard the boat tied up in Camden which will give you time to get to know your new surroundings.  It also means you can explore some of Camden’s splendid restaurants.

3 nights on the Windjammer Mercantile

Day 5-6

Maines Islands

Sailing Maine’s Islands

After a hearty breakfast Monday, get underway for a three-day adventure exploring

the Islands of Maine. Life aboard follows no set itinerary; where you go will depend on the winds and the tides, the only two things you can be certain of is that your Captain knows all the best bits and will share that knowledge with you and that sometime during your voyage there will be a lobster bake ashore. For the rest, it is time to relax and enjoy the sea air and the good food.

Day 7-8

Camden to Bar Harbor

Return to Camden Harbor by 10 a.m.

Upon returning to land, enjoy the quaint village of Camden before departing for Bar

Harbor, gateway to Acadia National Park.

2 nights Bar Harbor

Day 9

Bar Harbor to Portland

You have a choice of retracing your footsteps following Maine’s scenic coastline south to Portland or if you want to speed up, you can take the I-95 through Augusta. Portland has become a funky city filled with galleries, unique boutiques and shops, and incredible restaurants. Either way, you might like to stop in Freeport home to outlet stores and the renowned outdoor outfitter, LL Bean.

2 nights Portland

Day 10


A day to explore Portland’s historical centre and Old Port. We would recommend taking a picnic to Fort Williams Park overlooking Casco Bay and then visiting The Portland Head Light and Museum.

Day 11

Portland to Boston

This morning depart Portland for Boston Airport but on the way, take time to visit the artisan community of Kennebunkport.

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The View

A selection of images representing the areas and places you will be visiting to give you a glimpse of what lies in store during your holiday.

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Now we need to make the perfect holiday for you and give you a quotation.


Whether you would like to book this exact holiday or to tailor-make it to better suit you, please give one of our knowledgeable experts a call on 020 8776 8709 or send us an email.


Alternatively, take advantage of the Wishlist facility; simply add this itinerary, or any particular destinations or hotels to My Wishlist by clicking on the ADD TO WISHLIST buttons on all pages. To make it easier to save and change the details on your Wishlist at any time, why not register with us? You can also just send your completed Wishlist to us at any time; we will then contact you to discuss your holiday further and send you a detailed quotation.


We are here to make sure we tailor-make your holiday to suit your specific requirements and our friendly, knowledgeable staff are all ready to help.


Booking your holiday with us doesn't end when we send your confirmation out to you, either. Talk to us about adding excursions or room upgrades or even restaurant recommendations; we are here to offer advice all the way up to your departure date. Even when you have left the UK, we are still here to help. For example if your flight that we have booked is delayed or cancelled due to ash cloud, strike, etc, it is down to us to re-arrange your travel. We will do everything we can to make sure your holiday runs smoothly. And better still, we are fully bonded with ATOL and ABTA, so your money is completely protected.

Further Details for this Suggested Itinerary -



Your boat will be the Mercantile, often referred to as the "Prettiest coaster on the Bay." Built in 1916 and restored in 1989, she is 115 feet overall (80 feet on deck) and has accommodations for 29 passengers. A shoal-draft vessel, she was designed to take on and discharge cargo in out of the way places inaccessible to deeper draft vessels. Today, this feature allows her to explore secluded ports including some that the Mercantile originally served as a cargo vessel. The Mercantile has fourteen double cabins with either a double bed or two twin beds, and there is one private single cabin. All have full standing headroom and a window or porthole for light and ventilation. There are three heads in passenger areas and a hot, fresh water shower below decks.


NB Longer cruises on the Mercantile and other vessels are available on request.

If you have a party of 6, we can charter your own vessel for you..

Minimum age 12 unless for a private charter.


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Tailor-making YOUR perfect holiday

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This suggested itinerary is our recommendation but can be tailored to match your requirements

  • We can tailor this trip to suit your specific requirements
  • We can change everything from the hotels & tours to the durations & destinations.