60 days in Maine & Florida Keys Itinerary

60 days in Maine & Florida Keys Itinerary

Created using Inspirock United States trip itinerary planner

Plan created by another user. Make it yours
Drive
1
Bar Harbor, Mount Desert Island
— 7 nights
Drive
2
Camden
— 5 nights
Drive
3
Boothbay Harbor
— 3 nights
Drive
4
Portland
— 8 nights
Fly
5
Key West
— 16 nights
Drive
6
Marathon
— 6 nights
Drive
7
Islamorada
— 8 nights
Drive
8
Key Largo
— 6 nights
Fly

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7
nights
Bar Harbor, Mount Desert Island

Bar Harbor is a town on Mount Desert Island in Hancock County, Maine, United States. The Seal Cove Auto Museum and Whopaints Gallery are good opportunities to explore the local culture. Get outdoors at Shore Path and Champlain Mountain & Beehive Loop Trail. Go for a jaunt from Bar Harbor to Winter Harbor to see Schoodic Point about 46 minutes away. There's lots more to do: play a few rounds at Pirate's Cove Miniature Golf, contemplate the waterfront views at Jordan Pond Path Trailhead, take in the dramatic natural features at Schoodic Peninsula, and take a memorable drive along Park Loop Road.

To see more things to do, maps, and tourist information, you can read our Bar Harbor travel route planner.

Montreal, Canada to Bar Harbor is an approximately 7.5-hour car ride. You can also do a combination of flight and car; or fly. Prepare for little chillier weather when traveling from Montreal in June: high temperatures in Bar Harbor hover around 23°C and lows are around 13°C. Cap off your sightseeing on the 8th (Mon) early enough to go by car to Camden.

Things to do in Bar Harbor

Parks · Outdoors · Nature · Trails

Side Trips

5
nights
Camden

Museum-lovers will appreciate Farnsworth Art Museum and Maine Lighthouse Museum. Visit General Henry Knox Museum / Montpelier and Owls Head Lighthouse for their historical value. Venture out of the city with trips to Penobscot Narrows Bridge and Observatory (in Prospect), Olson House (in Cushing) and Colby College Museum of Art (in Waterville).

For reviews, other places to visit, maps, and tourist information, use the Camden trip itinerary planning site.

Drive from Bar Harbor to Camden in 2 hours. Alternatively, you can take a bus. In June, daily temperatures in Camden can reach 23°C, while at night they dip to 12°C. Finish your sightseeing early on the 13th (Sat) to allow enough time to drive to Boothbay Harbor.

Things to do in Camden

Museums · Parks · Historic Sites · Nature

Side Trips

3
nights
Boothbay Harbor

Boothbay Harbor is a town in Lincoln County, Maine, United States. Your inner history buff will appreciate Pemaquid Point Lighthouse and The Wilson Memorial Chapel. Get in touch with nature at Boat Tours & Water Sports and Reid State Park. Explore the numerous day-trip ideas around Boothbay Harbor: Doubling Point Lighthouse (in Arrowsic), Rockland Breakwater Light (in Rockland) and Round Pond Art Gallery and Shoppe (in Round Pond). There's more to do: step off the mainland to explore Cabbage Island and see the interesting displays at Boothbay Railway Village.

To find reviews, more things to do, ratings, and more tourist information, read our Boothbay Harbor trip itinerary tool.

Traveling by car from Camden to Boothbay Harbor takes an hour. Alternatively, you can do a combination of bus and taxi. In June, daytime highs in Boothbay Harbor are 26°C, while nighttime lows are 13°C. Finish your sightseeing early on the 16th (Tue) so you can drive to Portland.

Things to do in Boothbay Harbor

Historic Sites · Museums · Nature · Outdoors

Side Trips

8
nights
Portland

The Forest City

Maine's biggest and perhaps most vibrant city, Portland was established as a fishing village in 1633 and grew to become New England's largest port.
Discover out-of-the-way places like Portland Head Light and Boat Tours & Water Sports. Let the collections at Ogunquit Museum of American Art and Victoria Mansion capture your imagination. Explore the numerous day-trip ideas around Portland: York Beach (Long Sands Beach & Short Sands Beach), Nubble Lighthouse (in York) and Kennebunkport (St. Ann's Episcopal Church & Ocean Ave). The adventure continues: explore the striking landscape at Perkins Cove, make a trip to Portland Observatory, kick back and relax at Wells Beach, and appreciate the extensive heritage of Marginal Way Walkway.

To find maps, ratings, where to stay, and more tourist information, refer to the Portland itinerary planner.

You can drive from Boothbay Harbor to Portland in 1.5 hours. Other options are to do a combination of taxi and bus; or do a combination of taxi and train. In June, plan for daily highs up to 26°C, and evening lows to 14°C. Wrap up your sightseeing on the 24th (Wed) to allow time to travel to Key West.

Things to do in Portland

Parks · Outdoors · Beaches · Historic Sites

Side Trips

16
nights
Key West

Conch Republic

Located just 140 km (90 mi) from Cuba, Key West is an island only about 6.4 km (4 mi) long and 1.6 km (1 mi) wide.
Your cultural itinerary includes sights like The Ernest Hemingway Home and Museum and Key West Museum of Art & History at the Custom House. Appreciate the collections at Florida Keys Eco-Discovery Center and Fort East Martello Museum. Spend the 27th (Sat) exploring nature at Dry Tortugas National Park. There's much more to do: explore the gorgeous colors at Vandenberg Wreck, get interesting insight from Tours, take in the architecture and atmosphere at St. Paul's Episcopal Church, and look for all kinds of wild species at Key West Butterfly & Nature Conservatory.

For traveler tips, more things to do, photos, and other tourist information, refer to the Key West road trip planning tool.

Traveling by flight from Portland to Key West takes 8.5 hours. Alternatively, you can drive; or do a combination of bus and train. While traveling from Portland, expect a bit warmer days and much warmer nights in Key West, ranging from highs of 36°C to lows of 30°C. Wrap up your sightseeing on the 10th (Fri) early enough to drive to Marathon.

Things to do in Key West

Museums · Parks · Outdoors · Shopping

6
nights
Marathon

Heart of the Florida Keys

A tiny city just 16 km (10 mi) long, Marathon is spread across several islands in the middle of the Florida Keys.
You'll discover tucked-away gems like Dolphin Research Center and Boat Tours & Water Sports. Get a sense of the local culture at Crane Point Museum & Nature Center and San Pablo Catholic Church. There's still lots to do: explore the gorgeous colors at Sombrero Reef, identify plant and animal life at The Turtle Hospital, stroll through Sombrero Beach, and snap pictures at Old Seven Mile Bridge.

To see traveler tips, ratings, maps, and other tourist information, use the Marathon driving holiday planner.

You can drive from Key West to Marathon in 1.5 hours. Another option is to take a bus. In July in Marathon, expect temperatures between 39°C during the day and 32°C at night. Finish your sightseeing early on the 16th (Thu) so you can drive to Islamorada.

Things to do in Marathon

Parks · Wildlife · Outdoors · Beaches

Side Trips

8
nights
Islamorada

The Village of Islands

Islamorada, long recognized as one of the world's top spots for sport fishing, encompasses six islands in the Florida Keys.
Deepen your sense of the past at sights like Pasta Pantaleo Signature Gallery and Indian Key State Historic Site. Your cultural itinerary includes sights like History of Diving Museum and Lobster Trap Art Gift Shop and Gallery. There's much more to do: cast your line with a fishing tour, get outside with Neptune Charters, sample the tasty concoctions at Florida Keys Brewing Company, and examine the collection at Florida Keys History & Discovery Center.

To find traveler tips and tourist information, go to the Islamorada tour itinerary website.

You can drive from Marathon to Islamorada in an hour. Alternatively, you can take a bus. Expect a daytime high around 39°C in July, and nighttime lows around 32°C. Wrap up your sightseeing on the 24th (Fri) to allow time to drive to Key Largo.

Things to do in Islamorada

Outdoors · Parks · Museums · Nature

Side Trip

6
nights
Key Largo

Diving Capital of the World

The northernmost island of the Florida Keys, Key Largo provides stunning scenery, a number of watersports opportunities, and plenty of areas to relax on vacation.
Explore hidden gems such as Molasses Reef and Fishing Charters & Tours. Get in touch with nature at Spiegel Grove and Key Largo Dry Rocks. There's still lots to do: look for all kinds of wild species at Florida Keys Wild Bird Rehabilitation Center, admire the majestic nature at John Pennekamp Coral Reef State Park, see the vivid underwater world at North Dry Rocks, and step aboard African Queen Canal Cruise.

To find out how to plan a trip to Key Largo, use our trip itinerary maker.

Key Largo is just a stone's throw from Islamorada. Expect a bit cooler evenings in Key Largo when traveling from Islamorada in July, with lows around 28°C. On the 30th (Thu), wrap the sightseeing up by early afternoon so you can travel back home.

Things to do in Key Largo

Parks · Wildlife · Outdoors · Nature

Maine travel guide

4.5
Beaches · Lighthouses · Mountains
The Pine Tree State
The easternmost state in New England, Maine features an indented coastline and forested interior, carved eons ago by receding glaciers. Maine includes more lighthouses and quaint resort villages than you could ever hope to explore in a single trip, but the state is also one of the country's most sparsely populated, the majority of its land pristine and uninhabited wilderness. The temperate coastal regions, historically supported by fishing and lobstering, contain most of the state's urban centers and are the most popular spots in the state for holidays. The sea is the focus here, so it shouldn't come as a surprise that water plays an important role in the distinct character of the state, shaping its economy, tourism, cuisine, politics, sports, and art.

Florida Keys travel guide

4.3
Scuba & Snorkeling · Landmarks · Wildlife Areas
An archipelago of about 1,700 islands extending in a gentle arc south and southwest of Florida's mainland, the Florida Keys divide the Atlantic from the Gulf of Mexico. Many visitors on vacation come to scuba dive in the coral reefs, fossilized and exposed as sea levels declined over thousands of years. In addition to being one of the world's top diving and fishing spots, the Keys feature hundreds of shops, restaurants, bars, and various tourist attractions, most of them crowded all year long with visitors on vacation. To soak up the Keys' atmosphere and discover writer Ernest Hemingway's former haunts, drive from one island to the other all the way to Key West, located just 140 km (90 mi) from Cuba.