First stop in Eastport-Sweeties Downeast to pick up the keys from Lisa. She is very nice and very helpful; you couldn't ask for a better person to rent from! At this point, the weather was a bit foggy and misty. It certainly added charm to the town, which is a blend of working fishing village and artist colony.
Because it was late afternoon, we decided to go to the Dog House first, then find dinner. The house is beautiful, no two ways about it. It's nicely decorated, very charming and cozy. Because the weather was a little bit dreary our first day, the gas fireplace was very welcome. The house was great for our family of four, but is definitely big enough to hold more if needed. The top floor deck is fantastic, and the view is superb - if you look to the left, you'll see a white triangle on land across the water. That's the Old Sow whirlpool, and it's really close. If you sit on either of the two decks for any length of time, you will see dozens of dolphins, and Minke whales.
The tides are huge, and in front of the house there's an island that will disappear and reappear 2x a day. The air is clear and cool at night, with more stars in the sky than you can imagine. On more than one night, my wife and I thought we heard whales singing.
It is well worth it to visit Campobello, St. Andrews, and East and West Quoddy lighthouses. Visit East Quoddy at low tide so you can make your way to the light house itself (it's not accessible at high tide). Don't forget to bring passports for Canada.
We went out whale watching two days with Captain Skip Harris. The first day we saw a Minke whale breach about 7 times; the second day there was no breaching, but still lots of whales, seals, dolphins and other wild life. Beachcombing is a must do - Clark Street beach is accessible by stairs and has a ton of cool sea glass, while the sand dollar beach at the end of High Street has lots of (!) sand dollars. I also found part of an old clay pipe that was probably dumped by a sailor back in the 1800s.
Food - Quoddy Bay is great, as is Landmark, Dastardly Dicks (coffee) and Moose Island Bakery. Chowderhouse is pretty good. Maine-ly Smoked Salmon in Perry is delicious! On several nights, we picked up dinner and took it back to the deck so we could enjoy the view and relax. One of the houses across the street has music coming from it often; sort of a celtic/folk sound. So beautiful. Eastport was well worth the trek, and we are looking forward to visiting again!