Now that I've returned from Iceland, planning is already underway for my next trip. I plan to drive from Chicago to Newfoundland this summer.
This will be a 28 day road trip that will cover more than 5,000 miles. I will spend 9 nights in Nova Scotia and 10 nights in Newfoundland. Once I reach the eastern coast of Nova Scotia, I'll drive my Prius onto the ferry. The ferry will take 17 hours to cross the Atlantic before reaching eastern Newfoundland. Later, I'll return to Nova Scotia from western Newfoundland. The return trip is a 7 hour cruise. I'm hoping for calmer seas than what the ferry experienced in this video:
The logistics involved with planning this trip was more complicated than for my past road trips. In addition to making my usual Hampton Inn reservations, I had to make arrangements with 8 separate B&B's in Nova Scotia and Newfoundland. I also had to make reservations for the ferry (for both me and my car) to get from Nova Scotia to Newfoundland and back. I have rented a cabin for the 17 hour overnight trip to Newfoundland.
Here's a preliminary itinerary for this journey:

Day 1: Toronto, ON
Day 2: Quebec City, QC
Day 3: Saint John, NB
Day 4: Halifax, NS - Halifax skyline, Citadel, Halifax Library, Province House, various churches
Day 5: Peggy's Cove, NS - Sunset at lighthouse and cove
Day 6: Lunenburg, NS - architecture and waterfront
Day 7: Lunenburg, NS - churches and harbor
Day 8: Pictou, NS - Pictou harbor and Hector Heritage Quay
Day 9: Whycocomagh, NS - Cape Breton Highlands National Park; Baddeck lighthouse
Day 10: Sydney, NS - Louisnbourg fortress
Day 11: Ferry from Nova Scotia to Newfoundland (17 hours)
Day 12: St. John's, NL - colorful houses of St. John's, Cape Spear lighthouse
Day 13: St. John's, NL - Signal Hill, Ferryland lighthouse
Day 13: St. Mary's, NL - Cape St. Mary's Ecological Reserve; Northern Gannets
Day 15: St. Mary's, NL - Cape St. Mary's Ecological Reserve
Day 16: Bonavista, NL - Village of Trinity, puffins of Elliston
Day 17: Bonavista, NL - Bonavista lighthouse, puffins of Elliston; harbor
Day 18: Rocky Harbour, NL - Gros Morne National Park
Day 19: Rocky Harbour, NL - Gros Morne National Park, Western Brook Pond boat tour
Day 20: St. Anthony, NL - fishing village
Day 21: St. Anthony, NL - L-anse aux Meadows Vikings settlement
Day 22: Channel-Port aux Bosques, NL
Day 23: Sydney, NS - ferry from Newfoundland to Nova Scotia (7 hours)
Day 24: Bangor, ME
Day 25: Albany, NY - State Capitol
Day 26: Albany, NY - City Hall, Cathedral of the Immaculate Conception
Day 27: Cleveland, OH
Day 28: Orland Park, IL