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Trip Overview
What's Included
Eight days. Two states. One unforgettable journey through the birthplace of America and the scenic coastlines of the Atlantic. From Colonial Williamsburg’s cobblestone streets and historic taverns to the beaches, lighthouses, and maritime villages of the Outer Banks, this carefully crafted OregonWest adventure showcases some of the most fascinating destinations on the East Coast.
Explore the places where American history began as you visit Colonial Williamsburg, Jamestown Settlement, and Yorktown. Experience the stories of early settlers, revolutionaries, and statesmen before continuing to the beautiful shores of Virginia Beach and North Carolina’s Outer Banks.
Along the coast, discover the remarkable story of flight at the Wright Brothers National Memorial, enjoy a scenic dolphin-watching cruise on Roanoke Sound, marvel at the iconic Cape Hatteras Lighthouse, and explore Roanoke Island Festival Park. Comfortable accommodations, excellent regional dining, and carefully planned sightseeing create a relaxed and enjoyable experience from beginning to end.
With included airfare, accommodations, transportation, hosted meals, sightseeing, and an OregonWest Tour Director accompanying the group throughout, every detail has been arranged so you can simply enjoy the journey.
** Prices based on airfare estimate. Price may be reduced if airfare is less than anticipated.
Included in Your Tour
✅ Round-trip airfare from Portland
✅ All ground transportation throughout the tour
✅ 7 nights hotel accommodations
- 3 nights Williamsburg
- 1 night Virginia Beach
- 3 nights Outer Banks (Nags Head)
✅ 13 hosted meals
- 7 breakfasts
- 1 lunch
- 5 dinners
✅ Welcome Dinner at the Williamsburg Lodge
✅ Colonial Williamsburg admission and guided touring
✅ Jamestown Settlement admission
✅ American Revolution Museum at Yorktown admission
✅ Historic Yorktown Village visit
✅ Virginia Beach Oceanfront stay
✅ Wright Brothers National Memorial admission
✅ Cape Hatteras National Seashore and Lighthouse visit
✅ Dolphin Watch Cruise on Roanoke Sound
✅ Roanoke Island Festival Park admission
✅ Great Bridge, Chesapeake visit
✅ All activities and admissions as described in the itinerary
✅ Services of an OregonWest Excursions Tour Director throughout
What’s Not Included
❌ Meals not specifically listed in the itinerary
❌ Personal expenses, beverages, souvenirs, and optional purchases
❌ Travel Insurance (strongly recommended)
❌Transportation to the airport as part of the package
Travel Notes
Flights
This tour includes round-trip airfare between Portland and Norfolk, Virginia. Final flight schedules will be confirmed closer to departure. Your OregonWest Tour Director will accompany the group throughout the journey and assist with airport procedures, transfers, and travel logistics.
Weather
May is one of the best times to visit both Virginia and the Outer Banks. Expect pleasant spring temperatures generally ranging from the upper 60s to upper 70s during the day, with cooler mornings and evenings. Comfortable layered clothing, a light jacket, and comfortable walking shoes are recommended.
Walking
This tour features moderate walking throughout historic districts, museums, waterfront villages, and coastal attractions. Most walking occurs on paved surfaces, although some historic areas include uneven sidewalks, brick pathways, and occasional cobblestones. Guests should be comfortable walking approximately one to two miles throughout a typical day, often broken into shorter segments with frequent opportunities to rest.
Guests should be comfortable with moderate walking, standing during guided tours, and occasional stairs. Most activities are senior-friendly and designed with a relaxed pace, but some historic sites and outdoor attractions require walking over uneven surfaces.
Travel Documents
A government-issued Real ID-compliant driver’s license or other TSA-approved identification is required for domestic air travel. Travel insurance is strongly recommended.
Activity Level
Moderate: Level 2 Activity Tour
Activity Level 1
Leisurely Primarily easy-paced days with minimal physical activity. Guests should be comfortable walking short distances (up to 45 minutes at a time – an example would be a guided museum tour) on mostly level surfaces. Some standing during guided tours and occasional steps when boarding transportation. Suitable for travelers who prefer a more relaxed experience with limited walking.
Activity Level 2
Moderate A balanced mix of sightseeing and leisure. Guests should be comfortable walking or standing for periods of up to 60 minutes at a time (an example would be a guided walking tour or guided museum tour), which may include some uneven surfaces, gentle slopes, and occasional stairs. Tours may require boarding various modes of transportation, including motor coaches, boats, or trains. Suitable for travelers with an average level of mobility.
Activity Level 3
Active Days may include extended periods of walking or standing—up to 75 minutes at a time (an example would be a guided walking tour or guided museum tour) —on varied terrain such as uneven surfaces or cobblestones. Expect to navigate stairs and board multiple modes of transportation, including motor coaches or boats. This level is best suited for guests who are comfortable being on their feet and handling a more active pace.
What Our Travelers Are Saying
Real stories from guests who explored, connected, and created unforgettable memories with us.
Nothing speaks louder than the people who’ve experienced it.
I had the opportunity to travel with Oregon west twice this year and they are a great company to travel with! They are thorough and make traveling easy!
— Bob Cave
★★★★★
It was my first time traveling with OregonWest. I had a terrific time. The trip was well organized. Chris is wonderful tour guide. I look forward to travelling with OWE in the near future.
— J North
★★★★★
This is a great tour company. They take care of everything and make sure you have a good experience. I will be taking more excursions with OregonWest.
— Lee Evans
★★★★★
Went to Shore Acre with a friend. Chris was the best tour director, very informative. Nazeer was great driver helping to get us on and off the bus. Will be taking another trip with them.
— Barb Smith
★★★★★


