Colonial Shores & Outer Banks

May 14 – 21, 2027

Discover the history, beauty, and coastal charm of America’s first shores on this unforgettable journey through Virginia and North Carolina. From the living history of Colonial Williamsburg and Jamestown Settlement to the windswept beaches and maritime heritage of the Outer Banks, this tour combines fascinating stories, scenic landscapes, and memorable experiences at a relaxed pace designed for OregonWest travelers.

Your adventure begins in Williamsburg, where you’ll step back into the 18th century while exploring America’s largest living-history museum. Discover the stories of the nation’s founding at Colonial Williamsburg, visit Jamestown Settlement where English America began, and experience the American Revolution Museum at Yorktown. Along the way, enjoy charming taverns, historic villages, and the timeless atmosphere of Virginia’s Colonial Triangle.

The journey continues along Virginia’s coast with time to enjoy the waterfront charm of Yorktown and an overnight stay at Virginia Beach before crossing into North Carolina’s legendary Outer Banks. Here, you’ll visit the Wright Brothers National Memorial, stand before the iconic Cape Hatteras Lighthouse, cruise the calm waters of Roanoke Sound in search of dolphins, and explore Roanoke Island Festival Park, where the story of England’s first attempted colony comes to life.

With oceanfront accommodations, thoughtfully paced touring, fascinating history, beautiful coastal scenery, and plenty of time to relax and enjoy the experience, Colonial Shores & Outer Banks offers the perfect blend of discovery, comfort, and classic American travel.

** Prices based on airfare estimate. Price may be reduced if airfare is less than anticipated.

What Is 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

** Prices based on airfare estimate. Price may be reduced if airfare is less than anticipated.

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.

Activity Level

Level 2–3

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.

Click Here for Itinerary & Booking

** Prices based on airfare estimate. Price may be reduced if airfare is less than anticipated.

Click Here for a Flyer

This Tour is a Level II – click here to learn more

Click Here For Trip Insurance

For Insurance use our Tour Operator Location Number: 376005

Reserve Your Place This tour is limited to 30 guests and our tours fill quickly. To reserve your place or speak with our team, call us at (503) 585-3979, Monday–Friday, 9:00 AM–5:00 PM.