Our journey to America's colonial heartland begins today as we fly from Portland to Norfolk, Virginia. After arriving at the airport and completing the transfer to Williamsburg, we check in to our magnificent home for the next three nights — the iconic Williamsburg Lodge, set at the very heart of Colonial Williamsburg. With the evening before us, we gather for a warm welcome dinner right at the Lodge, savoring good food and the company of new friends as we look ahead to the extraordinary days to come.

Our journey to America's colonial heartland begins today as we fly from Portland to Norfolk, Virginia.

After arriving at the airport and completing the transfer to Williamsburg, we check in to our magnificent home for the next three nights — the iconic Williamsburg Lodge, set at the very heart of Colonial Williamsburg.

Check in to Williamsburg Lodge, Autograph Collection, Williamsburg, VA for the next three nights.

With the evening before us, we gather for a warm welcome dinner right at the Lodge, savoring good food and the company of new friends as we look ahead to the extraordinary days to come.

After a leisurely breakfast at the Lodge and a brief orientation with your Tour Director, we set out on foot into one of the most extraordinary places in America.

Colonial Williamsburg is a living, breathing recreation of 18th-century colonial life, and our private guide leads us through the Capitol area, along the grand sweep of Duke of Gloucester Street, and past the workshops of blacksmiths, printers, and cabinetmakers still practicing their trades as they have for centuries. The sights, sounds, and stories of the colonial era come vividly to life around every corner.

The afternoon is yours to explore the Historic Area at your own pace. Your Tour Director will provide a map with suggested stops — whether you are drawn to the apothecary, the courthouse, a demonstration of colonial-era crafts, or simply a quiet stroll through the beautifully preserved streets.

Lunch is on your own, with wonderful choices just steps away in the charming Merchants Square district.

The evening is yours to discover dinner on your own among the fine dining options in Merchants Square and the surrounding streets — all an easy walk from the Lodge.

Optional evening programming through Colonial Williamsburg brings the 18th century to life after dark, with dramatic courthouse performances, lantern-lit ghost tours, and musical entertainment.

Overnight at Williamsburg Lodge, Autograph Collection, Williamsburg, VA.

We begin the day with breakfast at the Lodge before heading to Jamestown Settlement, the vivid state-operated living history museum that recreates the story of America's first permanent English colony.

Walk through recreated Powhatan Indian and English fort villages, go aboard full-scale replicas of the three ships that carried the original colonists across the Atlantic in 1607, and bring to life the extraordinary convergence of cultures that shaped a nation. Our private group visit allows us to move at our own pace through this remarkable place.

Following a group lunch, we continue to Yorktown to visit the American Revolution Museum.

Through immersive 4D film, re-created Continental Army encampments, and richly detailed interactive galleries, we trace the arc from those first fragile settlements to the decisive final chapter of the Revolution fought on the very ground beneath our feet.

We return to the Lodge in the early evening with time to rest and freshen up before a group dinner at a beloved colonial tavern just a short walk through the Historic Area. The setting is pure 18th-century elegance — costumed servers, period-inspired dishes, and the warmth of candlelight — a fitting close to a day spent so fully in America's founding story.

For those with energy to spare, an optional evening program at Colonial Williamsburg begins at 8:30 and adds one more memorable chapter to a remarkable day.

Overnight at Williamsburg Lodge, Autograph Collection, Williamsburg, VA.

We begin our final Williamsburg morning with breakfast and a leisurely hour to enjoy any remaining time in the Historic Area — our hotel reservation includes two included Colonial Williamsburg tickets per guest, perfect for a final wander through the grounds at your own pace.

Mid-morning we check out and make our way to the Yorktown waterfront, where we board the free Yorktown Trolley for a guided circuit of this beautifully preserved village. The trolley winds past the Victory Monument, Historic Main Street, the scenic Yorktown Beach, and the Riverwalk waterfront — your Tour Director providing context on the 1781 siege that sealed American independence.

After the trolley tour, time is yours to explore Yorktown at leisure — a stroll along the waterfront, lunch on your own at one of the charming restaurants overlooking the York River, or a quiet walk up to the Victory Monument.

At 2:00 PM we depart for Virginia Beach, arriving at our oceanfront hotel by mid-afternoon with time to settle in and take in the spectacular views.

Overnight: Hilton Virginia Beach Oceanfront, Virginia Beach, VA

The Virginia Beach Oceanfront is yours this evening. Three miles of one of America's most celebrated boardwalks stretch in both directions from our hotel, with the Atlantic rolling in just beyond the dunes.

Dinner tonight is on your own — the boardwalk and surrounding streets offer a lively mix of fresh seafood and local favorites — a welcome evening of freedom after three full days of history.

The morning is entirely your own at the Virginia Beach Oceanfront — a rare and welcome gift of unstructured time. Walk the famous boardwalk, watch the waves from the beach, take a dip in the pool, or simply settle in with a coffee and the view.

We depart mid-morning for the Outer Banks of North Carolina, crossing the Wright Memorial Bridge onto the barrier island strand that has captured the imagination of travelers for generations.

After arriving on the Outer Banks and enjoying lunch on your own in Kill Devil Hills, we make our first stop at the Wright Brothers National Memorial.

The visitor center brings the story of Orville and Wilbur Wright to life with original artifacts, first-flight markers, and the extraordinary tale of two bicycle mechanics who changed the world.

We then check in to our home for the next three nights, the Surf Side Hotel in Nags Head, with its oceanfront setting and sweeping views of the Atlantic.

This evening we travel a short distance to a wonderfully atmospheric local restaurant for our first group dinner on the Outer Banks — a Victorian house tucked beneath a canopy of live oaks, where the menu celebrates the freshest local seafood and the warmth of genuine Southern hospitality.

We set out early for the great coastal drive south along NC-12, one of the most dramatically beautiful highway stretches on the Eastern Seaboard. Ocean and sound flank both sides of the barrier island as we make our way down to Hatteras Island and the Cape Hatteras National Seashore. Our destination is the legendary Cape Hatteras Lighthouse — at 199 feet the tallest brick lighthouse in America, moved 2,900 feet inland in a feat of engineering in 1999 to save it from the encroaching sea. The visitor center and beautifully maintained grounds tell the full story of this sentinel of the Graveyard of the Atlantic.

Lunch is on your own at a local Hatteras Island institution just a short distance from the lighthouse — renowned for its award-winning clam chowder and the only sushi bar on the island.

We then return north along the same scenic coastal corridor, arriving back in the Nags Head area for an afternoon excursion onto the Roanoke Sound aboard a soundside pontoon vessel for a dolphin watch cruise. The calm protected waters of the sound offer exceptional wildlife viewing, and encounters with the resident bottlenose dolphin pods are a reliable and delightful highlight of any Outer Banks visit.

After returning to the hotel to freshen up, we gather for a group dinner at one of the Outer Banks' most storied seafood institutions — an OBX dining tradition since 1978, where fresh local catch, Angus beef, and genuine coastal hospitality have made it a favorite of locals and visitors alike for nearly fifty years.

Overnight: Surf Side Hotel, Nags Head, NC

We cross to Roanoke Island this morning for a visit to the Roanoke Island Festival Park — one of the most compelling living history sites on the East Coast. Here the story of the Lost Colony, America's first attempt at permanent European settlement, unfolds through the reconstructed Elizabeth II sailing vessel, an authentically recreated Elizabethan settlement site, an American Indian Town, and the engaging Adventure Museum. The site is steeped in mystery and wonder, and our visit leaves ample time to explore at your own pace.

Following the Festival Park, we make our way to the charming waterfront of downtown Manteo — a beautifully preserved village that serves as the cultural heart of the Outer Banks. Lunch is yours to enjoy on your own along the waterfront boardwalk, where local cafés and delis make for a relaxed midday hour with boats drifting past and the Shallowbag Bay shimmering in the afternoon light. The balance of the afternoon is free — a last chance to walk the beach, browse local shops, or simply rest and reflect on a week well spent.

Tonight we gather for our farewell dinner at one of the Outer Banks' most beloved restaurants — a family-owned Nags Head institution perched above the Roanoke Sound, where every seat commands a panoramic view of the water, local ospreys nest just outside the windows, and the menu celebrates the catch brought in daily by local fishing boats. It is a perfect final evening — good food, good company, and one last lingering look at the extraordinary coast that has been our home this week.

Overnight: Surf Side Hotel, Nags Head, NC

Our final morning begins with a relaxed breakfast and time to pack and prepare before a comfortable mid-morning departure.

Depart Surf Side Hotel at 10:30 AM for transfer to Chesapeake, VA.

Arrive Great Bridge, Chesapeake around 12:00 PM for leisure time (approx. 75 min) in the historic waterfront community, with artisan shops, a bakery, boardwalk, and battlefield park.

Depart Great Bridge at 1:15 PM for transfer to Norfolk International Airport (ORF), arriving around 1:45–2:00 PM for check-in for departing flights.

Check in for departing flights at Norfolk International Airport (ORF). Recommended earliest flight departures from 4:00 PM onward.