Take one history-major daughter and one mom whose last getaway was to Bermuda 10 years ago and what do you have? A recipe for a perfect jaunt to a “triangle” of another sort, America’s historic triangle of Jamestown, Williamsburg and Yorktown.

Colonial Williamsburg. Photo: Visit Williamsburg
Jetting from one colonial capital — Boston (BOS) — to another via an hour-long flight to Richmond (RIC) is easy with several carriers offering direct routes along the East Coast (we used Delta Air Lines and JetBlue). Grab a rental car for less than $100 for a long weekend like we did and you can be in the heart of charming Williamsburg just in time for lunch. You’ll find good things do come in three’s with three days and two nights to explore — or if you hit up the Blue Talon for lunch, as the French countryside-inspired bistro will keep scooping its transcendent chocolate mousse until you say stop (although admittedly, only about three scoops fit the strawberry and chocolate-lined bowl). Decadent macaroni and cheese with Virginia ham, chicken and mushroom crepes, and nicoise salad for those with lighter palates all await in the heart of brick-lined Merchant’s Square. If you’ve got enough time, some shopping is in order and there are plenty of curios and clothing boutiques to pop into or, for a bit of a detox, the Spa at Colonial Williamsburg offers up some relaxation with treatments that are an homage to the apothecaries of yore. Sip the signature apple and mint tea or blends inspired by the 16th–20th centuries before heading in for a colonial orange and ginger scrub. Ginger aids in digestion and oranges are an excellent source of vitamins, used long ago by those making the long journey over across the ocean. Here, the only “waves” that await you are from the indoor hot tub.
Get ready for more relaxation and one of three opportunities to raise a glass at Silver Hand Meadery, where this fermented honey drink is expertly explained with intimate tastings both in terms of history and flavor profiles. Virginia wildflower honey, some tinged with New Jersey blueberry notes, and others with such revolutionary flavors as avocado prove the tipple has come a long way from its roots as the saccharine beverage of choice in Beowulf.

Cheese Shop. Photo: Visit Williamsburg
It’d be wise to save some room for the vintages at Fat Canary, one of Williamsburg’s fanciest restaurants that manages elegance on a plate without being overwrought and devoid of stuffy service. You will, however, most likely be stuffed if you opt for all three courses. (Insider tip: you can order half portions of some main dishes, not listed on the menu.) Those on a limited budget can also opt for a sandwich from the adjoining Cheese Shop at lunchtime, or pick up a bottle of wine from the in-house shop for a picnic.
Almost everything is within walking distance in Williamsburg, making it an ideal choice for those who’ve had a glass or two or just enjoy a pleasant stroll. It’s easy to get around and even better knowing The Cedars B&B — and its heavenly beds — is waiting at the end of the day. Each room in the three-story Georgian brick home offers a slice of history in terms of nomenclature and decor, especially as told by innkeeper Alex Vlk, a former history teacher whose knowledge of the past and pop culture could easily earn him a spot on Jeopardy. Have a chat over an expertly cooked breakfast before stepping back in time to the region’s gem: Colonial Williamsburg.
You can spend the better part of a day here, chatting with historical re-enactors who don’t break character as they answer every little question about what it was like to be a seamstress and how fabrics were diverted for use in the war for independence, what it was like to own a coffeehouse (and warm up with a free sip!) and even enjoy a fife-and-drum parade. Time truly flies watching all of the action, and laughing at kids skipping around in period dress over their jeans, gloriously iPhone-free.

© Visit Williamsburg
If that’s not too much history, more living-history at another corner of the triangle — Yorktown — beckons; despite harkening back to the 1700s, the paint is barely dry on the exquisite exhibit spaces at the American Revolution Museum just a 20-minute drive away. Open for just a year, period furniture, instruments, paintings and more all await the curious visitor.
Mugs, jugs and drinking glasses will get you in the mood for a brew at Virginia Beer Company, insanely popular despite only celebrating two years in business. Craft lovers and novice tipplers alike love ordering a Flight Plan for ample samplings of eight rotating and regular beers. Pair them with the grub from the rotating food trucks at the outdoor beer garden (which is pet-friendly, too!), or be sure to save some room for locally sourced seafood and produce at Waypoint Seafood and Grill.
Schnitzel from German-born chef Hans Schadler will keep that Bavarian beer hall theme going, or move onto some more local fare in the form of Chesapeake specialties like oysters on the half shell, oyster stew, rockfish or crab cakes.
After such an evening smorgasbord, it would seem impossible you’d have room for Sunday brunch, but you can fill up on that and history by finishing the weekend with a grand finale. The Settlement at Jamestown opens at 9 a.m. daily, and chronicles the struggles — and triumphs — of America’s first multicultural society and its growth. Perhaps you’ll learn about how each landowner was required to plant 12 grape vines in order to grow wine, though the most successful crop was by far tobacco until the practice of grafting came along. It’s cool to hear about it before moving on to Williamsburg Winery for a sample of the delicious results. Red, white or rosé, the tour and tasty sips are almost as delicious as the brunch bites out on the porch overlooking the arbor.
Read This Next
#WhereverFamily
Insta FeedHotels
Jun 12, 2025Summer Adventure Awaits Family Travelers at Four Seasons Resort and Residences Jackson Hole
Family travelers can experience a taste of cowboy life at Four Seasons Resort and Residences Jackson Hole, offering adventure, amenities and access to all the destination has to offer.
Awards
Jun 12, 2025Join Us at the 2025 The Trazees & Wherever Awards
This August, celebrate the winners of The Trazees, the awards voted on by the readers of trazeetravel.com, and the Wherever Awards, the awards voted on by the readers of whereverfamily.com.
Cruises
Jun 11, 2025HX Expeditions Partners with Inuit Communities on New Excursions in Arctic Canada
Expedition cruise line HX Expeditions recently launched a first-of-its-kind excursion in Arctic Canada in partnership with local Inuit communities. The community-led excursions launch this summer on HX’s 26-day Northwest Passage sailings.
Caribbean
Jun 10, 2025Barbados Welcomes Families Back to Blue Monkey Hotel and Beach Club
Prepare to be impressed with your next stay in Barbados when you book a room at Blue Monkey Hotel and Beach Club, where years of planning and revamping are about to pay off. What was once Tropical Escape Hotel and Blue Monkey Bar underwent a complete redesign and retrofit to showcase luxury, relaxation and Caribbean beauty. The property prepares for a summer reopening when it will unveil its new look and vibe along with its new name.
Hotels
Jun 10, 20253 Nostalgia-Inspired Hotels
With nostalgia travel on the rise, many family travelers look to bring their children to places they visited when they were kids. These properties around the country offer nostalgic travel experiences for the whole family.
Hotels
Jun 9, 2025Nautical News, Birds of Prey Encounters, Beachside Events and More Await at Whiteface Lodge This Summer
Did you know the term “vacation” was created in the Adirondack Mountains by 19th-century New Yorkers seeking summer air and relaxation in the mountains? Family travelers today continue to vacation to this beautiful destination and its surrounding areas every summer for fun, adventure and quality family time.
ShareThis