Planning the Perfect Williamsburg Itinerary

Is there anything better than discovering a destination you thought you knew actually has even more to offer? Our Greater Williamsburg itinerary just about knocked our little Colonial breeches off, y’all.

Williamsburg was the capital of the Virginia Colony from 1699 to 1780 — and if that was the end of the story, this place would be fascinating enough. But there’s so much more! The New York Times named Williamsburg as one of its 52 Places to Visit in 2019, and as we found while filming our show, there are more than enough reasons for the honor.

You are going to love our latest episode of The Jet Sisters where we take you along on our weekend in Williamsburg!

Williamsburg Itinerary

Why Visit Williamsburg Va?

Where else can you find so many things that The Jet Sisters are obsessed with in one place? Thrilling theme park attractions, world class food, historical sites featuring our boy Alexander Hamilton and costumes, and all just a few hours from Washington, D.C.?! It’s like Williamsburg was just waiting for us to “discover” it all this time, though clearly we were beaten by the English by about 400 years, and the Native Americans since well before that. 

Did you know? A trip to Greater Williamsburg means you’re actually experiencing three destinations at once!

Greater Williamsburg / Williamsburg / Colonial Williamsburg

Surprise, surprise, Greater Williamsburg is not the same thing as Colonial Williamsburg, the largest living history museum in the world. This may be the greatest misconception about the area, also known as the historic triangle comprising Jamestown, Yorktown and Williamsburg.

A Colonial Williamsburg vacation is a blast, whether you’re a history buff or not, and we can attest that kids of all ages will love it. Check out the Governor’s Palace, Duke of Gloucester Street, the Capitol and the Courthouse. You can grab an ale or a hot pie in a historic tavern and meet colonial folks like blacksmiths, shopkeepers and carriage drivers all along the way.

Even though Colonial Williamsburg is a must-see when you’re here, we didn’t include it in the episode because we figure it’s a given that you’ll go there, and we wanted to highlight some spots you might miss. We’ll share more about our experience at Tarpley, Thompson and Co. in a future post and video, but if you’re at all into costumes, this is your No. 1 stop in Colonial Williamsburg!

To book advanced tickets to Colonial Williamsburg, click here.

Jamestown / Historic Jamestowne

Did you know? Historic Jamestowne is the original site of the first permanent English settlement in the U.S., where Pocahontas and John Rolfe were married. The site was rediscovered in the 1990s, and is often confused with Jamestown Settlement, a living history museum with re-creations of a Powhatan village, sailing ships and a colonial fort. Today, you can visit both on a visit to Greater Williamsburg.


HAMILTON WAS HERE. Yorktown is known for the Revolutionary War battle of 1781, a huge surrender from the British and the beginning of the end of the end for the Empire’s rule in the Colonies. Today it’s the third point in the Historic Triangle, with main attractions including the Yorktown Battlefield, American Revolution Museum and even Segway tours through the town with Patriot Tours, It’s also where you board the Schooner Alliance!

If you haven’t checked out The Jet Sisters : Williamsburg yet, start here and then return to this post for details and bookable links for activities, accommodations and dining options for 48 hours in Williamsburg, Va.

The Jet Sisters Way

If you’ve got a stack of shiny gold coins to splurge or are in a period of pence-pinching, we’re on a mission to show you how to get the most out of your travels, no matter where you go. Hold on to your petticoats, we’ve got a Williamsburg itinerary for every budget.

Since we’re sisters on either end of the Millennial spectrum, we designed our weekend in Williamsburg adventure on what we would like to see, do and eat. The best part for you? Our itineraries work for anyone who likes fun. DO YOU LIKE FUN? Then you’re going to love our adventures in Virginia. Just set a budget and pick and choose what works for you! Together, we’ll help you decide where to splurge and where to save when you visit the Greater Williamsburg area.



Looking for things to do in Williamsburg? We’ve got lots of tips for your next vacation! Check out the resorts, activities and restaurants throughout Williamsburg. See you there!

Looking for things to do in Williamsburg? We’ve got lots of tips for your next vacation! Check out the resorts, activities and restaurants throughout Williamsburg. See you there!

Looking for things to do in Williamsburg? We’ve got lots of tips for your next vacation! Check out the resorts, activities and restaurants throughout Williamsburg. See you there!


Ready for 48 hours in Williamsburg Va with The Jet Sisters?

Looking for things to do in Williamsburg? We’ve got lots of tips for your next vacation! Check out the resorts, activities and restaurants throughout Williamsburg. See you there!

Rachel shares quirky, budget friendly accommodations, must-try eateries and activities that provide lots of bang for the buck. Expect to spend anywhere from $100-$500 per day.

Looking for things to do in Williamsburg? We’ve got lots of tips for your next vacation! Check out the resorts, activities and restaurants throughout Williamsburg. See you there!

Angie’s itineraries feature upscale accommodations, one-of-a-kind experiential dining opportunities and memorable activities. Expect to spend anywhere from $500-$1,500 for two for Angie’s day of adventure.

Follow our adventures on Instagram

@TheJetSisters | @AngieAway | @RaeAway


Rachel’s Budget Friendly Williamsburg Itinerary

Looking for things to do in Williamsburg? We’ve got lots of tips for your next vacation! Check out the resorts, activities and restaurants throughout Williamsburg. See you there!

Looking for things to do in Williamsburg? We’ve got lots of tips for your next vacation! Check out the resorts, activities and restaurants throughout Williamsburg. See you there!

Budget Friendly Accommodations in Williamsburg

This area of Virginia attracted early settlers for a variety of reasons and one has to be this: it’s absolutely gorgeous. Surrounded by rivers, lush trees and rolling hills, I was moved to song more than once! Disney’s animated Pocahontas film got a whole lot wrong historically, but now having “run the hidden pine trails of the forest,” I can say that part was spot on!

Greater Williamsburg’s attractions are spread over a wide area, so choosing a central spot to camp out is a great idea. And I’m serious about camping out. For my budget friendly accommodation, I chose a yurt at the 180-acre Williamsburg KOA. KOA’s yurt was a perfect choice for us, because we love camping but kinda hate packing for camping, setting up the tent, etc. We checked in, went straight to our yurt, a circular cross between a tent and a cabin, and were ready to explore without any muss or fuss. Community bath houses are 60 seconds away and bed linens, towels and air conditioning are included.

From the door of our yurt, it was just 10 minutes to Colonial Williamsburg and 15 minutes to Busch Gardens – super central! But for the days when you just want to enjoy the great outdoors, the KOA has a heated pool, splash pad, jumping pillows and walking trails. It’s also pet friendly and offers Kamp K9 amenities and dog park – wish we brought Sheba the adventure dog!

Check pricing and availability at KOA Williamsburg

4000 Newman Rd, Williamsburg, VA 23188


Things to Do in the Historic Triangle

It wouldn’t be a proper Jet Sisters adventure without a Hamilton encounter – surely y’all know this about us by now! For my budget friendly activity, and inspired by our favorite hit Broadway musical, we set out to explore historic Yorktown while singing, loudly, The Battle of Yorktown… 1781!

If you’re a Hamilton fan like us, you know more already about this historic Revolutionary War site than most. You know that Hamilton, Lafayette, Washington and the ragtag boys of the Revolution showed up. Young, scrappy and hungry, they had no business defeating the superior British army. And yet, through a series of events that shouldn’t have happened, as the awesome Ranger Mac told a rapt tour group and as Lin-Manuel Miranda told us on stage, we won, we won, we won, WE WON!

I’m purposely oversimplifying the story because I want you to come here and experience it for yourself. The world was truly turned upside down and it happened right here. There’s nothing like yelling ROCHAMBEAU and HERCULES MULLIGAN on the battlefield and just getting goosebumps all over. (And really, really weird look from our fellow tourists.)

In Yorktown, there’s more than the battlefield, so if you have time, be sure to check out Cornwallis’ Cave, the Nelson House and schedule a sunset sail on the schooner Alliance, which sails from Riverwalk Landing Pier in historic Yorktown and takes you up the tidewaters of the Chesapeake Bay on a 105 foot gaff-rigged ship.

1000 Colonial Pkwy, Yorktown, VA 23690

More attractions in Yorktown


Where to Eat and Drink in Williamsburg

The word “whiskey” comes from the Gaelic for “water of life,” which seems counterintuitive if you’ve ever had one too many cocktails on a night out. Back in the day, untreated water came with all sorts of parasites and bacteria, making fermented spirits like wine, beer and whiskey, the safer option for hydration. It’s no surprise then that breweries are still as big part of Greater Williamsburg’s landscape as they were in colonial times.

Fortunately, there’s an easy way to make sure you get a taste of colonial times and the modern craft booze scene – the Williamsburg Tasting Trail! There are nine official stops on the trail, featuring award-winning breweries, wineries, distilleries and even a meadery, so you can pick and choose as your budget allows. We stopped in at Alewerks Brewing Company and Virginia Beer Company for tasting flights, and then we had dinner at Amber Ox Public House for small plates of local goodies.

Take your Williamsburg Tasting Trail brochure to each stop on the trail for a stamp. If you collect all nine, you get a free glass! Please note, you should definitely not drive this route if you’re sampling all the beers on the trail, know what I mean? You can book a variety of brewery tours and transportation options if you really want to experience them all, and Uber is available as well. Be safe!

Aleworks – 189 Ewell Road, Williamsburg, VA 23188
Virginia Beer Company – 401 Second Street, Williamsburg, VA 23185
Amber Ox Public House – 525 Prince George Street, Williamsburg, VA 23185

Total Cost for Rachel’s Williamsburg Itinerary: $175


Angie’s Upscale Williamsburg Itinerary

Looking for things to do in Williamsburg? We’ve got lots of tips for your next vacation! Check out the resorts, activities and restaurants throughout Williamsburg. See you there!

Looking for things to do in Williamsburg? We’ve got lots of tips for your next vacation! Check out the resorts, activities and restaurants throughout Williamsburg. See you there!

Luxury Resorts in Williamsburg Va

The Kingsmill Resort is a sprawling resort with more accommodation options than even the staff can count! We stayed in a pretty typical hotel room, but there are also lovely waterfront cottages, full-sized vacation homes and The Estate, a mansion recently outfitted with all Restoration Hardware furnishings and fixtures. The Estate sits on a bluff overlooking the James River, comes with its own staff and chef, infinity pool and hot tub, and room for 8.

Like just about every stitch of land in the Historic Triangle, Kingsmill has some interesting roots. The 17th hole of the famous River Course is the site of a colonial shipping dock, the remnants of which you can still see from the tee box.

And there’s plenty to do if golf isn’t your bag, like a huge spa, lazy river, multiple pools, restaurants and a marina with jet skis and boats you can rent to cruise around the James River.

There’s a free shuttle from the resort to Williamsburg’s top attractions, so you don’t even have to think about parking or driving once you’re checked in.

Check pricing and availability at the Kingsmill Resort

136 Francis Street East, Williamsburg, VA 23185


Fun Things to Do in Williamsburg

You know if there’s a theme park to be found, the Jet Sisters are going to be right up in it! Busch Gardens is one of the most popular Williamsburg VA attractions and has been named World’s Most Beautiful Theme Park every year since 1990, and it lived up to the title with greenery, hills, animals and a European theme carried throughout.

We were lucky to be in town for the annual Food & Wine Festival, featuring 43 dishes from around the world, including new kiosks from Mexico, Jamaica and the Philippines. The festival only runs through June 30, but it’ll be back next summer so plan ahead!

With our limited time, we decided to do the Elite VIP Tour to get front-of-the-line access, behind-the-scenes knowledge, food and drinks and our own personal guide for the day. We got to choose our seats for every single ride – front row is a must on Griffon, a floorless coaster that dangles you over the edge of a 205-foot cliff before dropping you straight at the ground at 75 miles per hour. Words don’t do it justice – you absolutely have to see the episode to believe how bananas this ride is!

The coasters were so, so good, I couldn’t pick a favorite if I tried. Do not miss Alpengeist or Apollo’s Chariot – they were amazing as well. Also check out the Roller Coaster Insider Tour if you’re interested in how rides work. You still get to ride them all and skip the lines, so it’s a bargain.

Explore tickets to Busch Gardens Williamsburg and Water Country USA water park

1 Busch Gardens Blvd, Williamsburg, VA. 23185


Fine Dining in Williamsburg

Cuisine in Greater Williamsburg has come a long way since colonial times and nowhere is that more evident than the Rockefeller Room at the historic Williamsburg Inn.  Just steps from Colonial Williamsburg, this is the place for a fancy night out on the old town.

First, we took our time as the sun set. It reminded me so much of Bath! The Regency architecture, the way the sun looks on the warm stone.

Chef Matthias Maihoefer provided us with a tasting menu, so we ate a little of everything, shrimp and grits, oysters, beef tenderloin. The wine selection was extensive.

136 Francis St E, Williamsburg, VA 23185

Total cost for Angie’s Williamsburg Itinerary: around $1,200


Looking for things to do in Williamsburg? We’ve got lots of tips for your next vacation! Check out the resorts, activities and restaurants throughout Williamsburg. See you there!

Looking for things to do in Williamsburg? We’ve got lots of tips for your next vacation! Check out the resorts, activities and restaurants throughout Williamsburg. See you there!

We love that Greater Williamsburg has both a fascinating past and an exciting future. When you visit Williamsburg, you’re going to be so amazed at how much fun you have. Our only complaint is that we didn’t spend enough time at each stop, but you know what? We’re going to fix that on our next visit.


If you loved our episode in Williamsburg, we have amazing news! The Jet Sisters and Visit Williamsburg are partnering to give one lucky prizewinner and three guests a fun weekend in Greater Williamsburg, Virginia! The winner will stay in a yurt at the KOA Williamsburg, experience the American Revolution Museum at Yorktown and Jamestown Settlement, experience two locations on the Williamsburg Tasting Trail, Virginia Beer Company and Silver Hand Meadery, and explore the world’s most beautiful theme park, Busch Gardens Williamsburg. Terms and conditions are included in the widget below. Good luck!

Airfare and ground transportation not included. Please consult the terms and conditions for more information.

a Rafflecopter giveaway

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Thank you to Visit Williamsburg and its partners for hosting us and supporting independent content creators like us! And thank you, readers, for supporting the partners that keep Angie Away and The Jet Sisters a free travel resource. Please note, contains affiliate links. If you make a purchase using these links, we may earn a commission at no extra cost to you. 

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  • June 20, 2019

    I just watched your video! I loved it!!!!! Y’all are so cute and fun and now I’m dying to go to Williamsburg! Love you cutie Jet Sisters!

    • June 21, 2019

      Thank you! Girls trip? I think we need to get this on the calendar.

    • July 14, 2019

      The video was so funny! I have always wanted to do a VIP tour. Thinking it’s a must next time I’m at a theme park.

  • June 20, 2019

    Great video! Wish I had gone along. Adorable costumes btw! I now have a new place on my bucket list.

    • June 21, 2019

      Next time you can come with us. You would LOVE it.

  • June 21, 2019

    I want to go to Williamsburg to dress up like that! Maybe not in the summer though 🙂 So fun!

    • June 21, 2019

      I think I’ve found my next career… costumed shopkeeper in Williamsburg!

  • June 21, 2019

    Sounds like there is something for everyone in Williamsburg and while I was there many many many years ago now, I still learned a few new things from your video! <3

  • June 21, 2019

    Watched your video and as usual it is a stellar piece. You girls have the best time in everything you do !

  • June 24, 2019

    So fun! Can’t wait to go. Also that cute guy in your roller coaster photo kinda stole the show lol.

  • June 24, 2019

    Cool blog! Thanks for sharing!

  • June 28, 2019

    I want to visit Williamsburg to dress like this… this reminds me of Portia “Merchant of Venice”.. Its really nice post with budget and all its great…

  • July 04, 2019

    I recently moved to Texas from California. I can’t wait to get out on the road in my RV and explore the Eastern part of this great country. I’m a history buff so I am especially looking forward to visiting Williamsburg. This is my first visit to your blog and I love the way you each do a separate itinerary covering budget and luxury.

  • July 11, 2019
    Christina Gabs

    Everything looks amazing. I can’t wait for our trip next year. You actually have me considering a yurt!

  • July 12, 2019
    Amanda Warren

    This looks like so much fun, I’d love to take my kids to one of the Yurts 🙂

  • July 12, 2019
    Jennifer Anderson

    I ❤️ Williamsburg!

  • July 12, 2019
    Kristin W

    I would love to take my family to Williamsburg! I grew up in Virginia and I remember taking field trips there. I would love to show them around and see it as an adult now. We love learning about history and plus I could see my sister there !

  • July 14, 2019
    Maigan Czarnecki

    I love see your guys’ adventures 🙂 next time you guys come visit we have to hang out and talk about all the wild places you’ve been! Maybe one day I’ll follow behind and check them out too, including Williamsburg! 🙂

  • July 14, 2019

    This looks like such a fun trip. I appreciate that you guys offer budget & luxury options!

  • July 18, 2019

    Such great info and advice! This trip looks like a ton of fun!

  • July 18, 2019
    Jennifer Walton

    So fun!!! Williamsburg is such a great place!

  • July 18, 2019
    Kelly D

    I want to visit Williamsburg because it is so family friendly with lots of fun attractions.

  • July 19, 2019

    I’d love to visit Williamsburg to learn more about the history of the areas. Plus, anywhere with roller coasters gets a vote from me!

  • July 23, 2019

    My family has visited Williamsburg many times and we keep going back because we love it! We’ve stayed at a lot of different hotels including our favorite place to stay, Kingsmill Resort, but we’ve never stayed in a yurt! And we love Busch Gardens too!

  • July 30, 2019
    kristen s

    I need a vacations!

  • July 31, 2019
    Cassandra D

    Looks like so much fun and a great opportunity to visit historical sites, as well.

  • May 17, 2020

    Thanks for the fresh Williamsburg ideas! We were just there for New Years and were thinking about a return shortly so I was searching for itineraries and ideas. The “rollercoaster inside tour” is a really fun idea. Next time you’ll have to make it a little further to Richmond, too!

  • September 18, 2020

    Well you two lovely ladies are without a doubt living your absolute best lives and that is so inspiring to see! You’ve sparked joy in my heart and I can’t wait for my sister to come traveling with me in Williamsburg so we maybe can capture some of the magic you’ve caught! Thanks for sharing this beautiful post!

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