London, Dover and Southeast England: A Family Adventure (Where Mom Conquers Left-Side Driving and Lives to Tell the Tale!)
- Jess
- Feb 17
- 8 min read
This quick example showcases a Jess trip through Southeastern England, starting from London. Think of it as a teaser—our real, custom British vacation itineraries include way more personalized details, insider tips, and unforgettable experiences.
Let me tell you about the time I channeled my inner British racing driver (okay, more like nervous American mom) and took on UK roads with my crew. Picture this: Me, two boys who oscillate between history nerds and walking appetites, and five days to explore Southeast England. Spoiler alert: We survived! And, you probably will too. Now, we have some epic tales (and travel tips) to share!
Day 1: London Calling (Or Rather, My Boys Actually Looking Up From Their Phones!)
Let's talk about landing at Gatwick with a jet-lagged family and somehow making it through that first crazy day in London. First off, whoever designed the immigration hall clearly never traveled with hangry teenagers. But here's my secret weapon: I packed a Mary Poppins-worthy bag of snacks. My eleven year old was laying down everywhere like there was a carbon monoxide leak.
After surviving the Gatwick Express (we were standing in the aisle like a Calcutta commuter train), we made our way to the CitizenM Tower of London. Why this hotel? Because after 15 years of family travel, I've learned that location and cool factor are everything. The rooms are actually designed for families who still want to speak to each other after a 7-hour flight, and the view of Tower Bridge made even my "I'm too cool to be impressed" 14-year-old grudgingly admit it was "pretty sick" - which in teen speak is basically a standing ovation.
To combat the jet lag zombie apocalypse, I booked us on a Thames River cruise. My 11-year-old, bless his history-loving heart, actually stayed awake somehow, while my teenager, who normally treats his phone like it's surgically attached to his hand, actually started taking photos.
For dinner, I pulled off what I'm calling my greatest mom triumph of 2024 - scoring one of those coveted igloos at Coppa Club Tower Bridge. Booked it three months in advance, and it was worth every minute of planning. The boys thought we were eating in a spaceship with a view of Tower Bridge, and I thought I was in parent heaven because they were both actually excited about something that didn't involve WiFi. My 14-year-old demolished a truffle and mushroom pizza while my 11-year-old tried to convince me that the chocolate fondant was essentially breakfast food because "we're still on New York time, Mom." When he's right, he's right.
Day 2: Castle Life (Because Every Kid Needs a Medieval Phase)
Today was all about the Tower of London, and let me tell you - nothing tests your mom skills quite like navigating medieval history with two boys who think the most exciting part will be the torture chamber. Pro tip: Get there at opening (9 am sharp - you're welcome) because the Crown Jewels line gets longer than my teen's list of excuses for not doing homework.
Here's the real game-changer though: Book the "Opening Ceremony" ticket. Watching the Yeoman Warders unlock the tower is like getting a behind-the-scenes pass to the world's coolest history show. My 11-year-old was literally bouncing with excitement (a sight I usually only see when Taco Bell is involved). The Yeoman Warder who led our tour, complete with dad jokes and gruesome tales, managed to keep both boys entertained.
Lunch was a strategic move to Borough Market because nothing soothes hangry boys like Europe's oldest food market. Between the legendary grilled cheese at Kappacasein (trust me, it's life-changing) and the chocolate covered strawberries, I briefly achieved "cool mom" status.
Pro tip: Get the truffle honey grilled cheese - it's the kind of thing you'll dream about months later. My 11-year-old declared it "better than pizza" which is basically the kid equivalent of a Michelin star.
For the afternoon, I risked it all with a bold move - afternoon tea at Fortnum & Mason. Yes, I made my boys wear collared shirts. Yes, there was initial grumbling. But here's the secret: tell them the tiny sandwiches are "basically sliders" and the scones are "British cookies," and suddenly they're food critics. My teen even used a napkin voluntarily, which I'm adding to my list of parenting wins. The staff at F&M deserves a medal for treating my boys like proper gentlemen while they inhaled three tiers of treats in record time.
By the end of the day, we'd managed to turn medieval history into an adventure, street food into a cultural experience, and afternoon tea into something two American boys would actually admit to enjoying (though I'm sure their friends back home will never hear about the tiny sandwiches part).
Day 3: The Great British Road Trip Begins (Mom vs. Roundabouts)
This is where it gets interesting, folks. I picked up our rental car and learned that nothing tests your zen quite like navigating a roundabout while your family shouts "LEFT, STAY LEFT!" from the backseat.
First stop: Canterbury. The cathedral is stunning, but the real win was finding The Goods Shed for lunch - it's this amazing farmers' market/restaurant combo where my perpetually hungry sons actually tried new vegetables voluntarily. While it's pretty filled up with tourists during the day, a car gifts you the freedom of staying well after they leave. But, don't stay too long....you are moving into a castle!
Leeds Castle, to be exact, would be our home the next few nights. That place is what Disney imagines in their wildest dreams. We're talking moats, towers, and enough medieval vibes to make even my phone-addicted teen look up in wonder. The real MVP here was the maze - turns out nothing brings out family bonding quite like getting completely lost in a hedge labyrinth for an hour. My 11-year-old appointed himself navigation expert, which went about as well as you'd expect. Three wrong turns and one "mom, I swear it's this way" later, we finally found the center, and I've never seen two boys more proud of their "survival skills."
Day 4: Coastal Vibes and Medieval Times
This day was all about stepping back nearly a thousand years and standing in the footsteps of history. We centered everything around the Battle of Hastings - the clash that changed England forever. And let me tell you, Joe was into more than the kids, which says something.
We started with a quiet breakfast while the boys slept in. There's something about sipping coffee in a castle that makes you feel like you're getting away with something. But the peace didn't last long - we had a date with 1066.
Our first stop? Battle Abbey and the battlefield itself. Walking the grounds where William the Conqueror's Norman forces defeated King Harold's Anglo-Saxons was surreal. The audio guide gave us the gory details - and yes, my 11-year-old became an instant expert, gleefully explaining medieval battle tactics to anyone who would listen. We stood on the spot where King Harold likely fell, arrow-in-eye and all. It's hard to get more hands-on with history than that.
After the battlefield, we explored the abbey ruins. The boys climbed over ancient stones (as much as you're allowed to, anyway), and we tried to imagine what it was like when monks prayed here centuries ago. My teen even put down his phone long enough to say, "This is actually kinda cool." Victory.
By lunchtime, we headed to Hastings Old Town for a bite. We grabbed sandwiches from a small cafe and walked along the seafront. The old fishing boats and weathered net huts made for some great photos - and a perfect backdrop to explain to the kids why this town became a strategic hotspot after the battle.
Of course, we couldn't skip the Smugglers Adventure caves. They're touristy, sure, but wandering through dimly lit tunnels while learning how contraband tea and brandy fueled an underground economy? Totally worth it. Plus, we needed a break from the battle talk before the kids mutinied.
We ended the day back at our castle, with fresh seafood and a sunset over the Sussex countryside. As we clinked glasses, my youngest declared that history is "way cooler when you get to stand on it." I couldn't agree more.
Day 5: White Cliffs and English Beach Dreams
Listen, if there's one day that made me feel like a travel planning genius, this was it. Dover and the Ramsgate Tunnels might sound like just another history lesson, but trust this mom who's seen enough beach towns to write a guidebook - this combo is pure gold.
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The White Cliffs walk was both majestic and a lesson in British weather preparedness. Picture this: crystal clear morning, stunning views... and me shivering because I somehow forgot that "sunny" in England is more of a suggestion than a weather forecast. Thank goodness for my 14-year-old's oversized hoodie, which he graciously lent me while rolling his eyes so hard I thought they might stick. Pro mom tip: Pack layers. Then pack more layers. Then throw in a windbreaker because trust me, you'll need it.
Ramsgate, though? While a sleepy English beach town doesn't sound like the kind of place a Floridian used to hot and humid beaches would flock, we aren't your typical beach goers. You can't appreciate what you have until you see the difference.....and we saw it! Desolate and cold, the beach left us giddy at how the English run into the water in Florida in December and consider it warm! But, that wasn't why were here.
The Ramsgate Tunnels are the perfect way to sneak history into a little adventure. These tunnels served as a hideout for the people of Ramsgate during WW2. Here's the game-changer: Go with a guide. Yes, they'd rather run ahead. Yes, your teens will complain. But five minutes in, my history buff was schooling me on WW2 raids like he was auditioning for a BBC documentary.
We capped off the day grabbing the most common ethnic food available in England, Indian. Samosas, butter chicken, and garlic naan was cozy and comforting. We warmed up from the "beachy" vibes and rested our feet from the miles of tunnel walking. The King Fisher and a pack of UNO made for some quality family time. And, my picky eater, who usually treats new foods like they're poisonous, actually asked for seconds of the chana masala. I considered having this moment bronzed.
Between the cliff walks, tunnel exploring, and garam masala conquering, this day basically wrote itself into family legend. Though I'm pretty sure my teenagers' version will focus more on how mom nearly got blown off a cliff and less on the historical significance of medieval fortifications. But hey, memories are memories, right?
The Rental Car Reality Check: Look, driving on the left is weird. Your brain will hurt. You'll reach for the windshield wipers instead of the turn signal approximately 847 times. But here's the truth - it's totally doable. Get an automatic (trust me, dealing with a manual transmission while sitting on the "wrong" side is a therapy session waiting to happen), spring for the full insurance (peace of mind is priceless), and download Waze because British road signs are basically a foreign language. And yes, roundabouts are terrifying at first, but by day three, you'll be channeling your inner Mary Poppins.
Want your own perfectly planned UK custom vacation without the roundabout anxiety? Hit us up at Jess.Travel - we'll create a custom itinerary that makes you look like a travel genius to your family. Because let's be honest, someone needs to make sure you're not accidentally booking a hotel next to a construction site or missing out on the best scones in Canterbury.
Remember: The best souvenirs are stories, and the best stories usually start with "well, that wasn't in the guidebook..." And sometimes, the most memorable moments come from watching your kids discover history isn't just something in their textbooks - even if they'll never admit it to their friends back home.
And no, I didn't drive on the wrong side of the road once. Though I may have ditched into a roundabout for what felt like eternity while my backseat drivers provided increasingly dramatic commentary. But that's a story for another day...
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