Inspiration for your own tailor-made trip
Savannah - Charleston - Jekyll Island - Anna Maria
100% customisable for you
Wake up and wave goodbye to England – today marks the start of your road trip adventure. Head to the airport, speed through security and relax in the lounge before boarding your eight-hour flight to Philadelphia.
After landing, collect your bags and grab a snack before you board your second (and final) flight, taking you to your destination – Charleston, the gem of South Carolina and one of the most romantic cities in the South. From Philadelphia, the flight is just two hours, landing in the evening (Charleston time).
After touching down, you’ll be privately transferred to your historical hotel, ready to collapse onto your plush bed and catch some much needed shut eye.
Rise bright and early ready for today’s two-hour walking tour around Charleston’s charming downtown. Stroll through 300 years of history and hear the surprising stories behind the city’s colourful past as you take a tour of the pastel-coloured homes of Rainbow Row; the historic waterfront Battery; the impactful Civil War Landmarks; and the hidden gardens, courtyards and churches.
Tour ticked off, your next stop is Fort Sumter, a 19th-century sea fort located in the middle of Charleston Harbour. Accessible only by ferry, you’ll cruise over and learn a little of the fort’s history along the way. On the island, visit the museum which is filled with artifacts and information on the construction of the fort; stroll the grounds to see the cannons and wayside markers; and soak in the sweeping city views from atop the fort.
Kick off your second full day in Charleston with a visit to the magnificent Magnolia Plantation. Blooming with flowers year-round, the 24 hectares make up the oldest public garden in the United States – perfect for a romantic stroll.
After a morning following the garden’s oak-lined paths, exploring the nature-rich wetlands and walking the boardwalks of the swamp, the rest of the day is yours to spend how you please. Stretch out on one of the city’s six beaches (for shell hunting and surf, head to Folly Beach or, for a quieter vibe, check out Sullivan’s Island); tuck into a plate of iconic shrimp and grits; or try your hand (and feet) at some Charleston dancing in one of the artsy bars over on Upper King Street.
Get ready to hit the road – today you’ll be collecting your hire car ready to explore the South coast. After loading up the boot and deciding the designated driver, set your satnav to Savannah, the oldest city in the state of Georgia. The drive is around two-and-a-half hours (109 miles), giving you plenty of time to soak in the surrounding natural landscapes.
Park up at your hotel in Savannah’s historic district and check into your hotel, where a quick refresh will set you up for exploring the city’s nighttime attractions. The local historic district is particularly charming after dark with its moss-draped oaks, cobblestone streets and photogenic squares.
Over the next two days, discover what the historical streets of Savannah have to offer. Included in your itinerary is a walking tour with a local resident, who can share their insider knowledge while showing you around the picturesque squares, parks and churches. With Savannah being the filming location of Forrest Gump, you’ll even get to visit the iconic bench sat on by Tom Hanks.
With the city explored, it’s now your chance to further take another look at anything that caught your eye. If Savannah Theatre stole your attention, ask your local Concierge to book you into one of their award-winning performances. Or if the storefronts had you pining over their products, take some time to find the perfect Savannah keepsake.
Come evening, enjoy a taste for Savannah’s vibrant nightlife. Myrtle & Rose is a top spot for a romantic rooftop dinner or if you want river views and people watching, grab a seat in a bar over on River Street.
Bid a fond farewell to Savannah as you begin today’s hour-and-a-half (93-mile) drive to Jekyll Island. As you cruise over the bridge that connects the island to the mainland, the stunning ten miles of white beaches will slowly come into view. This peaceful barrier island is known for its quiet beaches, Gilded Age cottages and abundant natural beauty.
Check into your waterfront resort, slip straight into your swimsuits and head to the nearby beach for an afternoon of cocktail-sipping and sun-tanning.
Feast on a refreshingly fruity breakfast under the sun before getting stuck into today’s activity – a trip to Georgia’s only sea turtle education and rehabilitation facility. Here, you’ll have the chance to learn about the important work that goes into rehabilitating turtles before they’re released into the wild, and educational displays provide interesting information about the turtles.
The rest of the day is yours to explore Jekyll Island. We recommend checking out Driftwood Beach at sunset, where the tangles of dead trees create a stunning contrast against the twilight sky.
It’s goodbye Georgia and hello Florida as you set off for Fernandina Beach, a speedy one-hour-and-15-minute drive from Jekyll Island. Relax into your beachfront hotel and spend the rest of the day as you please. Fernandina Beach gives charming, small-town vibes with Victorian architecture, pristine beaches and a lively downtown district.
If you’re craving some city sites, head to Centre Street, the main artery of Fernandina Beach’s small centre. Browse the collection of art galleries, shops and restaurants and take a seat in a bar in time to watch the sunset with a cocktail in hand.
Today, you’ll leave the mainland behind as you take a trip to Cumberland Island. Head to St Mary’s, a short drive away from your hotel, and board the 45-minute ferry to Georgia's largest barrier island. Spend the day exploring the protected beaches and maritime forests, and make sure not to miss the Dungeness Ruins – the fascinating remains of a mansion built by Thomas Carnegie, brother and partner of steel tycoon Andrew Carnegie. After exploring, board the ferry back to mainland for an evening of slurping oysters at your hotel’s waterfront restaurant.
Buckle up ready for today’s one-and-a-half-hour (80-mile) drive to St Augustine. Built by the Spanish in 1565, this city is commonly thought to be the oldest in the USA, and the Hispanic influences live on in its streets, hotels and restaurants.
Check into your historical hotel and set out for a day of exploring: stroll around the Colonial Quarter, a living museum depicting city life in the 1700’s; climb to the top of the lighthouse with its swoon worthy views across the bay; or kick back on one of the long beaches (with 42 miles of silky sand, you won’t have to be elbow to elbow with tourists).
Fuel up with some coffee before the four-hour (230-mile) drive to Anna Maria Island, a barrier island tucked away on Florida’s southwest coast.
It’s a longer journey so either persuade your travel companion to take turns behind the wheel (easier said than done) or stop off in one of the many cities en route.
Upon arrival, relax into your boutique hotel, a delightful oasis that’ll be your home for the next three nights.
Life on Anna Maria Island is best experienced in the slow lane – with days spent flip-flopping between sand and sea, and indulging in seafood served fresh at the waterfront restaurants. If you fancy hopping on a boat tour to see dolphins and manatees in the wild, your local Concierge can book you onto the best. Further inland, head to Bridge Street and unleash your inner shopaholic in the large selection of stylish boutiques.
Come evening, head back to the beach and settle into a cosy cocktail bar. Anna Maria Island is spoilt with a west-facing sunset, so as the sun sinks into the sea be sure to raise a toast to your trip.
Enjoy one final lazy morning on Anna Maria Island before hitting the road for Tampa. The drive is just over an hour (55 miles), and you’ll be saying goodbye to your trusty set of wheels.
After dropping off the car, head into the airport and relax in the lounge before boarding your eight-and-a-half-hour flight home, landing the following morning.
Each of our trips is entirely tailor-made with originality, quality and cultural immersion in mind. Our team of destination specialists will craft itineraries based on your tastes, using their first-hand knowledge and the help of our in-country team of Concierges and guides. All trips are accompanied by a wide range of additional services, including a 24-hour helpline, the Original Travel app, fast-track airport services and much more.
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Our team of destination experts will get to know you and your unique requirements for your holiday
We work with you to build an ultra-personalised holiday itinerary with your choice of accommodation, experiences and activities
All of our holidays include little extras designed to make a big difference to your trip, from fast-tracking you through airport check-in and security to our network of local Concierges
