From the moment a seaplane sets you down on Puget Sound and you step off the dock into a place that has been quietly magnificent since 1886, to the night your paddle cuts through water that glows green in the Pacific Northwest dark — from a wild orca surfacing six feet from your boat to a cannon firing across the harbor at sunset while five flags come down and every woman on that dock holds her breath — this is not a vacation, it is a discovery. You did not know places like this still existed. They do. We found one.

Condé Nast Traveler — “In Washington State’s San Juan Islands, Time Stands Still and Nature Reigns Supreme” 

Forbes — “Island Hopping in the San Juans Off the Washington Coast” 

Travel + Leisure — “This Wildly Scenic Island in Washington State has Rocky Beaches, Great Seafood, and Beautiful Coastal Trails”

The Points Guy — “Pacific Northwest Road Trip: The San Juan Islands and Olympic Peninsula” 

Inside Hook — “Washington’s Island Getaway: How to Do the San Juan Islands” 

Travel + Leisure, World’s Best Awards, #2 Best Islands in the Continental U.S. 

USA Today 10Best, #1 Best Washington Attraction 

Roche Harbor Resort, #1 Best Harbor Pacific Region, US Harbors 

Roche Harbor Resort, 4.6 Google Rating ⭐

Overall Trip Highlights

• Jekyll Island Club Resort — A Living Gilded Age Estate You are not staying at a hotel — you are sleeping inside a National Historic Landmark where Rockefellers, Vanderbilts, and Morgans once wintered, beneath live oaks draped in Spanish moss on the banks of the Jekyll River.
• CJ White Private Hotel History Tour — Jekyll Island Club Resort Your own personal historian unlocks the secret life of America’s most exclusive Gilded Age retreat — the Federal Reserve was born in this building.
• Faith Chapel — Original Tiffany Stained Glass Window A Louis Comfort Tiffany window personally signed and installed in 1921, inside a chapel where the Vanderbilts and Rockefellers once prayed, free and open at dawn.
• J.P. & Co. Gilded Age Portrait Studio You dress as a Jekyll Island Club lady of leisure in authentic period costume and walk away with a portrait that belongs on a wall.
• Private Horse-Drawn Carriage Tour — Historic District at Dusk Two private carriages carry your group through cobblestone streets at twilight, past Millionaires’ Village, as the last Georgia light disappears through the Spanish moss.
• Macabre Tales Ghost Tour — Lantern-Lit Dubignon Cottage An after-dark lantern tour inside the most paranormally active building on the island — cold spots, orbs, and a hundred years of secrets.
• Georgia Sea Turtle Center — Behind the Scenes A working sea turtle hospital where rescue, rehabilitation, and release happen every single day — and where grown women cry happy tears.
• Cumberland Island — Wild Horses & Dungeness Ruins A ferry to a protected National Seashore where wild horses roam Carnegie mansion ruins and pristine beaches untouched by time.
• Lands & Legacies Guided Tour — Cumberland Island A private van carries you deep into the island’s interior — Plum Orchard Mansion, First African Baptist Church, and the raw beauty of America’s last wild places.
• Horseback Beach Ride — The Stables at Frederica, St. Simons Island Your horse crosses a bridge through coastal marsh and carries you straight onto Sea Island beach — dolphins in the water, eagles overhead.

The Jekyll River catches the last light of a February evening as your carriage rolls through a century of secrets, past Gilded Age cottages draped in shadow and Spanish moss, toward supper and firelight and a sky thick with Georgia stars. You are coming home a different woman, and you will spend the rest of your life telling this story.

Itinerary subject to change

Day One: Arrival & The Golden Isles Welcome

The Georgia coast has a way of slowing everything down the moment you cross onto the island. The causeway opens up to salt marsh on both sides, Spanish moss trailing from ancient live oaks, the Jekyll River catching the afternoon light — and just like that, the world you left behind begins to feel very far away.

We settle into the Jekyll Island Club Resort, a National Historic Landmark that has stood on the banks of the Jekyll River since 1886. This is not a hotel — it is a living piece of American history, where the Rockefellers, Vanderbilts, and Morgans once wintered beneath these same oaks, in these same buildings, breathing this same salt air. Your room is steps from where the most powerful families in America came to rest. Tonight, so do you.

Today is designed for arrival and ease. Check in, unpack, breathe. Let your personal historian CJ White unlock the secrets of this extraordinary property on a private guided tour — then gather your group on the river pier for welcome cocktails as the Jekyll River turns gold at dusk. As the evening settles in, a fire is waiting for you at the pool, and so are the s’mores.

This is where your journey begins.

Highlights

• Arrival and check-in at the Jekyll Island Club Resort — a National Historic Landmark on the Jekyll River
• Private CJ White Hotel History Tour — the secret life of America’s most exclusive Gilded Age retreat, told by the man who knows it best
• Welcome cocktails on The Wharf — over the Jekyll River as the sun goes down
• Welcome dinner at The Wharf — Southern favorites, river views, your people around the table
• S’mores by the fire pit under a Georgia sky thick with stars — no agenda, no schedule, just the night

FUN FACT 

In November 1910, a group of the most powerful bankers and politicians in America slipped away to Jekyll Island Club in total secrecy — and in nine days, drafted the plan that became the Federal Reserve Act of 1913. The financial system of the United States was born in this building. Tonight, you sleep here.

Day Two: Jekyll Island — Yours to Discover

The island wakes up slowly in February, the morning air carrying salt and something quieter — the particular stillness that only comes when a place hasn’t been touched yet by the day. For those who rise early, two vans leave before sunrise, headlights cutting through Spanish moss toward Driftwood Beach, where ancient oaks stand knee-deep in the Atlantic and the sky turns colors that don’t exist anywhere else. For those who sleep in, nobody is keeping score. This is your trip.

Breakfast is a quick stop at The Pantry before the morning opens into something rare — unscheduled time in one of the most beautiful historic districts in America. Faith Chapel is free and open before ten, and it is worth every quiet minute inside. A Tiffany window, a Vanderbilt pew, and the kind of stillness that reaches into a woman and rearranges something. When the shops open at ten, the Historic District comes alive — Lilly Pulitzer and Dune Jewelry at 31•81, local Georgia craftspeople at the Georgia Grown Signature Shoppe, and the moment every woman on this trip will remember: stepping into J.P. & Co. Gilded Age Photo Studio to dress as a Jekyll Island Club lady of leisure and have her portrait taken in timeless style.

Noon lands at Eighty Ocean Kitchen and Bar — oceanfront, open-air, woodfired pizza and a raw bar and the Atlantic spread out in front of you. After lunch the afternoon belongs to the Georgia Sea Turtle Center, where a working hospital rescues and rehabilitates sea turtles, and where grown women have been known to cry. As the sun falls toward the marshes, two private horse-drawn carriages carry your group through the Millionaires’ Village at twilight — cobblestone under hoof, lantern light on Gilded Age stone — before the carriage drops you at Zachry’s Riverhouse for dinner on the Jekyll River. The night finishes with a lantern-lit ghost tour inside the most haunted building on the island. You will not sleep immediately.

Today is the kind of day you will describe for years.

Highlights

• Optional Driftwood Beach sunrise — ancient oaks standing in the surf, sky turning colors you cannot name, 7:15 AM
• Faith Chapel — free and open before 10 AM, home to a Louis Comfort Tiffany window personally installed in 1921 and a silence that stops you cold
• Historic District shopping — J.P. & Co. Gilded Age Photo Studio, 31•81 (Lilly Pulitzer, Dune Jewelry), Georgia Grown Signature Shoppe, Jekyll Island Sweets, North Pole South year-round Christmas shop
• Eighty Ocean Kitchen and Bar — oceanfront lunch, open-air, woodfired pizza, raw bar, walk the beach after
• Georgia Sea Turtle Center — a working sea turtle rescue hospital, behind-the-scenes access, deeply emotional
• Private Horse-Drawn Carriage Tour — two private carriages, Historic District at dusk, Millionaires’ Village by lantern light, drops your group at dinner
• Dinner at Zachry’s Riverhouse — local legend since 1987, Georgia shrimp, hot butter sauce, crab cakes, riverfront deck
• Macabre Tales Ghost Tour — lantern in hand, inside Dubignon Cottage after dark, cold spots, orbs, and a hundred years of secrets

FUN FACT

The Tiffany stained glass window inside Faith Chapel was not shipped and installed by a crew — it was brought to Jekyll Island and personally installed by Louis Comfort Tiffany himself, on Good Friday, March 25, 1921. It has not moved since. You will stand ten feet from it this morning, and it will cost you nothing.

Day Three: Cumberland Island — The Day You Will Never Stop Talking About

The ferry leaves at nine, and there is no other way in. No bridge, no road, no shortcut. Cumberland Island does not accommodate convenience — it asks you to come on its terms, and its terms are a forty-five minute boat ride across water that has been doing exactly this for centuries, carrying people toward one of the last truly wild places left on the Eastern seaboard. By the time the dock disappears behind you, something in the air already feels different.

The island is enormous and almost entirely untouched. Ninety percent of it is protected as a National Seashore, and only three hundred people are allowed here each day. You are among them. The Lands and Legacies tour carries your group deep into the island’s interior — past Plum Orchard Mansion, past the First African Baptist Church that has stood since 1893, past the kind of American history that does not make it into textbooks. The unpaved roads are bumpy and the oak canopy is dark and the air smells like nothing you have smelled before. Pay attention. This is the part where women go quiet.

After the tour, the afternoon belongs to you. The Dungeness ruins sit at the southern end of the island — what remains of the Carnegie family’s fifty-nine room mansion, open to the sky now, wrapped in vines, surrounded by palmettos and the sound of the Atlantic. And somewhere nearby, moving through the trees as if your group is not there, the wild horses of Cumberland Island are doing exactly what they have done every day for over a hundred years. They do not perform. They do not pose. They simply live here, and if you are still enough, they will walk within ten feet of you, and something inside you will shift permanently. This is the threshold moment. This is why you came.

You will be tired tonight. You will also be changed. Both of those things are true at the same time.

Highlights

• Cumberland Island ferry — the only way in, a 45-minute crossing to one of the most protected and pristine barrier islands in the United States
• Lands & Legacies guided van tour — Plum Orchard Mansion, First African Baptist Church (1893), deep interior wilderness, and the raw history of an island that Carnegie money could not fully tame
• Wild horses of Cumberland Island — descendants of Carnegie-era horses, running free for over a century, entirely unbothered by the world beyond this island
• Dungeness Ruins — the skeletal remains of the Carnegie family’s 59-room winter mansion, open to the Georgia sky, surrounded by palmettos and Spanish moss and the sound of surf just beyond the tree line
• Pristine Atlantic beach — miles of undeveloped shoreline with no hotels, no umbrellas, no commerce — just the ocean, the sky, and the women beside you
• Dinner at Willet’s Lowcountry on the return — lowcountry boil, fresh Georgia snapper, handcrafted cocktails, and the particular satisfaction of a meal earned

FUN FACT

On September 21, 1996, John F. Kennedy Jr. and Carolyn Bessette slipped away from New York and married in total secrecy inside the First African Baptist Church on Cumberland Island — the same church you are standing in today. There were forty guests. No press. No cameras. The island kept the secret for nearly a day before the world found out. You will walk through that door, and you will feel exactly why they chose this place.

Day Four: St. Simons Island — Sea Air, Horseback, and the Best Dinner of the Trip

St. Simons Island sits thirty minutes from Jekyll by van, connected by a causeway that crosses salt marsh in every direction, the water flat and silver in the morning light. It is a different kind of beautiful than Jekyll — more alive, more village, more lived-in — and after the solitude of Cumberland Island, it feels like exactly the right thing. Today has three distinct acts, and every one of them earns its place.

The morning belongs to the horses. The Stables at Frederica sit in the middle of the island, and from there a trail crosses a short bridge through coastal marsh and delivers you onto the beach at Sea Island, where the Atlantic opens up in front of you and a horse is doing what horses do when they are exactly where they belong. Dolphins move through the water. Herons stand at the marsh edge without flinching. Ospreys cut overhead. For women who have never ridden a horse, this is the moment they realize they can. For women who have, this is the moment they remember why. Nobody talks much. There is nothing to say.

After lunch at Southern Soul BBQ — and if you have never had smoked brisket eaten outside with your boots still on from the beach, you have missed something — the afternoon opens into St. Simons Village for two hours of wandering. The lighthouse has been standing since 1872. Fort Frederica is older than the country itself. The live oaks along the village streets are thick with Spanish moss, and if you look closely at some of them — actually look at the bark — you will find carved faces staring back at you. The Tree Spirits of St. Simons Island. Women always stop when they find them. Then the vans take you back to Jekyll to dress for the finest dinner of the entire trip, and Halyards does not disappoint. It never does.

You came here four days ago as a traveler. Tonight at dinner, look around the table. These are your people now.

Highlights

• Grand Dining Room breakfast — the proper send-off before a big island day, buffet and live piano at the Jekyll Island Club
• Horseback beach ride — The Stables at Frederica — trail through coastal marsh, bridge crossing, onto Sea Island beach with dolphins in the water and eagles overhead
• Southern Soul BBQ — named one of the best barbecue restaurants in America, smoked brisket and pork and hoppin’ john and collard greens, counter service, eaten outside
• St. Simons Village — the lighthouse standing since 1872, Fort Frederica National Monument, Christ Church, the famous Tree Spirits carved into ancient oaks along the village streets
• Dress for Halyards — 1.5 hours back at the resort, the nicest dinner of the trip deserves the occasion
• Dinner at Halyards Restaurant — ⭐ 4.7, #4 of 104 restaurants on St. Simons, stuffed flounder, Georgia shrimp and grits, seared scallops, a private dining room, and a wine list that earns its reputation

FUN FACT

In July of 1742, a small force of British soldiers under General James Oglethorpe — the founder of Georgia — ambushed a vastly larger Spanish army in the marsh at St. Simons Island and stopped the Spanish advance cold. The Battle of Bloody Marsh was over in minutes. Historians argue it was one of the most consequential battles ever fought on American soil — had Spain won that day, the entire southeastern United States might have become Spanish territory. You are walking the ground where that happened. Fort Frederica, which Oglethorpe built in 1736, still stands. It was the southernmost British military installation in the colonies, and it held the line.

Day Five: Last Morning on the Island — Goodbye, Jekyll

Nobody wants to be the first one to say it, so nobody does. The bags are packed and stacked in the hallway, the rooms look the way they looked before you arrived, and somewhere in the lobby a woman you did not know five days ago is holding your hand and neither of you can quite explain why this particular morning feels so heavy. This is what happens when a trip works. This is what BB does.

Breakfast is quiet and unhurried, the last one in the Grand Dining Room with these women, at this table, on this island. The live oaks are doing what they have done every morning — draped in moss, lit sideways by February sun, entirely unbothered by the fact that you are leaving. Check out. Load the vans. Take one last look at the Clubhouse before the door closes. The Jekyll River is right there, exactly as it was when you arrived, and the Spanish moss is moving in the same slow way, and for a moment it is very hard to go.

The drive to Savannah follows the coastal highway north through some of the most quietly beautiful landscape in America. The Jekyll Island causeway crosses the salt marsh with water on both sides, and then the Sidney Lanier Bridge rises up over the Brunswick River — one of the most dramatic bridges on the Eastern Seaboard — and on a clear February morning the view from the top of that bridge stops conversation in both vans. From there it is US-17 north through the Georgia coast, marsh and pine and low country light all the way to Savannah, where Savannah/Hilton Head International Airport (SAV) waits, and where the next chapter of your life — the one where you are different than you were — officially begins.

You came as strangers. You are leaving as something else entirely.

Highlights

• Last breakfast — Grand Dining Room — unhurried, together, the final morning at one of the most historic resort tables in America
• Checkout — Jekyll Island Club Resort — say goodbye to the live oaks, the river, and the Clubhouse that started it all in 1886
• Jekyll Island causeway — the drive off the island across open salt marsh, the Atlantic visible in the distance, one last look back
• Sidney Lanier Bridge — Brunswick, Georgia — a dramatic cable-stayed bridge rising 480 feet over the Brunswick River, one of the most striking views on the entire coastal drive
• Scenic coastal drive — US-17 North — salt marsh, coastal pines, Georgia low country for ninety minutes of beautiful, peaceful transition
• Arrival — Savannah/Hilton Head International Airport (SAV) — no flights departing before 3:00 PM

FUN FACT

Jekyll Island was so beloved by its Gilded Age members that the Jekyll Island Club had a strict cap — never more than 100 member families, ever. The waiting list stretched for years. Even John D. Rockefeller had to wait his turn. In 1947, the state of Georgia purchased the entire island from its private owners for $675,000 and opened it to the public — so that every American, not just the wealthiest hundred families in the country, could stand under these live oaks and breathe this air. That decision is why you were here this week.

Add-On Night | Day Six: Savannah — One More Night

Add-on pricing: $900 Single Occupancy $700 Double per person. Includes hotel, hosts, exploring, dinner, and breakfast.

The hotel is close to the airport, rooms are easy, and by five o’clock everyone is checked in and the evening is beginning. February means Savannah after dark — which is not a consolation prize. It is a gift. The squares glow under antique streetlamps, the live oaks go enormous and black against the sky, and the cobblestones on River Street have been catching light like this since cotton was king. Savannah at night is Savannah at its most itself.

The hosts take the group downtown — a short drive, an easy walk, no agenda beyond being present in one of the most beautiful cities in America on the last night of a trip that earned this sendoff. A few squares. River Street. The Cathedral of St. John the Baptist lit against the February sky. Then dinner — a real one, unhurried, with the women who know you now, at a table that belongs to all of you for exactly as long as you need it to. Back to the hotel when it feels right. Breakfast in the morning. Then home.

Simple. Perfect. Done.

Highlights

• Hotel check-in — near SAV airport — drop your bags, freshen up, and let the evening begin with nothing on the agenda but a beautiful city waiting thirty minutes away
• Savannah by night — a stroll through the squares — your hosts take you on a leisurely walk through the lantern-lit squares, past fountains and antebellum mansions and live oaks so old they have names, giving you a taste of a city you may just have to come back to see properly
• Cathedral of St. John the Baptist — twin spires rising against the February sky, one of the most breathtaking buildings in the South, more beautiful at night than most things are in daylight
• River Street — cobblestones worn smooth by two hundred years of foot traffic, the Savannah River wide and dark beside you, old cotton warehouses lit warm from within — stop for an ice cream cone and eat it on the waterfront like you have all the time in the world
• Group dinner — downtown Savannah — the final table of the trip, your hosts, no rush, no agenda, just the women beside you and a meal that closes six days the way six days like these deserve to be closed
• Back to the hotel — easy return, comfortable night, the city still glowing behind you
• Breakfast included — unhurried morning, hotel breakfast, then the short drive to SAV and the flight home to the life that is waiting for you — different now than when you left

FUN FACT

On December 21, 1864, General Sherman reached Savannah at the end of his March to the Sea — a path of total destruction across Georgia. When he arrived here, he stopped. Four days later he sent President Lincoln a telegram: “I beg to present you as a Christmas gift the city of Savannah.” He spared it completely. Every square you walk through tonight exists because of that decision. You are having dinner inside a Christmas gift from 1864.