The Undiscovered Caribbean: Nevis, St Eustatius, & St Kitts
10 Days
10 days/9 nights—$8,976 /person (single add $1724)
Couples, Friends, and Solos
Feb 13—22, 2025
All Breakfasts, 6 Lunches, 7 Dinners
The Undiscovered Caribbean: Nevis, St Eustatius, & St Kitts
You’ve been to the Caribbean... Now prepare yourself for an eye-opening & undiscovered-pampered experience to 2 of the most beautiful and manicured historic islands no one knows about. You’ll be the talk of the town and you deserve it. Serene, upscale Nevis sits just 2 miles off the coast of St Kitts by water taxi, where resort tranquility awaits. Lady Di chose here to bring the boys for peaceful luxury, and we’ll stay at The Montpelier Plantation, her favorite hotel in the world. Alexander Hamilton’s home, Mt Nevis, your own private beach, and afternoon tea, await you by day, with sizzling island restaurants by night. St Eustatius is an unspoiled slice of Dutch paradise your friends will envy as you point out this little unknown dot to them on the map. How can this be in the 21st century? We found it for you! Known as Statia by the locals, its heyday was the 1700’s and its “Upper” and “Lower” town are still perfectly preserved as you stroll back through history with your jaw open in amazement. Pirates, colonial architecture, legendary “blue beads” to collect, and a world famous volcano—the Quill- are here for you to marvel on this island of just 3000 that treasures its high-end guests. Top off your adventure by staying on one of the most magnificent tropical properties on the globe, the Golden Rock Spa and Resort nestled on 40 acres of water’s edge. Just say yes!
Highlights
Taste, touch, and see greatly sought-after upscale serenity in the Caribbean, the world’s most naturally beautiful island chain, and do it with an Army Ranger & author whose care for his people earned the Bronze Star in Iraq.
Travel at ease with Joe to 2 of the loveliest destinations in the Caribbean, Nevis & St Eustatius. Far from the maddening crowd, and tailored to the taste of the seasoned traveler, rejuvenate your body & soul in the luxury you deserve.
Take up 4 nights residence fit for a Royal at Princess Diana’s favorite resort hotel, The Montpelier Plantation, and enjoy the private beach, lovely landscaped Sugar Mill grounds, and afternoon teas that made so many memorable times for her and the young Princes.
Visit the home of Alexander Hamilton, Nevis’s favorite son, hike leisurely up to Mt Nevis, or book a spa treatment at the Montpelier Plantation.
Enjoy world class sunsets each afternoon with a cocktail before thrilling your palate—every single night—to incredible island fare at Nevis’s most iconic restaurants
Travel back to Colonial times: the lore of Pirates, rum, and buried treasures on the island of St Eustatius, known to the locals as Statia. Stroll its well preserved “Upper” and “Lower” Town taking in the history, shops, and dramatic views of the waves below.
Stay 3 nights at perhaps the most enchanting property you’ve ever been to — The Golden Rock Dive Hotel & Spa—paradise on 40 acres of priceless green coast, manicured with 100,000 plants, 3 fine restaurants, courts, spa, and its very own train around the property.
Start one morning off with a hike to The Quill’s crater, a volcano-lover’s dream; Keep a sharp eye out for blue beads along the way! Be back in time for a phenomenal island breakfast. Then go for a swim or book a healing treatment at the spa, or both!
Explore the island on a guided tour of a Dutch fort and perfectly preserved home from the 1700’s in the Upper town, and cobble down the last remaining Slave Walk in the western hemisphere to stop for a coffee (or something stronger) at the Old Gin House in the Lower Town. Sample a fresh catch on the waterfront at the Barrel House at sunset dinner.
Spend the final 1 1/2 days on the big island of St Kitts—time to capture a few well-curated activities and last hoorah for shopping, or sandy beachfront time at the Koi resort.
Trek out to Timothy Overlook for a postcard shot of the vista and maybe some playful monkeys. Cruise into Basseterre on our way to the Batik factory and either continue out to Brimstone Fortress or back to the resort.
What better finale than sunset dinner on Frigate Bay at Boozies on the Beach for Dora’s island specialties and outlandishly good cocktails to toast the best vacation ever.
Who’s Your Host?
Captain Joe Sacchetti is a U.S. Army Ranger-qualified paratrooper in the 82nd Airborne and author of Guts, Smarts & Love, who served 2 tours in Iraq and was awarded the Bronze Star for actions in combat.
A Track & Field All-American and Welterweight Boxing Champ in the 82nd Airborne, Joe escorted the Olympic torch through his Pennsylvania hometown in 1980 on the way to Lake Placid as a kid, and from that moment knew he wanted to see the world!
After MIT’s Business Exec Ed program, Joe started Highroads Traveler to make sophisticated global travel easily accessible to small groups of 20 by “hosting” them, now via Legacy Collectibles.
It’s rare to mesh the world of combat vet and sophisticated traveler, yet Joe is on a journey to be the world’s first Army Ranger to visit every country on the globe. 160 out of 227 so far, and it’s much more than stamping a passport.
Connecting with people around the globe in their language makes every trip more fun. From European roots, Joe is comfortable in half a dozen or so, and always learning more.
Playing music is another fantastic people connector so he & his wife Domenica always keep an eye out for a piano to gather round at happy hour. It doesn’t take much nudging from her to get Joe to play either!
Why “Hosted?”
Go with a Pro.
You’ve saved up and are ready to take the trip of a lifetime. Do you really have time to plan all the details and get it all perfect? If yes, great! Yet for most, pretty much no way. And how about when you get there making your way to the best hotels, sites and restaurants? Most say… daunting. Our solution – let’s go together and make your greatest trip ever.
“Taste, touch and see what the world has to offer” is Joe & Domenica’s mantra, and now you’re invited to come share the journey to the best places in the world with their small-group hosted tours.
Day by Day
Day 1
Day 1
St Kitts/Nevis— Fly into friendly St Kitts. We’ll meet at 10am at the Koi Resort in St Kitts to start your vacation and drive to the dock for a 12 minute water taxi across the 2-mile shallows, to Nevis.
A short ride from Oualie Pier in Nevis will take us to Drift restaurant on the beautiful rocky northside of the island for owner & artist Vikki Fuller’s art and an oceanfront lunch. It’s sea-to-table on the veranda from chef Nicole Merchant!
After lunch, we’ll check into the royally tranquil Montpelier Plantation. Relax & get to know the 60-acre shangrila that became Princess Diana’s idyllic retreat with her sons, and join new friends for afternoon tea.
Meet at the main house before sunset for a short ride up to the lush Hamilton Estate for dinner at Bananas, a plantation style restaurant with colorful owner Gillian and great island specialties.
Day 2
Nevis— Enjoy a leisurely morning starting with an early sunrise walk along the grounds—or chill in your Plantation room reveling in the view, before strolling to the main house for a lovely breakfast.
Tour the island capitol of Charlestown & Cannonade grounds, and visit the well kept home & museum of Alexander Hamilton, Nevis’s favorite son.
Then head up into the green hills of Nevis Peak to the iconic Golden Rock Inn (featured in the movie One Year Off) for lunch high up on the hill in the tropical gardens.
Enjoy the rest of the afternoon on the beach with a book and suntan lotion, book a spa treatment, or join your fellow travelers for afternoon tea at 4pm. Soak in the dreamy sunset at 6:20.
Put on your shorts and flip flops for a casual bite to eat at Pinney’s Beach, home to a row of pubs and shacks in the sand. If we’re lucky, we’ll join Sunshine, the most colorful bar owner on the island, for a drink!
Day 3
Nevis— Put on some athletic gear today! Before a great breakfast, join in the “square hike” on the Plantation to get the blood flowing.
At 10am, hop the shuttle and head over to the Plantation’s private beach with cabanas and lovely manicured grounds,
OR
Grab your racquet for Pickleball. Hit the courts for a few games first and then join the rest of the gang at the beach to cool off.
After a killer day in the sun, head back to the hotel for afternoon tea.
Tonight for dinner we are off to the Chrishi Beach Club, a super spot with good eats & beach and vivacious owners Hedda and Christian
Day 4
Nevis– Wake up leisurely with nowhere special to be today after a robust breakfast except under the glorious sun in paradise.
Today is a day to do what you want: book a spa treatment, get sun in your favorite chaise lounge on the beach, hike Mt Nevis, rent scooters and explore the island, find some shopping, or just sit by the pool and read.
Stop back in for afternoon tea and make plans for your last night in Nevis.
Be sure to soak up every bit of charm at Montpelier and take pictures.
Enjoy lunch & dinner on your own today either at the Plantation or on the island. We can help with suggestions!
Day 5
Nevis/St Eustatius—Say farewell to Nevis as we get an early start and take the ferry to the nearby Dutch island of St Eustatius that the locals call Statia. You’ll think you stepped back into Colonial times as you enter port under the watchful protection of 2 Dutch forts and The Quill volcano.
Start off the day with an island tour that begins in Lower Town with a cup of coffee at the Old Gin House. From there we walk up the last remaining Slave Path in the western hemisphere from Lower to Upper Town past the Fort and Church to well preserved stores and shops.
Stop at the top to capture remarkable views at the edge of Upper Town. Meet Misha the Curator and step inside the Museum of Nevis History for a look at colonial life in a perfectly preserved 18th century house with the beds still made and china set out on the table.
Stop for a must-try Super Burger in town before heading out to your slice of paradise at the Golden Rock Resort on 40 acres of tropical oceanfront.
The property’s private train will take you to your room where you can settle in and explore—don’t forget the suntan lotion!
Meet later for Happy Hour and a surprise as the sun sets, and enjoy a memorable dinner al fresco as you pinch yourself that you really are living your dream on a unique island!
Day 6
St Eustatius– Volcanologists from all over the world come to Statia to see The Quill from the crater’s rim, and so will we. Rise early today as we head out to the Quill Trail just after sunrise and head up to the rim of the crater. Rest here, or actually continue down into the crater with me—your choice!
Earn your Crater certificate and check volcano off your bucket list over oceanfront breakfast.
Spend the rest of the day and evening at your own leisure with a variety of activities.
How about any of the following:
-Relax & read poolside or at the beach
-Book a spa treatment or play tennis on a grass court
-Enroll in a dive class at the resort dive center
Enjoy lunch & dinner on your own - in town or at the resort.
Whatever you decide, we can help.. you deserve it!
Day 7
St Eustatius—Sleep in as late as you like and enjoy a relaxed morning in paradise.
Relish a sun drenched morning with nowhere to be except here in the moment.
Gaze across panoramic views of the ocean and neighboring St Barths over healthy lunch at Breeze.
It’s your choice of casual or dressy for an afternoon ride into town to catch a couple last places to shop and learn about the legend of Statia’s blue beads. Islanders say, “you don’t find them, they find you.” Perhaps you’ll get lucky!
Then we’ll settle in dockside for a rustic sunset dinner at The Barrel House for the perfect finish to a great day.
Day 8
St Eustatius/St Kitts— Start your day with one more workout in the fitness center or train ride around the property. Walk about and emblazon the image of this slice of heaven in your mind forever.
Meet at lunchtime and head into sunny Lower Town for a casual snack before boarding the 1-hour afternoon ferry to St Kitts.
Arrive at St Kitts and unpack your flip flops at the beachfront Koi Resort by Hilton. Step outside the door onto the golden sand until it’s time for Happy Hour and a surprise on the pool deck.
Enjoy dinner on your own onsite at restaurant Jaya or nearby on the island. We can help with suggestions to a few gems within minutes.
Day 9
St Kitts—Rise unhurried to the sounds of the ocean from your room. Try the local Kittitian breakfast favorites along with tasty classics at the Koi Resort with your fellow island friends on a laidback morning.
Join a well-curated 4-hour tour of St Kitts past the 1690 UNESCO Brimstone Hill Fortress enroute to the Caribbean’s oldest rum distillery founded in 1681 by Thomas Jefferson’s great grandfather. Sample some hand made fabrics at the Caribelle Batik Factory where they demonstrate the artisan process. Then we’ll finish at iconic Timothy Hill for a dramatic photo worthy of your next holiday postcard. If the monkeys are out, you’ll get a pic of them too!
What better way to finish off your life-changing 10-day escape than sunset dinner on the beach at Frigate Bay at Boozies on the Beach.
Will this be your best island vacation ever? After Miss Dora’s outlandish icy cocktails & island specialties, you decide!
Day 10
St Kitts —Wake up on the island and enjoy a final workout & breakfast before your morning stroll on the beach.
End your trip at checkout with a fond hug till next time and head back home refreshed and tanned!
What's Included
-
All Breakfasts, Selected Lunches, Selected Dinners
-
Bon Voyage gift(s) for your International Tour
-
Expertise and service from your Highroads Traveler Host, Joe
-
Additional regional guides and experts on several trips
-
Comprehensive Trip Detailer with all-you-need-to-know info
-
Guided tours at historic sites and select attractions as noted in the Trip Detailer
-
All gratuities at hotels and restaurants
-
Special events, including wine tastings and select attractions as mentioned in the Trip Detailer
-
Park and other entry fees
-
Fares for trains, ferries and other modes of travel as listed in the Trip Detailer
-
Select coach transfers
-
Baggage transfers
Not Included:
Leader gratuities, transportation to and from your Highroads Traveler trip start & end locations, and on-your-own meals & activities.
Ready to Embark on Your Next Adventure?
You've read about the incredible experiences waiting for you on this tour—now it's time to turn that dream into reality! Imagine exploring stunning landscapes, immersing yourself in vibrant cultures, and creating memories that will last a lifetime. Don't wait any longer to make this trip happen.
Start Planning Your Journey Today!
Click the button below to book your tour and secure your spot. Adventure awaits!
Gallery & Testimonials
As an Army Ranger for 25 years, I served as Joe Sacchetti‘s 2nd-in- command during Desert Storm, and there is nowhere in the world that I wouldn’t follow him, He cares about people. If I had the money, I would go on every trip he takes.
Master Sergeant Al A. , 45th anniversary D-Day (1994) Jump Team, Army Ranger, Green Beret, Bronze Star, Master Parachutist
We first met Joe on the island of Martinique while he was leading his group on a New Year’s trip. Ooh la la, he lives life like a true Frenchman! C’est Bon, such joeux de vie!
Christian C. , Sergeant, French Maritime Marines
