Charter Smarter Newsletter | July 24, 2025
The Best All-Inclusive Trip in the U.S. (That You Probably Didn't Even Know Existed)
Think all-inclusive means crowds, wristbands, and overstuffed buffets? Think again.
One of the best all-inclusive trips in the U.S. isn’t a resort at all — it’s a private sailing catamaran experience in the U.S. Virgin Islands. And yes, it can actually cost less than a typical resort stay. This isn't just a trip — it's an adventure-meets-luxury getaway that feels like something off your bucket list.
If you're planning your next tropical getaway, here's your deep dive into why yacht vacations are transforming the travel game—especially in the stunning Virgin Islands.
Your Own Private Chef—No Buffets, No Lines
Forget waiting in line for the breakfast buffet or reserving a table at the only decent on-site restaurant. With a yacht charter, your meals are curated just for you. Before your trip even begins, you'll fill out a preference sheet detailing your favorite meals, allergies, and dietary restrictions.
From plant-based to pescatarian, keto to kid-friendly, everything is tailored. Your private chef will serve up meals that match your tastebuds and your schedule, whether it's a sunrise smoothie bowl on the flybridge or a sunset lobster dinner under the stars.
All-Inclusive Rates = No Hidden Costs
One of the biggest perks? It’s all included. No surprise bills at checkout, no added gratuities you didn’t expect. Your meals, drinks, and snacks are covered in your weekly rate. That’s five-star dining without the five-dollar coffee charges or $25 buffet breakfasts. And yes, the cocktails are unlimited.
Your Crew is Your Concierge, Captain, and Best Kept Secret
The Ultimate Local Guides
Unlike a resort concierge who hands you a preprinted map and sends you off with a voucher, your yacht crew is on board with you—literally. They're island insiders who know the Virgin Islands better than any travel brochure ever could.
Want to visit a hidden beach on St. John that most tourists never find? Done. Curious about the best snorkel spot with zero crowds? You’ll be there before lunch. Your crew doubles as your private tour guide, safety expert, and storyteller.
Personalized Itineraries You Can Actually Change
With a yacht charter, your itinerary is flexible. Want to stay longer at Soggy Dollar on Jost Van Dyke or detour to a quiet anchorage off Norman Island? No problem. You don’t need to go through a front desk or fight for a last-minute booking—the sea is your playground, and your crew is ready to adapt.
You’re Not Stuck in One Spot
Every Day, a New Island
The Virgin Islands are made up of over 60 islands, cays, and islets. Why choose just one resort when you can visit a dozen breathtaking destinations in a week?
Each morning, you’ll wake up to a new view—from the dramatic cliffs of Virgin Gorda to the beach bar vibe of White Bay, Jost Van Dyke. No taxis, no transfers. Just smooth sailing.
No More Extra Charges for Fun
At a resort, everything "extra" costs extra—kayaks, paddleboards, beach chairs, even WiFi. On a yacht charter, most of that is already included. Watersports gear, snorkeling equipment, and paddleboards are standard. You get access to the full experience without nickel-and-diming along the way.
Why the Virgin Islands Are the Ultimate Destination
Ideal Sailing Conditions
With consistent trade winds, calm seas, and short distances between islands, the US and British Virgin Islands are a sailor’s paradise. It’s one of the safest and most scenic destinations for yacht charters—perfect for both first-time guests and seasoned adventurers.
Culture, Cuisine, and Coral Reefs
It’s not just about beautiful beaches (though there are plenty of those). You’ll find beach bars with live reggae, family-owned rum distilleries, and coral reefs teeming with marine life. You’ll swim with turtles, dine on conch fritters, and watch the sunset from a new angle every night.
Common Misconceptions
Myth 1: Yacht Charters Are Just for the Rich
Not anymore. Yacht charters are becoming increasingly accessible—especially with companies like Charter Smarter, which offers luxury sailing experiences at affordable rates. You’re essentially getting a floating all-inclusive villa, personalized service, and daily excursions all rolled into one.
Myth 2: It’s Complicated to Plan
It’s actually easier than booking a resort. Charter companies help you pick the right boat, walk you through the preference sheet, and match you with the ideal crew. No stress, no micromanaging.
What’s Included in a Virgin Islands Yacht Charter
Private chef and gourmet meals
Captain and crew services
Daily housekeeping
All non-alcoholic and standard alcoholic drinks
Onboard water toys (kayaks, paddleboards, snorkel gear, floaties)
Flexible itinerary
Who Should Book a Yacht Charter?
Families who want bonding time without fighting for beach chairs.
Couples looking for a romantic getaway with total privacy.
Groups of friends planning birthday trips, bachelorette parties, or just a long-overdue escape.
Adventure lovers who hate the idea of being trapped in one place.
Ready to Island Hop?
If you’re dreaming of turquoise water, soft sand, and unforgettable memories—but you want something more personal than a cookie-cutter resort—this is your sign to charter a yacht.
With top-tier service, island-hopping freedom, and all-inclusive luxury, a yacht vacation in the Virgin Islands isn’t just better than a resort stay—it’s in a league of its own.
Whether you’re celebrating a special occasion or simply craving a better way to unwind, Charter Smarter is here to help you book your dream trip at a price that makes sense.
Trending Now: The Yacht Everyone’s Talking About
If there’s one post lighting up our social media, it’s Evenstar—our 55-foot luxury sailing catamaran that’s redefining what it means to truly unplug.
This isn’t your average boat day. Evenstar is the trip you book when you want zero stress, total comfort, and next-level service from the moment you step onboard. With four spacious, air-conditioned cabins and four full bathrooms, it’s built for up to eight guests to spread out, relax, and enjoy the best of the Virgin Islands in style.
This charter comes with a private gourmet chef—and yes, it's all-inclusive. Think beautifully plated meals, tropical cocktails, and decadent desserts, all customized to your taste. You won’t be lifting a finger… except to toast your next island stop.
Whether you're planning a birthday, honeymoon, or “just because” escape, Evenstar is built to create epic, sun-soaked memories for you and your crew.
🎥 Catch the full vibe on our Instagram!
📲 And if you’re not already, follow us on social for yacht inspo, behind-the-scenes content, and sneak peeks at our most popular charters each week.
New Flights to the Virgin Islands Make Yacht Travel Better ✈️
Southwest Airlines is officially launching nonstop service to St. Thomas in early 2026 — its first new Caribbean route in years. And it’s not just a new flight—it’s a complete shift in how guests can access private charters in the Virgin Islands. Here’s what this means for your next yacht escape — and why now is the time to start planning smarter.
What’s Happening?
Southwest will soon offer direct flights from the U.S. mainland to Cyril E. King Airport (STT) in St. Thomas. While exact cities haven’t been confirmed, likely candidates include Dallas, Orlando, Chicago, and Baltimore, all major Southwest hubs.
With over 900,000 travelers flying into the USVI last year — and visitor numbers climbing fast — this new route brings even more momentum to the region. But for savvy travelers, this isn’t just about cheaper flights. It’s about unlocking smarter, more streamlined luxury travel.
Why This Matters for Yacht Travelers
1. It’s Never Been Easier (or Cheaper) to Arrive
Southwest is famous for:
No change fees
Affordable pricing
That means your group can fly into paradise with zero stress and no surprise fees.
2. More Access = More Charter Opportunity
With added connectivity from key U.S. cities, guests can book a 7-night escape without complicated layovers or premium flight costs. This opens up yacht travel to:
Families planning school break trips
Couples looking for getaways
Groups coordinating from multiple U.S. cities
3. A Smarter Split: Fly Commercial, Sail Private
Chartering a yacht no longer needs to feel like a logistical hurdle. Guests can fly Southwest into St. Thomas and immediately board a private yacht—no transfers, no delays, no time wasted. You get the efficiency of a commercial airline with the exclusivity of a luxury charter.
📞 Ready to Build a Smarter Charter?
Spring 2026 is closer than you think.
Whether you’re flying in with Southwest or arriving by private plane, Charter Smarter is ready to meet you at the dock.
Contact us today to get matched with yachts that sync perfectly with Southwest’s arrival schedule. Or better yet? Let us build your entire itinerary — flight to float.
CHARTER TIP 💡
Book Early to Secure Your Dream Yacht! The best yachts, crews, and itineraries are often reserved months—sometimes even a year—in advance, particularly for high-demand yachts and peak travel seasons. Booking early not only ensures the widest selection, but also gives you ample time to personalize every detail of your charter experience.
Emily Busichio
Yacht Charter Specialist
