Sail the Leeward Islands

Luxury Yachts for All Sizes

the Leeward Islands Yacht Charters

Our Favorite Crewed Yachts In The Leeward Islands: Explore St Martin/St Barth's/Anguilla and More!

SUNMOON-All Inclusive Caribbean Winter 10 Guests, 5 Cabins Starting from €41,000 /Week SUNMOON-All Inclusive Caribbean Winter. 10 Guests, 5 Cabins. Greece. From €41,000 per week
TWO OCEANS 8 Guests, 4 Cabins Starting from $26,000 /Week TWO OCEANS. 8 Guests, 4 Cabins. Virgin Islands. From $26,000 per week
ABIDE 6 Guests, 3 Cabins Starting from $90,000 /Week ABIDE. 6 Guests, 3 Cabins. Leeward Islands. From $90,000 per week
ASCENSION 8 Guests, 4 Cabins Starting from $38,000 /Week ASCENSION. 8 Guests, 4 Cabins. Virgin Islands. From $38,000 per week
LE REVE L620 ESSENCE 6 Guests, 3 Cabins Starting from $42,000 /Week LE REVE L620 ESSENCE. 6 Guests, 3 Cabins. Virgin Islands. From $42,000 per week
RITMO 6 Guests, 3 Cabins Starting from $20,500 /Week RITMO. 6 Guests, 3 Cabins. Virgin Islands. From $20,500 per week
NDS EVOLUTION 9 Guests, 4 Cabins Starting from €55,000 /Week NDS EVOLUTION. 9 Guests, 4 Cabins. Virgin Islands. From €55,000 per week
MISCHIEVOUS 12 Guests, 5 Cabins Starting from $96,000 /Week MISCHIEVOUS. 12 Guests, 5 Cabins. Virgin Islands. From $96,000 per week
WONDERFUL 8 Guests, 4 Cabins Starting from $55,000 /Week WONDERFUL. 8 Guests, 4 Cabins. Virgin Islands. From $55,000 per week
VIVI 8 Guests, 4 Cabins Starting from $55,000 /Week VIVI. 8 Guests, 4 Cabins. Virgin Islands. From $55,000 per week
OUT OF THE BLUE 8 Guests, 4 Cabins Starting from $32,000 /Week OUT OF THE BLUE. 8 Guests, 4 Cabins. Virgin Islands. From $32,000 per week
ANDIAMO 8 Guests, 4 Cabins Starting from $32,000 /Week ANDIAMO. 8 Guests, 4 Cabins. Virgin Islands. From $32,000 per week
LUNAR ARC 6 Guests, 3 Cabins Starting from $32,000 /Week LUNAR ARC. 6 Guests, 3 Cabins. Virgin Islands. From $32,000 per week

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Location Details

Explore the Leeward Islands

St. Maarten/St. Barth’s/Anguilla

The Leeward Islands in the Caribbean are a favorite home base of charter yachts each winter, when guests flock to enjoy the quiet harbors, pretty beaches, and warm sunshine. Many islands remain minimally developed, while others offer world-class dining and shopping. A yacht charter here can truly be anything that you want it to be, whether you are interested in “getting away from it all” or sampling the finest of the Caribbean’s culture. If you have already chartered in the British Virgin Islands and are looking for a new destination to try out, The Leeward Islands is often close enough so that you can explore a new region while still enjoying your favorite Virgin Island yacht and crew.

Where will your journey take you?

Leeward Islands: Exploring St Martin, St. Barth’s & Beyond!

7-Night Leeward Islands Crewed Yacht Charter Itinerary

St. Martin • Anguilla • St. Barth’s

Average Cruising Speed: 8 knots

Daily Sailing Time: 2–4 hours

Route Style: Protected anchorages & short scenic island hops

Day 1
St. Martin → Anguilla (Road Bay)
DISTANCE: 12 NM DURATION: ~1 hr 30 min
Your crew welcomes you aboard in St. Martin, one of the Caribbean’s premier yachting hubs. After a safety briefing and settling into your cabins, set sail north across the Anguilla Channel.
Arrive at Road Bay in Anguilla, known for powder-soft sand and calm waters. Spend the afternoon swimming or relaxing on deck with a cocktail as the sun dips over the horizon.
Optional evening ashore:
• Dinner at Blanchards Beach Shack or Sandy Ground restaurants
• Beach walk along the quiet shoreline
Day 2
Anguilla → Prickly Pear Cays
DISTANCE: 8 NM DURATION: ~1 hr
Enjoy a leisurely breakfast before sailing to the Prickly Pear Cays, an uninhabited marine park with some of the clearest water in the Leeward Islands.
Highlights include:
• Exceptional snorkeling reefs
• Paddleboarding and kayaking in protected turquoise lagoons
• Relaxed beach barbecue prepared by your chef
Spend the evening under the stars in this peaceful anchorage.
Day 3
Prickly Pear → St. Barth’s (Gustavia)
DISTANCE: 24 NM DURATION: ~3 hrs
Set sail southeast toward the glamorous island of St. Barthélemy (St. Barth’s). Arrive in Gustavia Harbor, famous for its superyachts, chic boutiques, and French-Caribbean charm.
Afternoon options:
• Shopping in designer boutiques
• Beach time at Shell Beach
• Sunset cocktails overlooking the harbor
Dinner ashore offers world-class French cuisine.
Day 4
Gustavia → Colombier Bay
DISTANCE: 4 NM DURATION: ~30 min
A short scenic cruise brings you to Colombier Bay, one of the most protected anchorages on St. Barth’s. Surrounded by green hills and accessible only by boat or hiking trail, this bay feels wonderfully secluded.
Activities:
• Snorkeling with sea turtles
• Paddleboarding along the cliffs
• Relaxing on the yacht’s floating dock
Enjoy a quiet evening onboard with dinner under the stars.
Day 5
Colombier → Grand Case (St. Martin)
DISTANCE: 15 NM DURATION: ~2 hrs
Cruise back toward St. Martin, arriving in Grand Case, often called the culinary capital of the Caribbean.
Afternoon highlights:
• Beach bars and calm swimming
• Creole bakeries and cafés
• Optional sunset stroll through the charming waterfront village
Dinner ashore is highly recommended at one of the island’s renowned French restaurants.
Day 6
Grand Case → Tintamarre
DISTANCE: 8 NM DURATION: ~1 hr
Sail to Tintamarre Island, a protected nature reserve with calm anchorages and long natural beaches.
Things to enjoy:
• Snorkeling with turtles
• Exploring deserted beaches
• Kayaking and paddleboarding in protected waters
This tranquil stop offers a true “desert island” experience.
Day 7
Tintamarre → Simpson Bay Lagoon (St. Martin)
DISTANCE: 10 NM DURATION: ~1 hr 30 min
Return toward Simpson Bay Lagoon, one of the largest and most protected natural harbors in the Caribbean.
Spend your final afternoon:
• Enjoying water sports
• Visiting beach clubs at Maho or Mullet Bay
• Celebrating your last evening with a farewell dinner prepared by your chef.
Day 8
Disembarkation in St. Martin
Enjoy a final breakfast onboard before disembarking in St. Martin, taking with you unforgettable memories of sailing the Leeward Islands.
✔ Why This Route Works Well
Ideal for luxury crewed catamaran charters
Short comfortable sailing distances
Multiple well-protected anchorages
Combines Anguilla’s beaches, St. Barth’s glamour, and St. Martin’s dining

What Our Clients Say

Five Star Business Reviews

      EXCELLENT  
   Based on 17 reviews 
    
 
 
 
   
 
 
       Posted on Google  
   
   Theodore Guhr 
 
 
 
 Trustindex verifies that the original source of the review is Google. June 2026 BVI Charter- Karma
Well Kristen and Harry, this trip far exceeded our expectations; your hospitality, flexibility, and warm welcome was just what we needed this week, The two of you worked your butts off this entire week, and that hard work did not go unnoticed. Thank you for the amazing food that was prepared everyday. Thank you for providing healthy food options for Mads. Thank you pivoting every single day for Jake's interviews. Thank you for being so calm during the dives and during the entire week. We are so grateful that the two of you have entered and been part of our journey through life; we feel blessed as well as humbled. We look forward to sharing lots of adventures with you. With much love and gratitude,

-Ted, Wendy, Madeline, Theo, Jake, and Ben
  
 
      Posted on Google  
   
   Laura Siegler 
 
 
 
 Trustindex verifies that the original source of the review is Google. So much to say…..everything was perfect from my 1st contact with Mandy through until we arrived home.  She was responsive to all of our questions and helped us choose the right boat for our family. Everything was exactly as she said it would be from
the initial booking, making payments, giving her advice on different boats and sending links to help us with the ferry!  Mandy was a delight to work with and I would recommend her to everyone!!

We arrived in Tortola and we were met by Nick our captain and Jade our chef!  They are young. Smart, energetic, fun and aimed to please!  They even came along in the waters while we snorkeled and led us to all their favorite spots.  We swam with everything in the sea!

Jade’s cooking was awesome!! Every meal and snack was well thought out, interesting and delicious!!  And I mean delicious!! No wonder she won the culinary award last fall!!

Our week with our boys and their wives can be summed up in my Mother’s Day letter that I received a few days after we got home.  He said , it wasn’t just the sailing , the boat, the waters and the delicious food but I will never forget spending  the week with all my favorite people I!! Those words made it all worthwhile and I know we will all never forget it!!

Owner's reply
Hi Laura! I am so glad you were able to book Kismet this season with Nick and Jade! They will be amazing on Earnout next season
  
 
      Posted on Google  
   
   Amy Grove 
 
 
 
 Trustindex verifies that the original source of the review is Google. This was a dream vacation. The boat, C'Est La Vie, could not have been better and the crew was incredible. The food, the cocktails, the toys, the excursions, and just the overall experience was beyond our expectations in every way. This is the ultimate crew on the ultimate boat.

Owner's reply
Hi Amy, I am so happy your family were able to get together for this charter yacht vacation in The BVI. We look forward to working with you in the future for wherever you are interested in chartering next! Cheers Mandy
  
 
      Posted on Google  
   
   Ted Sulger 
 
 
 
 Trustindex verifies that the original source of the review is Google. Happened upon Mavis @ WLMS yacht Charters thru a recommendation, and after providing trip specs, priorities, group demographics and dietary preferences, she provided 4-5 available boats to consider for our trip. Amazing what you can discern reading and re-reading the vibe of each crew and the water toys they emphasize and the boat's features they promote. Given we aspired to dive everyday, be active everyday, as well stay and eat on the boat every night, we filtered the alternatives quickly. Luckily, we found Karma and its crew of Harry & Kristen available for our blissful week of joy and laughter and too many Rum specials and spectacular dives, and impeccable Just so attention and gourmet, i mean Bib Gourmand Michelin style breakfast, lunches, dinners and everything in between. The attention to detail was perfect, never too much when a book and nap were close at hand, but daily schedule highlights, hustle when necessary and just a refined level of engagement and enjoyment in what the crew was providing. it was the most impressive 24/7 service, while not being intrusive, which is a delicate task on a 50 foot yacht.I know i'm forgetting so much, but i just wanted to highly recommend Mavis for her help getting started with the daunting process, but also to Harry & Kristen for going above and beyond and making our special trip as wonderful as they did

Owner's reply
Thanks Ted! We are so happy you ended up booking Karma with us, hope you have a great rest of your spring!
  
 
      Posted on Google  
   
   Leigh Kelleher 
 
 
 
 Trustindex verifies that the original source of the review is Google. Four female friends (ages 60+) chartered the Sandy Cinco in early April, 2026. One of us had cruised the BVI on two prior boats, and this one was by far the best!  The boat is spacious, clean, and very well managed. The upper deck is a game changer (most don’t have this). The Captain, Mike, is an excellent sailor, and he went out of the way to show us places in the BVI that no others ever took us. He knows all the best mooring places. Lizzy’s cooking was excellent in flavor and presentation. We ate like Queens!  We felt at home as soon as we stepped on the boat. They paid careful attention to our Preferences forms and gave us exactly what we were looking for. On top of all that, we were blessed with fantastic weather the entire time. And, when we went onshore, Mike and Lizzy were well known to the locals, who would literally welcome us with hugs.  If you plan to charter for four to eight people, USE THIS BOAT AND CREW! You won’t regret anything. In fact, we hope to return in another year or two and won’t consider any other team or boat. Kudo’s to Mandy Walker, our broker,  who helped match us to this boat and helped with logistics.

Owner's reply
Thank you Leigh! I am so glad you had a wonderful charter with Mike and Lizzy on Sandy Cinco! Mike and Lizzy really enjoyed their time with you as well! I look forward to working with you in the future whenever you are ready.
  
 
      Posted on Google  
   
   pete haubenschild 
 
 
 
 Trustindex verifies that the original source of the review is Google. We had an amazing experience from start to finish with WLMS charters throughout the booking process as well as on the charter we did with the Colibiri crew -they were the ultimate hosts and crew which made our 50th birthday trip an experience we will never forget.  We are already planning to return with our teenagers!  Thank you to Graham, Kristiann and Matilda for being so gracious and fun to be around - the food and drinks were also amazing!
Pete and Stacy Haubenschild

Owner's reply
Thanks Pete! So glad Stacy had a great birthday celebration and look forward to working with you in the future!
  
 
      Posted on Google  
   
   Teri Norton 
 
 
 
 Trustindex verifies that the original source of the review is Google. As first time clients, our experience was exceptional from the guidance we received in booking our charter with Mandy to the accommodations on board Southern Charm.  Mandy ensured all of our travel needs were met and was with us every step of the way, setting up transportation as well as recommending pre and post charter lodging. She asked questions and listened to our requirements, recommending the perfect match for our charter aboard Southern Charm. Once aboard, it was obvious that the owners/crew had worked diligently to give us the very best experience possible. Every delicious meal was prepared exquisitely, every destination was postcard of beauty, and every activity was filled with fun and adventure. We will be talking out this trip for many years to come.

Owner's reply
Hi Teri, Thank you for booking with us. You guys were a wonderful group to work with and Southern Charm (Kevin and Elizabeth) loved having you onboard as well! Look forward to working with you in the future!
  
 
      Posted on Google  
   
   Kelly Hennessy 
 
 
 
 Trustindex verifies that the original source of the review is Google. This was our second trip using Mandy, and of course, everything was perfect! It was for my 50th birthday with our closest friends, and it could not have been better.  The boat (On A Whim) and crew were nothing short of amazing, and Mandy did such a good job pairing us with them.  Our captain, Alex, and first mate, Renee, made our week with them more memorable than we could have ever expected!  Please reach out to Mandy if are looking for someone to create an unforgettable vacation for you.

Owner's reply
Hi Kelly! So glad On A Whim delivered a wonderful trip for your 50th birthday!!!!
  
 
      Posted on Google  
   
   Betsy Dewberry 
 
 
 
 Trustindex verifies that the original source of the review is Google. Just returned from the most amazing family yacht charter in the British Virgin Islands aboard the stunning Wanderlust — and wow, what a trip! Charne and Dean are the absolute best crew!

From the phenomenal food prepared by the best crew ever, to snorkeling with sea life , zooming through the water on underwater  sea scooters , every moment was magic. We explored islands and hidden caves, watched breathtaking sunrises and sunsets, and even got massages on a floating spa boat!
We made unforgettable memories—from beach motes (beach buggies ) in Anegada to jumping off the plank at Willie T’s and sipping painkillers at the iconic Soggy Dollar. Nights were filled with card games, laughter, and family bonding under the stars.
Huge thanks to the incredible crew of Wanderlust who made this journey so special. Truly a trip of a lifetime !

Thank you Mandy for helping  us put this together ! Wanderlust and the crew , Charne and Dean were absolutely amazing !

Owner's reply
Hi Betsy! Thankyou for taking the time to post a review of Wanderlust-I will share with Dean and Charne. Look forward to catching up and working with you in the future. I'm so glad you got to experience The BVI with your family! Cheers Mandy
  
 
  
  
 
    Verified by Trustindex  Trustindex verified that these reviews were published on WLMS Yacht Charters's Google Business Profile. Learn more