Promote Health & Wellness aboard TELLSTAR


Next up on the meeting agenda is Health and Wellness of yourself and of your company or family.  It is your responsibility to create a healthy life-work balance for your employees and to live it out by example.  Step aboard TELLSTAR to enjoy quality family or couples time.  
  • Let the chef create meals from local island farms or fresh fish from the sea to satisfy the health part of your week.  
  • Let the captain and crew promote wellness through activities on land and in the water–island hiking trails and nature walks through the lush vegetation or enjoy the numerous water sports and toys.  
  • Let the fresh sea air and warm island breezes cure you.  

Whatever you chose to fill your days, we promise you’ll come back renewed, refreshed and CHILLAXED!


Call Robyn at 847-867-9181

Or email

TELLSTAR is a brand new, 2019, 77ft. Lagoon.  She will be splashed in France in December to make her journey to the states.  We’ll be introducing her at the Miami boat show in February and are excited to have her first client booking for Spring Break  
TELLSTAR accommodates up to 8 guests in 4 spacious ensuite queen size cabins including an amazing master stateroom.  Plus the port aft cabin can be either two single beds of converted to a queen berth.
She will have all of the fun water toys for your entertainment such as tubes, water skis, kneeboard, floating mats, stand-up paddle boards, kayak and of course plentiful snorkeling equipment as well as outfitted with fishing gear. Certified divers will also have the opportunity to dive from the boat to enhance the charter adventure.
Even though this brand new yacht is amazing, the crew might be our favorite part!!!  Captain Jack and Chef/Hostess Jaimey have been chartering the Caribbean over 9 years and boy do they know how to have fun while making guests happy.  Their love for living on the water and traveling the islands is absolutely contagious!  
Contact to learn more about booking the crew and boat specifics and to book your Chillaxin’ Charter vacay aboard TELLSTAR!




Call Robyn at 847-867-9181

Or email

For a full brochure and pricing of TELLSTAR or
for other crewed yacht options, email
Let us book your CHILLAXIN CHARTER Vacation!

Motivate with Travel Incentives like a Charter Vacation aboard OUR HERITAGE



Travel incentives motivate performance, so let us splash a wave of motivation across your company.  Book OUR HERITAGE for an employee incentive trip and watch the return on investment grow.




Call Robyn at 847-867-9181

Or email


OUR HERITAGE is a Westport 112 built in 2015.  The owner takes pride in outfitting it with the finest furniture and decor so your guests are surrounded by complete luxury.  He also limits the amount of charters aboard so the crew and boat are guaranteed to be at their best.  
OUR HERITAGE sleeps 8 guests in 4 cabins. She boasts an array of toys for the guests enjoyment. Chartering the Caribbean this winter and New England in the Summer months.  
Toys & Features
35 ft. Boston Whaler Outrage with Triple 300hp Mercury Engines
15 ft. Novurania with 90hp Engine
2 New Sea-Doo Waverunners
2 Paddleboards
Ample Snorkeling Gear
All new Fishing Gear, Tackle and Rods/Reels for inshore and offshore fishing
Jacuzzi on Fly Bridge 
Enclosed Air-Conditioned Shower/Bathroom located near the Jacuzzi
2 New Sea Bobs
Shalom and Tandem Skis
Wake Board 
Knee Board
2 Person Tube
Floating Pool
For a full brochure and pricing of OUR HERITAGE or
for other crewed yacht options, email
Let us book your CHILLAXIN CHARTER Vacation!

LADY COPE: Ready to Entertain Your Clients and Chillax with Your Top Executives


A perfect match for thanking a client and rewarding your top executive is a Charter Yacht vacation. LADY COPE offers comfort, luxury, service and fun all wrapped up into a one beautiful vacation that will leave a lasting impression with your top clients and return your top executives refreshed and ready to conquer the next deal!




Call Robyn at 847-867-9181

Or email

LADY COPE is s 2012 Princess yacht with 2016 Refits to keep her fresh and welcoming.  Her dedicated and fun crew is ready to entertain and pamper.  She has a spacious main aft deck with a 46” Sun Brite TV for outdoor entertainment on the main level and a sun deck that is complete with a wet bar, entertainment center, sliding sun roof, a jacuzzi for 6 and custom sun pads.  The main salon has a large wrap around sofa and boasts direct TV and Bose Sound system along with a large formal dining area.  All four staterooms are ensuite and equip with luxury linens.
The toys and crew are ready to entertain all ages!
**29’ Everglades center console w/ twin Yamaha 300hp, setup with fishing gear.  (GREAT for fishing!)
-2 x 2 person wave runners. 1 – Yamaha & 1 – Sea Doo
-2 x Inflatable Paddle boards
-1 x Inflatable Slide 
-1 x Tube
-2 x Adult wakeboards
-1 x Adult waterskies
-1 x Inflatable Floating Island for 8 
-Snorkeling Gear 
-Beach Games; Bocchi ball, beach toys, etc. 
-Beach Set Up
For a full brochure and pricing of LADY COPE or
for other crewed yacht options, email
Let us book your CHILLAXIN CHARTER Vacation!

Pick a Regatta and Discover Your Inner Sailor!

Are you a classic sailor?  A sailor wanna-be? Or, just a sun-goddess who likes to relax and enjoy the sun shimmering off the water, sparkling upon the sails while watching everyone else do the work?  (That would be me!)


Whatever you are, we know you won’t want to miss out on the excitement and festivities of upcoming Regatta and Race Season!  

Check out the partial list of the season’s events and CONTACT US to book your crewed charter yacht.  Your crew will help you and your guests experience the festivities up close and personal while pampering you along the way!  Race events are both monohull and catamaran friendly for spectators and you’ll even see the big motor yachts hanging around as it’s hard to resist the excitement of a chartered race course!  And if you like a good dock party, you’ll certainly enjoy the post celebration!


Charter Catamaran Cartouche

Let us know what sounds good to you and we’ll set you up! We are, of course, a little partial to the Caribbean events, but don’t discount the U.S. NE Coast to connect with your true inner sailor!  
BVI Spring RegattaMarch 26 – April 1
Antigua Classic Yacht Regatta Antigua April 18-23 
Figawi Race Weekend – Hyannis, MA May 26-28
New York Yacht Club Annual Regatta – Newport, RI  June 8-10
Edgartown Race Weekend – Edgartown, MA July 21
Candy Store Cup – Newport, RI July 26 – 28
Nantucket Race Week – Nantucket, MA August 17-18
Opera House Cup – Nantucket, MA August 19
Panerai Herreshoff Classic Yacht Regatta – Bristol, RI August 23-24
Indian Harbor Yacht Club Classic YAcht Regatta – Greenwich CT Sept 14-15
ASK US about more opportunities and about the 2019 Caribbean Events to book ahead!
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BVI Spring Regatta


YES! The BVI Is Ready to Greet You on Your Crewed Charter Yacht Vacation!

Chillaxin’ Charters is happy to report via first hand experience that the BVI is ready and waiting for you to visit aboard your charter yacht!  A recent guest to Coco Locos Beach Bar on Jost captured it best with this quote: “Irma was a bitch, but now she gone!”  IMG_6058

The following recap of our 10 day charter aboard EUPHORIA gives you insight into some excellent itinerary options for YOUR upcoming charter.  What?!  You don’t have one booked yet? Call us, and we’ll make it happen! 

Day 1:  Our energetic crew, Captain Chester and Chef Jen, welcomed us aboard the beautiful Sunreef Catamaran, EUPHORIA and we raised a glass of Veuve to toast the trip ahead! Our pick-up in Trellis Bay on Beef Island, Tortola showed remains of Irma’s power as a handful of boats still lay at rest on shore. Despite the displacement of the beached boats, we look past them and feel the breath of life projected by a handful of surviving palm trees along with the lush green landscape and the awe of the indisputable shades of turquoise blue water and immediately know that “Beauty” has already overcome the “Beast” of Irma.



Day 2:  Waking up on relaxed “Island Time”, our morning view of Guana Island and the dolphins playing around our boat after breakfast set the Chillaxin’ tone for the day.  The word around the BVI is that there have been many more dolphin sightings Post-Irma, so no guarantees, but your odds are better for a little dolphin time frolic than they used to be.  We counted 6 in our pod of friends playfully bobbing about as if on cue for a charter photo session!


Dolphin Fun!

A morning cruise took us to Jost Van Dyke on our first full day as we were anxious to check in on our friends at White Bay.  The beach was clean and the beach bars were genuinely thankful for the charter boats to be there.  “Thank-you for coming” was our greeting from each bartender we met (and we might have met up with a few!) Soggy Dollar and Hendo’s Hideout not only had cold drinks and tasty lunch menus, but their gift shops were stocked with the perfect island souvenirs.  Coco Locos was also looking fine and didn’t disappoint in the rum punch department either!  Gertrudes is actively rebuilding and should be ready to roll before you know it.  One Love will be getting some extra love in the near future too.  The soft white sand of the beach with the spectrum of blue to gaze upon simply continues to make White Bay a true “Happy Place!”


Painkillers & RumPunch Please!


Still Beautiful!




Foxy’s was the next stop.  It was 2 days before their annual NYE Party and it felt like we were at a set-up for Kenny Chesney concert.  Kenny’s One Love Charity workers were actively building a new stage on the beach and it was looking good.  Foxy greeted us with new stories and his bright beautiful smile.  If you have never taken the time to actually sit and talk—I mean listen—to Foxy, you are missing out!  It’s actually something to consider for your bucket list. Let’s say, #12. Spend time listening to Foxy share a few stories and jokes while sipping on a rum punch!”  You’ll never forget it!  We again found ourselves saddened by Irma’s remains around Great Harbour, only to be encouraged by the very people who lived through it with their smiles and stories.  “Thank-you for coming.”



A sunset cruise over to Cane Garden Bay never disappoints and since we wanted to pop into Myett’s to show some support, we thought it would be a nice spot to moor for the evening. Myett’s still has a beautiful view of the Bay.  It was certainly quieter than normal, and once again we heard, “thank-you for coming, so happy to have you here!”

Day 3:  Waking up surrounded by the hillsides of Cane Garden Bay and the roosters crowing at dawn along with the mist of the sea air are the sights, sounds and smells (fresh sea air) of a charter that somehow become an engrained part of your vacation psyche.  We were glad we did our quick visit to Cane Garden.


Cane Garden Bay, Dec 30, 2017

Next up was Christmas Cove to support our friends at Pizza Pi and show the USVI some charter love! All we can say is YummmmO!!!!   It’s a great cove to paddle board and snorkel as well! 




A short cruise took us over to St. John to moor at Waterlemon Cay for the afternoon where we hit land to explore the Old Sugar Mill Plantation.  We’d highly recommend it!  Views are breathtaking and the history is evident in the walls of the remaining structures–fun for all ages.    



Day 4:  Another specially prepared breakfast by Chef Jen followed by a morning snorkel and then off to Norman Island.  A quick stop in Soper’s Hole showed a mix of new and old which was beginning to be the pattern of the trip.  Yes, we still see remains of the storm– missing windows or worse yet, an entire building we knew should be there was just gone–heartbreaking.  Yet, in the same panoramic view, there is life getting back to the new normal.  Time. The full rebuild is going to take time and is made possible with a heavy dose of island love and giant splash of island spirit. 

Next, we arrived to Norman Island to find our view filled with charter boats of all sizes gathering for New Year’s Eve.  We moor at Treasure Point for our best ever snorkel at The Caves.  No crowds.  With The Caves all to ourselves, we could take our time and truly enjoy the underwater treasures waiting to be discovered.  After our snorkel, we settled in near Pirates Bight, got into our island “fancy” cloths and enjoyed a Beach BBQ New Year’s Eve Party!  Charter crews, guests, and locals alike all danced until our sparklers were lit at Midnight to flip the calendar to the possibilities of 2018!  By the way, kudos to The Bight!  It looks amazing!  And thanks to the crew of FOXY LADY for organizing the NYE beach party filled with a fabulous buffet, live music, dj & dancing, beach bonfire and excellent family fun!






Day 5:  Waking up on New Year’s Day surrounded by fellow Charter boat friends was the best way to start the new year.  Le Reve, Shangri-La, Nenne, Foxy Lady, Mrs. Happy, Where’s Waldo, Ipharra, Stop Work Order, A3, Ulta, Blue Moon, and many others were all waking up with happy guests and crews thankful to be in the BVI!  I must admit, I was also secretly happy that I did not wake up to news that Kenny Chesney made a surprise appearance at Foxy’s!  (There was a moment I suspected he could, he might, but he didn’t.  Whew, I didn’t miss anything! It might be on my Bucket List to party in the Caribbean with Kenny Chesney! It could happen, right!?)

A morning Sail to The Baths on Virgin Gorda set the Chillaxin’ tone for the morning followed by all of the adventure and untouched beauty The Baths has to offer.  Irma could huff and puff, but she was no match for those boulders!  There were a number of charter boats and even a few mega-yachts there to dinghy guests in and enjoy the walking paths, but we never even passed another group along our walk.  We ventured to The Top of the Baths to simply soak in the awe inspiring views (and maybe enjoy a delicious rum punch too!;).  If you have not yet experienced The Baths, it is a must on your Bucket List!  


Probably my one and only itinerary disappointment of the week was that we had hoped to visit CocoMaya next after The Baths, but they were closed on New Years Day.   We were not able to squeeze CocaMaya back into the itinerary.  Sorry Coca Maya–Next time!  If you can, be sure to visit them along your charter itinerary!

On to Plan B….A sunset cruise to Leverick Bay to moor for the evening.  Our Chillaxin’ sail gave us time to enjoy some Kenny Chesney music, sip on refreshing coctails and discuss the tradition of giving everyone on the boat a Pirate name for the trip.  One has to “earn” their pirate name in some fashion during the trip.  Some earn their pirate names sooner than others.  At this point, we had affectionately named our Captain “Barracuda Bait”! (Sorry, we can’t tell you why or else you’ll have to walk the plank!) We also had a “Princess Pirate”, a “Flipper Pirate”, a “Captain Crash” and a Greybeard with a few people yet to earn their Pirate patch!  

Day 6:  Another leisurely breakfast and then it was SPA time–Yay!  Who doesn’t love a massage during vacation?!  Lucky for us, the SPA at Leverick Bay is up and running and didn’t disappoint! All 6 of our guests took 60 minutes to zone out….Aaahhhhhh! 


Leverick Bay 1/2/18


The Spa at Leverick Bay

Off to Oil Nut Bay to enjoy a leisurely lunch at their Beach Club Restaurant.  Oil Nut Bay will soon be re-opening their Villas (March 1st), and currently are welcoming charter boat guests to enjoy the restaurant, swim up bar, pools, and watersports when they dine at The Beach Club Restaurant for lunch.  We’ll let the pictures of Oil Nut Bay speak for themselves!  Stunningly beautiful property, exceptional staff and more than one, “Thank-you for coming to visit us!”  


Oil Nut Bay Pool


Chillaxin’ Time!


Beach Club for Lunch


Swim Up Bar–CHEERS!

After a Chillaxin’ afternoon at Oil Nut, it was time to enjoy a sail over to Anegada.  Our Chef extraordinaire, Jen, made another dinner on-board that left us wondering how she can possibly mastermind such deliciousness (is that a word?) with provisions from a boat galley and make it seem like she is running a 5-star restaurant.  Even with a few differing preferences among the group–she’s probably laughing out loud at my use of the term “a few!”–she served up a meal each night to make everyone happy! Thanks Jen!

Day 7:  Excited to wake up to our view of Anegada and hit the paddle boards for some morning exercise.  Today’s adventure started mid-morning with our open-air taxi to visit Big Bamboo Loblolly and Cow Wreck Beach Bar.  Both greeted us with a “Thanks so much for coming to visit us!”  Each were in great condition, serving cold drinks, full menus and shared smiles, laughter and a few extra stories.  Both beaches are still beautiful, but Cow Wreck forever holds an extra special place in our hearts.  Another “Happy Place”.  Ann & Andrew, of Cow Wreck Beach Bar, don’t forget to give us a shout before your next trip to LOTO! 


Potters By The Sea, Dinghy Dock–WELCOME to Anegada!


Big Bamboo, Loblolly Time to fly the drone!


Cow Wreck Beach 1/3/18


Next up, a late afternoon Chillaxin’ sail back over to Leverick Bay to hit Michael Beans
“Happy Arrr” show! Michael is playing Monday – Wednesday 5pm-7pm this charter season and it’s a MUST on your charter route for extra pirate FUN! Call Leverick Bay ahead to confirm.


Michael Beans at Leverick Bay–Family Friendly Show!


Happy Arrrr!!


Day 8:  Captain Chester moved the boat for a Sunrise Cruise followed by breakfast and a swim at Sandy Cay.  We swam in for our own private island experience to walk around (1/2 way around at least) and search for coral treasures along the beach.  Next, back to White Bay because we had such an amazing day there the first time, we wanted more!  CRAZY what difference even 1 week can make!  Just 6 days later, Gertrudes had significant progress on it’s structure.  One Love had 10 guests from a day boat hanging out and bellied up to the “open air” bar.  And, Ivan’s had added beach chairs and signs in preparation to host an upcoming Sunday Funday for the Floatilla.  Our group found the adirondack chairs and sunk our toes in the sand while mixing in some beach walks and play time in the water.  A day of pure CHILLAXIN’!  


Cheers from White Bay!


At some point, we heard Kenny sing, Adios to Jost and it was that that time of day.  A move over to anchor in Peter Island’s Little Harbour provided the perfect opportunity to check an item off of one of our guest’s bucket lists–“To swim with the Tarpon Fish at night!”  Yep!  And she didn’t have to do it alone!  A few brave souls joined in (led by fearless Captain Chester of course) and we all had a magical night snorkel.  We were accompanied by a family of a mama, papa and baby sting rays and of course a zillion tarpon under the blue lights. 

Day 9:  A morning snorkel, paddle board, water sports and mini-hike started the day.  Our hike was “mini” as the path was overgrown from no use and this particular soul was not so brave!  With our last day looming over us, it was time to cruise closer to Trellis, so off to Guana we went to come full circle.  A final snorkel for the trip was a must and no place better to do it than at Monkey Point off Guana Island.  The reef here was colorful and the fish plentiful.  

Our last night onboard EUPHORIA was spent reflecting back on all of our “favorites” of the week.  The common answer, “It’s so hard to pick ONE thing because it was all amazing!” And, “I can’t pick ONE meal, they were all so delicious!” 

Day 10: An early morning move over to Trellis Bay for our last leisurely breakfast aboard EUPHORIA.  Sad goodbyes, a moment when our inner pirate personalities that evolved during the week thought about hijacking the boat (“I’m the Captain Now!”) to extend the vacation, and then the reality of de-boarding for our return to the cold sank in.  Family and friend memories made.  Lifetime friendships formed with our crew.  Island life alive and well among our favorite destinations.  


Thanks Jen and Chester for a great charter aboard EUPHORIA!

Our time on charter with “no worries” was the perfect way to reflect, refresh, reconnect and renew.   Our love for the islands is replenished and our efforts to advocate for island tourism and support of the rebuild process will continue, one Chillaxin’ Charter vacation at a time!  

Ready to explore booking YOUR crewed charter vacation?

Call Robyn at 847-867-9181 or email  

Robyn will help you select the best crewed catamaran or motor yacht that fits your group’s personality and budget.  Robyn will assist with all of your travel details so your only job is to sit back and CHILLAX!

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Want to support the USVI and BVI Hurricane Rebuild efforts?  Link to Kenny Chesney’s Love for Love City Foundation at

Want to more info. on land-based resorts and villas that are open for you to visit before or after your charter?  Visit: for the most up-to-date report.






To Charter, Or Not To Charter? That is the Question. Click for the answer!

The answer is YES!  Life is short, book the charter yacht vacation!  

Are you going to let a little whitehouseblogole’ hurricane called Irma or Maria change your winter vacation dreams on a crewed charter yacht?  I think not!

Ok, so they weren’t so little and our heart still breaks as they rocked the Caribbean world, changed many lives, and stripped away buildings–we continue to support all of those impacted and provide links below to reputable support efforts.  What remains?  Beauty. Island Love. Strength. Passion. Community. Oh, and don’t forget the painkillers and rum-runners! Not to mention the sea turtles, blue waters and white sand!

The B.V.I. Flotilla continues to come together at Soggy Dollar on Jost Van Dyke.  Check out and follow their community efforts to bring normalcy back to the islands: Click link:

The Yacht Charter community kicked off the winter charter season and already posting picture after picture of beautiful anchorages, snorkeling, diving sites, water activities and open restaurants/beach bar establishments.  Worried that provisioning for charter yachts will take away food supply for locals and those rebuilding the islands?  Remember that the charter yachts have been going “green” for the last several years so with their own water-makers on-board generating fresh water daily, and with access to stocked grocery stores for provisions, the charter yachts should not be seen as a draw on supplies in the main grocery stores that have reopened, there is no concern.  The yachts will, instead, be bringing the community tourism to promote regrowth!  Many of the island establishments are working hard to be able to greet guests with a smile, a beverage and maybe an old-school beach BBQ and certainly some heartfelt stories of survival.  Some are ready now, some will be soon! You can follow BVI Traveller’s website and Facebook to be notified of the most recent openings!  

Your destination options are wide open, and YES, it DOES include the U.S.V.I and B.V.I.! Some destinations, such as the Bahamas were relatively untouched and are always an excellent charter destination.  Others will have more of a story to tell and your charter crew will navigate the experience to make sure it’s customized and special!  Regardless of the destination, the answer to your question of “to charter or to not charter” is most certainly–YES!

Live by the motto:  “Life is Short! Book your yacht charter vacation! 

Chillaxin’ Charters specializes in matching clients with the best yacht and crew available for your vacation dates.  Our services are no cost to you and our experience will guide make the booking easy so you can countdown to a CHILLAXIN’ vacation!  We have yachts in:

√U.S.V.I. & B.V.I.

√The Bahamas

√St. Maartin and St. Barths

√St. Lucia, St. Vincent & The Grenadines



√The Florida Keys and Southern Florida Coastline 

Visit Chillaxin’ Charters Website to Inquire with Robyn for available charter yachts and itinerary possibilities within each destination.  

For immediate answers, call Robyn at 847-867-9181

email Robyn at

Please continue to support the V.I. recover efforts through the following fundraisers or another reputable foundation of your :


Link to this page for your choice of funding options:

Which Brand New SUNREEF Charter Yacht would YOU Pick?

Here’s the dilemma…You’ve got not 1, not 2, but 3 BRAND spanking new SUNREEF 74ft. Luxury Catamarans from which to choose.  SUNREEF is considered one of the leading designers and manufacturers of luxury sailing and power multihull yachts.  Their yachts are customized to the owners pleasure and specifications creating a unique feel on each SUNREEF you board.  Quality of the build surpasses competitors.  When you experience the quiet night’s sleep on these beauties, you’ll understand why we rave about a SUNREEF and love to book them!  

Back to the burning question! Check out these 3 new vessels built with love and tell us which one you would choose?  Will it be CALMAO?  DIANA? or ORION?  

Click on each yacht below for full brochure descriptions and report back!

WAIT! Before you click, know that their Winter Ports are open to the Caribbean and you can get your feet wet (pun intended;) in chartering in the Mediterranean next summer!  Corsica/Sardinia Itinerary for ORION and a Balearics home summer port for CALMAO with options of exploring into Spain and Croatia.  DIANA’s delivery expected in mid-February 2018 and base ports TBD.






Pricing ranges from $45K – $52K All Inclusive

Want to learn more about the crew or the amazing itineraries available??  Don’t delay, call Robyn at 847-867-9181 today! Or email at