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Catamaran Dianna Rose, 51ft, 6 passengers based in St Thomas, US Virgin Islands

Weekly Charter Rates

$15,000 (2 passengers 7 nights)
$18,000 (6 passengers 7 nights)*
*Price range is subject to change. Please Contact Us for pricing for various party sizes, number of nights and seasons. Best price guarantee: We endeavor to offer the lowest prices available and will always match lowest rates. We accept Visa, MasterCard and AMEX, no fees.


Guests Cabins Length
6 3 51ft
Guest cabin configuration:
1 Master Queen and 2 Queen en-suite cabins with AC
Designer Lagoon 500
Built 2012
Children Allowed Yes
Children Min. Age water safe
Half Board Available Yes
Home port Red Hook, St Thomas, US Virgin Islands
Scuba SCUBA available on board Available onboard
Dianna Rose 1 Dianna Rose 2 Dianna Rose 3 Dianna Rose 4 Dianna Rose 5 Dianna Rose 6 Dianna Rose 7 Dianna Rose 8 Dianna Rose 9 Outdoor dining area Spacious master cabin Master bath Luxurious queen bed Guest bath We keep a great assortment of water toys on board The dolphins love us! The master cabin lounge Meals are always a special event comfortable seating area in salon

Catamaran Dianna Rose Overview

Dianna Rose is a Lagoon 500 catamaran which accommodates up to 6 charter guests in three queen en-suite cabins (one a larger master suite).

The yacht is fully equipped with a variety of sporting equipment including kayaks, fishing gear, surf boards, stand up paddle boards, wake board, water skies, tow tube, professional beach volleyball net and snorkeling gear.

Every charter itinerary, drink list and meal plan is tailored to suit guest preferences. Come aboard Dianna Rose to experience a fun filled, adventurous vacation in comfort and style!

Ports and Available Cruising Areas

Home port: Red Hook, St Thomas, US Virgin Islands
Winter cruising area: Caribbean Virgin Islands
Summer cruising area: Caribbean Virgin Islands, Bahamas

Optional Half Board Details


Please inquire for details

Green Initiative: Purified water with reusable bottles made aboard. Reusable grocery bags are used for provisioning. No disposable plates or cups are used. Herbs are grown onboard.


DIANNA ROSE can accommodate 6 guests in 3 beautiful cabins all with queen-sized beds, electric heads and private showers. The Master cabin is a large "owner's suite" with a lounge area.


WiFi Internet: Not available
Air Conditioning: Full
Salon Stereo
Salon TV
Deck Shower
Hair Dryer
Board Games
Sun Awning
Ice Maker

Water toys

1-Man Kayak
2-Man Kayak
Adult Water Skis
Kids Water Skis
Knee Board
Snorkel Gear
Underwater Camera
Fishing Gear
Fishing Type: troling
Fishing Rods: 2
Dinghy: 14 FEET
Dinghy Outboard HP: 50hp
Other equipment includes:

2 Rigid Stand Up Paddle Boards, 1 inflatable SUP

SCUBA available on board

 SCUBA Details

Scuba Terms: Rent gear at around $180pp for up to 5 dives per week for certified divers.
Scuba Available Onboard: Yes
Captain's Scuba License: Instructor
Divers: 6
Number of dives per week: 5/week
Crew photo

Meet the Crew

Joseph & Britta Stiles

Joseph and Britta grew up a world apart but ended up finding true love in the Virgin Islands. He, from a small family farm in the Pacific Northwest and she from the white sandy beaches of Florida, they married in 2012 on the island of St Croix. Before moving to the Caribbean Joseph received degrees in both the Culinary Arts and Patisserie and Baking from Western Culinary Institute in Portland Oregon and in 2009 he packed his bags for the islands. He promptly bought his first sailboat and moved on board. Britta came to St. Croix as a PADI dive instructor in 2005 working at local dive shops and in the hospitality industry where she was able to take advantage of some of the best scuba diving in the Caribbean. Before the couple married they began to eagerly explore the Virgin Islands on their live aboard sailboat and have explored the entire scope of the Lessser Antilles.

Joseph comes to Dianna Rose by way of Motor Yacht Freedom a luxury yacht where he worked as the chef for 5 years. It was here that he took his restaurant philosophy and adapted it to yachting. He prides himself on sourcing from local farmers and fishermen and utilizing the relationships he has cultivated while in the restaurant industry in the Caribbean.

While the couple lived on St. John, Britta worked aboard Kiote, a 36 foot Pearson. Here she was able to give that special touch to the client experience, many of whom had never even been snorkeling before. Her love for everything underwater would quickly put her guests at ease and her knowledge as a dive instructor would allow her to point out and identify everything that swims and crawls below the oceans surface.

Now this chef turned captain and his mermaid wife bring to Dianna Rose the credentials to offer a vacation of a lifetime. The intricate knowledge of this world class sailing destination that they possess will leave guests breathless with memories to last a lifetime.

See reviews

Availability for Dianna Rose:

Listed below are any confirmed reservations or unavailability, as well as current holds / options. Note: this calendar is not always 100% current. Please contact us for more information about available dates aboard this yacht.

Upcoming 12 Months Reservation Calendar:

Available weekend day:
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Reservation Calendar with Port Locations:

Booked: Sunday, 26 February 2017 to Sunday, 5 March 2017: Booked: Red Hook to Red Hook
On Hold: Thursday, 23 March 2017 to Thursday, 30 March 2017: Option Taken: Compass Point, St Thomas* to Compass Point, St Thomas*
On Hold: Saturday, 8 April 2017 to Saturday, 15 April 2017: Option Taken: Red Hook to Red Hook
Booked: Saturday, 29 April 2017 to Saturday, 6 May 2017: Booked: West End, Tortola, BVI* to West End, Tortola, BVI*
Booked: Friday, 7 July 2017 to Friday, 14 July 2017: Booked: Red Hook, St. Thomas, USVI* to Red Hook, St. Thomas, USVI*

Hours required between charters: 24 hrs

Contact us

Contact us for rates and current availability or to book a charter aboard Dianna Rose!

Reviews for Dianna Rose with Joseph & Britta Stiles:

We had a wonderful trip. Joseph and Britta were awesome. They far exceeded our expectations. We could not ask for a better crew. The yacht was also great. Every detail was covered. Our favorite part of the yacht was the crew. Don’t get me wrong the yacht was great, but Britta and Joseph added such a personal touch for the whole event.

The food was spectacular. We ate every meal on board. We could not bring ourselves to eat anywhere except on board the Dianna Rose. We have been to the Virgin Islands several times and for the first time we actually had a culinary experience. The venues and voyage itself was also superior.

The crew was very accommodating with our desires. The whole experience was a 10 out 10. We would certainly recommend you, Sailing Directions, and the crew of the Dianna Rose. We will certainly utilize you in the future and recommend your organization.

Thanks so much for your assistance and making this trip a great success.

Shannon B, aboard Catamaran Dianna Rose sailing the Virgin Islands

We were absolutely blown away! The food and service were absolutely amazing! I have never had better food. I don't think there is a restaurant in Boston that can match Joseph's menu! The boat was impeccably clean. Britta was also an amazing host. We wanted for nothing! We will be back next year!

Deirdre G, aboard Catamaran Dianna Rose sailing the Virgin Islands

Additional reviews:

 I Have Never Had Better Food! Absolutely Amazing!
We were absolutely blown away! The food and the service were absolutely amazing! I have never had better food. I don;t think there is a restaurant in Boston that can matchvJosepths menu! The boat was impeccably clean. Britta wa also an amazing host! We wanted for nothing! We will be back next year! ~Deirdre G

 One Our Family\'s Greatest Trips
Thank you so much for guiding one of the greatest trips our family has ever been on. We appreciate all the amazing food, adventures, and company. We wish you all the best going forward, you two will be a huge success!

 Far surpassed all of my expectations
Amber & Diego,

What can I say?? This trip with the two of you has been a fabulous dream that far surpassed all of my expectations and it was because of y'all! The boat was perfect for us and was always perfect! We felt that the boat really was our home. Amber's food at each & every meal. . . WONDERFULLY DELICIOUS! I, definitely, hope to see you guys and the Dianna Rose again!


Doug & Donna Peacock

Yacht Dianna Rose review photo
Yacht Dianna Rose review photo
Yacht Dianna Rose review photo
 You guys are great at what you do
Amber & Diego

Probably the best thing we can say id this: if we evercome back and do this again we will do our best to make sure that you guys are the crew!

After having done this for the first time, we totally understand how important & critical the crew is to the total enjoyment of the trip.

You guys are great at what you do and we are sure you will continue to have great successin the future.

Thanks for a great trip!

Joe & Cyndy Dunlap

Yacht Dianna Rose review photo
 We had so much fun
Diego & Amber,

You made this trip the best we could ever expected. Steven and I don't travel much so this was a very special trip for us. We had so much fun. We loved the sun & water, so when Cyndy started talking about her bucket list wanting to plan the trip-- we were in. Awesome!

Thank you for the entertainment-food-friendship!

Steven & Penny

Yacht Dianna Rose review photo
 An Amazing Time
Diego & Amber,

Thank you for an amazing time this week! We loved the food, the jokes and the island hopping. The snorkeling was great! Thank you Diego for the snorkeling tour around the Indians. It was beautiful and you made it so interesting. Amber your food presentation was AMAZING! Thank you for keeping the rooms so clean.

You guys were the BEST CREW. We appreciate everything you did for us!!

Steve & Jo Linda Wallace

Robert & Debbie Daniels

Tom & Nancy Stark

Yacht Dianna Rose review photo
Yacht Dianna Rose review photo
 Wonderful, Inspiring and Peaceful
The most wonderful, inspiring and peaceful vacation thanks to the amazing hospitality and kindness of Amber + Diego. Like family<3

Food = fabulous (I'm jealous) Amber

Fun = Diego taking the kidsto kneeboard, drag and explore the deep.

The knowledge they both have of the customs, culture and wildlife only enhanced our love on this trip.

We do not look firwardto reality!

Thank you for spoiling us!

Kirk, Andrea, Bodie & Mack

Yacht Dianna Rose review image
Yacht Dianna Rose review photo
We hope to have the opportunity to do it again
Yacht Dianna Rose review photo
Yacht Dianna Rose review photo
Yacht Dianna Rose review photo
 You went above and beyond to ensure we had an amazing trip
Thank you, Amber & Diego, for a wonderful vacation! You took great care of us from the excellent food, drinks, snorkeling, and all the other details and little touches that made our experience special.

You both went above and beyond to ensure we had an amazing trip and your efforts did not go unoticed! We have all been to the BVI in the past, YOU GUYS made this experience unique and fabulous. Your personal efforts and love of the islands comes across in all that you do.

We are lucky to have found you -- thanks for sharing your knowledge, your home, and your personal experiences. We will be back!!

Love to you both,

Sharon, Mike, Shari, Sheldon, Leo & Karen xoxo :)

Yacht Dianna Rose review image
 We Could Not Have Asked for Anything Better!
Thank you so much for the amazing time here! We all truly enjoyed every minute and we are excited to see you again as soon as possible. Between the snorkeling, paddle-boarding delicious meals and left-handed Batmans we couldnt have asked for anything better. We enjoyed all the stories and were glad we got to shares new experiences with you. We learned a ton, too!

We wish you the best and we will come back so you can show us more amazing places. ~Tom, Jera, Trent and Paden

Yacht Dianna Rose review photo
Yacht Dianna Rose review photo
Yacht Dianna Rose review photo
 The Bar Was Set Very High For Any Future Trips
Diego was awesome. Very professional with the responsibilities of the boat as well as diving, our safety in the water and on shore. He was also super fun and great help to us and Amber with all her duties. I could not have been more pleased Amber was also awesome. Every meal was displayed beautifully and tasted wonderful. I probably gained 10 pounds from all the wonderful food. Haha. It was amazing Could not have asked for more. She was always asking if we needed anything and pretty much waited on us full time. Amber went to shore with us several times to show us around and where to shop.

The cabins were cleaned and beds made every day. The crew kept the boat very clean at all times. They required everyone to rinse off before coming on the boat if we were wet or sandy. I think that really helped keep everything nice. The rooms were well kept and clean.

We pretty much did everything we expected to do. There were some weather issues keeping us from a couple dives but Diego always had another plan or idea or place to go if something didn't work out.

The bar was set very high for any future trips. ~Hildebrands

Yacht Dianna Rose review photo
 A Great Pair to Go Sailing With
Captain Diego was fantastic. He was fun and new all the islands very well. He took us to places that met our desires, and it didn't mater if it was for a party atmosphere, peace and quiet, diving or just plainhanging out in paradise.

First Mate, Amber was outstanding. She not only made wonderful meals tha tasted like the best restaurant we have ever been to but her presentation of each meal was even more impressive. Amber and Diego make a great pair to go sailing with and we would HIGHLY recommend them. ~The Shepards

Yacht Dianna Rose review photo

WOW! What a great trip! What a great experience! Thank you so much for sharing your home with u and making it feel like our home. You really set the bar high Lori Hildenbran

1/29/16 Absolutely incredible you two! This was a trip of a lifetime thanks to you. Amber, the food and presentation was top notch. Thank you both so much.


Amber and Diego, Thank you, thank you, thank you for an amazing trip of a lifetime for us! Everything exceed our expectations and you were so awesome to adapt and personalize the trip to exactly what we wanted (and didn't even know we wanted all the time)! Trust me when I say we will be talking amongst the six of us for years to come about our amazing adventures aboard the Dianna Rose. You two are adorable too . :-) Thank you! Jill and Chad


Not much I can add to the above notes from the rest of our sixpack. It truly was an amazing experience because of your intimate knowledge of the area and your flexibility in adapting to a group like us. Amber's culinary skills were over the top amazing. Thanks for an outstanding vacation. You guys are the best!! Good luck to you in your future travels together (The Shepards (Richard and Linda)

Yacht Dianna Rose review image
Yacht Dianna Rose review image
Yacht Dianna Rose review image
 I Came Home With New Laugh Lines
We all had a fabulous week on the Dianna Rose. Captain Diego is an excellent captain. He navigates the sea well and we were able to get to all the places that we wanted to see,

dive and or snorkel. He was always concerned about our needs and safety.

Chef Amber prepared excellent meals for us all. She was able to accommodate Lacey and her gluten allergy in her food recipes -loved the gluten free chocolate brownies. She also used passion fruit to make some excellent mojitos.

We especially liked the layout of the Dianna Rose. Having an outside bar with ice maker, sink and refrigerator was perfect. Paul is an excellent drink meister and he was very at home

at this outside bar. The cabins/bathrooms were roomy and had plenty of

storage for all of our needs. When we boarded, our towels were rolled

like "snails" on the beds, so cute - thank you, Amber.

I came home with new laugh lines, so that is a visible sign of the fun

that we all shared. We all became friends with the crew during the charter and will continue

our friendships in the future.On behalf of Lacey, Christian, Jack, Danielle and Paul, we would all recommend the Dianna Rose and Captain Diego, Chef Amber to anyone who is

considering chartering in the Islands. ~The Morleys

Yacht Dianna Rose review image
Yacht Dianna Rose review image
Yacht Dianna Rose review image
 Russ and Suzie
Our honeymoon on the DianaRose was nothing short of fantastic!

The boat was incredibly luxurious, sailing was a rush, and watching the sunset as we enjoyed dinner on the deck, anchored near those breathtaking islands was out of this world. This charter exceeded our expectations in every way.

Thanks for giving us the best honeymoon ever.

Suzie and Russ, Toronto

Yacht Dianna Rose review image

Reviews for Dianna Rose with previous crew:

The most wonderful, inspiring and peaceful vacation. Thanks for the amazing hospitality and kindness of Amber & Diego - they're like family. Food = Fabulous. Fun = Diego taking the kids knee boarding and exploring the deep blue.

The knowledge they both have of the local customs, culture and wild life only enhanced out love of this trip. Thank you for spoiling us!

Kirk S, aboard Catamaran Dianna Rose sailing the Virgin Islands

Diego & Amber were they friendly, knowledgeable, attentive and accommodating. Although we did not have any real menu requests Amber listened to the conversations and adapted food choices and ingredients daily based on what we were saying. Top notch

I have been a lot of places in the Virgin Islands and Diego managed to bring us to places every day that I have never been (every day - not just once!).

I would recommend Diego, Amber and the Diana Rose to anyone. I also think you could tell families that these two would be wonderful for people with kids. I think Diego’s humor and energy and Amber’s ability to adapt to different personalities kids would have a blast.

Tom B, aboard Catamaran Dianna Rose sailing the Virgin Islands

sailing itinerary Sample Itinerary

Day 1.

Typically, we meet at the boat in Red Hook St Thomas. This is about a 20 minutes ride from the airport and makes a great place to start because of its close proximity to the British Virgin Islands. We would sail from there to Jost Van Dyke and clear BVI customs. In White Bay, guests enjoy swimming, kayaking or paddle boarding to the beach for cocktails at the famous soggy dollar bar. After sipping back a couple of their house drinks, the "Pain Killer", it doesn’t take long for the partying to get started. As the sun starts to set, we usually move the boat over to great harbor for a relaxing dinner then anchor there for the night. On shore the famous bar is Foxy's which is lively beach bar with live entertainment.

Day 2

Green Key and Sandy Key are two small uninhabited islands nearby with beautiful beaches and great snorkeling. Sandy key also has a short but interesting hiking trail. Little Jost van dyke is another great stop. It has a natural inland bubble pool created from the northerly swell. This also has a nice secluded anchorage where we often spend the night. If your preference is somewhere with restaurants and night life, it is just a short sail over to Cane Garden bay. There are numerous beach bars and restaurants there and often live music on the beach.

Day 3

Our next stop is Guanna Island which has a beautiful private secluded natural beach. No restaurants or bars but you can snorkel with 100's of fish including some tarpin almost 6 feet long and sea turtles. We like to head to our secret anchorage nearby in Cam bay for the evening and night. Most boaters don't know of this spot so we usually get the small bay, and beach to ourselves. There are several huge eagle rays in the bay and it is a great place to dine on the aft deck while watching the sun set, then enjoy a quite undisturbed evening onboard.

Day 4

We sail by Richard Branson's famous Neckar Island into North Sound. There are a variety of things to do their including beach volleyball, the Michael Bean happy hour at Leverick Bay (comedy routine which includes crab races, conch blowing contest and music), drinks, happy hour and dinner at Sabba Rock, and visiting the shops and bars at the Bitter End Yacht Club.

Day 5

We sail to Virgin Gorda. We have found a beautiful private beach surrounded by large boulders making it invisible from the water. Few people know of this spot so we often get it to ourselves. There are Outdoor grills and picnic tables here to so we often bring food to shore and have a beach BBQ. We of course make a visit to the baths where boulders, some the size of houses, have formed tunnels along the coast. This area gets very busy with day charters and tour buses so we like to go late afternoon when everyone is gone. Seeing the setting sun over the ocean through these huge rocks is spectacular!

Day 6

Norman Island is our next stop. The Indians and the caves at the mouth of the bay are 2 of the most spectacular snorkeling sights in the area. A trip to the BVI would not be complete without a visit to Willy T's (an old schooner converted into a floating bar). People tend to get a little out of hand there so be prepared for almost anything. A restaurant called the Pirates Bite on shore just reopened. It has great food and elegant beach dining. The Pirates Bite also features a fantastic beach bar which is somewhat tamer than Willy T's.

Day 7

We cross back into USVI waters for our final stop at Caneel Bay. Here, Honeymoon beach is great place to swim with sea turtles. On shore there is a beautiful resort built by the Rockefeller's on the ruins of an old sugar mill. It is well worth doing a tour of the grounds and perhaps having a drink or dinner in their open air restaurant overlooking the bay.

In the morning we head back to our starting place in Red Hook.

Contact Us

Interested in Dianna Rose? Contact us for rates, availability and details or to book your vacation!

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