“Round the Island Race”
The Big Event on Martha’s Vineyard
Martha’s Vineyard is one of the most beautiful and exclusive summer communities in our country. Arabella will take you there to participate in the “Round the Island Race.” This long distance race is the highlight of their yachting season. You’ll also have a great time visiting the picturesque towns, pristine beaches and impressive restaurants. And you’ll experience all of this while living onboard Arabella, one of the largest and most majestic superyachts in the fleet. This is your chance to experience Martha’s Vineyard.

The Thrill of Competition
The Round the Island Race is a 56 nautical mile marathon. It is patterned after the legendary Round the Isle Race in Cowes, England where the America’s Cup was born. Everyone onboard will have a chance to hear the captain, navigator and tactician discuss their strategies for finding the fresh breezes and favorable currents needed to win. Along the race course, you will also be rewarded with breathtaking scenery and a fleet of world-class racing yachts. Arabella is the perfect yacht for this long race because her cushions are soft, you read a book or nap, and our chef will be serving gourmet meals and drinks all day long. You can read more about the Round the Island Race here.

The Historic Edgartown Yacht Club
The host of the Round the Island Race is the prestigious Edgartown Yacht Club. This historic club is a beacon of classic New England charm and understated elegance. Established in 1905, this club blends a storied maritime tradition with modern comforts, offering an atmosphere that feels both exclusive and welcoming. And they like their racing and regattas. It is a great privilege to be invited by one of their members onto flagpole deck for a glass of rose wine at sunset.

Explore Martha’s Vineyard
Martha’s Vineyard is the summer playground of the rich and famous. Stroll through the island’s iconic towns, savor delicious local cuisine, and soak in the vibrant atmosphere of the island during this regatta. After the race is over, we will spend one extra day on the island so you can go sightseeing or visit one of the pristine beaches. This will be one of your best summer experiences ever.

Life Aboard Arabella
Life aboard Arabella during this week-long adventure is nothing short of exhilarating. This 157-foot luxury schooner becomes your home on the water, blending the thrill of yachting with the comforts of an elegant retreat. The camaraderie among guests grows each day. Evenings bring tranquil anchorages, where you can unwind with a glass of wine, savor chef-prepared meals, and take in breathtaking sunsets. Whether you’re a seasoned sailor or simply a lover of the sea, this unforgettable journey offers the perfect balance of spirited competition, luxury living, and the timeless allure of maritime adventure.
What’s Included
Relax in comfort and style aboard Arabella, your home for the week. Experience the Arabella Lifestyle with gourmet meals, stunning sunsets, and the camaraderie of fellow guests and sailing enthusiasts.
- 7 days and 6 nights of luxury accommodations on board, complete with gourmet dining.
- A spot onboard Arabella for the Round-the-Island Race.
- Invitations to regatta festivities and race-related social events.
- An extra day on Martha’s Vineyard to explore the picturesque towns and beaches.
- Bonus stopovers in Block Island and Newport!
Yes, take me to Martha’s Vineyard!
Start by joining the “Round the Island Race Email List” for more information & next steps.
The Itinerary – 7 Days & 6 Nights
Wednesday, June 18, 2025
Guests arrive onboard Arabella on Wednesday evening. She will be anchored in the harbor with views of the Manhattan skyline and the Statue of Liberty. Enjoy a welcoming cocktail, settle into your luxurious accommodations, and mingle with fellow guests over a gourmet dinner. As the sun sets, the lights of city come on and the view from Arabella’s aft deck are magical.
Thursday, June 19, 2025
At dawn, Arabella will weigh anchor, head up the East River and enter Long Island Sound. This will be a full day of steaming towards Block Island. We will enter the Great Salt Pond and drop anchor. You can head ashore to sample the local nightlife or stay onboard and bask in Arabella’s megayacht beauty.
Friday, June 20, 2025
We continue in the morning to Martha’s Vineyard, arriving off Edgartown by late afternoon. There will be regatta festivities this evening and you will be able to go ashore and meet some of the sailors from other yachts.
Saturday, June 21, 2025
Race day! Arabella will set off in the iconic ‘Round-the-Island Race, an all-day 56 mile challenge. We are hoping for strong breezes. After we finish, our team will celebrate at the regatta social events organized by the Edgartown Yacht Club. In addition to meeting other sailors, you may brush shoulders with some sailing legends.
Sunday, June 22, 2025
This is your well-deserved day of rest and your chance to leisurely enjoy Martha’s Vineyard You can visit the quaint towns, relax on the pristine beaches, or simply bask in yachting style onboard Arabella.
Monday, June 23, 2025
Arabella sets sail for Newport, RI, where guests can enjoy one last evening on board or ashore. You will have many great stories to share about the race and the incredible week of yachting.
Tuesday, June 24, 2025
Guests can disembark in Newport this morning or stay on Arabella for her return to NY Harbor. She will get underway early in the morning and plan to arrive back in the city around 10 pm. Guests will be able to disembark upon arrival.
Guests who cannot do the full cruise can still join Arabella for the Round the Island Race by flying in or out of Martha’s Vineyard.

StateRooms

All staterooms include:
- Single or Double Beds
- Individual Climate Control
- Electrical Sockets
- Ensuite Bath with Sink & Toilet
- Private Shower
- Hand & Bath Towels

Owners Stateroom
$3450
/ PER PERSON
- Largest and Most Luxurious Staterooms
- Queen Bed
- Located Amidships (the most stable part of the boat)
- 2 available each trip

Premier Stateroom
$3050
/ PER PERSON
- Queen Bed
- Located Amidships (the most stable part of the boat)
- 4 available each trip

Duluxe Stateroom
$2900
/ PER PERSON
- Queen Bed
- Located in the Forward Section of the Yacht
- 6 available each trip

Double Stateroom
$2200
/ PER PERSON
- Over/Under Single Bunks, ideal for singles
- Located in the Aft Section of the Yacht
- 4 available each trip

Single Stateroom
$2600
/ PER PERSON
- Single Berth
- Located in the Aft Section of the Yacht
- 2 available each trip

FAQs
Where do we meet Arabella?
Guests who join Arabella on Wed, June 18 will meet her in NY Harbor. You will arrive at the Manhattan Yacht Club in Jersey City and Arabella’s tender will bring you out to the yacht which will be anchored off Ellis Island. If you can’t join on the very first day of the cruise, you can still meet Arabella on Block Island or fly into Martha’s Vineyard and meet her off Edgartown.
What is the easiest way to get to New York City?
All major airlines fly to the Big Apple and the closest airport to the Manhattan Yacht Club is Newark (EWR). From Newark, you can take a 20 minute Uber/Lyft ride to the club.
Do I need to have racing experience in order to join this adventure?
No. This is what we call a “Regatta Experience.” It is one of the curated experiences created by Commodore Fortenbaugh and the Arabella team which form the basis of our “Arabella Lifestyle.” We love sailing and we also love racing. We want to share these incredible experiences with more people. So we have created these racing experiences. You can get a taste of the racing lifestyle without having to go through years of training first. If you like to be on a sailboat and also like a fun competition, you can do this. And in case we have not already said it, one of the best parts of any regatta are the social parties before and afterwards!
Do I need to even be a sailor to participate?
No you do not need to be a sailor to participate. But if you are not yet a sailor, we hope this experience will inspire you to get more involved int he world of sailing. The Manhattan Sailing School teaches adults how to sail every weekend in New York Harbor. As soon as you are ready, visit their website.
How much will be expected of me during the cruise and race?
During the cruise, our professional crew will manage the boat. But they would like your help whenever we need to raise the mizzen sail. This is our largest sail on the after-most mast (the mizzen mast). The mizzen sail is about 90 feet tall and we form a long line to pull the halyard. Not only does this promote teamwork and good feelings, but its a lot of fun and gets you pumped up as well. When we are cruising, the captain often allows guests to come up to the helm and help him steer Arabella. When in your life have you ever steered a 157-foot megayacht! This is your chance so have your camera ready. During the race, the captain, first mate or one of their designees will be steering at all times because of our need to keep Arabella moving as fast a possible. It’s a race, not a training session. But they will share their strategies, predictions and thought processes before and during the race so that you can follow along and be part of the action.
Will I have a chance to steer the boat or trim the sheets?
Yes, during the cruise you will have an opportunity to be involved in the sailing of Arabella. But during the race, the steering will be done only by the most experienced crew as designated by the captain only.
How should I pack?
Even though Arabella is a 157-ft megayacht, space onboard is at a premium. We encourage you to pack light. Please bring clothes in a soft duffle bag which can be folded up and stored in a cabinet. We discourage any hard suitcases because there will not be a place to store them in your room. For clothing, you will need enough to last the week and there are no laundry facilities on board. You can send laundry out in Martha’s Vineyard but it may pricey. Sailors specialize in making the most of a small wardrobe. All sailors look great in a blue blazer with a tie or scarf. You can get fancier from there as well. There is also be some special regatta gear which you can purchase before the event. Wearing the team gear to social events is usually well received. Most cabins have a few drawers for clothes storage plus a place for some hangers. The Premier and deluxe lines cabins have more storage space than the double and singe staterooms.
Are there electrical outlets in the cabins?
Yes. Each of the cabins has individual 110 volt electrical outlets. You will be able to charge your phone and computer each night. You can also run a hair dryer.
Are linens included?
Yes. The staterooms are fully stocked with linens and towels. Each cabin has a set of sheets, four pillows plus a fleece blanket and bed cover. Arabella does a “turnover” (where our stewardesses change the sheets) once per cruise, usually on the middle day, but sometimes staggered over two days (because there could be up to 20 guest cabins filled). It is recommended that you bring a small beach towel for your onshore excursions.
What is the situation with bathrooms and showers?
Each cabin also has its own private head (the nautical word for toilet), shower, and air conditioning. You will have privacy and be able to keep your room at your preferred temperature. However, water on a yacht is precious and we have to make all the water using our new Parker Aquamatic watermaker. Because our water supply is limited, please help us conserve it by taking “navy” showers or sharing with a friend. We appreciate your support and cooperation.
How is food and drink handled during the cruise?
All of your meals on Arabella are prepared by our gourmet chef. Arabella focuses on healthy eating and whenever possible, our provisioning is farm-to-table. Your cruise fare covers all breakfasts and lunches onboard during the trip plus four dinners. When you are on Martha’s Vineyard, those are the nights you eat ashore at any restaurant you choose. The cabin fare also includes non-alcoholic beverages. There is also a cash bar for beer, wine and mixed drinks which you may purchase while onboard.
Cancellation Policy
The Cruise Fare shall be deemed to be earned when paid and not refundable except as stated herein. If a guest cancels a trip 60 or more days in advance, they will receive a refund of all monies paid to ASA except 50% of the deposit. If a guest cancels a trip between 30 and 60 days, they will receive a refund of all monies paid except the full deposit. No cancelations are permitted within the final 30 days. If the guest fails to make an agreed-upon payment when due, they will be charged a $15 late fee for each additional day. If the guest fails to make a payment after 10 days after it was due, their contract can be canceled and no deposits will be returned.