“Round the Island Race”

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!

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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

  • Single or Double Beds
  • Individual Climate Control
  • Electrical Sockets
  • Ensuite Bath with Sink & Toilet
  • Private Shower
  • Hand & Bath Towels

Owners Stateroom

/ PER PERSON

  • Largest and Most Luxurious Staterooms
  • Queen Bed
  • Located Amidships (the most stable part of the boat)

Premier Stateroom

/ PER PERSON

  • Queen Bed
  • Located Amidships (the most stable part of the boat)

Duluxe Stateroom

/ PER PERSON

  • Queen Bed
  • Located in the Forward Section of the Yacht

Double Stateroom

/ PER PERSON

  • Over/Under Single Bunks, ideal for singles
  • Located in the Aft Section of the Yacht

Single Stateroom

/ PER PERSON

  • Single Berth
  • Located in the Aft Section of the Yacht