The Longest Johns Cordially Invite You

A Sailing Cruise through the Glorious Caribbean

March 10 - 18, 2024 / from $7495 per person


Imagine. . . a world-class sailing experience through the British Virgin Islands, aboard one of the world’s finest sailing yachts, with nightly entertainment provided by the Longest Johns – a dream come true!

In an exclusive partnership with US-based touring outfit ProRome Tours, the Longest Johns look forward to welcoming you onboard the Sea Cloud II for a week of song, fellowship and adventure next spring through the beautiful Caribbean.

Up through May 23, 2023 we are taking pre-registrations for this once in a lifetime voyage. We need to receive at least 80 pre-registrations, so sign up today to help make this dream come true! There are only 40 double occupancy cabins available, so act fast!

Make the dream come true

Pre-Register Today

Pre-registration is open through May 23, 2023. The operation of the trip is contingent on enough persons registering to fill the cabins: 80. Once 80 have pre-registered, registration will close and an invitation along with a link to formally register will be sent to each pre-registrant by email.

The Caribbean
Sea Cloud Cruises
The Art of Sailing

The Sea Cloud II

Our vessel is the Sea Cloud II, a three-mast barque complete with more than 3000 square meters of sail spread across 23 unique sails. Built to resemble the great ships of the old world, the Sea Cloud II does indeed hide in its hold two powerful diesel engines, designed to “Roll us Along” should the winds of the sunny Caribbean fail us.

Live Performances

Daily a capella performances led by the Longest Johns and a series of fascinating stories on the incredible history of maritime adventures will permeate the daily program.

Exclusive Itinerary

Sandy beaches, uninhabited island excursions and tours through the wonders of the Caribbean – created by both man and nature – make this itinerary unique and truly once in a lifetime.

A World-Class Vessel

Built in 2001, the Sea Cloud II perfectly combines spaciousness for up to 94 passengers with the lifestyle of a private yacht. Private luxury cabins, superb endless food and more await.

Fellowship and Fun

Sea Shanties have the incredible power of bringing people together. Through the music of the Longest Johns, together we will relive epic stories and build new and lasting friendships.

A Glance at the Itinerary

This incredible journey features one night at a four-star resort in St. Maarten and seven nights aboard the Sea Cloud II.

On March 10 we will rendezvous at the beautiful and all-inclusive four-star Maho Beach Resort in St. Maarten. That evening we will enjoy incredible sea views at a private welcome dinner hosted by The Longest Johns.

The next day we will board the Sea Cloud II, settle into our cabins, and join the captain on the lido deck for welcome cocktails as we put out to sea. Following a five-course welcome dinner we’re back out on deck for our first private concert with the Longest Johns. With the wind in our sails, we’re off to the British Virgin Islands!

For two days we will explore the channels, bays and islands once ruled by privateers and pirates. We will explore sandy beaches, hidden coves and colorful seaside villages. From Jost van Dyke to Virgin Gorda, we will experience a hidden world of stories and songs, with sea shanties led by the Longest Johns to keep us going along the way.

We then sail southwards, entering the Lesser Antilles and into the French territory of the “Îles des Saintes”, where we will explore the incredible beautiful islands of Terre-de-Haut and Dominica. Here we will explore the natural beauty and experience the cultural influences of the Old World, evident in the art, architecture and customs found here. 

Our last stop is Saint Barthélemy, a volcanic island fully encircled by shallow reefs, where we will marvel at elegant superyachts, browse in the shops for precious items, or enjoy a sundowner in the picturesque harbor surrounded by clusters of high class bars and restaurants. You may even consider snorkeling in the reefs before joining us on board for a farewell dinner and concert with the Longest Johns. 


Cabin Availability and Pricing


Below is the payment schedule.

$500 / Deposit due @ registration

50% Installment 1
due September 1, 2023
50% Installment 2
due November 1, 2023
We accept all major credit cards, checks, cash and bank transfers.

Cabins and Pricing

All cabins are double occupancy.

Prices are / per-person

Deluxe Cabins, $7495: 24 Available
Cabin Deck, 215-226 sf, Category D/E
Deluxe Cabins, $7995: 2 Available
Promenade Deck, 215 sf, Category C
Junior Suites, $9895: 14 Available
Promenade Deck, 247 sf, Category B


If you cancel, this policy applies.

Our Policy

180 days or more before tour
Full refund less $500 deposit
180-120 days before tour
50% Refund
Within 120 Days of Tour
No Refund

What's Included

One Night in St. Maarten

One night (March 10) lodging at the four-star Sonesta Maho Beach Resort in St. Maarten. Five-course dinner and bar package included.

Seven Nights Aboard the Sea Cloud II

Seven nights (March 11 - 18) lodging in cabin of your choosing aboard the Sea Cloud II.

All Meals and Touring Programs

All meals aboard the Sea Cloud II, free-flowing wine and beer, and all touring programs listed in the touring program. See brochure for full list of inclusions and exclusions.

01Registration Process

Top of the page, click “Pre-Register Now”
We are taking pre-registrations until May 23, 2023. The trip is contingent on the ship filling, so once 80 persons register the trip will move forward and a notice will be sent out to all of the pre-registrants. No payment is required to pre-register and your payment information will not be collected.
When you register please select the cabin that you would like occupy.

02Arrival and Departure

March 10 – 18, 2024
When we send you an invitation to formally register for the trip we will include flight information. Please arrange flights into Saint Martin on March 10, 2024 and out of Saint Martin on March 18, 2024. You should fly in and out of Princess Juliana International Airport (SXM). 

03What is included?

8 Nights Lodging, Most Meals and Tour Excursions
We have included one night lodging in St. Maarten and seven nights aboard the Sea Cloud II in the cabin of your choosing. The welcome dinner on March 10 in St. Maarten is included as are all meals aboard the Sea Cloud II. All tour excursions listed in the brochure are also included. Also included in the price are daily performances with the Longest Johns. Please see the brochure for a full list of inclusions and exclusions.

04What is not included?

Flights, Travel Insurance and Extras
ProRome Tours can help arrange your airfare as well as your travel insurance. When we send you a formal invitation to register we will also include information on how to book flights and travel insurance. Please note that meals on land are not included, as well as anything not explicitly listed in the brochure. Please see the brochure for a full list of inclusions and exclusions.

05What is the payment schedule and what is the cancellation policy?

See Below

When you formally register you will be prompted to pay a $500 deposit to hold your place on the trip. This amount is non-refundable.

The first 50% installment is due on September 1, 2023 and the second installment is due on November 1, 2023.

In the event that you must cancel, the $500 deposit is non-refundable. The remaining balance is fully refundable up until 180 days before departure (September 12, 2023) and the 50% refundable from 180 days until 120 days before departure (November 11, 2023). Within 120 days of departure (after November 11, 2023) the trip is non-refundable.

We highly recommend travel insurance for each traveler. We work exclusively with Allianz and will send you a complimentary quote upon your formal registration.