Sail No. XXIV — Caribbean Season 2026
Private Charters · Since 1994

The ocean
returns in chapters.

Crewed yacht voyages through the Virgin Islands, the Grenadines, the Aegean, and the Adriatic — orchestrated by brokers who know every captain by name.

A Note From The Helm

Thirty years
of sailing stories,
still unfolding.

Regency began as a two-person brokerage on a dock in Tortola. Today our quiet office still sits at Nanny Cay — but the fleet has grown to nearly three hundred crewed yachts, and the questions guests ask us have grown more interesting.

How do I cross the Atlantic in November? Where can a family of nine find a catamaran with a dive compressor and a proper chef? What does a private regatta weekend cost in Sardinia? These are good questions. Our brokers answer them in complete sentences, because yachting, at its best, is a conversation.

Read the full letter
32yrs
Advising Voyagers
287
Yachts in Fleet
41
Cruising Regions
96%
Returning Guests
Where You'll Anchor

Twelve seas,
one unhurried pace.

Every region has its season. Our brokers advise on weather, regattas, and the quiet weeks when a coastline belongs mostly to those who arrive by sea.

British Virgin Islands
Caribbean

British Virgin Islands

Dec — Apr  ·  64 yachts available
The Grenadines
Southern Caribbean

Grenadines

Nov — May
Greek Isles
Mediterranean

Greek Cyclades

May — Oct
Amalfi
Italy

Amalfi & Capri

Jun — Sep
Croatia
Adriatic

Dalmatian Coast

May — Sep
Currently Cruising

Three yachts,
three very different weeks.

A curated selection from the current season. Each is crewed, provisioned to specification, and available for private charter.

Featured Aurelia yacht
Motor Yacht Caribbean

Aurelia

142 ft· 10 guests· 6 cabins
From
$165,000 / week
View Yacht →
New Solis Mare
Sailing Catamaran Mediterranean

Solis Mare

78 ft· 8 guests· 4 cabins
From
$62,000 / week
View Yacht →
Orient Wind
Classic Sailing BVI

Orient Wind

118 ft· 6 guests· 3 cabins
From
$89,000 / week
View Yacht →
Voyages · Portfolio No. VII Family aboard a charter
Curated Itineraries

Voyages worth
telling twice.

01

Regatta Weeks

Chartered berths for St. Barth's Bucket, Les Voiles, and the BVI Spring Regatta — with shoreside access to the right parties.

02

Family Expeditions

Yachts outfitted with water toys, tutors, and crew trained for guests aged four to eighty-four.

03

Private Celebrations

Milestone birthdays, vow renewals, and the occasional surprise proposal at anchor off The Baths.

04

Dive & Discover

Yachts with PADI-certified crew, compressors aboard, and private guides for the Tobago Cays and Bonaire.

We've chartered through three brokers in twenty years. Regency is the one we stopped looking past. They know which captains laugh at our jokes and which chef knows our son's shellfish allergy by heart.
The Halberstam Family Seven Charters · 2014 — Present
The Journal

Notes from the water.

All Entries  →
Field Notes · Caribbean

Sailing the BVI Spring Regatta: four days aboard Tidal Pulse

Our senior broker files a dispatch from the rail of a 56-footer with a crew that does not believe in slow racing.

February 27, 2026  ·  8 min read
Planning

Mediterranean yacht routes worth planning twelve months ahead

February 23, 2026
Provisions

A chef's guide to eating your way around Virgin Gorda

January 30, 2026
Speak With A Broker

A good charter starts with
a long, honest conversation.

Tell us who's aboard, where you've already been, and where you'd rather not return. Our brokers will match you with three yachts within forty-eight hours — no sales, no pressure, no forms longer than they need to be.