☰ Menu
Caribbean · Winter 2026–27
Crewed sailing yachts
in the Caribbean
Three monohull sailing yachts for winter 2026–27, from a 32m Nautor Swan to a freshly refitted 29m yacht for eight, each with its own crew.
Our shortlist
A crewed sailing yacht is the classic way to see the Caribbean: steady trade winds, short hops between islands and a crew who handle everything. We chose these three for size, service and value.
The largest, at 32 metres
Il Mio Canto Libero
A 32m Nautor Swan, rebuilt at the Swan yard in 2026, for eight guests in four en-suite cabins.
- Guests
- 8
- Built
- 2014
- From / week
- €75,000
Oyster comfort, crew of four
Champagne Hippy
An 82ft Oyster refitted in 2023, with a crew of four looking after six guests.
- Guests
- 6
- Built
- 2014
- From / week
- €30,000
Fully refitted, crew of four
Free at Last
A 29m sailing yacht fully refitted in 2025–26, with a crew of four for up to eight guests.
- Guests
- 8
- Built
- 2001
- From / week
- €45,000
At a glance
Compare the three
| Il Mio Canto Libero | Champagne Hippy | Free at Last | |
|---|---|---|---|
| Best for | The largest, at 32 metres | Oyster comfort, crew of four | Fully refitted, crew of four |
| Builder | Nautor Swan | Oyster | Not listed |
| Built | 2014, refit 2026 | 2014, refit 2023 | 2001, refit 2025–26 |
| Length | 32 m (105 ft) | 25.2 m (82 ft) | 28.8 m (94 ft) |
| Guests · cabins | 8 · 4 | 6 · 3 | 8 · 3 |
| Crew | 4 | 4 | 4 |
| Where | Leewards, Windwards, BVI | Antigua | St Maarten: Leewards, Windwards, BVI |
| Terms | MYBA + 30% APA | MYBA + APA | MYBA + 30% APA |
| From | €75,000 | €30,000 | €45,000 |
| Up to | €85,000 (Jan–Mar) | €34,000 (Dec, Apr) | €45,000 (Jan–Apr) |
Rates are per week as published by each owner for winter 2026–27, in the currency the owner sets. MYBA rates add an advance provisioning allowance (APA) for fuel, food, drinks and port fees, plus any VAT or local tax. All yachts are subject to availability and confirmation at booking.
Your charter, arranged
From first message to first swim
Choose
Open a yacht to see every cabin, toy and rate. Tell us your dates and group.
Confirm
We check live availability with the owner and send a written proposal with the full price.
Sail
Sign with the owner, plan your route and preferences with the crew, and step aboard in the Caribbean.
iBoat International acts as your charter broker. Your charter contract is with the yacht’s owner or operator. Terms