Group Travel
Quarterly Group Voyages.
Four times a year, Paolo curates a group voyage for adults who want to sail together. Community-first. Adults-only. Virgin Voyages.
Upcoming Voyages
2026 — 2028
Forming now.
Eastern Caribbean & Bimini New Year's
Sisters at Sea — Bahamas
Western Caribbean & Bimini Beach Club
Red Hot Sailing Club — Greek Islands
Key West & Bimini New Year's
Q1 2028 Group Voyage
Rates subject to change. Daily gratuities excluded unless noted.
For More Info regarding Viator’s Worry Free Excursions (T&Cs) — Click Here
The Concept
Solo traveler.
Never alone.
Each quarterly voyage is curated for a group of 12–20 adults. You book your own cabin — no shared rooms — and join a community of like-minded travelers who are there to experience life at sea, not just tick a box.
Paolo sails with every group. You'll connect through Nautir — the adults-only social chat built for cruises. Familiar messaging, like WhatsApp, with privacy and security designed for travelers. Plus coordinated excursions and a welcome event on embarkation night.
Always Included
- ✦ WiFi
- ✦ All dining (20+ eateries)
- ✦ Beverages
- ✦ Fitness classes
- ✦ Entertainment
- ✦ Paolo sailing with the group
- ✦ Private group chat on Nautir
Group sailings — common questions
Do I need to bring anyone? Can I join a group solo?
Is there a single supplement on a group sailing?
How big is a group?
What is actually included beyond the cruise fare?
Who else will be on the trip?
What if I book and then cannot go?
Join the Community
Reserve your spot.
Sail together.
Spots fill fast. Once a voyage is confirmed, Paolo locks in the group rate and you'll be the first to know pricing and perks.