Day 1
Arrive in Miami
Embark in Miami. Private transfer from the airport to the port, where you'll board your ship and settle into your cabin. Sailaway dinner as the city lights recede.
Welcome dinner
Boutique 4★ / 5★ hotel
← All destinations
Cruise · Multi-island
Eastern Caribbean Cruise
Three islands, one ship, zero stress. Wake up somewhere new every morning.
Best season
Year-round (seasonal sailings)
Group size
2 — 12 travelers
Pace
Relaxed
Languages
English
Ideal for
Families with kids
Customization
Fully tailorable
Overview
Why this trip
feels different.
Three islands, one ship, zero stress. Wake up somewhere new every morning.
This 7 days itinerary is built around 4 hand-picked experiences across Multi-island. Hotels are selected for character — properties we've slept in, not just listed. Local guides are fluent in your language and trained to read the room: more time at the quiet vista, less at the crowded one.
The pace is intentional. Mornings tend to be active, afternoons quieter, evenings yours. We've designed it to feel less like a tour and more like the trip you'd plan if you had 18 years of travel-agent relationships in your back pocket — because that's exactly what's underneath it.
Day by day
7 days, unhurried.
A sample shape — every day on this itinerary can be adjusted to your interests, energy level, and pace. We treat this as a starting point, not a script.
- 1
- 2 Day 2
St. Maarten
Today centers on st. Maarten. Your private guide collects you after a leisurely breakfast for a thoughtfully-paced day that balances headlines with quieter moments away from the crowds. Lunch at a local favourite. Evening at leisure.
Breakfast & lunchBoutique hotel - 3 Day 3
St. Thomas
An early start (worth it) for st. Thomas. We've sequenced this day to put you ahead of the day-trippers, with mid-morning back at your hotel for a slow afternoon — pool, spa, or a wander on your own terms.
BreakfastBoutique hotel - 4 Day 4
Bahamas private island
Bahamas private island anchors today's itinerary. We pair the must-sees with a hand-picked detour your guide will reveal en route — usually a workshop, viewpoint, or family-run spot we keep quiet about for good reasons.
Breakfast & lunchBoutique hotel - 5 Day 5
Onboard spa & dining
A flexible day, themed around onboard spa & dining. Choose a deeper guided experience or trade it for a free day to wander — both options are pre-arranged so you can decide over breakfast.
BreakfastBoutique hotel - 6 Day 6
St. Maarten
Today centers on st. Maarten. Your private guide collects you after a leisurely breakfast for a thoughtfully-paced day that balances headlines with quieter moments away from the crowds. Lunch at a local favourite. Evening at leisure.
Breakfast & lunchFinal-night boutique stay - 7 Day 7
Disembark in Miami
A final breakfast onboard, then disembarkation and private transfer to the airport. We hope you're already plotting the next sailing.
Breakfast
Your route
4 stops, one journey.
01 Miami
Embark
02 St. Maarten
03 St. Thomas
04 CocoCay
Private island
- 01 MiamiEmbark
- 02 St. Maarten
- 03 St. Thomas
- 04 CocoCayPrivate island
Trip highlights
The moments you'll remember.
St. Maarten
Highlight 01
St. Thomas
Highlight 02
Bahamas private island
Highlight 03
Onboard spa & dining
Highlight 04
Gallery
Scenes from Multi-island.
What's in the box
No surprise line items.
Everything below is part of the price you see. The "not included" column is here so you know exactly where the extras are — never as a hidden upsell.
Included
- Selected cabin category onboard
- All onboard meals & main dining venues
- Onboard entertainment & enrichment
- Port taxes, fees, and pre-paid gratuities
- Pre-cruise hotel night where applicable
- Private transfers airport ↔ port
- 24/7 in-cruise support from your travel designer
- Pre-trip consultation calls
Not included
- International airfare (we can quote separately)
- Travel insurance (strongly recommended; we can quote)
- Visas & entry documents
- Meals not specified in the itinerary
- Optional excursions & activities
- Tips for guides, drivers, and hotel staff
- Personal expenses & laundry
Sample departures
When you might go.
These are sample windows we currently have inventory for. Custom dates are almost always available — we'll confirm based on your preferred travel month.
Departure 1
Jun 7
to Jun 13, 2026
Per person
$1,300
3
spots left
Departure 2
Aug 2
to Aug 8, 2026
Per person
$1,400
6
spots left
Departure 3
Oct 11
to Oct 17, 2026
Per person
$1,250
12
spots left
Ready when you are
Tell us where you'd love to wake up. We'll handle the rest.
A 30-minute discovery call with one of our travel designers — free, no commitment. You'll leave with a clearer idea of where to go, when to go, and what it might cost.
Eastern Caribbean Cruise
From $1,299 · 7 days