Bucket-List Cruise Adventure

7-Night Caribbean Cruise Adventure

Windstar · Wind Surf · round-trip from Philipsburg

$3,008 per person · next sails Feb 27, 2027 Book this cruise@ Cruisebound · same fare
Get there

Fly into Philipsburg (SXM)

Your gateway to the voyage. Arrive a day or two early — the best of the trip starts before you board.

Round-trip into SXM · $2,164 for two est.
Your voyage · 7 nights, day by day

Day by day — the unforgettable thing at every port

Your whole sailing in order: the day you board, every port it calls — each with the single bucket-list experience there and the operator who runs it — any days at sea, and the day you step off.

Day 1
Philipsburg Embark
Board in the afternoon — fly in at least a day early.
Day 2
Sopers Holeport guide →
The Baths of Virgin Gorda · $1,800 for two with Aristocat Chartershow to make it yours → ·
Days 2–3
Jost Van Dykeport guide →
Private Catamaran Charter · $1,600 for two with Honey Group Private Boat Chartershow to make it yours → ·
Day 4
Virgin Gordaport guide →
Private BVI Sailing Charter · $1,200 for two with BVI Yacht Charters (official)how to make it yours → ·
Day 5
Private Open-Top Mini Moke Island Tour of St. Barts · $130 for two with Ferry Voyager – St. Barths Tourshow to make it yours → ·
Day 6
Private Island Hopping · $120 for two with Junior's Glass Bottom Boat & Water Sportshow to make it yours → ·
Day 7
Falmouth Harbourport guide →
Antigua Full-Island Round Tour · $240 for two with Tuk-Tuk Adventures Antiguahow to make it yours → ·
Day 8
Philipsburg Disembark
Back where you started — disembark in the morning.
Home

Fly home from Philipsburg (SXM)

What this adventure runs estimated · for two
Your hotel
Flights round-trip into SXM · 2 travelers $2,164 est.
Hotel before you sail1 night · Philipsburg · Luxury~$200
Cruise fare7 nights · Windstar · 2 guests$6,016
Shore excursions6 bucket-list things, booked direct · for 2 · swap any at its port above ↑~$5,090
Transfersairport ↔ ship, private car~$180
Trip total$13,650
Flights are estimated from our best gateways (refine from your own airport above); the cruise fare is this sailing’s lead-in price for two; the hotel scales with the style you pick above; shore excursions are real book-direct operator prices, added as each port is curated; transfers are an estimate. We always build in at least one night ashore before you sail.
🚢 Book this cruise · $3,008 pp

Book your trip to Philipsburg

We may earn a commission when you book through these links, at no extra cost to you. Prices and availability are set by each partner.

Choose your line & sailing date

Every cruise line that calls at Philipsburg — round-trip from here or stopping by — pick the one that’s you, then your date.

Contemporary
Premium
Luxury
Book this cruise — $3,008 pp →

Same fare as booking direct. We earn a small commission — it costs you nothing.

★ Why Fantasize

We tell you the cruise to take — and the excursions to book.

Most cruise sites hand you a search box and leave you to it. We’re the concierge: the verdict, the plan, the trip of your life — at the exact same fare.

11,000 sailings to sift throughOne cruise, chosen for you
Search a catalog of excursions yourselfWe tell you the exact excursions to book
“Do your homework” on every portA free port-by-port plan, in your inbox
Booking fees and a pushy upsell callNo fees, no pressure — the same fare
Find your bucket-list cruise →

⚓ Your bucket-list concierge

Want this whole adventure in your inbox?

We'll email you this exact plan — where to fly in, the days before and after, the single most extraordinary thing to do at every port, and what it all runs.

We send the plan to your account’s own address — never to one typed into a box. Free, and Google works.

← Browse every bucket-list cruise