Bucket-List Cruise Adventure

10-Night San Juan to Bridgetown Cruise Adventure

Silversea · Silver Shadow · from San Juan

$5,750 per person · next sails Feb 6, 2027 Book this cruise@ Cruisebound · same fare
Get there

Fly into San Juan (SJU)

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

Open-jaw · fly into SJU, home from BGI · $1,810 for two est.
Before you sail

Bucket-list days near San Juan

Fly in at least a day early — every seasoned cruiser does, so a delay never costs you the ship. Here’s what’s worth that day, within reach of your port — not just the city you fly into.

49 mi from San Juan

Bioluminescent Bay Tour (Vieques)

0 mi from San Juan

Sunken City Scuba Diving Tour

Your voyage · 10 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
San Juan Embark
Board in the afternoon — fly in at least a day early (your day ashore here is just above).
Day 2
Jost Van Dykeport guide →
Private Catamaran Charter · $1,600 for two with Honey Group Private Boat Chartershow to make it yours → ·
Day 3
Private Open-Top Mini Moke Island Tour of St. Barts · $130 for two with Ferry Voyager – St. Barths Tourshow to make it yours → ·
Day 4
Port of Basseterreport guide →
Mt. Liamuiga Volcano Crater Hike · $150 for two with Duke of Earl Adventures (Earl Pemberton)how to make it yours → ·
Day 5
Little Bayport guide →
Soufrière Hills Volcano Exclusion Zone Helicopter… · $250 for two with Montserrat Aviation Services (MAS)how to make it yours → ·
Day 6
Iles des Saintesport guide →
Sunrise Hike to Le Chameau's Summit Fort · $86 for two with Self-guided via Office de Tourisme des Saintes trail map (local guide optional through Alexandra Randonnée)how to make it yours → ·
Day 7
Titou Gorge, Trafalgar Falls & Champagne Reef Priv… · $240 for two with Seacat Tours Dominica (Seacat Lugay)how to make it yours → ·
Day 8
Trois Iletsport guide →
★ La Savane des Esclaves — how to make it yours →
Day 9
Cosol Tours · $300 for two with Cosol Tours (official)how to make it yours → ·
Day 10
St. Georgesport guide →
Grenada Private Taxi Tour · $160 for two with Grand Tours Grenada (Call the Boss Taxi)how to make it yours → ·
Day 11
Bridgetown Disembark
Disembark in the morning.
Before you sail

Make it longer — by land from San Juan

The ship is the spine, not the whole trip. These are full land adventures within reach of your port.

234 mi from San Juan · fly SDQ

Barahona: The Dominican Coast You Haven't Heard Of Yet

Wild Coast & Mountain Culture

See the whole plan →
Home

Fly home from Bridgetown (BGI)

What this adventure runs estimated · for two
Your hotel
Flights open-jaw · fly into SJU, home from BGI · 2 travelers $1,810 est.
Hotel before you sail1 night · San Juan · Luxury~$484
Cruise fare10 nights · Silversea · 2 guests$11,500
Shore excursions8 bucket-list things, booked direct · for 2 · swap any at its port above ↑~$2,916
Transfersairport ↔ ship, private car~$180
Trip total$16,890
Flights are estimated from our best gateways (refine from your own airport above) — an open-jaw trip: out to the embark port, home from where you disembark; 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 · $5,750 pp

Book your trip to San Juan

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 San Juan — round-trip from here or stopping by — pick the one that’s you, then your date.

Contemporary
Premium
Luxury
Book this cruise — $5,750 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