Bucket-List Cruise Adventure

14-Night San Juan to Lisbon Cruise Adventure

Silversea · Silver Shadow · from San Juan

$7,000 per person · next sails Mar 9, 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 LIS · $1,556 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 · 14 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
Codringtonport guide →
Barbuda's Pink Sand Beach at Dawn, Private & Empty · $130 for two with Barbuda Bike & Sun (local guide co-op)how to make it yours → ·
Days 4–10
A day at sea
⛰ A day to savor the ship — the voyage itself is the experience, and it’s all included.
Day 11
Santa Cruz de La Palmaport guide →
Tajogaite Volcano · $162 for two with Graja Tours – Hiking on La Palmahow to make it yours → ·
Day 12
Santa Cruz de Tenerifeport guide →
Anaga Rural Park · $389 for two with ToursByLocals — John R. (Santa Cruz de Tenerife private guide)how to make it yours → ·
Days 13–14
A day at sea
⛰ A day to savor the ship — the voyage itself is the experience, and it’s all included.
Day 15
Lisbon Disembark
Disembark in the morning — or stay on for the days just below.
After you disembark

Bucket-list days near Lisbon

You end in a different port — stay on, and add what’s within reach before you fly home.

14 mi from Lisbon

Sintra Day Trip - Pena Palace

13 mi from Lisbon

Convent of the Capuchos Cork Lining & Underground Network

A 16th-century Franciscan monastery carved into living rock with corridors and chambers lined in cork for insulation—a radically austere labyrinth ref…

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 →
After you disembark

Make it longer — by land from Lisbon

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

4 mi from Lisbon · fly LIS

Sintra's Forests, Palaces & Coast: A Portuguese Masterpiece

Coastal Palace Adventure

See the whole plan →
Home

Fly home from Lisbon (LIS)

What this adventure runs estimated · for two
Your hotel
Flights open-jaw · fly into SJU, home from LIS · 2 travelers $1,556 est.
Hotel before you sail1 night · San Juan · Luxury~$484
Cruise fare14 nights · Silversea · 2 guests$14,000
Shore excursions4 bucket-list things, booked direct · for 2 · swap any at its port above ↑~$2,281
Transfersairport ↔ ship, private car~$180
Trip total$18,501
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.
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Every cruise line that calls at San Juan — round-trip from here or stopping by — pick the one that’s you, then your date.

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★ 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.

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“Do your homework” on every portA free port-by-port plan, in your inbox
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