Bucket-List Cruise Adventure

14-Night Lisbon to San Juan Cruise Adventure

Silversea · Silver Dawn · from Lisbon

$7,500 per person · next sails Nov 27, 2027 Book this cruise@ Cruisebound · same fare
Get there

Fly into Lisbon (LIS)

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

Open-jaw · fly into LIS, home from SJU · $1,556 for two est.
Before you sail

Bucket-list days near Lisbon

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.

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…

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
Lisbon Embark
Board in the afternoon — fly in at least a day early (your day ashore here is just above).
Day 2
A day at sea
⛰ A day to savor the ship — the voyage itself is the experience, and it’s all included.
Day 3
★ Pico do Arieiro to Pico Ruivo — how to make it yours →
Day 4
Santa Cruz de La Palmaport guide →
Tajogaite Volcano · $162 for two with Graja Tours – Hiking on La Palmahow to make it yours → ·
Day 5
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 6–7
A day at sea
⛰ A day to savor the ship — the voyage itself is the experience, and it’s all included.
Day 8
Private Full-Day São Vicente Island Discovery Tour · $224 for two with Green Line Tours Cabo Verdehow to make it yours → ·
Days 9–13
A day at sea
⛰ A day to savor the ship — the voyage itself is the experience, and it’s all included.
Day 14
Private Open-Top Mini Moke Island Tour of St. Barts · $130 for two with Ferry Voyager – St. Barths Tourshow to make it yours → ·
Day 15
San Juan Disembark
Disembark in the morning — or stay on for the days just below.
After you disembark

Bucket-list days near San Juan

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

49 mi from San Juan

Bioluminescent Bay Tour (Vieques)

0 mi from San Juan

Sunken City Scuba Diving Tour

Before you sail

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 →
176 mi from Lisbon · fly OPO

Salt, Sand and Natural Wine: The Aveiro Coast Done Right

Lagoon Coast Slow Adventure

See the whole plan →
After you disembark

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 San Juan (SJU)

What this adventure runs estimated · for two
Your hotel
Flights open-jaw · fly into LIS, home from SJU · 2 travelers $1,556 est.
Hotel before you sail1 night · Lisbon · Luxury~$450
Cruise fare14 nights · Silversea · 2 guests$15,000
Shore excursions4 bucket-list things, booked direct · for 2 · swap any at its port above ↑~$905
Transfersairport ↔ ship, private car~$180
Trip total$18,091
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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