San Juan to San Juan
Ocean Cruise Memorii Pick
Silversea Cruises  ·  Silver Shadow

San Juan to San Juan

From San Juan to San Juan  ·  Caribbean  ·  7 nights

Departure 20 Dec 2026
Return 27 Dec 2026
Duration 7 nights
Ports of call 6 ports
Ship Silver Shadow
Journey type Ocean Cruise
From
$2,977
per person
Request a Proposal
Voyage overview

What this voyage is

Silver Shadow & Whisper are elegant ships carrying just 392 privileged guests each, in beautiful style, with plenty of space and loads of facilities, whilst maintaining a nurturing intimacy.

We do enjoy stepping aboard these sleek ships, the second
generation from Silversea. Whilst maintaining the small ship feel,
they have the space to offer upgraded facilities and choices, not
to mention outstanding levels of service and hospitality, with
Italian flair and a family atmosphere.

Day By Day

Itinerary

1
20 Dec 2026
San Juan

Founded by the Spanish in 1521, Puerto Rico's capital is the second oldest European settlement in the Americas. Modern San Juan is a bustling city, home to over a third of the island's population, but the cobbled streets of the Old Town remain the biggest tourist draw. The colonial-era fortifications have been awarded UNESCO World Heritage status, crowned by the imposing waterfront El Morro fortress, and the Old Town is full of attractive, brightly coloured houses. Outside of the Old Town you can find designer shopping on Avenida Ashford, and the north of the city is fringed by beautiful beaches, including fashionable Condado with its hip hotels and bars.

Memory Tip: Don't miss Here in Puerto Rico it’s all about the history and the sea – you can’t miss the fabulous beaches, and you will enjoy the historic military buildings.
2
21 Dec 2026
Jost Van Dyke

The idyllic island of Jost Van Dyke, named after an early Dutch settler, is known for its laid back vibe and friendly beach bars, including the famous Foxy’s, which counts Keith Richards amongst its past customers. It’s a place to kick back and relax, and the clear blue waters are also perfect for snorkelling.

3
22 Dec 2026
Little Bay

Montserrat garnered global attention in 1995 when the Soufrière Hills volcano erupted, burying the island’s capital, Plymouth. Although an exclusion zone is still in place in the south, visitors are often surprised by how lush and unspoilt the rest of the island is, home to a colourful variety of birdlife.

4
23 Dec 2026
Castries

Castries, Saint Lucia’s diminutive capital, is home to some interesting markets and colonial buildings. The island’s highlights are situated elsewhere, however, and we’d recommend either heading south towards Soufrière, where the iconic Piton mountains guard a beautiful bay, or north to the bars, restaurants and beaches of Rodney Bay.

5
24 Dec 2026
Fort-de-France

The volcanic French Caribbean island of Martinique is a land of contrasts, from the lush rainforests of the north to the busy streets of the capital, Fort-de-France. There are plenty of lovely beaches geared towards relaxation, and the French influence also means that the cuisine is a cut above the usual Caribbean fare.

6
25 Dec 2026
At Sea
7
26 Dec 2026
Soper’s Hole (Tortola)
8
27 Dec 2026
San Juan

Founded by the Spanish in 1521, Puerto Rico’s capital is the second oldest European settlement in the Americas. Modern San Juan is a bustling city, home to over a third of the island’s population, but the cobbled streets of the Old Town remain the biggest tourist draw.

Memory Tip: Our tip Hunt out the very best chuletas Can-Can and pastelillos – local food at its best is great. Don’t settle for sorry imitations.
What is included

Fare inclusions

Alcohol included
Daytime activities
Gratuities included
Meals included
WiFi included
You might also consider

Similar voyages

Basslines & Beaches
Seven Seas Grandeur
Basslines & Beaches
10 nights  • 12 Mar 2029
Embark: Miami  →  Disembark: Miami
From $6,967 pp
Island Rhythms & Revelry
Seven Seas Grandeur
Island Rhythms & Revelry
9 nights  • 17 Feb 2029
Embark: Miami  →  Disembark: Miami
From $6,263 pp
Fete Afloat
Seven Seas Grandeur
Fete Afloat
10 nights  • 7 Feb 2029
Embark: Bridgetown  →  Disembark: Miami
From $6,872 pp