14-Day Leeward Island Jewels
Ocean Cruise Memorii Pick
Seabourn Cruises  ·  Seabourn Quest

14-Day Leeward Island Jewels

From Miami to Miami  ·  Caribbean  ·  14 nights

Departure 22 Nov 2026
Return 6 Dec 2026
Duration 14 nights
Ports of call 10 ports
Ship Seabourn Quest
Journey type Ocean Cruise
From
$7,831
per person
Request a Proposal
Voyage overview

What this voyage is

These spacious and elegant sisters are the perfect choice for a combination of contemporary style and expert hospitality.

When Seabourn built these 458-guest ships we were delighted. Not
only because each one is beautiful, but also because their
similarity means that they are interchangeable, enabling you to
travel all over the world in a familiar environment.

Day By Day

Itinerary

1
22 Nov 2026
Miami

Miami is a pulsating modern city, a cultural crossroads where Cuban émigrés rub shoulders with affluent New Yorkers topping up on winter sun, and where you're just as likely to hear Spanish or Caribbean patois being spoken as you are English. Downtown Miami is a destination in its own right, with a host of world class galleries including the fantastic MOCA (Museum of Contemporary Art), but it's still Miami Beach that draws the biggest crowds. The Art Deco district around South Beach is very much back in vogue, with new restaurants, bars and luxury developments sprouting up all over the place.

Memory Tip: Our tip Bill Baggs Cape Florida State Beach on the tip of Key Biscayne is a great place to get away from the crowds and spot some wildlife.
2
23 Nov 2026
At Sea
3
24 Nov 2026
At Sea
4
25 Nov 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.

5
26 Nov 2026
Road Bay

Tiny Anguilla is home to no less than 33 beaches, blessed with some of the most gloriously white sands in the Caribbean. A clutch of high end hotels and gourmet restaurants attract a well-to-do crowd, but the island has a more low key, laid back vibe than its glitzy neighbours, St Martin and St Barths.

6
27 Nov 2026
South Friars Bay

The beach at South Friars Bay is a lovely sweep of golden sand at the southern end of St Kitts, although it can get a little busy when the larger cruise ships are docked on the island. There are several bars and restaurants along this half-mile stretch, with watersports equipment and loungers available to rent.

7
28 Nov 2026
Roseau

The island of Dominica stands out from the rest of the Caribbean, a rugged natural paradise that remains blissfully free of mass market tourism. The capital, Roseau, is pleasant enough, but the island interior offers so much more, including thick jungle, bubbling hot springs, cascading waterfalls and abundant birdlife.

8
29 Nov 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.

9
30 Nov 2026
Terre-de-Haut

Eight tiny islands make up the Iles des Saintes, a sparsely inhabited archipelago off the southern coast of Guadeloupe. The most interesting island is hilly Terre-de-Haut, almost entirely populated by the fair-skinned descendants of Breton sailors and home to a beautiful bay reminiscent of a mini Rio de Janeiro.

10
1 Dec 2026
Montserrat

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.

11
2 Dec 2026
Virgin Gorda

Languid, laid-back Virgin Gorda is blessed with beautiful beaches and wonderfully friendly people. Life proceeds at a slower pace here, and highlights include The Baths, an unusual collection of granite boulders, grottoes and pools on the island’s southwest shore.

12
3 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.

13
4 Dec 2026
At Sea
14
5 Dec 2026
At Sea
15
6 Dec 2026
Miami

Downtown Miami is a destination in its own right, with a host of world class galleries, but it's still Miami Beach that draws the biggest crowds. The Art Deco district around South Beach is very much back in vogue, with new restaurants, bars and luxury developments sprouting up all over the place.

Memory Tip: Don't miss People watching in South Beach – glamorous gay guys on skates with miniature dogs in slings…
What is included

Fare inclusions

Alcohol included
Daytime activities
Gratuities included
Meals included
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