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From San Juan to San Juan

Windward Islands Surf & Sunsets

Dates:
8 Nov - 15 Nov 2026
Duration:
7 Nights
Journey type:
Cruise only (please call for flight options)
No. of ports:
7
Ship:
Star Pride
Cruise Line:
Windstar Cruises
Fares:

From £2,535 pp

Marigot, St Martin

From San Juan to San Juan

Windward Islands Surf & Sunsets

Dates:
8 Nov - 15 Nov 2026
Duration:
7 Nights
Journey type:
Cruise only (please call for flight options)
No. of ports:
7
Ship:
Star Pride
Cruise Line:
Windstar Cruises
Fares:

From £2,535 pp

Voyage Itinerary

8 November

Setting sail from 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.

Colourful street in San Juan, Puerto Rico
Chuleta Can Can, Puerto Rico

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.

9 November - At sea

10 November

Grenada: St George's

Browse the markets of charming St George’s, fragrant with the scent of cinnamon and nutmeg, and you’ll soon understand why Grenada is known as the ‘isle of spice’. This is one of the Caribbean’s most enchanting islands, fringed by gorgeous beaches and largely unsullied by mass market tourism.
Cannon overlooking St George's, Grenada

11 November

St. Vincent & Grenadines: Bequia

Bequia is an incredibly friendly, laid-back island blessed with pristine golden sand beaches and some excellent restaurants. It’s also a popular sailing destination; the yachts tend to congregate around Admiralty Bay, where you’ll find the little waterfront town of Port Elizabeth.
Admiralty Bay, Bequia

12 November

St. Vincent & Grenadines: Mayreau

Situated just to the west of the Tobago Cays, Mayreau is a tiny, barely inhabited island that can only be reached by boat. There is very little to do, which is the main attraction for those lucky few who wash up here; the palm-fringed beaches and gently lapping waters are the Caribbean island idyll par excellence.
Beach on Mayreau, St Vincent & The Grenadines

13 November

Guadeloupe: 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.
Terre-de-Haut, Iles de Saintes, Guadeloupe

14 November

Saint Martin: Marigot

Marigot is the gateway to an intriguing little Caribbean island with a dual personality: the Dutch side, St. Maarten, is the livelier of the two, with shopping malls, casinos and more of a nightlife scene, while French-speaking St. Martin is a more refined (and more expensive) affair, with a laid-back, continental air and a host of exclusive resorts and restaurants.
Marigot, St Martin

15 November

Arriving in 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.
Colourful street in San Juan, Puerto Rico
El Morro fortress, San Juan

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.

The ship

Star Pride

Capacity:
312 Guests
Crew:
204 Staff
Style:
This is laid-back luxury at its best with relaxed informal days, refined yet comfortable evenings and a friendly and welcomingcrew.

Windstar's Star Plus Class of vessels - Star Pride, Star Legend and Star Breeze - each carry just over 300 guests and are hugely popular for very good reason.

What we love

These small ships accommodate 312 guests in large all-suite accommodation, following the completion of the Star Plus refurbishment programme in 2021 which saw the ships lengthened. There's a choice of restaurants, comfortable lounges, and plenty of deck space, while the ship's marina ensures you can enjoy the complimentary watersports when anchored in hidden bays and tiny coves.

Learn more about Star Pride
Windstar Cruises - Star Breeze

inclusions

  • All meals in all venues including room service
  • Soft drinks, speciality coffees and teas
  • Champagne welcome reception
  • All onboard entertainment
  • Use of the Fitness Centre & yoga classes
  • Unlimited use of all watersports equipment

Tailor-make your trip

Ways to make it better
    • Room at El Convento hotel, San Juan, Puerto Rico

      Extend your stay in Puerto Rico

      If you want to stay in San Juan itself, El Convento is definitely the nicest choice. For resort hotels, we love the Ritz Carlton Reserve at Dorado Beach.

    • El Yunque rainforest, Puerto Rico

      Recommended excursions from San Juan

      In the El Yunque rainforest you will find the habitat of Puerto Rico's endangered wildlife - not to mention beautiful views.

    How can we help?

    Our frequently asked questions

    From cruise tips to travel protection, here are some of our most-asked questions

    visit our faqs

    Will I save by booking with Mundy Cruising?

    Absolutely. You'll save money and time by booking with us rather than directly with the cruise line and enjoy more flexibility in your travel arrangements. We have access to preferential rates and exclusive offers, and we offer expert advice on how to get the best value.

    Can you help with pre and post-cruise arrangements?

    From flights and transfers to hotels and tours, we can help with all your travel needs to make sure your trip is exceptional. What's more, we are members of ABTA and also offer full ATOL protection, not to mention a 24hr emergency contact, so we offer complete peace of mind.

    What are the benefits of a small luxury ship?

    Because small ships are able to reach smaller ports of call and provide a higher level of service than their big ship counterparts, we believe that small ship cruising is the very best way to travel. Usually they offer more space per person, and an attentive team to make sure you have the very best experience. Small ship cruising offers the very best of the best.

    Why Mundy?

    Who we are

    Founded in 1970, we have sold more luxury cruises for more years than anyone else in the UK.

    Mundy Cruising was the very first cruise specialist in the UK. We have been making the best cruise holidays even better since 1970.

    How? Simply by offering our clients more expertise, more personal service, more unique ideas, more fascinating add-ons, more fabulous freebies and more peace of mind.

    More about Mundy

    We're happy to do all of that over the phone. But if you prefer to chat face to face, why not visit us at our comfortable offices on London's High Holborn - we'd be delighted to see you.