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Discover the yachting islands of the Caribbean 2026 - 15 Days

15 days
From San Juan to Saint Thomas Island
4.2
30 traveler reviews

No departure dates available

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Plan your adventure:
Sailing
Catch the wind and set sail for new horizons
Fully Guided
An experienced guide will be with you for the entire tour
Low Intensity
Travelers can expect some light physical activities
Guided in English
Group Size 30 - 182
Ages 12+
Image of a map showing the route of the tour

Itinerary

  1. Day 1

    San Juan

    You'll arrive in San Juan and get transferred to your Emerald Cruises yacht. After checking in and settling into your cabin, the boat docks at 23:00, so you'll have the evening to get oriented before things really get going tomorrow.

  2. Day 2

    Culebra - Vieques

    A shuttle takes you to Flamenco Beach on Culebra, where you can spend the morning on the white sand and exploring the reefs. You'll grab lunch somewhere on the island, then sail over to Vieques and check out Esperanza with its waterfront area, beaches, and local spots to eat and wander around.

    Meals
    Breakfast, Lunch, Dinner

    Included Activities

    • Shuttle to Flamenco Beach

    Optional Activities

    • Kayaking in the Bioluminescent Bay at Mosquito Bay, Vieques (2 hours, Moderate activity level, must be pre-booked, extra expense)
    Landmarks
    Flamenco Beach
    Mosquito Bay
  3. Day 3

    St. John

    You've got two choices here. Take an included tour of St. John Island to see the old Annaberg sugar mill ruins from the 1700s, or go for the more active option and hike through Virgin Islands National Park with swimming included. Either way, you'll be based out of Cruz Bay, which has the ferry dock, restaurants, shops, and the nice Mongoose Junction area to walk through.

    Meals
    Breakfast, Lunch, Dinner

    Included Activities

    • St. John Island tour with Annaberg Plantation Ruins (3 hours, Easy activity level, open-air safari transportation)

    Optional Activities

    • EmeraldACTIVE: National Park Hike and Swimming along Lind Point Trail to North Shore with guided nature hike and swimming at secluded beach (3 hours, Strenuous activity level)
    Landmarks
    Annaberg Plantation Ruins
    Virgin Islands National Park
    Lind Point Trail
    Cruz Bay
    Mongoose Junction
  4. Day 4

    Jost Van Dyke

    Today you're visiting Jost Van Dyke, the smallest of the main British Virgin Islands and called 'The Last Virgin Island' for a reason. White Bay Beach is where you'll spend time, with rocky areas, colorful local culture, and some really nice Caribbean views from the shoreline.

    Meals
    Breakfast, Dinner

    Optional Activities

    • EmeraldPLUS: BBQ lunch on fully equipped beach with live band (lounge chairs, beach umbrellas, white sand, local music)
    Landmarks
    White Bay Beach
  5. Day 5

    Philipsburg, Sint Maarten

    Philipsburg offers a mix of Dutch and Caribbean vibes with a busy port atmosphere and colonial architecture that stands out. You can walk through historic sites and check out the street market for local food, arts, and crafts. The beaches here are nice too if you want to relax after exploring.

    Meals
    Breakfast, Lunch, Dinner

    Optional Activities

    • Island tour of Saint Martin / Sint Maarten covering both Dutch and French sides with historical sites, Border Monument, Philipsburg waterfront, Marigot market, and Fort Louis (3 hours, Easy activity level, extra expense)
    Landmarks
    Philipsburg
    Marigot
    Fort Louis
    Border Monument
  6. Day 6

    Saint-Barth (Gustavia)

    This French Caribbean island has mountainous terrain, great beaches, and historic wooden buildings scattered around. In Gustavia, you'll find jewelry shops, boutiques, and high-end restaurants. Take time to walk the charming streets and soak in the upscale colonial feel of the place.

    Meals
    Breakfast, Lunch, Dinner

    Optional Activities

    • Driving tour around the island in a private van, non-narrated (Colombier Viewpoint, Flamands Beach, St. Jean Bay, Eden Rock hotel, Atlantic coast, 2 hours 15 minutes, Easy activity level, extra expense)
    • Colombier Bay and Snorkelling at Colombier Bay and Gros Ilets with diverse marine species (2 hours, Moderate activity level, extra expense)
    • Catamaran Escape along St. Barths coastline with views of mega yachts, Colombier Bay swimming and relaxation, return to Gustavia (3 hours, Moderate activity level, extra expense)
    Landmarks
    Gustavia
    Colombier Viewpoint
    Flamands Beach
    St. Jean Bay
    Eden Rock
    Colombier Bay
    Gros Ilets
  7. Day 7

    Montserrat

    Montserrat is unusual because of its volcanic history. George Martin's Air Studios used to be famous here before the 1995 volcanic eruptions changed everything and destroyed the capital Plymouth. You'll see how the island has adapted and rebuilt after such a major event.

    Meals
    Breakfast, Lunch, Dinner

    Optional Activities

    • Volcano Views, Plymouth & Montserrat Volcano Observatory tour visiting the Soufrière Hills Volcano, Montserrat Volcano Observatory for insights into life with an active volcano, the Buried City of Plymouth with volcanic ash and debris layers, and historical contrast photographs (3 hours, Moderate activity level, extra expense)
    Landmarks
    Soufrière Hills Volcano
    Plymouth
    Montserrat Volcano Observatory
  8. Day 8

    Saint John's, Antigua

    After breakfast, you'll head into Saint John's to check out the cultural scene, the diverse population, and try some local food. The afternoon brings you back to the yacht for the second part of your journey, so plan your morning activities around an early afternoon return.

    Meals
    Breakfast, Lunch, Dinner
    Landmarks
    Saint John's
  9. Day 9

    Saint Barthélemy

    You'll have a full day to explore Saint Barthélemy on your own schedule. Start by walking through Gustavia's streets where you can browse luxury boutiques and jewelry shops, or if you'd rather just relax, head straight to one of the pristine beaches. If you want more structure, there are optional activities like a scenic drive around the island, snorkeling at Colombier Bay or Gros Ilets where the water is clear and great for seeing marine life, or a catamaran cruise along the coast with swimming stops included.

    Meals
    Breakfast, Lunch, Dinner

    Optional Activities

    • Driving tour around the island in private van (2.15 hours, Easy activity level)
    • Snorkeling at Colombier Bay and Gros Ilets (2 hours, Moderate activity level)
    • Catamaran Escape cruise along coastline with swimming stop at Colombier Bay (3 hours, Moderate activity level)
    Landmarks
    Gustavia
    Colombier Viewpoint
    Flamands Beach
    St. Jean Bay
    Eden Rock Hotel
    Colombier Bay
    Gros Ilets
  10. Day 10

    Îles des Saintes (Les Saintes)

    This small group of eight tropical islands blends French and Caribbean culture in quaint towns with stone buildings and white-sand beaches. Don't skip Fort Napoleon, which is historically significant and offers great views from up top. The whole place has that intimate island-hopping feel.

    Meals
    Breakfast, Lunch, Dinner

    Optional Activities

    • Fort Napoleon's and views of paradise tour with drive past multi-colored houses, exploration of Fort Napoleon originally built for defense against British invasions, stunning Princess Caroline Garden with tropical flowers and panoramic views, village charm including local church and picturesque streets with murals, boutiques, and friendly locals (3 hours, Moderate activity level, extra expense)
    Landmarks
    Fort Napoleon
    Princess Caroline Garden
    Itinerary Image 1
  11. Day 11

    Deshaies, Guadeloupe

    You'll visit this charming village surrounded by green hills and Caribbean waters. The locals are friendly, the natural beauty is genuine, and the cultural vibe here makes it feel like a real discovery. It's the kind of quiet Caribbean experience that doesn't get overhyped.

    Meals
    Breakfast, Lunch, Dinner

    Optional Activities

    • Tropical World Discovery tour of the Botanical Garden in Deshaies, ten-minute drive from the pier, exploring winding paths through lush oasis created by M. Michel Gaillard with exotic flora including wax rose, red ginger, bougainvillea, and orchids (3 hours, Moderate activity level, extra expense)
    Landmarks
    Botanical Garden of Deshaies
  12. Day 12

    Barbuda

    This full day in Barbuda focuses on history and nature. You'll have the option of a guided tour starting from the jetty that takes you through villages with stops at Martello Tower for views over the island, Codrington where important historical events took place, and Two Foot Bay to see a cave with ancient Arawak petroglyphs. The main event is a motorboat trip to the Frigate Bird Sanctuary where around 1,500 frigate birds nest, making it the world's largest colony of these birds.

    Meals
    Breakfast, Lunch, Dinner

    Optional Activities

    • Frigate Bird Sanctuary guided tour including Martello Tower, Codrington, Two Foot Bay, and motorboat to sanctuary (2.50 hours, Strenuous activity level)
    Landmarks
    Martello Tower
    Codrington
    Two Foot Bay
    Frigate Bird Sanctuary
  13. Day 13

    Virgin Gorda - Norman Island

    You'll spend the morning at Virgin Gorda exploring The Baths, which features sea caves and large granite boulders along the beach. Choose between a relaxing included visit or the EmeraldACTIVE option if you want to wade through caves and learn about the geology. Both options include a fruit smoothie at the Top of the Baths. Later in the afternoon, you'll sail to Norman Island, so plan to head back to the boat with time to spare before departure.

    Meals
    Breakfast, Lunch, Dinner

    Included Activities

    • The Baths excursion including safari wagon transport, beach exploration, swimming, and fruit smoothie (4 hours, Moderate activity level)

    Optional Activities

    • The Baths - EmeraldACTIVE option with cave wading through knee-deep water, geological interpretation of boulder formations, and fruit smoothie (4 hours, Strenuous activity level)
    Landmarks
    The Baths
    Norman Island
  14. Day 14

    Norman Island

    You'll spend your day at Norman Island, an uninhabited island known from Robert Louis Stevenson's 'Treasure Island' story. The beach here is fully set up with lounge chairs and umbrellas, so you can settle in for the day. If you choose the EmeraldPLUS package, lunch is BBQ served on the beach with a local band playing live music, letting you enjoy Caribbean rhythms while looking out at clear water.

    Meals
    Breakfast, Lunch (BBQ lunch on fully equipped beach with live band), Dinner

    Included Activities

    • BBQ lunch on fully equipped beach with live band entertainment
    Landmarks
    Norman Island
  15. Day 15

    St. Thomas

    Your Emerald Cruises voyage wraps up in St. Thomas. You'll be transferred from the yacht to the airport, heading home with Caribbean memories and probably a few days worth of salt in your hair.

    Meals
    Breakfast
    Landmarks
    St. Thomas
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What's Included

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  • Accommodation
  • Guide
  • Meals
  • Additional Services
  • Transport
  • Free eSIM
    TourRadar offers the lead traveler (the person who booked) a free 1GB eSIM for the trip. The eSIM is redeemable only through the TourRadar app 72 hours before departure.

What's Not Included

  • Flights
  • Insurance
  • Optional
  • Additional Services

Operated by

Emerald Cruises

Number of tours

564

Age Range

12 to 90 years old

Response time

within 2 days

Response rate

80%

There’s nothing quite like an Emerald Waterways river cruise. From Europe to...

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Cancellation Policy

A transparent overview of applicable fees.

Travel Insurance

Be covered for any unforseen circumstances.

Emerald Cruises Ship

  • Emerald Azzurra
    Emerald Azzurra
    Reaching an impressive 110 metres in length, our spectacular luxury yachts will exceed your ocean cruising expectations An abundance of spac… Read more
    Capacity
    Capacity
    Built
    2022
    Built
    2022
    Guests
    100
    Guests
    100
    Crew
    68
    Crew
    68
    Length
    110 metres / 360.9 feet
    Length
    110 metres / 360.9 feet
    Width
    Width
    Suites
    Suites
    Staterooms
    Staterooms
    Registry
    Registry
    Gross Tonnage
    5300 gt
    Gross Tonnage
    5300 gt
    Electricity
    Electricity
    Beam
    Beam
    Cruising Speed
    22 kn / 41 kph / 25 mph
    Cruising Speed
    22 kn / 41 kph / 25 mph
    Generators
    Generators
    Engines
    Engines
    Draft
    Draft
    Cabin
    50
    Cabin
    50
    Deck
    Deck
    Deck with Cabins
    Deck with Cabins

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2028

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Who is travelling?

AdultsAges 18 or above

2

ChildrenUnder 18

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Good to Know

Tour ID: 293360

  • Currencies
    Euro
    Guadeloupe and St Martin
    $
    US Dollar
    Puerto Rico, Virgin Islands, U.S. and Virgin Island, British
  • Plugs & Adapters

    As a traveler from USA, Canada you will need an adaptor for types C, E, F, D, M. As a traveler from England, Australia, New Zealand you will need an adaptor for types C, E, F, D, M, A, B. As a traveler from South Africa you will need an adaptor for types C, E, F, A, B.

    Type C
    Guadeloupe
    Type E
    Guadeloupe
    Type F
    Guadeloupe
    Type D
    Guadeloupe
    Type M
    Guadeloupe
    Type A
    Virgin Islands, U.S., Virgin Island, British and St Martin
    Type B
    Virgin Islands, U.S., Virgin Island, British and St Martin
  • Vaccines
    • These are only indications, so please visit your doctor before you travel to be 100% sure.
    • Hepatitis A - Recommended for Guadeloupe.Puerto Rico.Virgin Islands, U.S..Virgin Island, British. Ideally 2 weeks before travel.
    • Hepatitis B - Recommended for Guadeloupe.Puerto Rico.Virgin Islands, U.S..Virgin Island, British. Ideally 2 months before travel.
    • Yellow fever - Certificate of vaccination required if arriving from an area with a risk of yellow fever transmission for Guadeloupe. Ideally 10 days before travel.
  • Visa
    • Unfortunately we cannot offer you a visa application service. Whether you need a visa or not depends on your nationality and where you wish to travel. Assuming your home country does not have a visa agreement with the country you're planning to visit, you will need to apply for a visa in advance of your scheduled departure.
    • Here is an indication for which countries you might need a visa. Please contact the local embassy for help applying for visas to these places.
  • Payment information
    • For any tour departing before May 9th, 2026 a full payment is necessary. For tours departing after May 9th, 2026, a minimum payment of 100% is required to confirm your booking with Emerald Cruises. The final payment will be automatically charged to your credit card on the designated due date. The final payment of the remaining balance is required at least 95 days prior to the departure date of your tour. TourRadar never charges you a booking fee and will charge you in the stated currency.
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  • Cancellation Policy
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    Some tours are not suitable for mobility-restricted traveler, however, some operators may be able to accommodate special requests. For any enquiries, you can contact our customer support team, who are ready and waiting to help you.

Who is travelling?

AdultsAges 18 or above

2

ChildrenUnder 18

0

Select departure month

2026

Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec

2027

Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec

2028

Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec