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Discover the yachting islands of the Caribbean: 15 days San Juan to San Juan

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Operated by Emerald Cruises
Tripcode: NZ-ba0ec7e6ca4cc0ccd
Overview
Destination:
Puerto Rico
Start:San Juan, Puerto Rico
Finish:San Juan, Puerto Rico
Duration:15 days
Travel Period
December 2025 - January 2026

Island hop through the Caribbean by luxury yacht

Embark on an unforgettable Caribbean voyage exploring pristine beaches and coral reefs, island-hopping through diverse cultures, where the warmth of the locals will enhance your luxury yacht adventure.
Embark on this 15-day Caribbean cruise starting from San Juan, you’ll sail in contemporary luxury on board your Emerald Cruises yacht to Culebra, where azure waters thrive with marine life, hugging the golden sands of tranquil beaches. Explore the charming coastal town of Esperanza on Vieques Island and Cruz Bay on St. John Island, where an easy-going attitude makes city strolls a true joy. Continue exploring the Virgin Islands with a stop off in Jost van Dyke, before Gustavia on St. Barts promises a certain French je ne sais quoi. Proceed to Barbuda, a tranquil island with pink-sand beaches and crystal-clear waters before visiting Illes des Saintes and Deshaies in Guadeloupe. Each port offers a unique blend of culture, history, and natural beauty, making this cruise an unforgettable experience. Your cruise ends in San Juan, Puerto Rico.
Standard inclusions
  • 14 nights on board an Emerald Cruises luxury yacht
  • Airport transfers to and from the ship
  • The services of an Emerald Cruises Shore Excursion Manager
  • Port taxes and charges
  • All tipping and gratuities
  • 41 superb meals including 14 Breakfasts (B), 13 Lunches (L), 14 Dinners (D)
  • Including a Welcome and Farewell Reception & Dinner
  • Complimentary wine, beer, soft drinks & selected cocktails throughout the day.
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Itinerary
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Day 1 - San Juan, Puerto Rico

Your yacht cruise begins in San Juan, where you’ll be transferred to your Emerald Cruises luxury yacht and embark on your discovery of the Caribbean. 

Please book your flight to arrive into San Juan prior to 07:00 PM.

Day 2 - Culebra Island & Vieques Island, Puerto Rico

Culebra is widely known for its white-sand beaches and active reef and is one of the major islands in Puerto Rico’s archipelago. This island offers plenty for nature lovers, giving you peace and tranquillity in a truly pristine destination. There are more than 20 cays bustling with diverse marine life, making it an absolute paradise for underwater adventurers and casual beachgoers alike. 

Opportunity to spend the day swimming off the yacht and enjoying our marina toys. 

After lunch we set sail to Vieques Island. The quaint coastal town of Esperanza has a lovely waterfront with gorgeous beaches and a bustling strip of restaurants, bars, and guesthouses. One can walk along the boulevard and visit the various establishments for a glimpse into the local culture and activities on offer. Locals enjoy spending the afternoon at Sun Bay, the main urban beach located in the town’s eastern outskirts.  

Day 3 - St. John, U.S. Virgin Islands - Jost Van Dyke, British Virgin Islands

Cruz Bay is the economic and social hub of St. John, with a busy?inter-island ferry dock connecting it to other islands in the region. The busy bay is dotted with restaurants and shops, and beautiful Caribbean architecture can be seen in Mongoose Junction as one takes a gentle stroll through town.  

In the evening, set sail to Jost Van Dyke, one of the main islands in the British Virgin Islands. 

Day 4 - Jost Van Dyke, British Virgin Islands

Jost Van Dyke is the smallest of all four main islands comprising the British Virgin Islands, approximately eight square kilometres. Known as ‘The Last Virgin Island’, White Bay Beach on Jost Van Dyke is made up of rather rocky scenery combined with colourful local culture. The bay is by far one of the best beaches to relax on and savour splendid Caribbean views.   

Day 5 - Philipsburg, Sint Maarten (Saint Martin)- Gustavia, Saint Barthélemy

With its blend of Dutch and Caribbean influences, Philipsburg presents a bustling port town with a vibrant atmosphere, striking colonial architecture, and stunning beaches.  

It also offers a range of activities and attractions, including historic sites and a lively street market where you can sample the local cuisine, and peruse the island arts and crafts. You will set sailing to Gustavia in the evening. 

Day 6 - Gustavia, Saint Barthélemy

Named for Sweden’s King?Gustav III, Gustavia is the charming capital and main seaport of the island of Saint Barthélemy, also known as St. Barth. It is often considered to be one of the most beautiful islands in the Caribbean and a tropical paradise with French flair. You will enjoy the beauty of its large idyllic beaches, plus the charm and refinement of its old wooden houses. 

Opportunity to spend the day swimming off the yacht and enjoying our marina toys. 

Day 7 - Little Bay, Montserrat

Welcome to one of the most unusual and fascinating islands in the Caribbean. Prior to the recent volcanic eruptions that commenced in 1995, Montserrat was considered as one of the “Insiders” favourite Caribbean islands. It was also home to producer George Martin’s Air Studios Montserrat recording studio where some of the world’s most famous recording artists, including Eric Clapton, Little River Band and Paul McCartney among many others, used to record their albums. Recent history has brought some unfortunate blows to the island ranging from hurricanes (Hugo in 1989) to multiple volcanic eruptions that destroyed the lovely capital city of Plymouth. 

Day 8 - St John's, Antigua

After breakfast, take your time exploring Saint John's, Antigua, renowned for its cultural diversity, bustling cultural scene, and delicious cuisine. In the afternoon, step back on board your Emerald Cruises luxury yacht for the second leg of your journey. 

Day 9 - Barbuda, Antigua and Barbuda

Barbuda is a small island located in the Caribbean Sea, northeast of the island of Antigua. It is one of the two islands that make up the country of Antigua and Barbuda, along with Antigua. The island is known for its stunning beaches, including the famous Pink Sandy Beach, which is considered one of the most beautiful beaches in the world. It is also home to several wildlife reserves, including the Frigate Bird Sanctuary, which is a UNESCO World Heritage Site. The island has a strong sense of community and a relaxed atmosphere, making it a popular destination for those looking for a peaceful and secluded getaway. 

Day 10 - Îles des Saintes, Guadeloupe

Îles des Saintes, known as Les Saintes, is a miniature archipelago of eight tropical islands with a distinctive French and Caribbean culture fusion. Discover the quaint towns, with their collection of petite stone buildings and small white-sand beaches. Don’t miss Fort Napoleon, a significant historical site with incredible views of one of the islands.    

Day 11 - Deshaies, Guadeloupe

Located on the northwest shores of the Caribbean Island of Guadeloupe, this picturesque village is renowned for its traditional fishing village atmosphere, colourful Creole architecture, and stunning beaches framed by verdant hills. Not surprisingly, Deshaies has emerged as a popular destination, attracting visitors with its friendly locals, and delicious French-Caribbean cuisine. 

Day 12 - Gustavia, Saint Barthélemy

The capital of the lovely Caribbean Island of Saint Barthélemy, Gustavia was named after Sweden’s King Gustav III, who boldly declared it his own exclusive island getaway in 1785. In this vibrant city, uncover distinctive treasures in the historic downtown shopping enclave, photograph the brightly painted wooden houses, and feast on unique cuisine that fuses French and Creole culinary influences. 

Opportunity to spend the day swimming off the yacht and enjoying our marina toys. 

Day 13 - Virgin Gorda, British Virgin Islands

The Island of Virgin Gorda, named after its resemblance to a reclining woman, is part of the British Virgin Islands and popular for its laid-back pace and picturesque landscapes. Among the natural wonders of Virgin Gorda, The Baths are arguably the most famous, a series of pools and grottoes created by a collection of massive granite boulders formed by volcanic eruptions.  

Day 14 - Norman Island, British Virgin Islands

Renowned for its beautiful beaches, crystal-clear waters, and vibrant marine life, Norman Island offers a variety of activities, including hiking trails and caves to explore.  

The island is also steeped in pirate lore, with local legend implying that this was a favourite hiding spot for pirates who buried their treasure on the island; hence why it has been nicknamed ‘Treasure Island’ by locals and visitors alike. Without doubt, this is the perfect destination for those seeking a tranquil and alluring tropical getaway.  

Opportunity to spend the day swimming off the yacht and enjoying our marina toys. 

Day 15 - San Juan, Puerto Rico

Your Emerald Cruises luxury voyage draws to a close in San Juan. From the yacht, you will be transferred to the airport for your journey home. 

*Please verify with the Shore Excursion Manager onboard whether a DiscoverMORE tour is available on disembarkation day. 

Please book your flight to depart out of San Juan after 11:00 AM.

The itinerary is a guide only and may be amended for operational reasons. As such Emerald Cruises cannot guarantee the cruise will operated unaltered from the itinerary states above. Please refer to our terms and conditions for further information.

Departure dates

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Travellers

Operator
Emerald Cruises

Discover the world with Emerald Cruises. Whether you’re travelling to unspoilt islands or bustling metropolises, our fleet of river-cruising Star-Ships and ocean-going luxury yachts guarantee an unparalleled voyage. Enjoy modern exploration, pairing authentic adventures with inimitable luxury. Founded in 2013, and first sailing as Emerald Waterways in 2014, Emerald Cruises is an award-winning travel operator specialising in deluxe river cruises and luxury yacht cruises. Just one year later, in 2014, the first Star-Ship, Emerald Sky, set sail. Our extensive fleet of Star-Ships are custom-built to sail Europe’s iconic Rhine, Main, Moselle, Danube, Rhȏne, Saône and Douro rivers, as well as the majestic Mekong River in Southeast Asia, with each ship featuring a range of stylish innovations. Whether you’re travelling by river or sea, your luxury vessel will dock in the heart of amazing destinations. In 2024, we celebrate 10 years of Emerald Cruises by introducing the next generation of superyachts: Emerald Kaia, launching in early 2026.

Important Information
*Terms and conditions
Please note: We are proud to be an independent agent to travel providers of hotels, flights and other related services. We are not a tour operator. Details and information on the offer are provided by 3rd party businesses and although we do our best to verify the information, we cannot guarantee its accuracy on all occasions. These offers are not available in conjunction with any other offer unless otherwise stated. Pricing and availability are subject to change without notice. For more information, please see Terms of Use
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