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Explore colorful Gustavia

Round Trip St. Maarten

Example 7 Day Cruise aboard Vela
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Set a course for the Leeward Islands and discover a treasure trove of breathtaking beaches, old forts, and seaside villages on this unforgettable 7-day Caribbean cruise. The Leeward islands offer cultural diversity and stunning natural beauty along with a perfect balance of small islands and larger ports with just the right amount of hustle and bustle. Board your comfortable ship and set off on an incredible journey. 
Play in the brilliant blue waters of the CaribbeanA stunning sunset over the CaribbeanRelax on the beaches of the CaribbeanGustavia Harbor in St. BarthsExplore colorful Gustavia
  • Discover Philipsburg's French and Dutch sides
  • Take a stroll on your own private slice of brilliant white sand at Anguilla
  • Explore tiny Pigeon Island, home to Jacque Cousteau’s underwater reserve
  • Enjoy fishing, kayaking and snorkeling at Monserrat Island
Trip Type:
  • Small Ship
Activity Level: Relaxed

Full Itinerary

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Day 1: Philipsburg, St. Maarten

One island, two countries.  One side French, the other side Dutch. Does that make it twice as nice? We think so! Put your money on red in a world-class casino, or shop in the chic local boutiques. Sail the America’s Cup, and celebrate your victory with a bottle of champagne at the beach. Sint Maarten / St. Martin, in any language, is a slice of paradise!

Day 2-6: Sailing the Caribbeam

  • Ship
  • 5 Breakfasts, 5 Lunches, 5 Dinners
The captain and crew will set a course following ideal weather, providing a truly custom trip. Some of the destinations you may visit include:

Take a romantic stroll on your own private slice of brilliant white sand. Hunt for seashells, feel the breeze and gaze at incredible horizons. Indulge in the delicious cuisine offered at casually sophisticated island restaurants. Late nights will find you enjoying the local music scene, as the rhythm of reggae and string quartets fill the night air. It’s everything you’ve heard, and more! Anguilla will be your paradise found.

You can trace Antigua’s English roots to Admiral Horatio Nelson and the Royal Navy, who took shelter in the picturesque harbors over 200 years ago. Today, Antigua offers a variety of unforgettable experiences: from helicopter rides to romantic horseback riding, and a different beach for every day of the year, Antigua has it all.

Shaped like a butterfly, Guadeloupe’s wings flutter into your adventure-loving heart. Beach lovers head east to Grand-Terre for miles of white sand and aqua shores. Hikers, history buffs and those looking to shop may prefer the west wing of Basse-Terre, with its winding trails, lush plant life, and tempting boutiques. Snorkelers and Scuba Divers should check out tiny Pigeon Island, home to Jacque Cousteau’s underwater reserve.

When the volcano erupted in 1997, the locals had already abandoned their homes and businesses in the capital of Plymouth. Nearly two-thirds of the island is located in the Exclusion Zone. Tours are offered when weather permits and the still-active volcano is dormant. To the North, Montserrat’s beaches are a lovely shade of pearl grey that shimmers in the sunlight. Sport fishing, kayaking, and snorkeling are popular activities.

Halos of white puffy clouds float high atop Nevis Peak, a perfect backdrop to the idyllic scenery below. Picturesque gingerbread-house-style cottages and old plantations dot the countryside. Take a hike, play golf, or spend a decadent day doing nothing but sifting sand through your toes on a perfect beach. And don’t miss the Killer Bees at Sunshine’s!

St. Barths
Millionaires, rock stars and sailors like you eat cheeseburgers in paradise at Le Select, the inspiration for Jimmy Buffet’s song. Marvelous beaches, gastronomical delights, and bistros made for people watching and sipping fine French wines…it’s an ooh-la-la kind of day, St. Barth’s style!

Day 7: Philipsburg, St. Maarten

Disembark this morning for your continued journey home.




Dates & Prices

My Preferred Start Date

Per person starting at
Cabin 3
Select a Date
Cadet Solo
Cabins #1-2. Single occupancy cabins with a raised berth and a compact, all-in-one bathroom.
Cabin 2
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Standard Cabin
Cabins #3-4. Feature a wider lower and single upper berth and an all-in-one shower/bathroom.
Cabin 1
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Deluxe Cabin
Cabins #5-6. Feature a double lower and single upper berth and a private bathroom with shower.
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Staysail Cabin
Cabins #11-15. Feature a roomy double berth and private bathroom with shower.
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Compass Cabin
Cabins #16-17.located in the aft section of the ship. These spacious cabins feature a queen size bed (no upper bunk) and an ensuite bathroom with shower.
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Topsail Cabin
Cabin #9. Features a queen size bed and luxury bathroom
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Owners’ Suite
Cabin #7. Features a king size bed and large bathroom. There are portholes in both the cabin and the bathroom.


The above itinerary is just an example of what you may experience on your tall ship sailing cruise. Your captain may make changes based upon the weather, local activities, and several other factors. The captain may decide to include one of many other hidden island jewels on your itinerary. 

Cruise rates include meals, beverages (water, juice, soda, beer, wine, and rum punch), cabin service, port charges and taxes, and complimentary use of snorkel gear for the week. You’re welcome to bring your own spirits on board to mix your favorite drinks.

Not included in cruise fare: Daily island excursions are optional and are not included in the cruise fare.



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