Have questions? We're here.
Explore colorful Gustavia

Round Trip St. Maarten

Example 7 Day Cruise aboard Vela
Talk with an expert
Customize any aspect of your Caribbean trip. 1.406.541.2677
Help Me Plan My Trip
“To the Indies!” shouted explorers and pirates from the decks of tall ships. Set a course for the Leeward Islands and discover a treasure trove of breathtaking beaches, old forts, and seaside villages waiting to be conquered by adventurers like you. Choose the Leewards if you’re looking for cultural diversity along with a nice balance of small islands and larger ports with just the right amount of hustle and bustle. 

Day-by-Day Summary

Day 1 : Philipsburg, St. Maarten
Days 2-6 : Sailing the Caribbeam
Day 7 : Philipsburg, St. Maarten


  • Discover Philipsburg French and Dutch sides
  • Take a stroll on your own private slice of brilliant white sand at Anguilla
  • Check out tiny Pigeon Island, home to Jacque Cousteau’s underwater reserve
  • Enjoy Sportfishing, kayaking and snorkeling across Monserrat Island



Places Visited

  • Caribbean
  • Anguilla
  • Antigua
  • Guadeloupe
  • Leeward Islands
  • Lesser Antilles
  • Montserrat
  • Nevis
  • Philipsburg
  • St. Barth
  • St. Martin
  • Virgin Islands


Trip Type

  • Small Ship

Activity Level


Trip Snapshots

Explore colorful Gustavia Play in the brilliant blue waters of the Caribbean A stunning sunset over the Caribbean Relax on the beaches of the Caribbean Gustavia Harbor in St. Barths

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 on black — the little black dress that you discovered in a chic boutique. Sail the America’s Cup, and celebrate your victory with a bottle of champagne at an "au naturel" beach. Sint Maarten / St. Martin, in any language, is your kind of paradise!

Day 2-6 Sailing the Caribbeam

  • Ship
  • 5 Breakfasts, 5 Lunches, 5 Dinners
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 delightfully 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.

Pinkies up! 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 is more than high tea and crumpets. 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 weather permitting and when the still-active volcano is dormant. To the North, Montserrat’s beaches are a lovely shade of pearl grey that shimmers in the sunlight. Sportfishing, kayaking and snorkeling are popular activities.

Halos of white puffy clouds floating high atop Nevis Peak remind us that we’re close to heaven on earth. Gingerbread-trimmed 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. Bart’s style!

Day 7 Philipsburg, St. Maarten

  • 1 Breakfast
Disembark this morning for your continued journey home.


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
Select a Date
Standard Cabin
Cabins #3-4. Feature a wider lower and single upper berth and an all-in-one shower/bathroom.
Cabin 1
Select a Date
Deluxe Cabin
Cabins #5-6. Feature a double lower and single upper berth and a private bathroom with shower.
Select a Date
Staysail Cabin
Cabins #11-15. Feature a roomy double berth and private bathroom with shower.
Select a Date
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.
Select a Date
Topsail Cabin
Cabin #9. Features a queen size bed and luxury bathroom
Select a Date
Owners’ Suite
Cabin #7. Features a king size bed and large bathroom. There are portholes in both the cabin and the bathroom.


- Rates are in US funds, per person based upon double occupancy, unless noted otherwise. Rates are inclusive of all onboard meals and snacks, beverages (water, juice, soda, beer, wine, and rum punch), port charges and taxes, and complimentary use of snorkel gear for the week.
- Daily tours are optional and are not included in cruise fare.

- Children aged 12-18 receive a $100 discount and must be accompanied by an adult.

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.
Payment & Cancellation Policies
Travel Agents
headshot Kevin Moore
Kevin M

We Love to Talk Travel

Call 1.800.344.6118
Chat Now
Our guide and driver were very good with their knowledge and were very helpful with our questions. It was a very pleasant visit that would have been impossible to do on our own. Hotels and restaurants were fantastic. The special places we got to go to, like the kitchens, were great. Enjoyed the entire trip!
Meyer Smolen

Caribbean Travel Guide

Favorite Caribbean Tours & Cruises

Why Travel With Adventure Life

More Reasons

Recognized By

All News