USVI Island Paradise – 8 Days Sample Itinerary

Set Sail for Unforgettable Memories with Summerwind Sailing Adventures – Discover Your Perfect Itinerary!

This itinerary takes you on an unforgettable adventure through the stunning U.S. Virgin Islands. Get ready to discover hidden coves, pristine beaches, and vibrant island life!

Day 1:

  • Morning: Depart from St. John’s after a leisurely breakfast on Summerwind or exploring the local markets (depending on arrival time). Consider alternative activities like kayaking in Maho Bay or visiting the Annaberg Plantation ruins.
  • Afternoon: Arrive at Honeymoon Beach for some swimming, stand-up paddleboarding (SUP) rentals, and a relaxing beach lunch prepared by the yacht’s crew.
  • Evening: Enjoy a welcome dinner on board the Summerwind, prepared by our onboard chefs.

Day 2:

  • Morning: Hike Waterlemon Cay for panoramic views and explore the underwater world with a guided snorkeling tour on the vibrant Waterlemon Reef.
  • Afternoon: Set sail for Great Harbor, Jost Van Dyke, soaking up the Caribbean sunshine on deck or trying your hand at light fishing.
  • Evening: Anchor near Foxy’s Bar on Yost Van Dyke. Enjoy live music or stargazing from the deck while sipping on cocktails prepared by the crew.

Day 3:

  • Morning: Relax and enjoy a leisurely brunch on board before anchoring near Foxy’s Bar on Yost Van Dyke.
  • Afternoon: Join the lively atmosphere at Foxy’s for their famous “Painkiller” cocktails and delicious Caribbean fare.
  • Evening: Enjoy a sunset cruise towards Norman Island, indulging in canapés and drinks prepared by the crew.

Day 4:

  • Morning: Explore the fascinating underwater world of Norman Island’s Pirate Caves with a guided snorkeling tour.
  • Afternoon: Savor a delicious lunch on board prepared by the chef, followed by some free time for swimming, sunbathing, or onboard activities like games or reading.
  • Evening: Enjoy a relaxing dinner under the stars at Willie T’s restaurant on Norman Island.

Day 5:

  • Morning: Sail to Cooper Island and spend a relaxing day at the beautiful Cooper Island Beach Resort. Enjoy water sports like kayaking or windsurfing (rentals available), or simply lounge on the beach with a refreshing beverage.
  • Afternoon: Opt for a guided nature walk on Cooper Island to discover the island’s unique flora and fauna, or join a beach volleyball tournament organized by the resort.
  • Evening: Enjoy a delicious barbecue dinner on deck prepared by the crew. Watch the sunset as you share stories and laughter with your fellow travelers.

Day 6:

  • Morning:Cruise to Road Town, Tortola, for some shopping and exploring the island’s capital. Visit Pusser’s Marina for local crafts and souvenirs, or stroll through the historic Main Street.
  • Afternoon:Unwind on a relaxing sail to Spanish Bay on Virgin Gorda.

Evening: Enjoy a gourmet dinner prepared by the chef at the renowned Cocoa Maya restaurant on Virgin Gorda.

Day 7:

  • Morning: Explore the Baths National Park on Virgin Gorda. Hike through the granite boulders and explore the hidden pools, taking in the breathtaking scenery.
  • Afternoon: Depending on the red flag warnings, consider a guided kayak tour through The Baths or a relaxing afternoon at Leverick Bay Resort. Enjoy water sports rentals, unwind by the pool, or grab a bite at one of the resort’s restaurants.
  • Evening: Enjoy a farewell dinner on board the Summerwind, celebrating the memories made throughout the charter.

Day 8 (Optional):

  • Morning: Choose your adventure! Explore Virgin Gorda further with a jeep tour, or visit Anegada for some world-class bonefishing. Alternatively, set sail for another Virgin Island, depending on your preferences and wind conditions.

Please note that these itineraries are suggestions, and the specific destinations and activities can be customized to your interests. Be sure to research each island to discover hidden gems and create your perfect Caribbean adventure!

Additional Considerations:

  • This itinerary offers a mix of relaxation and exploration, with opportunities to customize based on your preferences.
  • Discuss activity options and meal preferences with the yacht crew in advance to personalize your experience.
  • Be sure to factor in potential weather changes and adjust the itinerary accordingly.
  • Consider including some downtime on board to soak up the sun, read a book, or simply enjoy the serenity of being at sea.


Sailing with Marty was my first experience as an adult sailing off the coast. We had a wonderful trip starting in St Augustine. First, we were given some basic information about the boat and safety, the other crew members and our destination. Then we were off. We sailed up to Amelia Island for most of the day and then docked at Fernandina Beach marina. We had a short walk into downtown and had a wonderful meal. It was also a great way to really get to know the other members of the crew. The next morning we set off and sailed north to Cumberland Island. Once on the island, we explored the ruins, had a nice hike and enjoyed dinner on the boat. The next step was amazing. We headed off into the sunset on the boat and sailed all night. It was truly exhilarating sailing through the night. At all times, I felt safe but the excitement got me hooked on sailing. Marty is honest, helpful, and always cheerful; exactly what you want in a captain.


This past summer my husband and I had an awesome time on Summerwind. The weather was warm so it was a great time sailing to downtown St Augustine and simply grabbing a mooring ball eating a yummy lunch with our family and diving off the back for a refreshing dip. The following day we took the boat several miles out in the ocean with all the sails up, music on in the cabin; a complete escape from work etc. At day’s end we sailed right up to Caps On The Water restaurant for my birthday where we enjoyed a seafood dinner and drinks. We can’t wait to plan another visit aboard Summerwind, It was a complete vacation over only a single weekend. Many thanks.


Sailing with Marty is truly a treat... He and his trusty Yacht are one with the mighty ocean. Years at sea and behind the helm show, and pay off in high seas or calm. But don't get too comfortable because he is always game to teach you the ropes and be sure you are part of the adventure. There is nothing more peaceful and fulfilling than a day at sea with Marty. Thanks for the memories!


We had such a peaceful experience taking in the joys of the sea while sailing with Marty. He was willing to let us take on roles to help sail the boat (and willing to let us fail, too!) We brought along our two little children (2.5 years and 10 months) and they enjoyed playing below deck and seeing the beautiful scenery sailing by. We were grateful for Marty’s expertise, generosity and passion for sailing!

Claire L / DAPHNE, AL

I've sailed with Captain Marty several times and it was a joy. One of the trips was a longer sail from Puerto Rico to Saint Augustine, Florida in May, 2013. We had a great time and I felt totally comfortable with Marty as our Captain. His sailing and navigating experience made me feel very at ease while on the water - he is a safety conscious sailor. I would give the trip 5 stars!


Being a novice on boats, this was a very exciting time for me. Marty and the crew made me feel very comfortable aboard the Yacht. We sailed down the Cooper River, under the incredible Arthur Ravenel Jr. Bridge and into Charleston Harbor. I enjoyed seeing the USS Yorktown and the submarines. The view of the city of Charleston and the historic homes was amazing! Marty is very knowledgeable about historic sites. Seeing Fort Sumter from the water was also a memorable experience. I would rate this sail as 5 stars


My family and I have sailed many times over the last ten years with Marty and his crews including wonderful afternoons off the coast of St. Augustine. We have had many fabulous overnight trips to places like Fernandina Beach and Cumberland Island. Summerwind is a beautiful Yacht and she sails like a dream. Some our family’s greatest moments have been sailing on Summerwind with the sails up on a beautiful day with gentle breezes moving along the ocean effortlessly. We strive to create lifelong memories with our family by having experiences together and a day on Summerwind is an unforgettable experience. We give Summerwind and the amazing crew 5 stars and can’t wait for our next sailing Adventure.


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