Sample Day Trip Itineraries from St. John

🚤 Itinerary 1: Adventure Lovers

For travelers who want their day to feel like a true island expedition.

• Whistling Cay (USVI): Snorkel with sea turtles along the reef drop

• Newfound Bay (USVI): Off-the-map reef exploring

• Lunch: Casual beach break at Pirates Bight (Norman Island) or Willy T

• Lee Bay, Great Camanoe (BVI): Cliff jumping + deep blue swimming

Love City Captain’s Tip: Conditions change daily—this itinerary is best on calmer days when visibility is high.

🥂 Itinerary 2: Luxury + Leisure

Smooth water, scenic cruising, and refined barefoot luxury.

• Whistling Cay (USVI): Easy snorkel + calm morning waters

• Manchioneel Bay, Cooper Island (BVI): Swim and drift in turquoise water

• Lunch: Waterfront dining at Cooper Island Beach Club

• Great Harbour, Peter Island (BVI): Quiet anchorage + float time

Love City Captain’s Tip: Order dessert and espresso at Cooper—they roast their own beans and make ice cream on site.

🌴 Itinerary 3: Family-Friendly Fun

Calm water, easy swimming, and stops everyone will love.

• Maho Bay (USVI add-on): Turtle spotting warm-up

• Whistling Cay (USVI): Protected snorkeling stop

• Lunch: Laid-back meals at Hendo’s Hideout or Soggy Dollar Bar (Jost Van Dyke)

• End the day enjoying the sunshine before heading back to St John

Love City Captain’s Tip: Bring your playlist—this route pairs perfectly with island music and a relaxed pace. 

🗿 Itinerary 4: Virgin Gorda Explorer

A signature BVI day — dramatic landscapes and unforgettable adventure.

• Cross the Channel: Scenic run across open water toward Virgin Gorda

• The Baths, Virgin Gorda (BVI): Explore massive granite boulders, grottoes, and sea pools

• Devil’s Bay: Swim and relax on one of the most stunning coves in the BVIs

• Lunch: Cruise back south and enjoy a relaxed Caribbean lunch at Pirates Bight, Norman Island

• Optional Extend the Day: And head to White Bay for an afternoon Cocktail

Love City Captain’s Tip: Head out early. Customs  \is best completed first thing!