Your 8 Tuff Miles Road Race Itinerary
Time your U.S. Virgin Islands getaway to coincide with St. John’s 28th annual 8 Tuff Miles Road Race Festival on Feb. 27, 2027. This exciting run routinely draws more than 1,000 participants on a foot race from Cruz Bay to Coral Bay. Our suggested five-day itinerary pairs race-day fun with immersive experiences on the islands of St. Thomas and St. John.
Arrive on St. Thomas
The 8 Tuff Miles Road Race Festival adventure begins on Thursday, Feb. 25, when your flight arrives at Cyril E. King Airport (STT) on St. Thomas, where warm sea breezes set the tone for your trip. Arrange for a licensed taxi driver to take you to The Westin St. Thomas Beach Resort & Spa at Frenchman’s Reef, a dreamy waterfront retreat set on a peninsula with stunning bay views.
Following check-in, take some time to relax — perhaps with a stroll along the shoreline to take in the scenery — before dinner at Isla Blue at the Buoy Haus Beach Resort St. Thomas, Autograph Collection. Enjoy fresh, island-inspired seafood dishes complemented by signature cocktails and sunset views. Then, get a good night’s sleep for a fun-filled day ahead.
Take a Ferry to St. John
Wake up at The Westin refreshed on Friday and start the day with breakfast at the resort’s Shorebird restaurant. Depart mid-morning for the Red Hook Ferry Terminal. The ferry ride to Cruz Bay on St. John offers a breezy, scenic crossing that takes about 20 minutes over sparkling blue waters, with panoramas of neighboring cays and lush hills rising in the distance.
After arriving at Cruz Bay, take a guided island tour — good options include Star Fish Tours & Taxi Services and Ocean Surfari’s Jeep Surfari tours — for an overview of the island, including scenic stops and highlights of Virgin Islands National Park, which covers about 60 percent of St. John. The park’s unspoiled beaches, lush greenery, sugar plantation ruins and coastal vistas define the landscape. Stop for lunch and order a taco or burger sided with a tropical drink at The Windmill Bar, known for its sweeping hilltop views of the surrounding islands. Back in Cruz Bay soak up the town’s vibrant island charm, dotted with an array of colorful buildings, open-air shops and palm-lined streets.
Walk to Virgin Islands National Park’s Cruz Bay Visitor Center to pick up your race bib. Linger here to view exhibits on the island’s history, culture and protected landscapes that help add context to the terrain that runners will encounter. By early evening, return via ferry to your hotel on St. Thomas — you’ll want to get a good night’s rest for the big race.
Get Revved for the 8 Tuff Miles Road Race
Before sunrise on Saturday, hire a taxi to take you to Red Hook in time to board the 6 a.m. ferry to Cruz Bay. It’s a beautiful sight to see the first light of day ripple across the water as you cruise to St. John. Check in for the race at 6:30 a.m. at the Cruz Bay Visitor Center, pumped up by the energy of fellow runners eager to hit the road.
At 7:15 a.m., set off on the 8 Tuff Miles Road Race course that stretches from Cruz Bay in the west to Coral Bay on the east side of the island. Follow a challenging but rewarding 8.38-mile route framed by rolling hills (the highest elevation on the course is 999 feet), ocean views and stretches of tropical landscape. Along the way, water stations support participants — hydration is encouraged the day before, during and after the race, as daytime temperatures will be in the mid- to high-80s.
Celebrate completing the course at the finish line in Coral Bay. Have lunch at Skinny Legs for a casual, post-race meal of hearty comfort fare like burgers and sandwiches that are perfect for refueling. After dining, return to Cruz Bay for the 4 p.m. awards ceremony at Mongoose Junction. Unwind on the ferry ride back to St. Thomas for an evening of leisure.
Boat Cruise & Spa Treatments
After the active race day, shift the pace on Sunday with a schedule designed for restoration and pampering. Have breakfast at The Westin, then head to a morning appointment at the Heavenly Spa by Westin for a 50-minute relaxation massage to soothe post-race muscles.
In the afternoon, take a 15-minute drive to Oasis Cove Marina, where you’ll board a private boat charter. The excursion includes swimming and snorkeling in clear waters among brightly colored tropical fish and marine life. You’ll cruise along the scenic St. Thomas shoreline and stop for lunch at an unexpected spot. Lime Out is literally an on-the-water dining experience, with fresh, flavorful tacos and tropical drinks served from a floating restaurant in Lindbergh Bay.
Cruise back to the marina, then head to The Westin to freshen up. Your day will end with dinner at Pesce Italian in Red Hook. The elegant restaurant’s refined menu features Italian classics such as crispy calamari, homemade gnocchi, truffle-mushroom pappardelle and chicken Marsala.
Depart Paradise
Your trip concludes on Monday. Enjoy breakfast at The Westin one last time. Before checking out, savor your final USVI moments by taking a dip in the infinity pool, squeezing in a workout at the fitness center or simply lounging along the waterfront.
More Things to Do on St. John and St. Thomas
Best St. John snorkeling spots & tours
St. John tours & excursions: Explore the island & waters