8 days in U.S. Virgin Islands Itinerary
Created using Inspirock U.S. Virgin Islands trip itinerary planner
Start: Chicago
Fly
1
St. Croix
— 2 nights
Fly to St Thomas SPB, Taxi to East End
2
East End, St. Thomas
— 3 nights
Ferry
3
Cruz Bay, St. John
— 2 nights
Ferry to Red Hook, St Thomas, Fly to Chicago
End: Chicago
Wed, Feb 22 - Wed, Mar 1
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St. Croix — 2 nights

Twin City
The largest of the U.S. Virgin Islands, St.St. Croix is known for wildlife, adventure, and beaches. Your trip includes some of its best attractions: see the vivid underwater world at Buck Island Reef National Monument, kick back and relax at Rhythms at Rainbow Beach, identify plant and animal life at St. Croix Ultimate Bluewater Adventures (SCUBA), Inc., and tour the pleasant surroundings at Sandy Point National Wildlife Refuge.
For where to stay, photos, reviews, and tourist information, you can read our St. Croix online route planner.
Chicago, USA to St. Croix is an approximately 9.5-hour flight. The time zone difference moving from Central Standard Time (CST) to Atlantic Standard Time (AST) is 2 hours. Plan for much warmer temperatures traveling from Chicago in February, with highs in St. Croix at 85°F and lows at 72°F. Cap off your sightseeing on the 24th (Fri) early enough to travel to East End.
Highlights from your trip
East End, St. Thomas — 3 nights

St.East End is known for beaches, wildlife, and zoos & aquariums. Your trip includes some of its best attractions: stroll through Magens Bay, don't miss a visit to St. Thomas Synagogue, enjoy the sand and surf at Coki Point Beach, and head off the coast to Water Island.
To find traveler tips, more things to do, ratings, and other tourist information, go to the East End travel route planner.
You can do a combination of flight and taxi from St. Croix to East End in 3 hours. Alternatively, you can do a combination of flight and ferry. In February, plan for daily highs up to 84°F, and evening lows to 73°F. Wrap up your sightseeing on the 27th (Mon) early enough to ride a ferry to Cruz Bay.
Side Trips
Highlights from your trip
Cruz Bay, St. John — 2 nights
Love City
The gateway to the island of Saint John, Cruz Bay represents the island's largest town, port, and commercial center.Kick off your visit on the 28th (Tue): look for gifts at Vibe Jewelry, contemplate the long history of Annaberg Sugar Plantation, and then enjoy the sand and surf at Trunk Bay Beach. Here are some ideas for day two: tour the pleasant surroundings at Caneel Bay Beach and then paddle through the water with a kayaking and canoeing tour.
For maps, traveler tips, ratings, and other tourist information, read our Cruz Bay online road trip planner.
You can ride a ferry from East End to Cruz Bay in an hour. Alternatively, you can ride a ferry. February in Cruz Bay sees daily highs of 84°F and lows of 73°F at night. Finish your sightseeing early on the 1st (Wed) to allow enough time to travel back home.
Side Trips
Highlights from your trip
U.S. Virgin Islands travel guide
America's Paradise
Three main and a number of minor islands that make up U.S. Virgin Islands treat visitors to a blend of historical sites and picture-perfect beaches. Though officially American territory--nicknamed "America's Paradise"--these islands boast a mix of cultures that make for culturally enriching vacations. A no-passport-required status makes holidays in U.S. Virgin Islands extremely popular with American tourists, who flock to this tropical heaven to enjoy scenic beaches, outdoor activities, and tasty local food. The islands are also a duty-free shopping destination, which also makes them appealing to shopaholics from across the world.