8 days in Caribbean Itinerary

Created using Inspirock Caribbean trip planner
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Fly to Charlotte Amalie, Ferry to Cruz Bay
1
Cruz Bay, U.S. Virgin Islands
— 3 nights
Ferry to Red Hook, St Thomas, Fly to Isla de Vieques
2
Isla de Vieques, Puerto Rico
— 2 nights
Fly
3
Simpson Bay, St. Maarten-St. Martin
— 2 nights
Fly

S M T W T F S
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Cruz Bay, U.S. Virgin Islands — 3 nights

Love City

The gateway to the island of Saint John, Cruz Bay represents the island's largest town, port, and commercial center.
You'll get in some beach time at Magens Bay and Maho Bay Beach. You'll explore the less-touristy side of things at Hawksnest Beach and Bamboo Studio. Change things up with a short trip to Sapphire Beach in East End (about 40 minutes away). There's still lots to do: enjoy the sand and surf at Trunk Bay Beach and tour the pleasant surroundings at Caneel Bay Beach.

To find more things to do, other places to visit, traveler tips, and tourist information, you can read our Cruz Bay tour app.

San Diego, USA to Cruz Bay is an approximately 14.5-hour combination of flight and ferry. Traveling from San Diego to Cruz Bay, you'll lose 4 hours due to the time zone difference. Traveling from San Diego in July, expect Cruz Bay to be somewhat warmer, temps between 90°F and 80°F. Finish your sightseeing early on the 27th (Thu) to allow enough time to travel to Isla de Vieques.
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Parks · Outdoors · Beaches · Nature
Side Trips

Isla de Vieques, Puerto Rico — 2 nights

Isla Nena

For sixty years until 2003, most of the Isla de Vieques was closed off to the public, with the US Navy using the island's beaches and surrounding waters for drills and testing of new military machinery, such as bombs.
Start off your visit on the 28th (Fri): take a leisurely stroll along Malecon and then kick back and relax at Balneario Sun Bay. Keep things going the next day: kick back and relax at Playa La Chiva and then tour the pleasant surroundings at Playa Caracas.

Plan a trip to Isla de Vieques easily and quickly by telling Inspirock to suggest an itinerary.

Traveling by combination of ferry and flight from Cruz Bay to Isla de Vieques takes 5.5 hours. In July, plan for daily highs up to 88°F, and evening lows to 79°F. Wrap up your sightseeing on the 29th (Sat) to allow time to fly to Simpson Bay.
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Parks · Outdoors · Beaches

Simpson Bay, St. Maarten-St. Martin — 2 nights

Simpson Bay offers luxury resort living and good access to the main areas of the island.
Kick off your visit on the 30th (Sun): enjoy the sand and surf at Cupecoy Bay Beach, then contemplate the waterfront views at Mullet Bay Beach, and then stroll through Maho Beach.

To find more things to do, traveler tips, and other tourist information, read Simpson Bay sightseeing planning tool.

Traveling by flight from Isla de Vieques to Simpson Bay takes 6 hours. In July in Simpson Bay, expect temperatures between 87°F during the day and 79°F at night. On the 31st (Mon), wrap the sightseeing up by early afternoon so you can fly back home.
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Parks · Outdoors · Beaches · Nature
Side Trips