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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31
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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 Hawksnest Beach. You'll explore the less-touristy side of things at Caneel Bay Beach and Cinnamon Bay Beach. 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, tour the pleasant surroundings at Maho Bay Beach, and look for gifts at Bamboo Studio.

To see where to stay, traveler tips, maps, and tourist information, use the Cruz Bay route maker website.

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. Plan for somewhat warmer temperatures traveling from San Diego in July, with highs in Cruz Bay at 90°F and lows at 80°F. Cap off your sightseeing on the 27th (Thu) early enough to travel to Isla de Vieques.
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Find places to stay Jul 24 — 27:

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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Beaches · Outdoors · Parks
Find places to stay Jul 27 — 29:

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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Find places to stay Jul 29 — 31: