18 days in Caribbean Itinerary

The most commercialized part of the Turks and Caicos, Providenciales remains the islands' tourism heaven, boasting many resorts, hotel chains, and condominiums.

Step out of the city life by going to Grace Bay Beach and Scuba & Snorkeling. Bring the kids along to Little Water Cay and Coral Gardens Reef. There's more to do: enjoy the sand and surf at Half Moon Bay and don't miss a visit to Leeward Beach.

To find reviews, where to stay, traveler tips, and tourist information, go to the Providenciales online trip maker.

Madison, USA to Providenciales is an approximately 9.5-hour flight. The time zone difference when traveling from Madison to Providenciales is 1 hour. Traveling from Madison in June, you will find days in Providenciales are somewhat warmer (89°F), and nights are warmer (80°F). Wrap up your sightseeing on the 10th (Sat) early enough to fly to Punta Cana.

In an area boasting beaches that face both the Atlantic Ocean and the Caribbean Sea, vacations in Punta Cana have been popular with tourists since the early 1970s.

Kids will appreciate attractions like Zipline and Destiny Caribbean Tours. Get outdoors at Bavaro Beach and Macao Beach. And it doesn't end there: relax and rejuvenate at Flavio Acuna Spa Natural Center, examine the collection at Aromas Museum, and stop by Jellyfish Shop.

To see maps, traveler tips, reviews, and tourist information, read Punta Cana itinerary maker website.

You can fly from Providenciales to Punta Cana in 5 hours. Due to the time zone difference, you'll lose 1 hour traveling from Providenciales to Punta Cana. June in Punta Cana sees daily highs of 87°F and lows of 76°F at night. Finish your sightseeing early on the 13th (Tue) so you can travel to Cruz Bay.

The gateway to the island of Saint John, Cruz Bay represents the island's largest town, port, and commercial center.

We've included these beaches for you: Magens Bay and Caneel Bay Beach. Bring the kids along to Trunk Bay Beach and Jumbie Beach. When in Cruz Bay, make a side trip to see Coral World Ocean Park in Smith Bay, approximately Smith Bay away. The adventure continues: contemplate the long history of Annaberg Sugar Plantation, contemplate the waterfront views at Hawksnest Beach, get interesting insight from Caneel Bay Kayak, Hike & Snorkel Adventure - Virgin Islands Ecotours, and see the interesting displays at Cinnamon Bay Archeology Museum & Lab.

To find photos, other places to visit, where to stay, and more tourist information, read our Cruz Bay trip tool.

Traveling by combination of flight and ferry from Punta Cana to Cruz Bay takes 6 hours. June in Cruz Bay sees daily highs of 89°F and lows of 79°F at night. Cap off your sightseeing on the 16th (Fri) early enough to catch the ferry to Virgin Gorda.

Thankfully lacking some of the commercialism of other islands nearby, Virgin Gorda offers a relaxing place to holiday, and maintains a feeling of intimacy despite its reputation as an exclusive destination.

Start off your visit on the 17th (Sat): take in the dramatic natural features at The Baths, stroll through Spring Bay, and then explore the activities along Savannah Bay. On the 18th (Sun), you'll have a packed day of sightseeing: stroll through Honeymoon Beach, then see some colorful creatures with Sunchaser Scuba Ltd., and then relax and rejuvenate at some of the top local wellness centers.

To see other places to visit, reviews, traveler tips, and other tourist information, you can read our Virgin Gorda trip itinerary planning site.

Getting from Cruz Bay to Virgin Gorda by ferry takes about 2.5 hours. Other options: do a combination of ferry and flight. In June in Virgin Gorda, expect temperatures between 88°F during the day and 80°F at night. Wrap up your sightseeing on the 18th (Sun) to allow time to travel to St. Jean.

Start off your visit on the 19th (Mon): tour the pleasant surroundings at Anse de Grande Saline and then tour the pleasant surroundings at St. Jean Beach. On your second day here, tour the pleasant surroundings at Anse des Flamands and then stroll through Colombier Beach.

To see maps, reviews, ratings, and more tourist information, you can read our St. Jean trip builder site.

Do a combination of flight, car, and ferry from Virgin Gorda to St. Jean in 4.5 hours. Alternatively, you can fly. Finish your sightseeing early on the 20th (Tue) so you can fly to Bridgetown.

Bridgetown is the capital and largest city of Barbados. Kids will enjoy Boat Tours & Water Sports and Carlisle Bay. Get some cultural insight at Andromeda Botanic Gardens and Sunbury Plantation House. Step out of Bridgetown to go to Saint Philip Parish and see Bottom Bay, which is approximately 36 minutes away. There's much more to do: Head underground at Harrison's Cave., take in nature's colorful creations at Hunte's Gardens, take in panoramic vistas at Gun Hill Signal Station, and enjoy the sand and surf at Pebbles Beach.

Inspirock's itinerary builder makes planning a Bridgetown trip simple and quick.

Fly from St. Jean to Bridgetown in 7.5 hours. In June, daytime highs in Bridgetown are 86°F, while nighttime lows are 78°F. Wrap up your sightseeing on the 23rd (Fri) early enough to fly to Seven Mile Beach.

Seven Mile Beach is a long crescent of coral-sand beach on the western end of Grand Cayman island. Start off your visit on the 24th (Sat): take an in-depth tour of Cayman Islands National Museum, then get a new perspective on things with Slackem Fishing Charters, and then enjoy the sand and surf at Seven Mile Beach.

To find maps, photos, other places to visit, and more tourist information, refer to the Seven Mile Beach trip itinerary builder.

Traveling by flight from Bridgetown to Seven Mile Beach takes 9.5 hours. The time zone difference moving from Atlantic Standard Time (AST) to Eastern Standard Time (EST) is minus 1 hour. In June in Seven Mile Beach, expect temperatures between 88°F during the day and 79°F at night. Wrap up your sightseeing by early afternoon on the 25th (Sun) to allow enough time to travel back home.