22 days in Caribbean Itinerary

22 days in Caribbean Itinerary

Created using Inspirock Caribbean tour itinerary maker

Make it your trip
Fly to Owen Roberts International Airport, Drive to Seven Mile Beach
1
Seven Mile Beach, Cayman Islands
— 2 nights
Fly
2
Ocho Rios, Jamaica
— 2 nights
Fly
3
Providenciales, Turks and Caicos
— 2 nights
Fly
4
Punta Cana, Dominican Republic
— 3 nights
Shuttle to Santo Domingo, Fly to Palm - Eagle Beach
5
Palm - Eagle Beach, Aruba
— 3 nights
+2
Fly to St Maarten, Ferry to Anguilla, Taxi to West End Village
6
West End Village, Anguilla
— 2 nights
+2
Taxi to Anguilla, Ferry to Sint Maarten, Fly to Virgin Gorda
7
Virgin Gorda, British Virgin Islands
— 2 nights
Fly
8
Culebra, Puerto Rico
— 2 nights
Ferry
9
Cruz Bay, U.S. Virgin Islands
— 3 nights
Ferry to Red Hook, St Thomas, Fly to Tulsa

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Seven Mile Beach, Cayman Islands

— 2 nights
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 11th (Fri): explore the striking landscape at Hell Gift Store, laugh and play at Cayman Turtle Centre: Island Wildlife Encounter, and then stroll through Seven Mile Beach. On the 12th (Sat), you'll have a packed day of sightseeing: look for gifts at Cayman Islands National Museum and then discover the deep blue sea with a scuba or snorkeling tour.

To see more things to do, traveler tips, photos, and other tourist information, read our Seven Mile Beach travel itinerary planner.

Tulsa, USA to Seven Mile Beach is an approximately 14.5-hour combination of flight and car. You can also fly. The time zone changes from Central Standard Time (CST) to Eastern Standard Time (EST), which is usually a 1 hour difference. Traveling from Tulsa in June, expect somewhat warmer with lows of 79°F in Seven Mile Beach. Wrap up your sightseeing by early afternoon on the 12th (Sat) to allow time for the flight to Ocho Rios.

Things to do in Seven Mile Beach

Parks · Wildlife · Outdoors · Theme Parks

Side Trips

Ocho Rios, Jamaica

— 2 nights
A trip to Ocho Rios, the tourist hub of Saint Ann Parish, offers travelers a staggering amount of activities and cultural attractions.
Start off your visit on the 13th (Sun): walk around Konoko Falls, take in the dramatic scenery at Dunn's River Falls and Park, and then admire the sheer force of Benta River Falls.

To see photos, reviews, more things to do, and more tourist information, go to the Ocho Rios online journey planner.

Fly from Seven Mile Beach to Ocho Rios in 4.5 hours. In June, daytime highs in Ocho Rios are 90°F, while nighttime lows are 78°F. Wrap up your sightseeing by early afternoon on the 14th (Mon) to allow enough time to fly to Providenciales.

Things to do in Ocho Rios

Parks · Nature · Trails · Outdoors

Side Trip

Providenciales, Turks and Caicos

— 2 nights
The most commercialized part of the Turks and Caicos, Providenciales remains the islands' tourism heaven, boasting many resorts, hotel chains, and condominiums.
On the 15th (Tue), enjoy the sand and surf at Half Moon Bay, explore the gorgeous colors at Little Water Cay, and then stroll through Grace Bay Beach. Get ready for a full day of sightseeing on the next day: see the vivid underwater world at Smith's Reef and then see some colorful creatures with a scuba or snorkeling tour.

To find maps, more things to do, photos, and tourist information, read our Providenciales route planner.

Traveling by flight from Ocho Rios to Providenciales takes 5 hours. June in Providenciales sees daily highs of 89°F and lows of 80°F at night. Wrap up your sightseeing on the 16th (Wed) early enough to fly to Punta Cana.

Things to do in Providenciales

Outdoors · Parks · Wildlife · Beaches

Side Trip

Punta Cana, Dominican Republic

— 3 nights
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.
Spend a day of island exploring on the 18th (Fri) at Saona Island. The adventure continues: get a new perspective on things with Destiny Caribbean Tours, tour the pleasant surroundings at Bavaro Beach, look for gifts at HARRISON'S Fine Caribbean Jewelers, and relax and rejuvenate at Flavio Acuna Spa Natural Center.

To see maps, traveler tips, other places to visit, and other tourist information, refer to the Punta Cana trip planner.

You can fly from Providenciales to Punta Cana in 5 hours. Traveling from Providenciales to Punta Cana, you'll lose 1 hour due to the time zone difference. June in Punta Cana sees daily highs of 87°F and lows of 76°F at night. Wrap up your sightseeing by early afternoon on the 19th (Sat) to allow time for travel to Palm - Eagle Beach.

Things to do in Punta Cana

Parks · Outdoors · Nature · Tours

Side Trip

Palm - Eagle Beach, Aruba

— 3 nights
A long stretch of powdery white sand and aquamarine waters, Palm - Eagle Beach remains one of Aruba's most visited vacation spots.
Go for a jaunt from Palm - Eagle Beach to San Nicolas to see Baby Beach about 48 minutes away. And it doesn't end there: stroll through Eagle Beach, kick back and relax at Hadicurari Beach, enjoy the sea views from California Lighthouse, and get engrossed in the history at Fort Zoutman Historical Museum.

To see more things to do, traveler tips, ratings, and other tourist information, refer to the Palm - Eagle Beach trip planner.

Traveling by combination of shuttle and flight from Punta Cana to Palm - Eagle Beach takes 8 hours. In June, plan for daily highs up to 90°F, and evening lows to 80°F. Wrap up your sightseeing on the 22nd (Tue) early enough to travel to West End Village.

Things to do in Palm - Eagle Beach

Parks · Beaches · Outdoors · Wildlife

Side Trips

West End Village, Anguilla

— 2 nights
A pleasant coastal town giving access to some of Anguilla's most pristine and picturesque beaches, West End Village attracts visitors looking for a beach resort holiday.
On the 23rd (Wed), stroll through Meads Bay, enjoy the sand and surf at Rendezvous Bay Beach, and then contemplate the waterfront views at Maundays Bay. Get ready for a full day of sightseeing on the next day: tour the pleasant surroundings at Little Bay and then enjoy the sand and surf at Shoal Bay.

To find ratings, where to stay, and more tourist information, refer to the West End Village travel app.

You can do a combination of flight, ferry, and taxi from Palm - Eagle Beach to West End Village in 9.5 hours. In June, plan for daily highs up to 87°F, and evening lows to 78°F. Finish your sightseeing early on the 24th (Thu) so you can travel to Virgin Gorda.

Things to do in West End Village

Parks · Beaches · Outdoors · Nature

Side Trips

Virgin Gorda, British Virgin Islands

— 2 nights
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.
Kick off your visit on the 25th (Fri): enjoy the sand and surf at Honeymoon Beach, see some colorful creatures with Sunchaser Scuba Ltd., and then get outside with Fusion BVI. Get ready for a full day of sightseeing on the 26th (Sat): relax and rejuvenate at some of the top local wellness centers, take in the dramatic natural features at The Baths, and then enjoy the sand and surf at Spring Bay.

To find reviews, other places to visit, more things to do, and other tourist information, go to the Virgin Gorda online trip itinerary maker.

You can do a combination of taxi, ferry, and flight from West End Village to Virgin Gorda in 6 hours. June in Virgin Gorda sees daily highs of 88°F and lows of 80°F at night. Cap off your sightseeing on the 26th (Sat) early enough to catch the flight to Culebra.

Things to do in Virgin Gorda

Outdoors · Beaches · Parks · Tours

Culebra, Puerto Rico

— 2 nights

Little Island

With much of Culebra a nature refuge, the tropical island has been protected from overdevelopment, chain hotels, and the cruise set.
Kick off your visit on the 27th (Sun): tour the pleasant surroundings at Playa Punta Soldado Beach and then enjoy the sand and surf at Flamenco Beach. On the 28th (Mon), you'll have a packed day of sightseeing: visit a coastal fixture at Culebrita Lighthouse, head off the coast to Culebrita, and then stroll through Zoni Beach.

To find traveler tips, other places to visit, maps, and more tourist information, read Culebra trip itinerary planning app.

Fly from Virgin Gorda to Culebra in 6.5 hours. Expect a daytime high around 89°F in June, and nighttime lows around 79°F. Finish your sightseeing early on the 28th (Mon) so you can ride a ferry to Cruz Bay.

Things to do in Culebra

Parks · Beaches · Outdoors · Nature

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.
On the 29th (Tue), contemplate the long history of Annaberg Sugar Plantation, then enjoy the sand and surf at Trunk Bay Beach, and then enjoy the sand and surf at Jumbie Beach. Get ready for a full day of sightseeing on the next day: get up close and personal with brilliant marine life at Coral World Ocean Park, then kick back and relax at Magens Bay, and then stroll through The Butterfly Garden.

To see maps, other places to visit, traveler tips, and other tourist information, read our Cruz Bay trip maker website.

Traveling by ferry from Culebra to Cruz Bay takes 2.5 hours. In June, daily temperatures in Cruz Bay can reach 89°F, while at night they dip to 79°F. Wrap up your sightseeing by early afternoon on the 1st (Thu) to allow enough time to travel back home.

Things to do in Cruz Bay

Parks · Beaches · Outdoors · Zoos & Aquariums

Side Trips