8 days in Caribbean Itinerary

8 days in Caribbean Itinerary

Created using Inspirock Caribbean travel route maker

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Route & dates

8 days in Caribbean Itinerary

Start: Springfield, United States
Fly:  13​h
1
San Juan, Puerto Rico
— 1 day
Fly:  3​h 45​min
2
Shoal Bay Village, Anguilla
— 1 night
Fly:  3​h 45​min
3
Santo Domingo, Dominican Republic
— 2 nights
Fly:  7​h 15​min
4
Seven Mile Beach, Cayman Islands
— 2 nights
Fly:  6​h 15​min
End: Springfield, United States

1
day
San Juan, Puerto Rico

San Juan ©
Founded by the Spanish in 1521, San Juan is the oldest city under U.S.
Start off your visit on the 22nd (Wed): contemplate the long history of San Juan National Historic Site and then wander the streets of Old San Juan.

Find out how to plan San Juan trip without stress by asking Inspirock to help create an itinerary.

Springfield, USA to San Juan is an approximately 13-hour flight. The time zone difference when traveling from Springfield to San Juan is 2 hours. Traveling from Springfield in May, expect nights in San Juan to be warmer, around 76°F, while days are a bit warmer, around 88°F. Finish your sightseeing early on the 22nd (Wed) to allow enough time to travel to Shoal Bay Village.

Things to do in San Juan

Historic Sites Neighborhoods
Find places to stay May 22 — 23:
Highlights from your plan
Old San Juan ©
Old San Juan
San Juan National Historic Site ©
San Juan National Historic Site

1
night
Shoal Bay Village, Anguilla

Shoal Bay Village ©
Start off your visit on the 23rd (Thu): kick back and relax at Rendezvous Bay Beach and then kick back and relax at Shoal Bay.

To see reviews, photos, ratings, and more tourist information, go to the Shoal Bay Village trip planning site .

You can fly from San Juan to Shoal Bay Village in 4 hours. Alternatively, you can do a combination of flight and ferry. In May in Shoal Bay Village, expect temperatures between 86°F during the day and 76°F at night. Finish your sightseeing early on the 23rd (Thu) to allow enough time to travel to Santo Domingo.

Things to do in Shoal Bay Village

Outdoors Beaches Parks

Side Trip

Rendezvous Bay Beach
Find places to stay May 22 — 23:
Highlights from your plan
Shoal Bay ©
Shoal Bay
Rendezvous Bay Beach ©
Rendezvous Bay Beach

2
nights
Santo Domingo, Dominican Republic

Santo Domingo ©
Santo Domingo, the capital of the Dominican Republic, remains the oldest continuously inhabited settlement in the New World.
On the 24th (Fri), appreciate the history behind Columbus Lighthouse (Faro A Colon), then step into the grandiose world of Alcazar de Colon, then contemplate in the serene atmosphere at Catedral Primada de America, and finally take in the architecture and atmosphere at Basilica Cathedral of Santa Maria la Menor. Get ready for a full day of sightseeing on the 25th (Sat): admire the masterpieces at Amber Museum and then don't miss a visit to Zona Colonial.

To find more things to do, ratings, photos, and other tourist information, go to the Santo Domingo online trip itinerary planner .

Getting from Shoal Bay Village to Santo Domingo by flight takes about 4 hours. Other options: do a combination of ferry and flight; or do a combination of flight and shuttle. Finish up your sightseeing early on the 25th (Sat) so you can travel to Seven Mile Beach.

Things to do in Santo Domingo

Historic Sites Museums Shopping
Find places to stay May 23 — 25:
Highlights from your plan
Alcazar de Colon ©
Alcazar de Colon
Zona Colonial ©
Zona Colonial
Catedral Primada de America
Catedral Primada de America

2
nights
Seven Mile Beach, Cayman Islands

Seven Mile Beach ©
Seven Mile Beach is known for wildlife, beaches, adventure, spas, and golf. Your plan includes some of its best attractions: stroll through Seven Mile Beach, laugh and play at Cayman Turtle Centre: Island Wildlife Encounter, look for all kinds of wild species at Wildlife Areas, and sample the fine beverages at Cayman Spirits Co. Distillery.

For ratings, other places to visit, maps, and tourist information, you can read our Seven Mile Beach trip planner .

You can fly from Santo Domingo to Seven Mile Beach in 7.5 hours. Other options are to do a combination of shuttle and flight; or do a combination of bus, shuttle, and flight. You'll gain 1 hour traveling from Santo Domingo to Seven Mile Beach due to the time zone difference. In May in Seven Mile Beach, expect temperatures between 87°F during the day and 77°F at night. Finish your sightseeing early on the 28th (Tue) to allow enough time to travel back home.

Things to do in Seven Mile Beach

Wildlife Parks Outdoors

Side Trips

Grand Cayman, Cayman Spirits Co. Distillery, Cayman Turtle Centre: Island Wildlife Encounter
Find places to stay May 25 — 28:
Highlights from your plan
Stingray City ©
Stingray City
Seven Mile Beach ©
Seven Mile Beach
Scuba & Snorkeling

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