28 days in Caribbean Itinerary

28 days in Caribbean Itinerary

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Route & dates

28 days in Caribbean Itinerary

Start: Philadelphia, United States
Fly:  8​h 30​min
1
Harbour Island, Bahamas
— 1 day
+2
ferry + taxi + Fly:  5​h
2
George Town, Bahamas
— 1 night
Fly + shuttle:  3​h
3
Nassau, Bahamas
— 2 nights
Fly:  4​h 30​min
4
Havana, Cuba
— 2 nights
Fly:  2​h
5
Seven Mile Beach, Cayman Islands
— 2 nights
Fly:  6​h
6
Oranjestad, Aruba
— 1 night
Fly:  1​h
7
Kralendijk, Bonaire
— 2 nights
Fly:  7​h 45​min
8
Isla de Vieques, Puerto Rico
— 3 nights
Fly:  1​h
9
St. Croix, U.S. Virgin Islands
— 2 nights
Fly:  2​h 15​min
10
San Juan, Puerto Rico
— 2 nights
Fly:  30​min
11
Culebra, Puerto Rico
— 3 nights
Fly:  3​h 45​min
12
Punta Cana, Dominican Republic
— 3 nights
shuttle + Fly:  4​h 30​min
13
Providenciales, Turks and Caicos
— 2 nights
Fly:  4​h 30​min
End: Philadelphia, United States

1
day
Harbour Island, Bahamas

The casual Bahamian vibee of Harbour Island comes through in its atmospheric seaside eateries, the colonial English architecture of its main urban zones, and its wealth of attractive coastal areas.
Start off your visit on the 1st (Sun): contemplate the long history of Dunmore Town, then discover the deep blue sea with a scuba or snorkeling tour, and then stroll through Pink Sands Beach.

For ratings, photos, other places to visit, and tourist information, refer to the Harbour Island trip builder tool .

Philadelphia, USA to Harbour Island is an approximately 8.5-hour flight. Finish your sightseeing early on the 1st (Sun) to allow enough time to travel to George Town.

Things to do in Harbour Island

Outdoors Wildlife Tours
Find places to stay Dec 1 — 2:
Highlights from your plan
Scuba & Snorkeling
Pink Sands Beach ©
Pink Sands Beach
Dunmore Town ©
Dunmore Town

1
night
George Town, Bahamas

Few island getaways are more idyllic than George Town, a small settlement on the east coast of the Bahamian island of Exuma.
Start off your visit on the 2nd (Mon): get a new perspective on things with Boat Tours & Water Sports, enjoy the sand and surf at Beaches of Stocking Island, then explore the different monuments and memorials at Rolle Town Tombs, and finally pause for some serene contemplation at St. Andrew's Anglican Church.

To see ratings, maps, where to stay, and more tourist information, refer to the George Town journey planner.

Getting from Harbour Island to George Town by combination of ferry and flight takes about 5 hours. Other options: ride a ferry. Finish your sightseeing early on the 2nd (Mon) so you can travel to Nassau.

Things to do in George Town

Outdoors Wildlife Tours

Side Trip

Great Exuma
Find places to stay Dec 1 — 2:
Highlights from your plan
Scuba & Snorkeling
St. Andrew's Anglican Church ©
St. Andrew's Anglican Church

2
nights
Nassau, Bahamas

Nassau ©
On a trip to Nassau you can immerse yourself in a dynamic city atmosphere or spend your days lazing on the soft golden sands.
Kick off your visit on the 3rd (Tue): kick back and relax at Cable Beach, then see some colorful creatures with a scuba or snorkeling tour, and then step into the grandiose world of Fort Fincastle. Here are some ideas for day two: steep yourself in history at Queen's Staircase, then get engrossed in the history at Pirates of Nassau Museum, then take in the spiritual surroundings of Christ Church Cathedral, and finally steep yourself in history at Fort Charlotte.

To find maps, photos, where to stay, and other tourist information, use the Nassau day trip app .

Traveling by combination of flight and shuttle from George Town to Nassau takes 3 hours. Alternatively, you can ride a ferry. Expect a daytime high around 82°F in December, and nighttime lows around 69°F. Wrap up your sightseeing on the 4th (Wed) early enough to travel to Havana.

Things to do in Nassau

Outdoors Historic Sites Wildlife
Find places to stay Dec 2 — 4:
Highlights from your plan
Cable Beach ©
Cable Beach
Christ Church Cathedral ©
Christ Church Cathedral
Scuba & Snorkeling

2
nights
Havana, Cuba

Havana ©
Cuba's capital and major commercial center, Havana manages to be very old and very modern at the same time.
On the 5th (Thu), kick back and relax at Playas de Este, explore the different monuments and memorials at Christopher Columbus Cemetery (Cemetario de Colon), then tour the pleasant surroundings at Santa Maria del Mar, and finally steep yourself in history at El Morro. On your second day here, pause for some serene contemplation at Oratorio San Felipe Neri, don't miss a visit to Revolution Plaza, then appreciate the extensive heritage of El Malecon, then contemplate the long history of Old Square (Plaza Vieja), and finally appreciate the extensive heritage of Old Havana.

To find other places to visit, traveler tips, photos, and tourist information, read Havana online road trip planner .

You can fly from Nassau to Havana in 4.5 hours. Plan for a bit cooler nights when traveling from Nassau in December since evenings lows in Havana dip to 64°F. Finish your sightseeing early on the 6th (Fri) to allow enough time to travel to Seven Mile Beach.

Things to do in Havana

Historic Sites Beaches Parks
Find places to stay Dec 4 — 6:
Highlights from your plan
Old Havana ©
Old Havana
El Malecon ©
El Malecon
Old Square (Plaza Vieja) ©
Old Square (Plaza Vieja)

2
nights
Seven Mile Beach, Cayman Islands

Seven Mile Beach ©
On the 7th (Sat), kick back and relax at Seven Mile Beach, then sample the fine beverages at Cayman Spirits Co. Distillery, then browse the exhibits of Pedro St. James National Historic Site, and finally kick back and relax at Rum Point. On the 8th (Sun), you'll have a packed day of sightseeing: cool off at Cayman Turtle Centre: Island Wildlife Encounter, make a trip to Hell, and then discover the deep blue sea with a scuba or snorkeling tour.

To see reviews, where to stay, ratings, and tourist information, you can read our Seven Mile Beach online attractions planner .

Getting from Havana to Seven Mile Beach by combination of flight and bus takes about 2 hours. Traveling from Havana in December, plan for somewhat warmer nights in Seven Mile Beach, with lows around 75°F. Wrap up your sightseeing on the 8th (Sun) early enough to travel to Oranjestad.

Things to do in Seven Mile Beach

Parks Outdoors Wildlife

Side Trips

Grand Cayman, Cayman Spirits Co. Distillery, Cayman Turtle Centre: Island Wildlife Encounter
Find places to stay Dec 6 — 8:
Highlights from your plan
Seven Mile Beach ©
Seven Mile Beach
Scuba & Snorkeling

1
night
Oranjestad, Aruba

Oranjestad ©
When vacationing on Aruba, don't miss taking a tour of Oranjestad, the capital of the small Caribbean island.
Start off your visit on the 9th (Mon): kick back and relax at Baby Beach, then identify plant and animal life at Donkey Sanctuary Aruba, and then enjoy the sand and surf at Eagle Beach. Get ready for a full day of sightseeing on the next day: experience rural life at The Butterfly Farm, enjoy the sea views from California Lighthouse, and then kick back and relax at Palm Beach.

To see maps, traveler tips, reviews, and more tourist information, you can read our Oranjestad day trip planner .

Do a combination of bus and flight from Seven Mile Beach to Oranjestad in 6 hours. The time zone difference when traveling from Seven Mile Beach to Oranjestad is 1 hour. In December, daytime highs in Oranjestad are 88°F, while nighttime lows are 78°F. Wrap up your sightseeing on the 10th (Tue) to allow time to fly to Kralendijk.

Things to do in Oranjestad

Parks Beaches Outdoors

Side Trips

Palm - Eagle Beach, California Lighthouse, Baby Beach, Donkey Sanctuary Aruba
Find places to stay Dec 8 — 10:
Highlights from your plan
Baby Beach ©
Baby Beach
Eagle Beach ©
Eagle Beach
Palm Beach ©
Palm Beach

2
nights
Kralendijk, Bonaire

Kralendijk ©
The capital city and main port Bonaire, Kralendijk possesses a rich and varied history and natural heritage to explore on an adventurous and diverse itinerary.
On the 11th (Wed), step off the mainland to explore Klein Bonaire, admire nature's wide array of creatures at Donkey Sanctuary Bonaire, then don't miss a visit to Slave Huts, and finally explore the striking landscape at Salt Flats. Get ready for a full day of sightseeing on the 12th (Thu): look for all kinds of wild species at Bonaire National Marine Park, then look for all kinds of wild species at Seru Grandi, and then contemplate the waterfront views at Lac Bay.

To see maps, photos, and tourist information, read our Kralendijk trip itinerary builder site .

Getting from Oranjestad to Kralendijk by flight takes about an hour. In December, daily temperatures in Kralendijk can reach 86°F, while at night they dip to 78°F. Finish your sightseeing early on the 12th (Thu) to allow enough time to travel to Isla de Vieques.

Things to do in Kralendijk

Parks Nature Wildlife

Side Trips

Bonaire, Seru Grandi
Find places to stay Dec 10 — 12:
Highlights from your plan
Klein Bonaire ©
Klein Bonaire
Donkey Sanctuary Bonaire ©
Donkey Sanctuary Bonaire
Lac Bay ©
Lac Bay

3
nights
Isla de Vieques, Puerto Rico

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.
You'll get in some beach time at Sun Bay and Media Luna Beach. Get outdoors at La Chiva and Caracas Beach. There's lots more to do: look for all kinds of wild species at Vieques National Wildlife Refuge, see some colorful creatures with a scuba or snorkeling tour, steep yourself in history at Puerto Ferro Lighthouse, and enjoy the sand and surf at Playa Monte Santo.

For reviews, maps, ratings, and more tourist information, go to the Isla de Vieques trip itinerary maker site .

Getting from Kralendijk to Isla de Vieques by combination of flight and car takes about 8 hours. December in Isla de Vieques sees daily highs of 84°F and lows of 75°F at night. Finish your sightseeing early on the 16th (Mon) so you can travel to St. Croix.

Things to do in Isla de Vieques

Outdoors Parks Beaches
Find places to stay Dec 12 — 16:
Highlights from your plan
Scuba & Snorkeling
Sun Bay ©
Sun Bay
Media Luna Beach ©
Media Luna Beach

2
nights
St. Croix, U.S. Virgin Islands

St. Croix ©
The largest of the U.S.
Start off your visit on the 17th (Tue): see the vivid underwater world at Buck Island Reef National Monument, contemplate the long history of Fort Christiansvaern, and then kick back and relax at Rhythms at Rainbow Beach. Keep things going the next day: see some colorful creatures with a scuba or snorkeling tour and then see the vivid underwater world at Cane Bay.

Ask Inspirock to suggest an itinerary and make planning a trip to St. Croix fast, fun, and easy.

Traveling by combination of car and flight from Isla de Vieques to St. Croix takes an hour. Alternatively, you can do a combination of ferry, shuttle, flight, and car. In December, daily temperatures in St. Croix can reach 85°F, while at night they dip to 74°F. Finish your sightseeing early on the 18th (Wed) to allow enough time to travel to San Juan.

Things to do in St. Croix

Wildlife Parks Outdoors
Find places to stay Dec 16 — 18:
Highlights from your plan
Buck Island Reef National Monument ©
Buck Island Reef National Monument
Cane Bay ©
Cane Bay
Scuba & Snorkeling

2
nights
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 19th (Thu): tour the pleasant surroundings at Condado Beach, then appreciate the extensive heritage of Old San Juan, and then appreciate the extensive heritage of San Juan National Historic Site. Get ready for a full day of sightseeing on the next day: kick back and relax at Pine Grove Beach, do some two-wheel cruising with Puerto Rico Electric Transporters, and then tour the pleasant surroundings at Luquillo Beach.

To find maps, traveler tips, reviews, and tourist information, you can read our San Juan holiday maker site .

Traveling by combination of car and flight from St. Croix to San Juan takes 2.5 hours. Expect a daytime high around 85°F in December, and nighttime lows around 75°F. Wrap up your sightseeing on the 20th (Fri) to allow time to fly to Culebra.

Things to do in San Juan

Parks Outdoors Beaches

Side Trips

Luquillo Beach, Puerto Rico Electric Transporters, Pine Grove Beach
Find places to stay Dec 18 — 20:
Highlights from your plan
Old San Juan ©
Old San Juan
Condado Beach ©
Condado Beach
Luquillo Beach ©
Luquillo Beach

3
nights
Culebra, Puerto Rico

Culebra ©
With much of Culebra a nature refuge, the tropical island has been protected from overdevelopment, chain hotels, and the cruise set.
You'll enjoy a bit of beach vacationing at Flamenco Beach and Tamarindo Beach. Escape the urban bustle at Zoni Beach and Culebra National Wildlife. There's lots more to do: head off the coast to Culebrita Island, examine the collection at Museo Historico de Culebra, enjoy the sea views from Culebrita Lighthouse, and tour the pleasant surroundings at Playa Punta Soldado Beach.

To see where to stay, ratings, reviews, and other tourist information, use the Culebra trip builder website .

Culebra is very close to San Juan. December in Culebra sees daily highs of 85°F and lows of 75°F at night. Cap off your sightseeing on the 23rd (Mon) early enough to travel to Punta Cana.

Things to do in Culebra

Outdoors Parks Beaches
Find places to stay Dec 20 — 23:
Highlights from your plan
Flamenco Beach ©
Flamenco Beach
Zoni Beach ©
Zoni Beach
Tamarindo Beach ©
Tamarindo Beach

3
nights
Punta Cana, Dominican Republic

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.
You'll get in some beach time at Bavaro Beach and Macao Beach. Visiting Safaris and Scuba & Snorkeling will get you outdoors. Explore the numerous day-trip ideas around Punta Cana: Altos de Chavon (in La Romana) and Basilica Catedral Nuestra Senora de la Altagracia (in Higuey). The adventure continues: stop by La Perla Dominicana.

To see photos, ratings, maps, and tourist information, read our Punta Cana attractions planner.

You can fly from Culebra to Punta Cana in 4 hours. Alternatively, you can do a combination of flight and shuttle; or do a combination of ferry, shuttle, and flight. Expect a daytime high around 85°F in December, and nighttime lows around 73°F. Finish up your sightseeing early on the 26th (Thu) so you can travel to Providenciales.

Things to do in Punta Cana

Outdoors Wildlife Tours

Side Trips

Basilica Catedral Nuestra Senora de la Altagracia, Altos de Chavon
Find places to stay Dec 23 — 26:
Highlights from your plan
Bavaro Beach ©
Bavaro Beach
Safaris
Macao Beach ©
Macao Beach

2
nights
Providenciales, Turks and Caicos

Providenciales ©
The most commercialized part of the Turks and Caicos, Providenciales remains the islands' tourism heaven, boasting many resorts, hotel chains, and condominiums.
On the 27th (Fri), see the vivid underwater world at Bight Reef, then find your balance on the water with some of the best stand-up paddleboarding in the area, then tour the pleasant surroundings at Grace Bay, and finally steep yourself in history at Sapodilla Bay Hill Rock Carvings. On the next day, trot along with a tour on horseback, explore the gorgeous colors at Smith's Reef, then see some colorful creatures with a scuba or snorkeling tour, and finally don't miss a visit to Thursday Fish Fry.

To see reviews, maps, photos, and more tourist information, read Providenciales trip planner .

Do a combination of shuttle and flight from Punta Cana to Providenciales in 4.5 hours. Alternatively, you can fly. The time zone difference when traveling from Punta Cana to Providenciales is minus 1 hour. In December, daytime highs in Providenciales are 83°F, while nighttime lows are 75°F. Cap off your sightseeing on the 28th (Sat) early enough to travel back home.

Things to do in Providenciales

Outdoors Wildlife Tours

Side Trip

Smith's Reef
Find places to stay Dec 26 — 28:
Highlights from your plan
Grace Bay ©
Grace Bay
Smith's Reef
Smith's Reef
Scuba & Snorkeling

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