38 days in Caribbean Itinerary

38 days in Caribbean Itinerary

Created using Inspirock Caribbean travel route builder

Plan created by another user. Make it yours
1
Havana, Cuba
— 4 nights
2
Santo Domingo, Dominican Republic
— 2 nights
3
Punta Cana, Dominican Republic
— 4 nights
4
San Juan, Puerto Rico
— 3 nights
5
Philipsburg, St. Maarten-St. Martin
— 4 nights
6
Kralendijk, Bonaire
— 4 nights
7
Oranjestad, Aruba
— 4 nights
8
Willemstad, Curacao
— 5 nights
9
Bridgetown, Barbados
— 3 nights
10
St. George, Bermuda
— 3 nights

S M T W T F S
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24
25
26
27
28
29
30
31
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4
nights
Havana, Cuba

Havana ©

Rome of the Caribbean

Cuba's capital and major commercial center, Havana manages to be very old and very modern at the same time.
Havana is known for historic sites, nightlife, and museums. Your plan includes some of its best attractions: appreciate the extensive heritage of Malecón of Havana, don't miss a visit to Plaza de la Catedral, contemplate the long history of Old Square (Plaza Vieja), and get engrossed in the history at Museum of the Revolution (Museo de la Revolucion).

To find where to stay, reviews, other places to visit, and other tourist information, you can read our Havana itinerary planning website.

Manila, Philippines to Havana is an approximately 27-hour flight. You'll gain 13 hours traveling from Manila to Havana due to the time zone difference. Traveling from Manila in October, expect a bit cooler with lows of 24°C in Havana. Wrap up your sightseeing on the 28th (Wed) early enough to travel to Santo Domingo.

Things to do in Havana

Side Trip

Find places to stay Oct 24 — 28:
Highlights from your trip
©
Must see
Old Havana
4.6
©
Historic Walking Area
Malecón of Havana
3.9
©
Landmark
El Capitolio
4.0

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.
Start off your visit on the 29th (Thu): appreciate the history behind Columbus Lighthouse (Faro A Colon), then examine the collection at Museo De Las Casas Reales, then explore the historical opulence of Alcazar de Colon, and finally explore the ancient world of Monasterio de San Francisco. Get ready for a full day of sightseeing on the next day: take in the architecture and atmosphere at Basilica Cathedral of Santa Maria la Menor and then don't miss a visit to Zona Colonial.

To see where to stay, reviews, other places to visit, and tourist information, you can read our Santo Domingo travel route planner.

Traveling by flight from Havana to Santo Domingo takes 5.5 hours. Traveling from Havana to Santo Domingo, you'll lose 1 hour due to the time zone difference. Finish your sightseeing early on the 30th (Fri) to allow enough time to take a shuttle to Punta Cana.

Things to do in Santo Domingo

Find places to stay Oct 28 — 30:
Highlights from your trip

4
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.
Step out of Punta Cana with an excursion to Altos de Chavon in La Romana--about 1h 20 min away. Spend a day of island exploring on the 31st (Sat) at Saona Island. There's still lots to do: look for all kinds of wild species at Dominicana.pro, relax and rejuvenate at Flavio Acuna Spa Natural Center, stop by HARRISON'S Fine Caribbean Jewelers, and try your luck at Hard Rock Casino Punta Cana.

For other places to visit and tourist information, read our Punta Cana day trip planning tool.

You can take a shuttle from Santo Domingo to Punta Cana in 2 hours. Other options are to drive; or fly. In October, daytime highs in Punta Cana are 36°C, while nighttime lows are 28°C. Wrap up your sightseeing on the 3rd (Tue) to allow time to travel to San Juan.

Things to do in Punta Cana

Outdoors · Parks · Nature · Tours

Side Trips

Find places to stay Oct 30 — Nov 3:
Highlights from your trip
©
Must see
Saona Island
4.4
©
Must see
Bavaro Beach
4.5
©
Historic Walking Area
Altos de Chavon
4.4

3
nights
San Juan, Puerto Rico

San Juan ©

Walled City

Founded by the Spanish in 1521, San Juan is the oldest city under U.S.
Change things up with a short trip to El Yunque Rain Forest in El Yunque National Forest (about 1h 10 min away). And it doesn't end there: get to know the fascinating history of Old San Juan, stroll through Pine Grove Beach, skim along the rocks with a canyoning and rapelling tour, and savor the flavors at Food & Drink.

To see ratings, maps, where to stay, and more tourist information, you can read our San Juan travel planning tool.

You can fly from Punta Cana to San Juan in 2.5 hours. Alternatively, you can do a combination of bus and ferry. In November, daytime highs in San Juan are 36°C, while nighttime lows are 28°C. Wrap up your sightseeing on the 6th (Fri) early enough to travel to Philipsburg.

Things to do in San Juan

Parks · Outdoors · Wildlife · Nature

Side Trips

Find places to stay Nov 3 — 6:
Highlights from your trip
©
Must see
Old San Juan
4.7

4
nights

Take a trip to Philipsburg, the capital of Sint Maarten, and enjoy dynamic nightlife and great shopping.
Philipsburg is known for shopping, beaches, and wildlife. Your plan includes some of its best attractions: race across the water with a speed boat tour, enjoy the sand and surf at Orient Bay Beach, explore the activities along Mullet Bay Beach, and tour the pleasant surroundings at Maho Beach.

To see reviews, more things to do, photos, and tourist information, go to the Philipsburg trip builder site.

You can fly from San Juan to Philipsburg in 4 hours. In November in Philipsburg, expect temperatures between 35°C during the day and 30°C at night. Wrap up your sightseeing on the 10th (Tue) to allow time to travel to Kralendijk.

Things to do in Philipsburg

Outdoors · Parks · Beaches · Wildlife

Side Trips

Find places to stay Nov 6 — 10:
Highlights from your trip
©
Must see
Speed Boats Tours
4.9
©
Beach
Maho Beach
4.4
©
Beach
Dawn Beach
3.6

4
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.
Get out of town with these interesting Kralendijk side-trips: Washington-Slagbaai National Park (Boka Chikitu, Boca Slagbaai, &more). The adventure continues: step off the mainland to explore Klein Bonaire, get outside with Landsailing Adventures, explore the activities along Lac Bay, and make a trip to Seru Largu.

To find ratings, more things to do, maps, and other tourist information, refer to the Kralendijk day trip planning website.

Fly from Philipsburg to Kralendijk in 6.5 hours. In November, daytime highs in Kralendijk are 36°C, while nighttime lows are 30°C. Wrap up your sightseeing on the 14th (Sat) early enough to fly to Oranjestad.

Things to do in Kralendijk

Parks · Nature · Outdoors · Wildlife

Side Trips

Find places to stay Nov 10 — 14:
Highlights from your trip
©
Island
Klein Bonaire
4.6
©
Water Body
Lac Bay
4.5

4
nights
Oranjestad, Aruba

Oranjestad ©
When vacationing on Aruba, don't miss taking a tour of Oranjestad, the capital of the small Caribbean island.
Take a break from Oranjestad with a short trip to Baby Beach in San Nicolas, about 32 minutes away. Next up on the itinerary: enjoy the sand and surf at Eagle Beach, contemplate the long history of Bushiribana Gold Mill Ruins, explore the striking landscape of Arikok National Park, and tour the pleasant surroundings at Donkey Sanctuary Aruba.

To see traveler tips, more things to do, maps, and other tourist information, read Oranjestad trip planner.

Getting from Kralendijk to Oranjestad by flight takes about 3.5 hours. In November, plan for daily highs up to 37°C, and evening lows to 30°C. Wrap up your sightseeing on the 18th (Wed) early enough to travel to Willemstad.

Things to do in Oranjestad

Parks · Outdoors · Beaches · Nature

Side Trips

Find places to stay Nov 14 — 18:
Highlights from your trip
©
Must see
Eagle Beach
4.8
©
National Park
Arikok National Park
4.4
©
Beach
Palm Beach
4.5

5
nights
Willemstad, Curacao

Willemstad ©
Willemstad is the capital city of Curaçao, an island in the southern Caribbean Sea that forms a constituent country of the Kingdom of the Netherlands. Willemstad is known for wildlife, nature, and adventure. Your plan includes some of its best attractions: snap pictures at Queen Emma Pontoon Bridge, kick back and relax at Mambo Beach, examine the collection at Mikve Israel-Emanuel Synagogue, and step off the mainland to explore Klein (Little) Curacao.

For traveler tips, ratings, where to stay, and more tourist information, use the Willemstad driving holiday planner.

You can fly from Oranjestad to Willemstad in 4.5 hours. Expect a daytime high around 36°C in November, and nighttime lows around 30°C. Wrap up your sightseeing on the 23rd (Mon) to allow time to travel to Bridgetown.

Things to do in Willemstad

Parks · Outdoors · Beaches · Nature

Side Trip

Find places to stay Nov 18 — 23:
Highlights from your trip
©
Speed Boats Tour
Powerboat Caribbean
5.0

3
nights
Bridgetown, Barbados

Bridgetown is the capital and largest city of Barbados. Start off your visit on the 24th (Tue): take in panoramic vistas at Gun Hill Signal Station, admire the natural beauty at Hunte's Gardens, then steep yourself in history at Andromeda Botanic Gardens, then see the interesting displays at Sunbury Plantation House, and finally stroll through Bottom Bay. Get ready for a full day of sightseeing on the next day: take in nature's colorful creations at Welchman Hall Gully, Head underground at Harrison's Cave., then see some colorful creatures with a scuba or snorkeling tour, and finally enjoy the sand and surf at Carlisle Bay.

For ratings, maps, photos, and more tourist information, use the Bridgetown vacation planner.

Fly from Willemstad to Bridgetown in 8 hours. In November, plan for daily highs up to 35°C, and evening lows to 29°C. Cap off your sightseeing on the 26th (Thu) early enough to travel to St. George.

Things to do in Bridgetown

Parks · Outdoors · Beaches · Wildlife

Side Trips

Find places to stay Nov 23 — 26:
Highlights from your trip

3
nights
St. George, Bermuda

St. George ©
Kick off your visit on the 27th (Fri): examine the collection at Bermuda National Trust Museum, admire the landmark architecture of St. Peter's Church, then tour the pleasant surroundings at Tobacco Bay, and finally contemplate in the serene atmosphere at The Unfinished Church. On your second day here, take an in-depth tour of World Heritage Centre - St. George, Head underground at Crystal & Fantasy Caves, and then get engrossed in the history at St. George's Historical Society Museum.

For more things to do, photos, reviews, and tourist information, use the St. George trip planner.

Use the Route module to find suitable travel options from Bridgetown to St. George. In November, St. George is little chillier than Bridgetown - with highs of 27°C and lows of 22°C. Finish your sightseeing early on the 29th (Sun) so you can travel back home.

Things to do in St. George

Parks · Museums · Historic Sites · Beaches

Side Trip

Find places to stay Nov 26 — 29:
Highlights from your trip
©
Beach
Tobacco Bay
4.3
©
Religious Site
The Unfinished Church
3.8

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