54 days in Caribbean Itinerary

54 days in Caribbean Itinerary

Created using Inspirock journey builder

Plan created by another user. Make it yours
1
San Juan, Puerto Rico
— 4 nights
2
Jost Van Dyke, British Virgin Islands
— 5 nights
3
The Valley, Anguilla
— 3 nights
4
Jolly Harbour, Antigua and Barbuda
— 5 nights
5
Willemstad, Curacao
— 11 nights
6
Oranjestad, Aruba
— 8 nights
7
Providenciales, Turks and Caicos
— 7 nights
8
Seven Mile Beach, Cayman Islands
— 8 nights

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4
nights
San Juan, Puerto Rico

San Juan ©

Walled City

Founded by the Spanish in 1521, San Juan is the oldest city under U.S.
Deepen your sense of the past at sights like Old San Juan and Paseo de la Princesa. You'll enjoy a bit of beach vacationing at Ocean Park Beach and Balneario El Escambron. When in San Juan, make a side trip to see La Marquesa Forest Park in Guaynabo, approximately Guaynabo away. There's still lots to do: contemplate the waterfront views at Condado Lagoon, get to know the fascinating history of La Muralla, glide peacefully along the water with some of the best stand-up paddleboarding in the area, and pause for some serene contemplation at Catedral Metropolitana Basilica de San Juan Bautista.

Discover how to plan a San Juan trip in just a few steps with Inspirock's itinerary builder.

Las Vegas, USA to San Juan is an approximately 12.5-hour flight. Traveling from Las Vegas to San Juan, you'll lose 4 hours due to the time zone difference. Expect somewhat warmer evenings in San Juan when traveling from Las Vegas in September, with lows around 78°F. Cap off your sightseeing on the 23rd (Wed) early enough to travel to Jost Van Dyke.

Things to do in San Juan

Outdoors · Parks · Historic Sites · Beaches

Side Trip

Find places to stay Sep 19 — 23:
Highlights from your plan
Campo Rico Ziplining Adventures ©
Campo Rico Ziplining Adventures
Old San Juan ©
Old San Juan
Paseo de la Princesa ©
Paseo de la Princesa

5
nights

Jost Van Dyke ©
Home to fewer than 300 residents and encompassing just 8 sq km (3 sq mi), Jost Van Dyke represents the smallest of the four main British Virgin Islands.
Kids will appreciate attractions like White Bay and Ocean Spa Bvi. Visiting Foxy's Charters & Water Taxi and The Bubbly Pool will get you outdoors.

To find ratings, maps, traveler tips, and more tourist information, refer to the Jost Van Dyke route maker site.

You can do a combination of flight and ferry from San Juan to Jost Van Dyke in 3.5 hours. In September, daytime highs in Jost Van Dyke are 89°F, while nighttime lows are 80°F. You'll set off for The Valley on the 28th (Mon).

Things to do in Jost Van Dyke

Outdoors · Parks · Adventure · Tours
Find places to stay Sep 23 — 28:
Highlights from your plan
White Bay ©
White Bay
Foxy's Charters & Water Taxi ©
Foxy's Charters & Water Taxi

3
nights
The Valley, Anguilla

The Valley ©
The Valley is the capital of Anguilla, one of its fourteen districts, and the main "town" on the island., it had a population of 1,067.HistoryHistorical landmarksThe Valley has few examples of colonial architecture due to the relocation of Anguilla's administration to St. Kids will enjoy Shoal Bay and Meads Bay. Step off the beaten path and head to Crocus Bay Beach and Cove Bay. And it doesn't end there: kick back and relax at Rendezvous Bay Beach, pause for some serene contemplation at St. Gerard Roman Catholic Church, take a tour by water with Vigilant Divers Anguilla, and soothe aching muscles at some of the top local wellness centers.

For photos, maps, where to stay, and other tourist information, read The Valley road trip tool.

Do a combination of ferry and flight from Jost Van Dyke to The Valley in 4 hours. In September in The Valley, expect temperatures between 89°F during the day and 78°F at night. Wrap up your sightseeing on the 1st (Thu) to allow time to travel to Jolly Harbour.

Things to do in The Valley

Outdoors · Parks · Beaches · Wildlife

Side Trips

Find places to stay Sep 28 — Oct 1:
Highlights from your plan
Meads Bay ©
Meads Bay
Shoal Bay ©
Shoal Bay
Rendezvous Bay Beach ©
Rendezvous Bay Beach

5
nights

Jolly Harbour is a township on Antigua island, in Antigua and Barbuda.GeographyThe town is located in the southwest coast of the island in Saint Mary Parish, close to Bolans and south of Five Island Harbour.TourismIt contains shops, restaurants, holiday villas, private houses, golf-course and a marina and boatyard. Get outdoors at Scuba & Snorkeling and Ffryes Beach. Explore hidden gems such as Jolly Beach and jetovator Antigua. There's much more to do: enjoy the sand and surf at Deep Bay Beach, play a few rounds at Jolly Harbour Golf Club, tour the pleasant surroundings at Hawksbill Bay, and browse the exhibits of Art At The Ridge.

To see other places to visit, reviews, photos, and other tourist information, read our Jolly Harbour trip planner.

Traveling by combination of taxi, ferry, and flight from The Valley to Jolly Harbour takes 5 hours. In October, plan for daily highs up to 87°F, and evening lows to 77°F. On the 6th (Tue), wrap the sightseeing up by early afternoon so you can travel to Willemstad.

Things to do in Jolly Harbour

Outdoors · Parks · Beaches · Wildlife

Side Trips

Find places to stay Oct 1 — 6:
Highlights from your plan
Scuba & Snorkeling
Turners Beach ©
Turners Beach
Ffryes Beach ©
Ffryes Beach

11
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. Fort Beekenburg and Fortkirche - De Fortkerk - The Fortchurch in Fort Amsterdam will appeal to history buffs. Visiting Scuba & Snorkeling and Playa Jeremi will get you outdoors. Go for a jaunt from Willemstad to Barber to see Museo di Ka'i Orgel about 1h 5 min away. Next up on the itinerary: enjoy the sand and surf at Blue Bay Beach, make a trip to Queen Wilhelmina Bridge, soothe aching muscles at some of the top local wellness centers, and Head underground at Boca Tabla.

For traveler tips, more things to do, maps, and more tourist information, refer to the Willemstad trip itinerary planner.

Traveling by flight from Jolly Harbour to Willemstad takes 9 hours. October in Willemstad sees daily highs of 91°F and lows of 80°F at night. On the 18th (Sun), you'll travel to Oranjestad.

Things to do in Willemstad

Parks · Outdoors · Beaches · Nature

Side Trips

Find places to stay Oct 6 — 18:
Highlights from your plan
Blue Bay Beach ©
Blue Bay Beach
Daaibooi Beach ©
Daaibooi Beach
Playa Jeremi ©
Playa Jeremi

8
nights
Oranjestad, Aruba

Oranjestad ©
When vacationing on Aruba, don't miss taking a tour of Oranjestad, the capital of the small Caribbean island.
You'll get in some beach time at Eagle Beach and Mangel Halto Beach. Discover out-of-the-way places like Boca Cataavlina and Seroe Colorado. You'll find plenty of places to visit near Oranjestad: San Nicolas (Cosecha in San Nicolas, Baby Beach, &more). There's much more to do: take your sightseeing to a higher altitude at Hooiberg, tour the pleasant surroundings at Manchebo Beach, kick back and relax at Arashi Beach, and explore the gorgeous colors at Malmok Reef.

To see where to stay, ratings, other places to visit, and more tourist information, use the Oranjestad driving holiday planner.

You can fly from Willemstad to Oranjestad in 4.5 hours. In October in Oranjestad, expect temperatures between 91°F during the day and 81°F at night. On the 26th (Mon), wrap the sightseeing up by early afternoon so you can travel to Providenciales.

Things to do in Oranjestad

Parks · Outdoors · Beaches · Wildlife

Side Trips

Find places to stay Oct 18 — 26:
Highlights from your plan
Mangel Halto Beach ©
Mangel Halto Beach
Eagle Beach ©
Eagle Beach
Manchebo Beach ©
Manchebo Beach

7
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.
Your itinerary includes some good beach time at Grace Bay Beach and Long Bay Beach. Your inner history buff will appreciate Cheshire Hall Plantation and Sapodilla Bay Hill Rock Carvings. Spend the 30th (Fri) exploring nature at Princess Alexandra National Park. The adventure continues: explore the activities along Sapodilla Bay Beach, let the river carry you with M & J's Charters, stroll through Smith's Reef, and tee off at Provo Golf Club.

For other places to visit, maps, photos, and more tourist information, read Providenciales trip itinerary maker website.

You can fly from Oranjestad to Providenciales in 9.5 hours. You'll gain 1 hour traveling from Oranjestad to Providenciales due to the time zone difference. October in Providenciales sees daily highs of 88°F and lows of 79°F at night. Wrap up your sightseeing by early afternoon on the 2nd (Mon) to allow enough time to travel to Seven Mile Beach.

Things to do in Providenciales

Parks · Outdoors · Wildlife · Nature

Side Trip

Find places to stay Oct 26 — Nov 2:
Highlights from your plan
Grace Bay Beach ©
Grace Bay Beach
M & J's Charters ©
M & J's Charters
Half Moon Bay ©
Half Moon Bay

8
nights
Seven Mile Beach, Cayman Islands

Seven Mile Beach ©
Seven Mile Beach is a long crescent of coral-sand beach on the western end of Grand Cayman island. Discover out-of-the-way places like Smith's Barcadere and Governors Beach. We've included these beaches for you: Seven Mile Beach and Royal Palms Beach Club. Step out of Seven Mile Beach with an excursion to Davinoff's Concrete Sculpture Garden in North Side--about 40 minutes away. Next up on the itinerary: tour the pleasant surroundings at Stingray City Grand Cayman, test your team's savvy at Locked Inn Cayman, step aboard Kittiwake Shipwreck & Artificial Reef, and cool off at Cayman Turtle Centre: Island Wildlife Encounter.

To see traveler tips, maps, more things to do, and more tourist information, go to the Seven Mile Beach online trip itinerary planner.

You can fly from Providenciales to Seven Mile Beach in 9 hours. In November, daily temperatures in Seven Mile Beach can reach 85°F, while at night they dip to 77°F. You will have some time to spend on the 10th (Tue) before leaving for home.

Things to do in Seven Mile Beach

Parks · Outdoors · Wildlife · Beaches

Side Trips

Find places to stay Nov 2 — 10:
Highlights from your plan
Locked Inn Cayman ©
Locked Inn Cayman
Seven Mile Beach ©
Seven Mile Beach
Smith's Barcadere ©
Smith's Barcadere

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