Caribbean Cruise — Feb 7–16, 2025

Map & Route Overview

Interactive view of the cruise path from San Juan, PR, through the Eastern Caribbean.

Fri, Feb 7 — Chicago, IL → San Juan, PR

Time	Location / Notes
9:33 AM – 9:56 AM	Driving: 17 mi (23 min) to Chicago O’Hare International Airport (ORD)
9:56 AM – 1:47 PM	At Airport: ORD (check-in / boarding)
1:47 PM – 9:07 PM	Flight: Chicago → San Juan, 2,074 mi (5 hr 20 min)
9:07 PM – 9:37 PM	Arrival: Luis Muñoz Marín International Airport (SJU)
9:37 PM – 9:44 PM	Driving: 3.3 mi (7 min) to 115 Cll Ismael Rivera
9:44 PM	Arrived: 115 Cll Ismael Rivera (End of Day)

Sat, Feb 8 — San Juan, Puerto Rico

Time	Location / Notes
10:23 AM – 10:40 AM	Driving: 4.5 mi from 115 Cll Ismael Rivera
10:40 AM – 11:41 AM	Walking: 0.7 mi exploring area
11:41 AM – 12:05 PM	Ostra Cosa (Plaza del Soportal): Meal stop
12:05 PM – 12:28 PM	Driving: 8.9 mi
12:28 PM – 1:25 PM	The Mall of San Juan: Shopping (Il Nuovo Mercato)
1:25 PM – 1:41 PM	Driving: 3.9 mi
1:41 PM – 2:36 PM	Plaza Las Américas: Visited Macy’s, Cheesecake Factory
2:36 PM – 2:50 PM	Driving: 2.5 mi
2:50 PM	Return: Back at 115 Cll Ismael Rivera (End of Day)

Sun, Feb 9 — Old San Juan & Cruise Embarkation

Time	Location / Notes
8:16 AM	Left 115 Cll Ismael Rivera: Drove 1.2 mi (7 min) to La Alcapurria Quemá (8:23 AM – 9:41 AM)
9:41 AM – 10:06 AM	Walking: 0.7 mi to Tresbé (10:06 AM – 10:08 AM)
10:08 AM – 10:14 AM	Farmacia Americana: Quick stop
10:14 AM – 10:21 AM	Walking: Back home
10:21 AM – 11:58 AM	At home: Rest
11:58 AM – 12:10 PM	Driving: 2.8 mi to San Juan Cruise Port (12:10 PM – 12:50 PM)

Mon, Feb 10 — Road Town, Tortola, British Virgin Islands

Time	Location / Notes
10:01 AM – 10:28 AM	Road Town Ferry Terminal: Arrival
10:50 AM – 11:13 AM	Brandywine Bay: Stop
11:13 AM – 11:39 AM	Driving: 3.7 mi / 26 min
11:39 AM – 12:02 PM	Terrance B. Lettsome Airport: Beef Island
12:02 PM – 1:25 PM	Driving: 12 mi / 1 hr 23 min
1:25 PM – 1:38 PM	Tropical Fusion Beach Bar & Grill: Lunch
1:38 PM – 1:55 PM	Driving: 1.1 mi / 17 min
1:55 PM – 3:02 PM	Smuggler’s Cove: Visit
3:02 PM – 3:48 PM	Driving: 8.3 mi / 45 min
3:48 PM → Feb 11 6:15 AM	On a ferry: 10 mi / 14 hr 27 min (Sailing)

Tue, Feb 11 — St John's, Antigua & Barbuda

Time	Location / Notes
6:15 AM – 8:33 AM	Green Bay: St John’s (Arrival)
8:33 AM – 8:51 AM	Walking: 0.2 mi / 18 min
8:51 AM – 9:10 AM	Saint John’s Cathedral: Visit
9:10 AM – 9:26 AM	Driving: 2.5 mi / 15 min
9:26 AM – 1:21 PM	Sandals Grande Antigua Resort: Stay
1:21 PM – 1:38 PM	Driving: 2.6 mi / 17 min
1:38 PM – 3:58 PM	Heritage Quay Complex: Shopping
3:58 PM → Feb 12 9:19 AM	On a ferry: 140 mi / 17 hr 21 min (Sailing)

Wed, Feb 12 — Bridgetown, Barbados

Time	Location / Notes
9:19 AM – 11:26 AM	Bridgetown Harbour Cruise Terminal: Arrival
11:34 AM – 2:26 PM	La Cabane: Batts Rock Beach
2:26 PM – 2:30 PM	Driving: 0.8 mi / 3 min
2:38 PM – 3:39 PM	Driving: 10 mi / 1 hr 1 min
3:39 PM – 5:57 PM	Bridgetown Harbour Cruise Terminal: Return
5:57 PM → Feb 13 6:53 AM	On a ferry: 54 mi / 12 hr 55 min (Sailing)

Thu, Feb 13 — Castries, St Lucia

Time	Location / Notes
6:53 AM – 7:43 AM	Pointe Séraphine Cruise Port: Castries (Arrival)
7:43 AM – 9:26 AM	Walking: 1.1 mi / 1 hr 44 min
9:26 AM – 9:32 AM	Driving: 1.7 mi / 6 min
9:32 AM – 9:42 AM	George F.L. Charles Airport: St Lucia
9:42 AM – 9:55 AM	Driving: 1.7 mi / 13 min
8:19 PM → Feb 14 8:48 AM	On a ferry: 16 mi / 12 hr 28 min (Sailing)

Fri, Feb 14 — St Maarten / Saint-Martin (NL/FR)

Time	Location / Notes
8:48 AM – 9:48 AM	Port of St Maarten: Great Bay (Arrival)
9:48 AM – 9:51 AM	Driving: 0.4 mi / 3 min
9:51 AM – 10:04 AM	Point Blanche Bay: Sint Maarten
10:04 AM – 10:20 AM	Driving: 4.8 mi / 16 min
10:20 AM – 10:29 AM	La Saintoise Boulangerie et Pâtisserie: Breakfast
10:29 AM – 10:34 AM	Driving: 1.2 mi / 4 min
10:34 AM – 11:21 AM	Villa Beauvoir: Stay
11:21 AM – 1:46 PM	Driving: 3.3 mi / 2 hr 24 min
1:46 PM – 3:32 PM	Sunset Bar and Grill: Simpson Bay
3:32 PM → Feb 15 5:24 AM	Driving: 117 mi / 13 hr 53 min (Sailing/Overnight)

Sat, Feb 15 — St Thomas, U.S. Virgin Islands

Time	Location / Notes
5:24 AM – 5:55 AM	On a ferry: 2.1 mi / 31 min
5:55 AM – 7:58 AM	Havensight Mall & Tap and Still Restaurant: Breakfast
7:58 AM – 8:06 AM	Walking: 0.2 mi / 8 min
8:18 AM – 8:30 AM	Catch of the Day: Coki Point Rd
8:30 AM – 8:41 AM	Walking: 0.4 mi / 11 min
8:41 AM – 8:49 AM	Louie’s Market: Smith Bay Rd
8:49 AM – 9:04 AM	Missing travel: 3.6 mi / 14 min
9:04 AM – 2:32 PM	Magen’s Point Bar & Grill: Lunch stop
2:32 PM – 2:53 PM	Driving: 3.6 mi / 22 min
2:53 PM – 4:15 PM	Havensight Mall: Return visit
4:15 PM → Feb 16 5:10 AM	On a ferry: 89 mi / 12 hr 54 min (Sailing)

Sun, Feb 16 — Return to Chicago

Time	Location / Notes
9:01 AM – 9:20 AM	Driving: 6.6 mi / 19 min
9:20 AM – 10:39 PM	Flying: 13 hr 19 min including layovers
8:39 PM – 9:21 PM (CST)	Chicago O’Hare International Airport: Arrival

Philosophical Takeaways

The rhythm of the ocean mirrors the journey of personal growth: constant, powerful, and demanding respect. It taught me that sometimes, the greatest adventures happen when you simply allow yourself to be carried by the current.

A thought from St. Thomas, USVI (Day 9)

Beyond the beautiful ports and precise timings of the log, this trip reinforced the necessity of embracing the unplanned. The "missing entries" in the original log represent moments where the digital compass was set aside, and the compass of the soul took over. Those are the moments that truly change you.