KEY WEST WATER ACTIVITIES FIELD GUIDE
Key West: Four Nights at the Southernmost Beach Resort — sun, salt and island pace
A 5-day, 4-night Key West escape based at the oceanfront Southernmost Beach Resort with included resort breakfast and a one-day hop-on, hop-off trolley pass—this guide lays out what to expect and how to plan your free-time adventures.
Key West: Four Nights at the Southernmost Beach Resort — sun, salt and island pace.
Located at the southern tip of the continental United States, Key West is a compact island where Atlantic surf, coral flats and a faded Caribbean architecture set the scene for slow days and active water play. This five-day escape centers on four nights at the Southernmost Beach Resort—an oceanfront property that puts you steps from Old Town and the Atlantic, private beaches, pools and a menu of on-site services to make island time simple and indulgent.
Highlights
Outing Highlights
Southernmost Beach Resort — six acres of oceanfront calm
Your base is the Southernmost Beach Resort, a six-acre oceanfront property at the edge of Old Town that offers two private beaches, three heated pools, multiple bars and an oceanfront restaurant, plus a fitness center, spa and daily resort activities—everything to balance downtime with easy access to island attractions.
Historic Duval Street and the Southernmost Point
The resort sits at the end of Duval Street where Old Town meets the Atlantic and places you within walking distance of Key West icons such as the Southernmost Point Buoy—90 miles from Cuba—plus Hemingway’s house, the Key West Lighthouse and the lively dining and shopping along Duval.
A playground of snorkeling, sailing and kayaking
Key West’s island setting invites water-based options during your free time—snorkeling on coral flats, sailing, fishing and kayaking are all popular pursuits and the resort’s concierge can help arrange excursions and sunset cruises.
What the day feels like
What this island escape feels like
The trip is built for choice: spend mornings with an included resort breakfast, linger on private sand and heated pools, and use a one-day hop-on, hop-off trolley pass to sample Key West’s compact attractions. Evenings mix laid-back seafood dinners or live music at the resort with the option to join sunset cruises or explore Duval Street’s nightlife—your days unfold around a comfortable oceanfront base and plenty of free time to pick your pace.
THE RESORT
Southernmost Beach Resort — six acres of oceanfront calm
Your base is the Southernmost Beach Resort, a six-acre oceanfront property at the edge of Old Town that offers two private beaches, three heated pools, multiple bars and an oceanfront restaurant, plus a fitness center, spa and daily resort activities—everything to balance downtime with easy access to island attractions.
THE SIGHTS
Historic Duval Street and the Southernmost Point
The resort sits at the end of Duval Street where Old Town meets the Atlantic and places you within walking distance of Key West icons such as the Southernmost Point Buoy—90 miles from Cuba—plus Hemingway’s house, the Key West Lighthouse and the lively dining and shopping along Duval.
THE WATER
A playground of snorkeling, sailing and kayaking
Key West’s island setting invites water-based options during your free time—snorkeling on coral flats, sailing, fishing and kayaking are all popular pursuits and the resort’s concierge can help arrange excursions and sunset cruises.
Suitability
Who it's for
Who this trip suits and who should reconsider.
Practical planner
Details to review before reserving
This is a five-day, four-night island stay (officially listed as 5 Days and 4 Nights). The advertised date context includes a January window (example dates provided: January 24–29, 2027).
Accommodations are at the Southernmost Beach Resort, an oceanfront property at the end of historic Duval Street with on-site dining, bars, pools, private beaches, fitness center, spa and concierge services for excursions and tours.
Four nights at the Southernmost Beach Resort and daily resort breakfast are included; the program also includes a one-day hop-on, hop-off trolley pass to explore the island.
Pack swimwear, sun protection, casual island clothing, comfortable walking shoes for Old Town, and any personal water-sport gear if you prefer—concierge services can arrange rentals and excursions for snorkeling, sailing, fishing or kayaking.
Review cancellation policies before reserving.
Frequently asked questions
Planning Your Outing
How long is the trip?
The program is five days and four nights.
Where do we stay?
Accommodations are at the Southernmost Beach Resort, an oceanfront resort located at the end of historic Duval Street where Old Town meets the Atlantic Ocean.
Are meals included?
Each morning a resort breakfast is included with your stay.
Is transportation around Key West provided?
The trip includes a one-day hop-on, hop-off trolley pass to help you explore the island; additional transportation and excursions can be arranged via the resort concierge.
What activities can I do during free time?
Popular free-time options listed include snorkeling, sailing, fishing, kayaking, visiting the Ernest Hemingway Home & Museum, Key West Butterfly & Nature Conservatory, the Harry S. Truman Little White House, sunset dinner cruises and trips to Dry Tortugas National Park.
What resort amenities are available?
The Southernmost Beach Resort features four bars, one oceanfront restaurant, three heated pools, two private beaches, a fitness center, spa, live music and daily resort activities, plus concierge services for excursions and tours.
How close is Key West to Cuba?
The Southernmost Point Buoy marks the southernmost point in the continental U.S. and sits roughly 90 miles from Cuba.