THOMPSON ISLAND

Information

We’ve invited a small group of our closest friends/family to stay with us on Thompson Island during the wedding weekend. Thompson Island is also where we’ll be hosting the Welcome Party and After Party, so staying here makes the weekend super easy (and a lot of fun).

Thompson Island is a private, gated island connected to Key West by a bridge for easy access, and it’s about 10 minutes from downtown. Thompson Island

Lodging

For those staying with us on the island, we’re asking guests for a portion of the lodging. We’ve structured the room rates to be meaningfully lower than comparable accommodations in Key West during this time, particularly for a waterfront setting.

Our intention is to make staying together both convenient and approachable for those who would like to be at the center of the weekend’s events.

What you’re getting by staying on Thompson Island

  • You’re on-site for the Welcome Party + After Party (no late-night Ubers required)
  • Transportation to and from the wedding via the trolley
  • A private island setup with great shared spaces
  • Easy access to Key West via the bridge
  • Kitchen/fridge access
  • Kayaks, beach volleyball court, private beach

Rooms + setup

Thompson Island has multiple room options across the main house + cottages.
We’ll coordinate:

  • who’s in which room

  • arrival timing

  • any issues/challenges

  • the airport is 4 minutes (1.4 mi) away and we can arrange a pickup if needed

How booking/payment will work

Digital Payment (venmo/zelle/cash app): We have reached out to everyone who is invited to stay with us. If you are able, please send us the discussed amount.

Zelle – 706-834-5705

More details about the property are here:

https://thompsonislandkeywest.com/

Location

Thompson Island
4095 South Roosevelt Boulevard, Key West, FL 33040
Google Maps
Apple Maps

Quick expectations

  • This is a shared, group weekend house vibe (fun + respectful of the space).

  • If you’re staying here, you’re also in the middle of the action for the Welcome/After Party—so expect some lively energy.

FAQs

💌 When is the RSVP deadline?

We kindly ask that you RSVP by January 15th, 2026.

📍 What are the addresses of the venues?

-Welcome Party & After Party:
Thompson Island
4095 South Roosevelt Blvd, Key West, FL 33040

-Wedding & Reception:
Ernest Hemingway Home & Museum
907 Whitehead St, Key West, FL 33040

🏠 Where should I stay?

Please see our Accommodations page for our favorite recommendations.
We’ve reserved a hotel block at the Perry Hotel and Marina — the perfect waterfront spot near Thompson Island. You can book directly here or call and ask for the Diller–Baker wedding party rate.

We also love exploring the island’s unique lodging options — from cozy Airbnbs and VRBOs to houseboats and tiny homes at Boyd’s Key West Campground. Adventure encouraged!

👗 What is the dress code?

Dress code for the welcome party is tropical or destination casual.

The wedding ceremony is cocktail / semi-formal.  

Don’t be afraid to lean into bright, bold tropical colors! 

For the After Party, anything goes — think fun and comfortable.

☀️ Will the events be indoors or outdoors?

  • Welcome Party & After Party: Indoor and outdoor areas available.

  • Wedding & Reception: Entirely outdoors (with a rain plan in place).

🌙 What is the After Party like?

This one’s for the night owls! Join us back at Thompson Island after the reception, where we’ll trade heels and ties for flip-flops and late-night fun. Expect loud music, snacks, dancing, and zero rules — we’ll celebrate until sunrise!

🚎 What’s the easiest way to get to and from the wedding venues?

🕔 Updated Schedule 12/7

  • Guests cannot enter the Hemingway Home until 5:45 PM.

  • The Old Town Trolley will pick up from the Perry Hotel at 5:00 PM, then depart Thompson Island at 5:25 PM to arrive at the Hemingway Home by 5:45 PM.

  • Travel time is approximately 20 minutes, so please plan to be ready a few minutes early to ensure a smooth departure.

🚎 Getting To and From the Wedding

We recommend traveling via the Old Town Trolley from either Thompson Island or the Perry Hotel.

  • Free parking is available at Thompson Island.

  • Limited paid parking is available in Old Town near the Hemingway Home.

  • The trolley will take you to the wedding and bring you back after the reception.

Other great options for getting around Key West include:

  • Uber / Lyft

  • Moped rentals (our favorite!)

  • Free Duval Loop bus

🚌 Trolley Schedule

  • To the Wedding: 5:00–6:00 PM departures from Thompson Island and the Perry Hotel

  • Return After Reception: 10:00–11:00 PM back to Thompson Island and the Perry Hotel

Exact departure times will be confirmed closer to the date.

Please plan your evening with these times in mind — this ensures everyone arrives together and can enter the Hemingway Home right as the celebration begins!

🧒 Can I bring a plus one or children?

We kindly ask that you do not bring additional guests or children unless explicitly invited.

🎁 Where are you registered?

Your presence is truly the greatest gift!
However, if you’d like to celebrate us with a gift, we are registered at Crate & Barrel
Please visit the Registry here for the direct link.

ACCOMMODATIONS

If you’re looking for accommodations — look no further!

We’ve reserved a block of rooms at the Perry Hotel and Marina, located right on the waterfront near Thompson Island. This is the most convenient option for our events and offers a true Key West marina vibe.

👉 Book your room here:
Reserve at the Perry Hotel & Marina (Diller–Baker Wedding Block)

Alternatively, you can call the hotel directly and ask to be booked under the Diller–Baker wedding party to receive the group rate.

🏝️ Other Recommended Stays

Some of our favorite local options include:

  • Boyd’s Key West Campground – Great for RVs, tent camping, and even tiny home rentals. This spot is close to the water and has a fun, community feel.

  • Houseboats & Floating Rentals – For a unique experience, check out the beautiful houseboats on Airbnb or VRBO. Several are docked nearby, offering a peaceful setting and unbeatable sunset views.

🏡 Vacation Rentals

Key West and Stock Island are full of wonderful Airbnb and VRBO options — from classic conch cottages to modern condos with ocean views.

  • Search for listings near Old Town (close to the Hemingway Home) or Stock Island (near Thompson Island).

  • Many rentals include bikes or kayaks — perfect for getting around and exploring!

No matter where you stay, you’ll be surrounded by turquoise water, tropical breezes, and that laid-back Key West charm.

RSVP

Event Registration Form (#3)

Event Attendance

Choose your events to help us with headcounts and logistics. Need clarity on activities, timing, or transport? Head to the FAQ.

GETTING TO KEY WEST

Fly (fastest)

  • Airport: Key West International (EYW), 10–15 minutes from Old Town.

  • Who flies here: American, Delta, United, JetBlue, Allegiant, Breeze (plus a couple of new/seasonal entrants). Routes change with the season, but there are nonstops from major hubs.

Budget-minded flyers

If nonstops to EYW are pricey, try a fly to MIA+ drive/shuttle combo:

  • Fly into Miami (MIA) for more (often cheaper) flight choices, then continue by shuttle, bus, or car (2.5–3 hours along the scenic Overseas Highway). Keys Shuttle runs door-to-door service between MIA and the Keys.

Drive (scenic)

  • From mainland Florida, take US-1/Overseas Highway all the way down the island chain (~165 miles from Miami). Consider splitting the drive with a lunch stop in Islamorada or Marathon.

 

GETTING AROUND

No car needed in Old Town

  • Free Duval Loop: Hop-on/hop-off bus that circulates through Old Town (great for bars, beaches, Southernmost Point, and the waterfront). Runs daily; frequencies vary by time of day.

  • Lower Keys Shuttle: Public bus linking Key West with Stock Island, Big Pine, Marathon, etc.—handy if you’re staying up the Keys.

  • Bikes, scooters & rideshare: Short distances, limited parking—two wheels or Uber/Lyft are easy. Scooters are the best way to get around Key West. If you do rent a car, plan for paid parking and narrow streets near Old Town.

Pro tips for guests

  • Compare two itineraries: (a) Fly EYW nonstop vs. (b) MIA/FLL + shuttle/drive—you’ll often save with plan (b), especially on peak weekends. If you’re looking to cruise in style, there are many luxury car rental options in Miami.

  • Don’t overpack: Old Town is walkable; many hotels have beach gear/bikes.

  • Skip a car if you can: Between the Duval Loop, Scooters (so fun!), bikes, and rideshare, you’ll be set—and you’ll avoid parking stress.