FR EA
1044-00004 · Client 1044 · Offering Memorandum & Disclosure
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[slide 1]

Disclaimer & Important Notice

This presentation is confidential and has been prepared solely for informational purposes in connection with the proposed offering of $400,000,000 aggregate principal amount of Senior Secured Notes due 2029 (the 'Notes') by Thalassa Shipping & Logistics SA and Thalassa Finance Pte. Ltd. (together, the 'Co-Issuers')

The Notes have not been and will not be registered under the U.S. Securities Act of 1933, as amended; offered only to qualified institutional buyers pursuant to Rule 144A and to non-U.S. persons in offshore transactions pursuant to Regulation S

This presentation does not constitute an offer to sell or a solicitation of an offer to buy any securities in any jurisdiction

This presentation must be read in conjunction with the Offering Memorandum dated September 12, 2022; in the event of any inconsistency, the Offering Memorandum shall prevail

Forward-looking statements involve risks and uncertainties including, without limitation, fluctuations in the Baltic Dry Index, charter rate volatility, vessel values, regulatory changes, and general economic conditions

Minimum denominations of $200,000 and $1,000 increments above

Lead Bookrunner and Initial Purchaser: Anchor Bay Securities LLC; Co-Manager and Initial Purchaser: Halcyon Partners International Ltd.

[slide 2]

Table of Contents

I. Executive Summary & Investment Highlights

II. Transaction Overview

III. Company Overview & History

IV. Fleet Profile

V. Market Overview & Industry Dynamics

VI. Business Operations & Trade Lanes

VII. Financial Highlights

VIII. Use of Proceeds & Capitalization

IX. Security Package & Collateral

X. Covenant Summary

XI. Ratings Overview

XII. Key Risk Factors

XIII. Appendix

[slide 3]

Executive Summary

Thalassa Shipping & Logistics SA ('TSL') is a Greek-headquartered private shipping and logistics company founded in 1997 by the Kallistratos family

Operates a diversified fleet of 50 vessels: 38 dry-bulk carriers (Supramax, Ultramax, and Kamsarmax classes) and 12 container feeder vessels

Integrated platform with port logistics and freight-forwarding operations across Eastern Mediterranean, Black Sea, and Southeast Asia trade lanes

Total fleet appraised at approximately $1.82 billion (June 2022, by Compass Marine Valuations Ltd.)

LTM Revenue of $687.4 million and LTM Adjusted EBITDA of $214.6 million (Q1 2022 annualized), representing a 31.2% EBITDA margin

Proposed offering: $400 million Senior Secured Notes due October 15, 2029, at an indicative coupon of 8.750% per annum

Pro forma net leverage of 1.59x and interest coverage of 6.13x

[slide 4]

Investment Highlights (1 of 2)

Leading independent operator with 25+ years of operational track record in dry-bulk and container feeder segments

Diversified fleet across multiple vessel classes reduces single-segment concentration risk

Integrated business model: vessel ownership, port logistics (via Thalassa Port Services FZCO), and freight forwarding (via Thalassa Freight Solutions Pte. Ltd.) provides multiple revenue streams

Young, well-maintained fleet with average vessel age of 9.2 years, well below industry average

Strategic positioning across high-growth Eastern Mediterranean, Black Sea, and Southeast Asia trade lanes

[slide 5]

Investment Highlights (2 of 2)

Conservative pro forma leverage: 1.59x net leverage vs. 3.50x incurrence covenant threshold

Robust collateral package: first-priority ship mortgages on 28 vessels valued at $1.175 billion (2.94x coverage ratio)

Strong interest coverage of 6.13x provides significant debt-service cushion

Experienced management team led by CEO Spyros Andreou with deep shipping industry expertise

Stable, long-term family ownership (Kallistratos family — 72.5%) with institutional validation from Pelagos Capital Partners Fund III LP (18.0%)

Simplified post-offering capital structure: single-tranche Notes replace bilateral facilities

[slide 6]

Transaction Overview

Co-Issuers: Thalassa Shipping & Logistics SA and Thalassa Finance Pte. Ltd.

Offering Size: $400,000,000 aggregate principal amount

Security: Senior Secured Notes due October 15, 2029 (7-year maturity)

Coupon (indicative): 8.750% per annum, payable semi-annually (April 15 and October 15)

Issue Price: 98.00% of par (OID of 2.00%); Yield to Maturity: approximately 9.12%

Format: Rule 144A / Regulation S; DTC / Thackeray Partners LLC / Ashgrove Enterprises

Governing Law: Singapore

Listing: Application to SGX-ST

Ratings: B+ (stable) from Polaris Ratings Group Ltd.; B1 (stable) from Oceanic Credit Assessments Inc.

[slide 7]

Transaction Parties

Co-Issuers: Thalassa Shipping & Logistics SA (Greece) and Thalassa Finance Pte. Ltd. (Singapore, UEN 202209345K)

Guarantors: Thalassa Dry Bulk Operations Ltd. (Malta), Thalassa Container Feeder Ltd. (Marshall Islands), Thalassa Port Services FZCO (Dubai), Thalassa Freight Solutions Pte. Ltd. (Singapore)

Parent Guarantor: Kallistratos Maritime Holdings Ltd. (BVI) — limited guarantee capped at $50 million

Lead Bookrunner / Initial Purchaser: Anchor Bay Securities LLC

Co-Manager / Initial Purchaser: Halcyon Partners International Ltd.

Indenture Trustee: Marlowe Asset Management Trust Company of Singapore Pte. Ltd.

Security Agent: Atlas Collateral Agency Pte. Ltd.

Rating Agencies: Polaris Ratings Group Ltd. (B+ stable); Oceanic Credit Assessments Inc. (B1 stable)

Fleet Appraiser: Compass Marine Valuations Ltd.

Auditor: Kestrel & White Chartered Accountants

[slide 8]

Company Overview — History & Milestones

Founded in 1997 by the Kallistratos family in Piraeus, Greece — one of the world's premier maritime hubs

Grew from a single-vessel operation to a 50-vessel diversified fleet over 25 years

Expanded into container feeder segment and integrated logistics services

2015: Recruited Spyros Andreou as CEO to professionalize management and drive operational excellence

Strategic investment by Pelagos Capital Partners Fund III LP (18.0% equity) — institutional validation of platform

ESOP trust holds 9.5% — aligning management incentives with long-term performance

Headquarters: 42 Akti Miaouli, Piraeus 185 35, Greece

[slide 9]

Organizational Structure

Kallistratos Maritime Holdings Ltd. (BVI) — 72.5% equity holder; 100% beneficially owned by Dimitrios Kallistratos

Pelagos Capital Partners Fund III LP (Cayman Islands) — 18.0% equity holder; 2 of 7 board seats

Management ESOP Trust — 9.5%

Thalassa Shipping & Logistics SA (Greece) — parent operating company

Thalassa Finance Pte. Ltd. (Singapore) — wholly-owned co-issuer SPV; holds intercompany loans ($365M) to fleet subs

Fleet-Owning Subsidiaries: Thalassa Dry Bulk Operations Ltd. (Malta — 22 bulkers), Thalassa Container Feeder Ltd. (Marshall Islands — 12 feeders)

Operating Subsidiaries: Thalassa Port Services FZCO (Dubai), Thalassa Freight Solutions Pte. Ltd. (Singapore)

[slide 10]

Management Team

Dimitrios Kallistratos — Chairman & Controlling Shareholder; 40+ years in shipping; founder's son

Elena Kallistratos-Pavlou — Vice Chairwoman; oversees fleet management and vessel operations

Spyros Andreou — Chief Executive Officer; former Westvale Advisors partner; joined TSL in 2015; drives strategic initiatives

Marina Demetriou — Chief Financial Officer & Sole Director of Thalassa Finance Pte. Ltd.; CPA (Greece); previously at Oceanus Dry Cargo Holdings

Alexandros Theodorakis — General Counsel; qualified in Greece and England & Wales; oversees legal and regulatory affairs

[slide 11]

Fleet Overview — At a Glance

Total Fleet: 50 vessels

Dry-Bulk Carriers: 38 vessels (Supramax, Ultramax, Kamsarmax classes)

Container Feeder Vessels: 12 vessels

Total Deadweight Tonnage (DWT): approximately 2.85 million

Average Vessel Age: 9.2 years

Total Fleet Appraised Value: $1.82 billion (June 2022, Compass Marine Valuations Ltd. desktop appraisal)

Collateral Vessels: 28 of 50 vessels, appraised at $1.175 billion

[slide 12]

Fleet Profile — Dry-Bulk Carriers

38 dry-bulk carriers across three vessel classes:

Supramax (45,000–60,000 DWT): versatile, geared vessels suitable for minor bulk trades and ports with limited infrastructure

Ultramax (60,000–65,000 DWT): larger variant of Supramax with enhanced cargo capacity and fuel efficiency

Kamsarmax (80,000–82,000 DWT): max-size Panamax vessels optimized for coal and grain trades

Owned and operated through Thalassa Dry Bulk Operations Ltd. (Malta)

Core trade routes: Eastern Mediterranean grain corridor, Black Sea coal/steel exports, Southeast Asia minor bulks

[slide 13]

Fleet Profile — Container Feeder Vessels

12 container feeder vessels

Serve intra-regional trade connecting hub ports to secondary ports

Owned through Thalassa Container Feeder Ltd. (Marshall Islands)

Complementary to dry-bulk operations — different demand drivers and cyclicality

Contract mix includes time charters and voyage charters, providing revenue diversification

[slide 14]

Fleet Profile — Vessel Age and Maintenance

Average vessel age of 9.2 years — well below global dry-bulk fleet average

Young fleet reduces near-term drydocking and special survey capital expenditure requirements

Compliance with IMO 2020 sulfur regulations and positioning for future environmental requirements

Well-maintained fleet supports higher charter rates and stronger resale values

Appraised fleet value of $1.82 billion reflects quality and condition

[slide 15]

Market Overview — Dry-Bulk Market Fundamentals

Dry-bulk shipping is a global industry driven by demand for raw materials (iron ore, coal, grain, minor bulks)

Baltic Dry Index (BDI) is the primary industry benchmark — reached approximately 3,400 in May 2022

Supply-side discipline: limited orderbook supports medium-term rate environment

Demand drivers: global trade growth, infrastructure investment, urbanization in emerging markets

TSL's Supramax/Ultramax/Kamsarmax segments benefit from fragmented market with strong spot-rate exposure

[slide 16]

Market Overview — Container Feeder Market

Container feeder vessels serve as critical connectors in global supply chains

Demand driven by hub-and-spoke network expansion and port congestion dynamics

Eastern Mediterranean and Southeast Asia are high-growth feeder markets

Feeder rates have benefited from broader container market strength

TSL's 12-vessel feeder fleet provides strategic diversification away from pure dry-bulk exposure

[slide 17]

Trade Lane Overview — Eastern Mediterranean & Black Sea

Eastern Mediterranean: key grain export corridor; strategic location connecting Europe, Africa, and Asia

Black Sea: major coal and steel export region; significant agricultural commodity flows

TSL's Piraeus headquarters provides operational proximity and local market knowledge

Long-standing port relationships and logistics infrastructure (via Thalassa Port Services FZCO, Dubai)

[slide 18]

Trade Lane Overview — Southeast Asia

Southeast Asia: rapidly growing trade volumes driven by industrialization and intra-regional commerce

TSL operates freight-forwarding services through Thalassa Freight Solutions Pte. Ltd. (Singapore)

Container feeder vessels serve hub-and-spoke networks connecting Singapore and other major ports

Growing minor-bulk trade (nickel, bauxite, palm oil) provides Supramax/Ultramax deployment opportunities

[slide 19]

Integrated Business Model

Vessel Ownership & Operations: core revenue driver — 50 vessels across dry-bulk and container feeder segments

Port Logistics: Thalassa Port Services FZCO (Dubai) — cargo handling, stevedoring, and port agency services

Freight Forwarding: Thalassa Freight Solutions Pte. Ltd. (Singapore) — end-to-end logistics solutions for customers

Integration creates revenue synergies, customer stickiness, and operational efficiency

Multiple revenue streams reduce dependence on any single market segment or charter type

[slide 20]

Financial Highlights — Key Metrics

LTM Revenue (Q1 2022 Annualized): $687.4 million

LTM Adjusted EBITDA (Q1 2022 Annualized): $214.6 million

EBITDA Margin: 31.2%

Cash on Balance Sheet: $58.3 million

Pro Forma Total Debt (post-offering): $400.0 million (Notes only — bilateral facilities fully refinanced)

Pro Forma Net Debt: $341.7 million

Pro Forma Net Leverage: 1.59x

Pro Forma Interest Coverage: 6.13x

[slide 21]

Financial Highlights — Revenue Diversification

Revenue by Segment: Dry-bulk vessel operations, container feeder operations, port logistics, freight forwarding

Revenue by Geography: Eastern Mediterranean, Black Sea, Southeast Asia, other

Multi-segment, multi-geography revenue base reduces concentration risk

Charter mix includes time charters, voyage charters, and contracts of affreightment

[slide 22]

Financial Highlights — Historical Financial Performance

Consistent revenue growth driven by fleet expansion and favorable market conditions

EBITDA margin expansion reflecting operational leverage and fleet optimization

Strong cash generation supporting fleet renewal and debt reduction

Financial statements audited by Kestrel & White Chartered Accountants

[slide 23]

Pro Forma Capitalization

Pre-Offering Debt: $310 million bilateral ship-finance facilities ($190M Meridian Maritime Bank AG + $120M Clearwater Shipping Finance Ltd.)

Post-Offering Debt: $400 million Senior Secured Notes due 2029 (only funded debt)

Cash on Balance Sheet: $58.3 million

Pro Forma Net Debt: $341.7 million

Fleet Appraised Value: $1.82 billion

Equity: 72.5% Kallistratos Maritime Holdings Ltd. / 18.0% Pelagos Capital Partners Fund III LP / 9.5% Management ESOP

[slide 24]

Use of Proceeds

Refinance Meridian Maritime Bank AG bilateral facility: $190,000,000

Refinance Clearwater Shipping Finance Ltd. bilateral facility: $120,000,000

General corporate purposes and fleet capital expenditures: $72,000,000

Estimated fees, expenses, and OID: $18,000,000

Total: $400,000,000

[slide 25]

Sources and Uses

Sources: $400M Senior Secured Notes (at par); net cash proceeds at 98% issue price = $392M; plus TSL cash contribution